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WO2023168301A2 - Compositions de soins à domicile comprenant de l'huile produite par voie microbienne et leurs dérivés - Google Patents

Compositions de soins à domicile comprenant de l'huile produite par voie microbienne et leurs dérivés Download PDF

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Publication number
WO2023168301A2
WO2023168301A2 PCT/US2023/063528 US2023063528W WO2023168301A2 WO 2023168301 A2 WO2023168301 A2 WO 2023168301A2 US 2023063528 W US2023063528 W US 2023063528W WO 2023168301 A2 WO2023168301 A2 WO 2023168301A2
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Prior art keywords
microbial oil
oil
home care
microbial
care composition
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WO2023168301A3 (fr
Inventor
Harold M. Mcnamara
Shara TICKU
David Heller
Corentin MOEVUS
Bowen Zhang
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C16 Biosciences Inc
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C16 Biosciences Inc
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Publication of WO2023168301A3 publication Critical patent/WO2023168301A3/fr
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/667—Neutral esters, e.g. sorbitan esters
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2093—Esters; Carbonates
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/38—Products with no well-defined composition, e.g. natural products

Definitions

  • the present disclosure relates to environmentally friendly and sustainable alternatives to plant-derived palm oil for home care compositions.
  • the palm oil alternatives are produced by oleaginous microorganisms and share one or more features with plant-derived palm oils. These alternatives may also be fractionated, treated, and/or derivatized based, on their intended use.
  • Palm oil is currently the most widely produced vegetable oil on the planet, as it finds uses in the manufacture of a large variety of products. Derivatives of palm oil are widely used in a number of everyday products, such as laundry' detergents, dishwashing detergent, household cleaners, and household items. The global demand for palm oil is approximately 57 million tons and is steadily increasing. However, the high demand for palm oil has resulted in environmentally detrimental practices related to the expansion of plantations devoted to palm oil-producing plants. Palm oil production is a leading contributor to tropical deforestation, resulting in habitat destruction, increased carbon dioxide emissions, and local smog clouds across South East Asia.
  • the present disclosure relates to a microbial oil and derivatives thereof.
  • the microbial oil comprises a fatty acid, profile of at least 30% saturated, fatty acids, at least 30% unsaturated faty acids, and less than 30% polyunsaturated fatty acids.
  • the microbial oil is refined, bleached, and/or deodorized.
  • the present disclosure relates to home care compositions and methods of producing home care compositions comprising a microbial oil and/or a derivative thereof.
  • the microbial oil derivative functions as a surfactant, emulsifier, wetting agent, ester, solvent, process aid, humectant, quaternary ammonium compound, antistatic agent, softening agent, rheology modifier, thickener, foam suppressor, anti-foaming agent, foam booster, stabilizer, or cleaning agent in the home care composition.
  • the present disclosure relates to methods of producing derivatives from a microbial oil comprising obtaining a whole cell or lysed microbial biomass, extracting crude microbial oil from the whole cell or lysed microbial biomass, wherein said extraction process removes toxins and produces a microbial oil safe for human use, and modifying the microbial oil to produce a derivative.
  • the modifying comprises fractionation, interesterification, transesterification, hydrogenation, steam hydrolysis, distillation, saponification, amination, ethyoxylation, sulfonation, oxidation, quaternization, or combinations thereof.
  • the disclosure relates to a derivative produced from a microbial oil.
  • the derivative is isostearyl palmitate, polyglyceryl-4 dipalmitate, sorbitan palmitate, poly glyceryl- 10 dioleate, polyglyceryl-4 oleate, retinyl palmitate, ascorbyl palmitate, sucrose palmitate, ethyl palmate, methyl ester sulfonate, or an esterquat.
  • FIG. 1 is a flow diagram illustrating examples of various methods of processing the microbial oil and the resulting derivatives (oleochemicals) which may be used in home care compositions.
  • FIG. 2A shows a chromatogram of the triglyceride composition analysis of exemplary crude microbial oil
  • FIG. 2B shows a chromatogram of the triglyceride composition analysis of exemplary crude palm oil
  • FIG. 2C shows a chromatogram of the triglyceride composition analysis of exemplary crude hybrid palm oil.
  • FIG, 3 is a flow diagram of fractions produced from microbial oil.
  • FIG. 4A is a photograph of a fractionation of erode microbial oil (left) and crude palm oil (right).
  • FIG. 4B is a photograph of a complete fractionation of crude microbial oil.
  • FIG. 4C is a photograph of an incomplete fractionation of erode microbial oil.
  • FIG. 5 is a bar graph showing gas chromatography-mass spectrometry (GCMS) data highlighting how the fractionation shifts the fatty acid profile in the olein and stearin layers.
  • GCMS gas chromatography-mass spectrometry
  • FIG. 6 is a bar graph of the data shown in FIG. 5 illustrating the overall balance of saturated fatty acids (SFA), monounsaturated fatty acids (MUFA), and polyunsaturated fatty acids (PUFA).
  • SFA saturated fatty acids
  • MUFA monounsaturated fatty acids
  • PUFA polyunsaturated fatty acids
  • FIG. 7A shows a chromatogram of the fatty acid composition analysis of exemplary erode microbial oil
  • FIG. 7B shows a chromatogram of the fatty acid composition analysis of exemplary crude palm oil
  • FIG. 7C shows a chromatogram of the fatty acid composition analysis of exemplary crude hybrid palm oil
  • FIG. 7D shows a bar graph of representative fatty acid compositions of microbial oil and palm oil.
  • FIG. 8 A is a flow diagram of fatty acids produced from microbial oil.
  • FIG. 8B is a flow diagram of fatty alcohols produced from microbial oil.
  • FIG. 9 shows a chromatogram of the tocopherols analysis of exemplary- erode microbial oil, crude palm oil, and crude hybrid palm oil. Notable peaks are annotated, with “External ISTD” illustrating the location of the standard.
  • FIG. 10A shows a representative chromatogram of the triglyceride profile showing the main TAG region.
  • FIG. 10B shows a representative chromatogram of the mono- and diglyceride profile showing the mono- and diglyceride regions.
  • FIG. 11A shows a flow chart, and corresponding images and specifications of crude, refined, refined and bleached, and RBD microbial oil samples processed with an antioxidant.
  • FIG. 11B shows a flow chart and corresponding images and specifications of erode, refined, refined and bleached, and RBD microbial oil samples processed without an antioxidant.
  • FIG, 12A-12D show total ion chromatograms for four different oil samples: an exemplary toruloides microbial oil of the disclosure (FIG. 12A); algae oil (FIG. 12B); crude palm oil (FIG, 7C); and refined, bleached, and deodorized (RBD) palm oil (FIG. 12D).
  • FIG. 13 shows a representative extracted peak for a compound of interest (ergosterol- TMS) from the total ion chromatogram of an exemplary microbial oil of the present disclosure.
  • FIG, 14A-14E show the electron-ionization spectra for five different deri vatized sterol s spiked into crude palm oil : ergosterol-TMS (FIG. 14A); cholesterol-TMS (FIG. 14B); campesterol-TMS (FIG, 14C); sitosterol-TMS (FIG, I4D); and stigmasterol-TMS (FIG, 14E).
  • FIG. 15A-15B show the results of a carotenoid analysis of agricultural palm oil.
  • FIG. 15A shows the overall UV/Vis absorbance spectrum.
  • FIG, 15B shows the HPLC-DAD chromatogram with absorbance at 450 nm.
  • FIG. 16A-16B show the results of a carotenoid analysis of a strong acid-extracted exemplary Ft toruloides microbial oii of the present disclosure.
  • FIG. 16A show's the overall UV/Vis absorbance spectrum.
  • FIG. 16B shows the HPLC-DAD chromatogram with absorbance at 450 nm.
  • FIG, 17A-17B show the results of a carotenoid analysis of a strong acid-extracted exemplary/ R. toruloides microbial oil of the present disclosure.
  • FIG. 17A shows the overall UV/Vis absorbance spectrum.
  • FIG, 17B shows the HPLC-DAD chromatogram with absorbance at 450 nm.
  • FIG, 18A-18B show the results of a carotenoid analysis of a weak acid-extracted exemplary R. toruloides microbial oil of the present disclosure.
  • FIG. 18A shows the overall UV/Vis absorbance spectrum.
  • FIG. 18B shows the HPLC-DAD chromatogram with absorbance at 450 nm.
  • FIG. 19A-19B show the results of a carotenoid analysis of an acid-free extracted exemplary Ft toruloides microbial oil of the present disclosure.
  • FIG. 19A shows the overall UV/Vis absorbance spectrum.
  • FIG. 1911 show's the HPLC-DAD chromatogram with absorbance at 450 nm.
  • FIG. 20A-20B show the results of a carotenoid analysis of an acid-free extracted exemplary R. toruloides microbial oil of the present disclosure.
  • FIG. 20A show's the overall UV/Vis absorbance spectrum.
  • FIG. 20B shows the HPLC-DAD chromatogram with absorbance at 450 nm.
  • FIG. 21A shows the results of faty acid methyl ester (FAME) analysis of the solid fraction resulting from solvent-based fractionation condition 1 in Example 17.
  • FIG. 21B shows a Differential Scanning Calorimeter (DSC) chromatogram for the solid fraction resulting from solvent-based fractionation condition 1 in Example 17.
  • DSC Differential Scanning Calorimeter
  • FIG. 22 shows the results of FAME analysis of the liquid fraction resulting from solvent-based fractionation condition 1 in Example 17.
  • FIG. 23A shows the results of FAME analysis of the solid fraction resulting from solvent-based fractionation condition 2 in Example 17.
  • FIG. 23B shows a DSC chromatogram for the solid fraction resulting from solvent-based fractionation condition 2 in Example 17.
  • FIG. 24A shows the results of FAME analysis of the solid fraction resulting from solvent-based fractionation condition 3 in Example 17.
  • FIG. 24B shows a DSC chromatogram for the solid fraction resulting from solvent-based fractionation condition 3 in Example 17.
  • FIG. 25A shows the results of FAME analysis of the solid fraction resulting from solvent-based fractionation condition 4 in Example 17.
  • FIG. 25B shows a DSC chromatogram for the solid fraction resulting from solvent-based fractionation condition 4 in Example 17.
  • FIG. 26A shows the results of FAME analysis of the solid fraction resulting from solvent-based fractionation condition 5 in Example 17
  • FIG. 26B shows a DSC chromatogram for the solid fraction resulting from solvent-based fractionation condition 5 in Example 17.
  • FIG. 27A shows the results of FAME analysis of the solid fraction resulting from solvent-based fractionation condition 6 in Example 17.
  • FIG. 27B shows a DSC chromatogram for the solid fraction resulting from solvent-based fractionation condition 6 in Example 17.
  • FIG. 28A shows the results of FAME analysis of the liquid fraction resulting from solvent-based fractionation condition 6 in Example 17
  • FIG. 28B shows a DSC chromatogram for the liquid fraction resulting from solvent-based fractionation condition 6 in Example 17.
  • FIG. 29A shows the results of FAME analysis of the solid fraction resulting from solvent-based fractionation condition 7 in Example 17.
  • FIG. 29B shows a DSC chromatogram for the solid fraction resulting from solvent-based fractionation condition 7 in Example 17.
  • FIG, 30A shows the results of FAME analysis of the solid fraction resulting from solvent-based fractionation condition 8 in Example 17.
  • FIG. 30B shows a DSC chromatogram for the solid fraction resulting from solvent-based fractionation condition 8 in Example 17.
  • FIG. 31A shows the results of FAME analysis of the solid fraction resulting from solvent -based fractionation condition 9 in Example 17.
  • FIG. 3UB shows a DSC chromatogram for the solid fraction resulting from solvent-based fractionation condition 9 in Example 17.
  • FIG. 32 A shows the results of FAME analysis of the solid fraction resulting from solvent-based fractionation condition 10 in Example 17.
  • FIG, 32B shows a DSC chromatogram for the solid fraction resulting from solvent-based fractionation condition 10 in Example 17.
  • FIG. 33A shows the results of FAME analysis of the solid fraction resulting from dry' fractionation condition 1 in Example 10.
  • FIG. 33B shows a DSC chromatogram for the solid fraction resulting from dry' fractionation condition 1 in Example 18,
  • FIG. 34A shows the results of TA (3- analy sis of the solid fraction resulting from dry fractionation condition 2 in Example 18.
  • FIG. 34B show's a DSC chromatogram for the solid fraction resulting from dry fractionation condition 2 in Example 18.
  • FIG. 35A shows the results of TAG analysis of the solid fraction resulting from dry' fractionation condition 3 in Example 18.
  • FIG. 35B show's the results of FAME analysis of the solid fraction resulting from dry? fractionation condition 3 in Example 18.
  • FIG. 35C shows a DSC chromatogram for the solid fraction resulting from dry' fractionation condition 3 in Example 18.
  • FIG. 36A shows the results of TAG analysis of the solid fraction resulting from dry' fractionation condition 4 in Example 18.
  • FIG. 36B show's the results of FAME analysis of the solid fraction resulting from dry/ fractionation condition 4 in Example 18.
  • FIG. 36C shows a DSC chromatogram for the solid fraction resulting from dry fractionation condition 4 in Example 18.
  • FIG. 37A shows the results of FAME analysis of the solid fraction resulting from dry' fractionation condition 5 in Example 18.
  • FIG. 37B shows a DSC chromatogram for the solid fraction resulting from dry' fractionation condition 5 in Example 18.
  • FIG, 38A shows a DSC chromatogram for an original microbial oi 1 and a liquid fraction and solid fraction derived therefrom.
  • FIG. 38B shows the same three curves as in FIG. 38A, but overlaid.
  • “Cleaning agent” as used herein is any substance used to remove dirt, dust, stains, and/or odor. They may also be classified as a disinfectant or anti-microbial.
  • a “fatty acid” is a carboxylic acid with a long aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, from 4 to 28. Fatty acids are usually not found free in organisms, but instead within three main classes of esters: triglycerides, phospholipids, and cholesteryl esters. Within the context of this disclosure, a reference to a fatty acid may refer to either its free or ester form.
  • “Fatty acid profile” as used herein refers to how specific fatty acids contribute to the chemical composition of an oil.
  • “Faty acid-ingredient” as used herein refers to a cosmetic grade ingredient. For example, whereas pure “stearic acid” is C18:0, in cosmetics when “stearic acid” is listed as an ingredient, it is a mixture of C16:0/C18:0.
  • fractionabie is used to refer to a microbial oil or lipid composition which can be separated into at least two fractions that differ in saturation levels and wherein the at least two fractions each make up at least 10% w/w (or mass/mass) of the original microbial oil or lipid composition.
  • the saturation levels of the fractions may be characterized by, e.g., their iodine value (IV).
  • IV of the fractions may differ by at least 10.
  • a “fraction” as used herein refers to a separable component of a microbial oil that differs in saturation level from at least one other separable component of the microbial oil.
  • Home care composition refers to products used for care and cleaning purposes in households.
  • Lipid means any of a class of molecules that are soluble in nonpolar solvents (such as ether and hexane) and relatively or completely insoluble in water. Lipid molecules have these properties, because they are largely composed of long hydrocarbon tails that are hydrophobic in nature.
  • lipids include fatty' acids (saturated and unsaturated); glycerides or glycerolipids (such as monoglycerides, diglycerides, triglycerides or neutral fats, and phosphoglycerides or glycerophospholipids); and nonglycerides (sphingolipids, tocopherols, tocotrienols, sterol lipids including cholesterol and steroid hormones, prenol lipids including terpenoids, fatty alcohols, waxes, and polyketides).
  • glycerides or glycerolipids such as monoglycerides, diglycerides, triglycerides or neutral fats, and phosphoglycerides or glycerophospholipids
  • nonglycerides sphingolipids, tocopherols, tocotrienols, sterol lipids including cholesterol and steroid hormones, prenol lipids including terpenoids, fatty alcohols
  • “Luxury soft oil” or “soft oil” refers to oils that are liquid at room temperature.
  • Microorganism and “microbe” mean any microscopic unicellular organism and can include bacteria, algae, yeast, or fungi.
  • Oleaginous refers to material, e.g., a microorganism, which contains a significant component of oils, or which is itself substantial composed of oil.
  • An oleaginous microorganism can be one that is naturally occurring or synthetically engineered to generate a significant proportion of oil.
  • Oleaginous yeast refers to a collection of yeast species that can accumulate a high proportion of their biomass as lipids (namely greater than 20% of dry cell mass).
  • An oleaginous yeast can be one that is naturally occurring or synthetically engineered to generate a significant proportion of oi l.
  • Oil refers to a chemical compound derived natural oils or fats, which could be from an animal, microbial, or plant source.
  • Home care composition or “home care product” as used herein relate to a broad category of compositions including, for example, laundry detergents, dishwashing detergents, household cleaners, and household items, such as air freshener, dryer sheets, antistatic spray, etc.
  • Polymer as used herein refers to a broad category of substances composed of the same, or similar, repeating subunits (monomers), and may be natural or synthetic.
  • RBD refers to refinement, bleaching, and deodorizing or refers to an oil that has undergone these processes.
  • Rhodosporidium toruloides refers to a particular species of oleaginous yeast. Previously called Rhodotorula glutims or Rhodotorula gracilis. Also abbreviated as R. toruloides. This species includes multiple strains with minor genetic variation.
  • single cell oils refers to microbial lipids produced by oleaginous microorganisms.
  • “Surfactants” as used herein refers to a broad category of compounds that lower the surface tension between two liquids, for example oil and water, between a gas and a liquid, or between a liquid and a solid. In some instances, they can act as an anti-microbial agent and/or a preservative.
  • “Tailored fatty acid profile” as used herein refers to a fatty acid profile in a microbial oil which has been manipulated towards target properties, either by changing culture conditions, the species of oleaginous microorganism producing the microbial oil, or by genetically modifying the oleaginous microorganism.
  • “Triglyceride(s)” as used herein refers to a glycerol bound to three fatty acid molecules. They may be saturated or unsaturated.
  • WAV or “w/w”, in reference to proportions by weight, refers to the ratio of the weight of one substance in a composition to the weight of the composition.
  • reference to a composition that comprises 5% w/w oleaginous yeast biomass means that 5% of the composition's weight is composed of oleaginous yeast biomass (e.g., such a composition having a weight of 100 mg would contain 5 mg of oleaginous yeast biomass) and the remainder of the weight of the composition (e.g., 95 mg in the example) is composed of other ingredients.
  • any terminology used herein referring to palm plant-based derivatives is intended to refer to the analogous derivative obtained from a microbial oil, e.g.. the corresponding derivative derived from an oil obtained from an oleaginous yeast.
  • ethyl palmate refers to the microbial oil derivative that is analogous to the palm plant derivative known in the art by this term.
  • the present disclosure relates to home care compositions comprising a microbial oil and/or derivative thereof.
  • these lipids may serve as palm oil alternatives and be processed and/or derivatized by any number of means known in the art.
  • the microbial oil or derivative thereof may be a surfactant, emulsifier, wetting agent, ester, solvent, process aid, humectant, quaternary ammonium compound, antistatic, softening agent, rheology modifier/thickener, foam suppressor/ antifoaming agent, foam booster/ stabilizer, or combinations thereof.
  • the microbial oil or derivative thereof may be used in a variety of home care products, including, for example, laundry' detergents, dishwashing detergents, household cleaners, and household items.
  • the present disclosure also relates to methods of producing compositions comprising a microbial oil and/or derivative thereof.
  • the microbial oil is derived from an oleaginous yeast.
  • An embodiment of the present disclosure relates to home care compositions comprising a microbial oil, or derivative thereof, derived from an oleaginous microorganism.
  • oleaginous microorganisms for lipid production has many advantages over traditional oil harvesting methods, e.g., palm oil harvesting from palm plants.
  • microbial fermentation (1) does not compete with food production in terms of land utilization; (2) can be carried out in conventional microbial bioreactors; (3) has rapid growth rates; (4) is unaffected or minimally affected by space, light, or climate variations; (5) can utilize waste products as feedstock; (6) is readily scalable; and (7) is amenable to bioengineering for the enrichment of desired fatty acids or oil compositions.
  • the present methods have one or more of the aforementioned advantages over plant-based oil harvesting methods.
  • the oleaginous microorganism is an oleaginous microalgae.
  • the microalgae is of the genus Botryococcus, Cylindrotheca, Nilzschia, or Schizochytrium .
  • the oleaginous microorganism is an oleaginous bacterium.
  • the bacterium is of the genus Arthrobacter, Acinetobacter, Rhodococcus , or Bacillus.
  • the bacterium is of the species Acinetobacter calcoaceticus, Rhodococcus opacus, or Bacillus alcalophilus .
  • the oleaginous microorganism is an oleaginous fungus.
  • the fungus is of the genus Aspergillus, Mortierella, or Humicola.
  • the fungus is of the species Aspergillus oryzae, Mortierella isabellma, Humicola lanuginosa, or Mortierella vinacea.
  • Oleaginous yeast in particular are robust, viabl e over multiple generations, and versatile in nutrient utilization. They also have the potential to accumulate intracellular lipid content up to greater than 70% of their dry biomass.
  • the oleaginous microorganism is an oleaginous yeast.
  • the yeast may be in haploid or diploid forms. The yeasts may be capable of undergoing fermentation under anaerobic conditions, aerobic conditions, or both anaerobic and aerobic conditions.
  • a variety of species of oleaginous yeast that produce suitable oils and/or lipids can be used to produce microbial lipids in accordance with the present disclosure.
  • the oleaginous yeast naturally produces high (20%, 25%, 50% or 75% of dry cell weight or higher) levels of suitable oils and/or lipids. Considerations affecting the selection of yeast for use in the invention include, in addition to production of suitable oils or lipids for production of food products: (1) high lipid content as a percentage of cell weight, (2) ease of growth; (3) ease of propagation; (4) ease of biomass processing; and (5) glycerolipid profile.
  • the oleaginous yeast comprise cells that are capable of producing at least 20%, 25%, 50% or 75% or more lipid by dry weight. In other embodiments, the oleaginous yeast contains at least 25-35% or more lipid by dry' weight.
  • Suitable species of oleaginous yeast for producing the microbial lipids of the present disclosure include, but are not limited to Candida apicola, Candida sp., Cryptococcus albidus. Cryptococcus curvatus, Cryptococcus terricolus, Cutaneolrichosporon oleagiriosus, Debaromyces hansenii, Endomycopsis vemalis, Geotrichum carabidarum, Geotrichum cucujoidarum, Geotrichum.
  • the yeast is of the genera Yarrowia, Candida, Rhodotorula, Rhodosporidium, Metschnikowkt, Cryptococcus, Trichosporon, or Lipomyces.
  • the yeast is of the genus Yarrowia.
  • the yeast is of the species Yarrowia lipolytica.
  • the yeast is of the genus Candida.
  • the yeast is of the species Candida curvata.
  • the yeast is of the genus Cryptococcus.
  • the yeast is of the species Cryptococcus albidus.
  • the yeast is of the genus Lapomyces.
  • the yeast is of the species Lipomyces starkeyi. In some embodiments, the yeast is of the genus Rhodotorula. In some embodiments, the yeast is of the species Rhodotorula glutinis. In some embodiments, the yeast is of the genus Metschnikowia. In some embodiments, the yeast is of the species Metschnikowia pulcherrima.
  • the oleaginous yeast is of the genus Rhodosporidium. In some embodiments, the yeast is of the species Rhodosporidium toruloides. In some embodiments, the oleaginous yeast is of the genus Lipomyces. In some embodiments, the oleaginous yeast is of the species Lipomyces Starkeyi.
  • the oleaginous microorganisms that produce the microbial lipids of the present disclosure are a homogeneous population comprising microorganisms of the same species and strain. In some embodiments, the oleaginous microorganisms that produce the microbial lipids of the present disclosure are a heterogeneous population comprising microorganisms from more than one strain. In some embodiments, the oleaginous microorganisms that produce the microbial lipids of the present disclosure are a heterogeneous population comprising two or more distinct populations of microorganisms of different species.
  • wild-type strains are subjected to natural selection to enhance desired traits (e.g., tolerance of certain environmental conditions such as temperature, inhibitor concentration, pH, oxygen concentration, nitrogen concentration, etc.).
  • desired traits e.g., tolerance of certain environmental conditions such as temperature, inhibitor concentration, pH, oxygen concentration, nitrogen concentration, etc.
  • a wild-type strain e.g., yeast
  • a feedstock of the present disclosure e.g., a feedstock comprising one or more microorganism inhibitors.
  • wild-type strains are subjected to directed evolution to enhance desired traits (e.g., lipid production, inhibitor tolerance, growth rate, etc.).
  • the cultures of microorganisms are obtained from culture collections exhibiting desired traits.
  • An embodiment of the present disclosure relates to home care compositions comprising a microbial oil, and/or a derivative thereof, wherein the microbial oil is derived from an oleaginous yeast.
  • the derivative is a surfactant, emulsifier, wetting agent, ester, solvent, process aid, humectant, quaternary ammonium compound, antistatic, softening agent, rheology rnodifier/thickener, foam suppressor/ antifoaming agent, foam booster/stabilizer, or combinations thereof.
  • the microbial oil comprises a fatty acid profile of at least 20% palmitic acid, at least 10% stearic acid, and at least 30% oleic acid.
  • the microbial oil comprises at least one of ergosterol, ⁇ - carotene, torulene, and torularhodin.
  • the microbial oil comprises one or more sterols. In some embodiments, the microbial oil comprises ergosterol. In some embodiments, the microbial oil comprises at least 50 ppm ergosterol. In some embodiments, the microbial oil comprises at least 100 ppm ergosterol.
  • the microbial oil comprises less than 100 ppm of a phytosterol, cholesterol, or a protothecasterol. In some embodiments, the microbial oil comprises less than 50 ppm of of a phytosterol, cholesterol, or a protothecasterol. In some embodiments, the microbial oil does not comprise a sterol selected from a phytosterol, cholesterol, or a protothecasterol. [93] In some embodiments, the microbial oil does not comprise plant sterols. In some embodiments, the microbial oil does not comprise one or more phytosterols. In some embodiments, the microbial oil does not comprise campesterol, ⁇ -sitosterol, or stigmasterol. In some embodiments, the microbial oil does not comprise cholesterol. In some embodiments, the microbial oil does not comprise protothecasterol.
  • the microbial oil comprises a pigment. In some embodiments, the microbial oil comprises at least one pigment selected from the group consisting of carotene, torulene and torulorhodin. In some embodiments, the microbial oil comprises carotene. In some embodiments, the microbial oil comprises torulene. In some embodiments, the microbial oil comprises torulorhodin. In some embodiments, the microbial oil comprises each of carotene, torulene and torulorhodin. In some embodiments, the microbial oil does not comprise chlorophyll.
  • the composition of the microbial oil may vary depending on the strain of microorganism, feedstock composition, and growing conditions.
  • the microbial oil produced by the oleaginous microorganisms of the present disclosure comprise about. 90% w/w tri acylglycerol with a percentage of saturated fatty acids (% SFA) of about 44%.
  • the most common fatty acids produced by oleaginous microbial fermentation on the present feedstocks are oleic acid (C18: 1), stearic acid (C18:0), palmitic acid (C16:0), palmitoleic acid (C16:1), and myristic acid (C 14:0).
  • the microbial oil comprises 5-15% C18:2 acid.
  • the microbial oil comprises myristic acid (C14:0). In some embodiments, the microbial oil comprises at least 0.1%, at least 0.2%, at least. 0.3%, at least 0.4%, at least 0.5%, at least 0.6%, at least 0.7%, at least 0.8%, at least 0.9%, at least 1%, at least. 2%, at least 3%, at least 4%, or at least 5% myristic acid.
  • the microbial oil comprises margaric acid (C17:0). In some embodiments, the microbial oil comprises at least 1%, at least 5%, at least 6%, at least 7%, at least 8%, at least 9%, at least 10%, at least 11%, at least 12%, at least 13%, at least 14%, at least 15%, at least 16%, at least 17%, at least 18%, at least 19%, at least 20%, at least 21%, at least 22%, at least 23%, at least 24%, or at least 25% margaric acid. In some embodiments, the microbial oil comprises 5-25% w/w margaric acid. In some embodiments, the microbial oil comprises 9-21% w/w margaric acid.
  • the microbial oil comprises at least 5%, at least 10%, at least
  • the microbial oil comprises C18:2 (linoleic acid). In some embodiments, the microbial oil comprises at least 0.1%, at least 0.2%, at least 0.3%, at least 0.4%, at least 0.5%, at least 0.6%, at least 0.7%, at least 0.8%, at least 0.9%, at least 1%, at least 2%, at least 3%, at least 4%, or at least 5% linoleic acid. In some embodiments, the microbial oil comprises at least 5% linoleic acid. In some embodiments, the microbial oil comprises less than 25% linoleic acid. In some embodiments, the microbial oil comprises 1- 25% linoleic acid. In some embodiments, the microbial oil comprises 5-15% linoleic acid.
  • the microbial oil comprises C18:3 (linolenic acid). In some embodiments, the microbial oil comprises at least 0.1%, at least 0.2%, at least 0.3%, at least 0.4%, at least 0.5%, at least 0.6%, at least 0.7%, at least 0.8%, at least 0.9%, at least 1%, at least. 2%, at least 3%, at least 4%, or at least 5% linolenic acid.
  • the microbial oil comprises C20:0 (arachidic acid). In some embodiments, the microbial oil comprises at least 0.1%, at least 0.2%, at least 0.3%, at least 0.4%, at least 0.5%, at least 0.6%, at least 0.7%, at least 0.8%, at least 0.9%, at least 1%, at least 2%, at least 3%, at least 4%, or at least 5% arachidic acid.
  • the microbial oil comprises C24.0 (lignoceric acid). In some embodiments, the microbial oil comprises at least 0.1%, at least 0.2%, at least 0.3%, at least 0.4%, at least 0.5%, at least 0.6%, at least 0.7%, at least 0.8%, at least 0.9%, at least 1%, at least 2%, at least 3%, at least 4%, or at least 5% lignoceric acid.
  • the microbial oil comprises C12:0. In some embodiments, the microbial oil comprises C15: 1. In some embodiments, the microbial oil comprises C16:1. In some embodiments, the microbial oil comprises C17: 1. In some embodiments, the microbial oil comprises C18:3. In some embodiments, the microbial oil comprises C20:1. In some embodiments, the microbial oil comprises C22:0. In some embodiments, the microbial oil comprises C22:1. In some embodiments, the microbial oil comprises C22:2.
  • the microbial oil comprises about 0.1%, about 0.2%, about 0.3%, about 0.4%, about 0.5%, about 0.6%, about 0.7%, about 0.8%, about 0.9%, about 1%, about 2%, about 3%, about. 4%, or about 5% of any one of these fatty acids. In some embodiments, the microbial oil comprises about 0-5% of any one of these fatty acids. In some embodiments, the microbial oil comprises about 0.1-2% of any one of these fatty acids.
  • the microbial oils of the present disclosure have differences from plant-derived palm oil. In some embodiments, these differences are useful and allow for manipulation of the microbial oil for the improved production of a given product compared to plant-derived palm oil.
  • the fatty acid profile of a microbial oil is tailored so as to produce a higher fraction of one or more fatty acids of interest for use in production of a product.
  • other parameters of the microbial oil are also able to be manipulated for increased production of a component of interest or decreased production of an undesired component relative to plant-derived palm oil.
  • the present compositions are also useful as environmentally friendly alternatives to plant-derived palm oil. Therefore, in some embodiments, the microbial oil has one or more properties similar to those of plant-derived palm oil. Exemplary properties include apparent density, refractive index, saponification value, un saponifiable matter, iodine value, slip melting point, and fatty acid composition.
  • the microbial oil has a fatty acid profile similar to that of plant- derived palm oil. In some embodiments, the microbial oil has a significant fraction of C16:0 fatty acid. In some embodiments, the microbial oil has a significant fraction of C18: 1 fatty acid. In some embodiments, the microbial oil comprises 10-45% C16 saturated fatty acid. In some embodiments, the microbial oil comprises at least 15% C16 saturated fatty acid. In some embodiments, the microbial oil comprises 10-70% C18 unsaturated fatty acid. In some embodiments, the microbial oil comprises 35-80% C18 unsaturated fatty acid. In some embodiments, the microbial oil comprises at least 40% C18 unsaturated fatty acid.
  • the microbial oil has a saturated fatty acid composition of about 20-80% and an unsaturated fatty acid composition of about 20-80%. In some embodiments, the microbial oil has about 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, or 85% saturated fatty acids. In some embodiments, the microbial oil has about 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, or 85% unsaturated fatty acids.
  • the microbial oil has a similar level of mono-unsaturated fatty acids as plant-derived palm oil. Some plant-derived palm oils contain approximately 40% mono-unsaturated fatty acids. In some embodiments, the microbial oil contains about 40% mono-unsaturated fatty acids. In some embodiments, the microbial oil contains about 30-50% mono-unsaturated fatty acids. In some embodiments, the microbial oil contains about. 5-60% mono-unsaturated fatty acids. In some embodiments, the microbial oil has about 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, or 70% mono-unsaturated fatty acids. In some embodiments, the microbial oil comprises 30-70% mono-unsaturated fatty acids.
  • the microbial oil has a similar level of poly-unsaturated fatty acids as plant-derived palm oil.
  • Some plant-derived palm oils contain approximately 10% polyunsaturated fatty acids.
  • the microbial oil contains about 10% polyunsaturated fatty acids.
  • the microbial oil contains about 5-25% polyunsaturated fatty acids.
  • the microbial oil has about 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, or 25% poly-unsaturated fatty acids.
  • the microbial oil comprises less than 25% poly-unsaturated fatty acids.
  • the microbial oil has a similar iodine value as plant-derived palm oil. Some plant-derived palm oils have an iodine value of about 50.4-53.7. In some embodiments, the microbial oil has an iodine value of about 45-80. In some embodiments, the microbial oil has an iodine value of about 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, or 80. In some embodiments, the microbial oil has an iodine value of 55-85. In some embodiments, the microbial oil has an iodine value of 62-76.
  • Table 1 shows ranges for the fatty acid composition of an illustrative plant-derived palm oil and ranges of values for the fatty acid composition of illustrative microbial oil.
  • the microbial oil has one or more fatty acid composition parameters similar to those of Table 1 .
  • the microbial oil has a value within the plant-derived palm oil range for a given fatty acid composition parameter.
  • the microbial oil has a value within the microbial oil ranges provided in Table 1 for one or more parameters.
  • Table 1 Illustrative fatty acid compositions of microbial oil
  • the microbial oil has a similar slip melting point to plant-derived palm oil. Some plant-derived palm oils have a slip melting point of about 33.8-39.2°C. In some embodiments, the microbial oil has a slip melting point of about 10-50°C. In some embodiments, the microbial oil has a slip melting point of about 10, 15, 20, 25, 30, 35, 40, 45, or 50°C. In some embodiments, the microbial oil has a melting point of 10-30°C. In some embodiments, the microbial oil has a melting point of 16-25°C.
  • the microbial oil has a saponification value similar to that of plant-derived palm oil. Some plant-derived palm oils have a saponification value of about 190- 209. In some embodiments, the microbial oil has a saponification value of about 150-210, In some embodiments, the microbial oil has a saponification value of about 150, 155, 160, 165, 170, 175, 180, 185, 190, 195, 200, 205, or 210. [118] In some embodiments, the microbial oil has a similar unsaponifiable matter content to that of plant-derived palm oil. Some plant-derived palm oils have an unsaponifiable matter content of about 0.19-0.44% by weight. In some embodiments, the microbial oil has an unsaponifiable matter content of less than 5% by weight.
  • the microbial oil has a similar refractive index to that of plant- derived palm oil.
  • Some plant-derived palm oils have a refractive index of about 1.4521-1.4541.
  • the microbial oil has a refractive index of about 1.3-1.6.
  • the microbial oil has a density of 0.8-1 g/cc. In some embodiments, the microbial oil has a density of 0.88-0.95 g/cc. In some embodiments, the microbial oil has a density of 0.9-0.92.
  • Tables 2 and 3 show ranges for the triglyceride composition of an illustrative plant- derived palm oil and ranges of values for the triglyceride composition of illustrative microbial oil.
  • the abbreviations used are as follows: S: Stearic fatty acid; P: Palmitic fatty acid; O: Oleic fatty acid.
  • S Stearic fatty acid
  • P Palmitic fatty acid
  • O Oleic fatty acid.
  • P-O-P the corresponding measurements for that molecule may also include other isomers, for example P-P-0 and O-P-
  • the microbial oil has a similar triglyceride content to that of plant-derived palm oil.
  • the total triglyceride content of sat-unsat-sat in plant- derived palm oil is approximately 49.53 and microbial-derived oil has approximately 49.42 in some embodiments.
  • the microbial oil has a value different than plant- derived palm oil.
  • plant-derived palm oil has approximately 9.04% sat-sat-sat chains, whereas microbial-derived oil has approximately 3.36% in some embodiments.
  • Some plant-derived palm oils have a triglyceride content of over 95%.
  • the microbial oil has a triglyceride content of 90-98%. In some embodiments, the microbial oil has a triglyceride content of about 90, 91, 92, 93, 94, 95, 96, 97, or 98%.
  • Table 2 Illustrative triglyceride compositions of microbial oil
  • the microbial oil has a similar triacylglycerol profile to plant- derived palm oil. Some plant-derived palm oils have over 80% C50 and C52 triacylgylcerols. In some embodiments, the microbial oil has a tri acylglycerol profile comprising at least 40% C50 and C52 triacylglycerols.
  • the microbial oil has a triglyceride profile wherein greater than 40% of the triglycerides have one unsaturated sidechain, and wherein greater than 30% of the triglycerides have two unsaturated sidechains.
  • a microbial oii derivative herein is a microbial triglyceride.
  • a microbial oil derivative herein is the product of hydrolysis of a microbial triglyceride, e.g., a free fatty acid or glycerin.
  • a microbial oil of the disclosure has a TAG saturation profile comprising less than 5% triglycerides with three saturated fatty acid chains. In some embodiments, a microbial oil of the disclosure has a TAG saturation profile comprising less than 2% triglycerides with three saturated fatty acid chains. In some embodiments, a microbial oil of the disclosure has a TAG saturation profile comprising less than 1% triglycerides with three saturated fatty acid chains. In some embodiments, a microbial oil of the disclosure has a TAG saturation profile comprising about 0.5% triglycerides with three saturated fatty acid chains.
  • a microbial oil of the disclosure has a TAG saturation profile comprising 25%-60% triglycerides with two saturated fatty acid chains and one unsaturated fatty acid chain. In some embodiments, a microbial oil of the disclosure has a TAG saturation profile comprising 30%-55% triglycerides with two saturated fatty acid chains and one unsaturated fatty acid chain. In some embodiments, a microbial oil of the disclosure has a TAG saturation profile comprising 35%-50% triglycerides with two saturated fatty acid chains and one unsaturated fatty acid chain. In some embodiments, a microbial oil of the disclosure has a TAG saturation profile comprising about 40%-47% triglycerides with two saturated fatty acid chains and one unsaturated fatty acid chain.
  • a microbial oil of the disclosure has a TAG saturation profile comprising 30%-65% triglycerides with one saturated fatty acid chain and two unsaturated fatty acid chains. In some embodiments, a microbial oil of the disclosure has a TAG saturation profile comprising 35%-55% triglycerides with one saturated fatty acid chain and two unsaturated fatty acid chains. In some embodiments, a microbial oil of the disclosure has a TAG saturation profile comprising 40%-50% triglycerides with one saturated fatty acid chain and two unsaturated fatty acid chains. In some embodiments, a microbial oil of the disclosure has a TAG saturation profile comprising about 43%-47% triglycerides with one saturated fatty acid chain and two unsaturated fatty acid chains.
  • a microbial oil of the disclosure has a TAG saturation profile comprising less than 25% triglycerides with three unsaturated fatty acid chains. In some embodiments, a microbial oil of the disclosure has a TAG saturation profile comprising less than 20% triglycerides with three unsaturated fatty acid chains. In some embodiments, a microbial oil of the disclosure has a TAG saturation profile comprising less than 15% triglycerides with three unsaturated fatty acid chains. In some embodiments, a microbial oil of the disclosure has a TAG saturation profile comprising about 5%-l 5% triglycerides with three unsaturated fatty acid chains.
  • a microbial oil of the disclosure comprises 10*30% POP triglycerides. In some embodiments, a microbial oil of the disclosure comprises at least 10% POP triglycerides. In some embodiments, a microbial oil of the disclosure comprises 1 -10% PLP triglycerides. In some embodiments, a microbial oil of the disclosure comprises 5-15% POS triglycerides. In some embodiments, a microbial oil of the disclosure comprises at least 5% POS triglycerides. In some embodiments, a microbial oil of the disclosure comprises 15- 40% POO triglycerides.
  • a microbial oil of the discl osure comprises 2.5*10% OSO triglycerides. In some embodiments, a microbial oil of the disclosure comprises 3-15% OOO triglycerides. In some embodiments, a microbial oil of the disclosure comprises at least 3% OOO triglycerides. In some embodiments, a microbial oil of the disclosure comprises 5-10% OOO triglycerides.
  • a microbial oil of the disclosure comprises less than 10% PPM, MOM, PPP, MOP, MLP, PPS, OMO, PLS, PLL, POLn, SOS, SLO, and/or OLO.
  • compositions comprising microbialfy produced oil and/or derivatives thereof
  • the disclosure teaches methods of producing a home care composition, comprising providing a microbial oil, or derivative thereof, and producing a home care composition.
  • the home care composition is a. laundry detergent, dishwashing detergent, household cleaner, or household item.
  • the household cleaner is a glass cleaner, all-purpose cleaner, floor cleaner, shower/tile cleaner, bathroom cleaner, toilet cleaner, wood cleaner, fabric stain remover, or carpet cleaner.
  • the household item is dry/ er sheets, fabric softener, air freshener, or antistatic spray.
  • the home care composition is a liquid, powder, pod, wipe, foam, spray, or gel .
  • the unsaturated lipids in vegetable oils are susceptible to oxidation over time, which can be accelerated when the oil is exposed to heat, light, or metals. Oxidation causes changes in the chemical, sensory, and nutritional properties of the oil, and can result in, among other things, an unpleasant odor.
  • the oxidative stability of the microbial oil described herein was analyzed by detection of peroxide using methods known in the art, for example, by titration reaction of iodine and peroxide with a starch indicator.
  • the peroxide value of the microbial oil was less than 2 mEq/kg, which is within the Malaysian Palm Oil Board (MPOB) specification.
  • the microbial oil is obtained from the oleaginous microorganism, it is subjected to some form of processing. In some embodiments, the microbial oil is refined, bleached, deodorized, fractionated, treated, and/or derivatized.
  • refinement removes certain minor components of the crude microbial oil with the least possible damage to the oil fraction (e.g., trans faty acids, polymeric and oxidized triacylglycerols, etc.) and minimal losses of desirable constituents (e.g., tocopherols, tocotri enols, sterols, etc.).
  • processing parameters are adapted for retention of desirable minor components like tocopherols and tocotrienols and minimal production of unwanted trans fatty acids. See Gibon (2012) “Palm Oil and Palm Kernel Oil Refining and Fractionation Technology,” incorporated by reference herein in its entirety, for additional details of oil processing that are useful for the present microbial oils.
  • a refined microbial oil refers to a microbial oil from which one or more impurities or constituents have been removed other than odor and pigment.
  • RBD as used herein and as applied to a microbial oil, indicates that the microbial oil has been each of refined, bleached, and/or deodorized.
  • the free fatty acids and most of the phosphatides are removed during alkali neutralization.
  • the non- hydratable phosphatides are first activated with acid and further washed out together with the free faty acids during alkali neutralization with caustic soda.
  • chemical refining comprises one or more steps of acid treatment, centrifugation, bleaching, deodorizing, and the like.
  • phosphatides are removed by a specific degumming process and the free fatty acids are distilled during the steam refining/deodorization process.
  • the degumming process is dry' degumming or wet acid degumming.
  • physical refining is employed when the acidity of the crude microbial oil is sufficiently high.
  • physical refining is employed for crude microbial oil with high initial free fatty acid (FFA) content and relatively low phosphatides.
  • the microbial oil is deodorized.
  • the deodorization process comprises steam refining.
  • deodorization comprises vacuum steam stripping at elevated temperature during which free fatty acids and volatile odoriferous components are removed to obtain bland and odorless oil.
  • Optimal deodorization parameters temperature, vacuum, and amount of stripping gas are determined by the type of oil and the selected refining process (chemical or physical refining) but also by the deodorizer design.
  • the microbial oil is bleached.
  • the bleaching is performed through the use of bleaching earth, e.g., bleaching clays.
  • the bleaching method employed is the two stage co-current process, the countercurrent process, or the Oehmi process.
  • the bleaching method is dry bleaching or wet bleaching.
  • bleaching is accomplished through heat bleaching.
  • bleaching and deodorizing occur concurrently.
  • the microbial oil is refined, bleached, and/or deodorized.
  • the microbial oil is not bleached or is only partially bleached.
  • the microbial oil still retains pigments after processing.
  • the microbial oil comprises any one or more of the pigments referenced herein. Therefore, in some embodiments, the microbial oil is refined and deodorized, but not bleached or not fully bleached.
  • the fatty acids may also be modified by amination, esterification, and reactions with amino acids to produce fatty amines, fatty esters, and amide carboxylates respectively.
  • Fatty amines may further be modified by oxidation, monochloroacetic acid (MCA) reaction, and quatemization to produce amine oxides, betaines, and quats respectively.
  • MCA monochloroacetic acid
  • the microbial oil or fraction thereof may also be modified by saponification to produce fatty acid salts. Any of these derivatives and intermediate products may be used in home care compositions.
  • the microbial oil is processed and/or modified via one or more of fractionation, hydrogenation, hydrolysis, distillation, saponification, esterification, interesterification, transesterification, amination, ethoxylation, sulfonation, oxidation, quaternization, MCA reaction, and/or reaction with amino acids.
  • Fractionation of is another means of processing the microbial oil described herein for use in home care compositions. Fractionation may be used to physically separate room temperature oil into saturated and unsaturated components. The melting points of full oil mixtures and their saturated/unsaturated components differ. Hydrophilization makes use of surface active agents (surfactants) that dissolve solidified fatty crystals and emulsify liquid oils. By centrifuging this hydrophilized suspension, fats can be separated into different fractions based on saturation.
  • surfactants surface active agents
  • the microbial oil is fractionable. In some embodiments, the disclosure teaches a method of fractioning a microbial oil. In some embodiments, the microbial oil is fractionable into two or more fractions. In some embodiments, the microbial oil is fractionable into more than two fractions. In some embodiments, the microbial oil is fractionable into two fractions, which may then be further fractionated.
  • the microbial oil is fractionable into two fractions.
  • the two fractions are microbial olein and microbial stearin.
  • each fraction comprises at least 10% of the microbial oil’s original mass.
  • the iodine value (IV) of the fractions differs by at least 10. In some embodiments, the iodine value of the fractions differs by at least 20. In some embodiments, the iodine value of the fractions differs by at least 30.
  • the microbial oil is fractionated. In some embodiments, fractionation is carried out in multiple stages, resulting in fractions appropriate for different downstream indications. In some embodiments, the microbial oil is fractionated via dry' fractionation. In some embodiments, the microbial oil is fractionated via wet fractionation. In some embodiments, the microbial oil is fractionated via solvent/detergent fractionation.
  • Hydrogenation is the process whereby liquid fats are made solid or partially solid by adding hydrogen. The extra hydrogen converts the double bonds in unsaturated fats to single bonds, generating saturated fats. Unless the process is controlled, some fats may be partially hydrogenated and this leads to “trans fats”, so named due to the trans configuration of the molecule. In the U.S., artificial trans fats have been banned from food products, however hydrogenated fats may still be used in home care compositions. Hydrogenated oils prevent the rancid odors caused by oxidation, thus increasing the shelf life of the product, and may also provide a thicker consistency.
  • the FAMEs produced by transesterification may be hydrogenated to produce fatty alcohols.
  • Fatty acids produced from hydrolysis may also be further modified via esterification to produce wax esters, which may then be hydrogenated to produce fatty alcohols.
  • Direct hydrogenation of fatty acids is also possible and produces fatty alcohols.
  • the oil is derivatized to fatty alcohols.
  • the disclosure teaches methods of fatty acid hydrogenation, wherein the fatty acids are derived from a microbial oil.
  • fatty alcohols derived from an oleaginous yeast are used in a home care item.
  • the fatty alcohols are further refined and/or distilled.
  • the fatty acids derived from the microbial oil are distilled.
  • the disclosure teaches methods of using free fatty acids from oleaginous microorganisms in home care compositions.
  • the disclosure relates to a home care composition comprising a fatty acid-ingredient derived from an oleaginous yeast- in some embodiments, the fatty acid-ingredients are selected from the group consisting of stearic acid, oleic acid, palmitic acid, and myristic acid.
  • a microbial oil derivative herein is a high palmitic acid fraction of a microbial oil. In some embodiments, a microbial oil derivative herein is a high oleic acid fraction of a microbial oil. In some embodiments, a microbial oil derivative herein is a palmitic acid, or a derivatized version thereof, e.g., an ester thereof. Amination
  • the disclosure teaches methods of producing fatty amines from fatty acids, triglycerides, and/or fatty esters derived from the microbial oil described herein.
  • the disclosure relates to home care compositions comprising fatty amines derived from a microbial oil.
  • the disclosure relates to home care compositions comprising amine surfactants derived from a microbial oil.
  • Saponification is the process whereby triglycerides or free fatty acids used as feedstock are converted to fatty acids salts (soaps), glycerol, and free fatty acids in the presence of a base.
  • the base may be for example, sodium hydroxide, which for example produces hard bar soaps, or potassium hydroxide, which for example produces softer bars or liquid soaps.
  • Saponification may be achieved via a hot or cold process.
  • the cold process uses the heat generated from the combination of the fatty acids in the melted oils and fats with sodium hydroxide (base). This process takes longer, and an additional curing phase is needed for the soap to harder.
  • the hot process uses heat to speed up the saponification process, and generally no additional curing step is required before use of the soap.
  • the disclosure teaches methods of using the microbial oil, free fatty acids, and/or triglycerides as feedstock in a saponification reaction to produce fatty acid salts, glycerol, and/or free fatty acids.
  • these fatty acid salts, glycerol, and/or free fatty acids are used in a home care composition.
  • the home care composition is soap.
  • Sodium stearate is produced by saponification of stearic acid, and it one of the most commonly used commercial surfactants in soap. It is also found in solid deodorants, rubbers, latex paints, and inks.
  • the disclosure relates to a sodium stearate produced from stearic acid, wherein the stearic acid is produced by an oleaginous yeast.
  • the disclosure relates to products and compositions comprising a sodium stearate derived from an oleaginous yeast.
  • Surfactants are a broad category of compounds that lower the surface tension between two liquids, for example oil and water, between a gas and a liquid, or between a liquid and a solid. Depending on the compound, they may act as an emulsifier, emollient, detergent, wetting agent, foaming agent, thickening agent, pearlescent, solubilizer, conditioning agent, co- surfactant, or dispersant. In some instances, they can act as an anti-microbial agent and/or a preservative. They can be classified by their head group as either non-ionic (neutral), anionic (negatively charged), cationic (positively charged), or amphoteric (both positive and negative charges).
  • Nonionic surfactants An embodiment of the present disclosure relates to home care compositions comprising a microbial oil, and/or derivative thereof, wherein the derivative functions as a nonionic surfactant in a home care composition.
  • microbially derived nonionic surfactants include, but are not limited to, C10-C16 alkyl dimethyl amine oxide, laureth-6, alcohols - C12-C16 ethoxylated, soy methyl ester ethoxylate, coco methyl ester ethoxylate, D-glucopyranose, oligomeric, C10-C16 - alkylglycoside, D-glucopyranose, oligomeric, decyl octyl glycoside, laureth-9, decyl glucoside, lauryl glucoside, capryl/myristyl glucoside, capryloyl/caproyl methyl glucamide, C8-C10 alkyl polygluco
  • An embodiment of the present disclosure relates to home care compositions comprising a microbial oil, and/or derivative thereof, wherein the derivative functions as an anionic surfactant in a home care composition.
  • microbially derived anionic surfactants include, but are not limited to, sodium laureth sulfate (also known as sodium lauryl ether sulfate), sodium C14-17 alcohol sulfate, MEA C1215 alkyl ether sulfate, and sodium lauryl sulfate.
  • the present disclosure relates to home care compositions comprising a microbial oil, and/or derivative thereof, and a non-microbially derived anionic surfactant.
  • Cationic surfactants An embodiment of the present disclosure relates to home care compositions comprising a microbial oil, and/or derivative thereof, wherein the derivative functions as a cationic surfactant in a home care composition. In another embodiment, the present disclosure relates to home care compositions comprising a microbial oil, and/or derivative thereof, and a non-microbially derived cationic surfactant.
  • the microbially derived cationic surfactant may be a quaternary' ammonium compound (“quats” or “QACs”). Quats are widely used as surface disinfectants, but can also function as antistatic agents (i.e. fabric softeners) and as the active ingredient in sanitizers. Quats can be derived from naturally occurring fats and oils, such as tallow, corn oil, soybean oil, cottonseed oil, castor oil, linseed oil, safflower oil, palm oil, peanut oil and the like. In some embodiments, the disclosure teaches methods of producing a quat derived from a microbial oil. In some embodiments, the disclosure relates to home care compositions comprising a quat derived from a microbial oil.
  • Esterquats are a type of cationic quat having two long C16-C18 fatty acid chains with two weak ester linkages. They function as fabric conditioning agents and can replace dialkyl dimethyl ammonium salts as a biodegradable alternative (Mishra S. and V.K. Tyagi, Ester Quats: The Novel Class of Cationic Fabric Softeners, J. of Oleo Sci. 2007, 56(6): 269-276).
  • esterquats can be derived from naturally occurring fats and oils using methods well known in the art, they can also be derived from the microbial oil described herein. Thus, in some embodiments, the disclosure teaches methods of producing esterquats from a microbial oil. In some embodiments, the disclosure relates to home care compositions comprising esterquats derived from a microbial oil.
  • esters have fruit-like odors and occur naturally in essential oils of plants, and may be used in fragrances to mimic those odors.
  • the microbial oil is derivatized to esters.
  • esters derived from an oleaginous yeast are used in a home care composition.
  • the esters are used as a fragrance in a home care composition.
  • the microbial oil is modified via interesterification.
  • the interesterification is enzymatic.
  • the interesterifi cation is chemical.
  • the microbial oil is modified via transesterification.
  • the oil is derivatized to fatty acid methyl esters (FAMEs).
  • Methyl esters may be used in home care compositions, for example, they may be a carrier for an active ingredient, an emollient, or viscosity regulator.
  • the FAMEs derived from oleaginous yeast are used in a composition of matter.
  • the methyl esters are hydrogenated to produce fatty alcohols. Direct hydrogenation of fatty acids is also possible and produces fatty alcohols.
  • the oil is derivatized to fatty alcohols.
  • fatty alcohols derived from an oleaginous yeast are used in a home care composition.
  • the disclosure relates to a composition of matter comprising cetearyl alcohol derived from fatty alcohols produced by an oleaginous yeast.
  • Solvents dissolve solutes, resulting in a solution. Some solvents are harmful to the environment. Recent research shows that vegetable oil, such as palm oil, can be used as nontoxic bio-based solvent (Noppawan P., et al., Green Chem., 2021, 23, 5766-5774). However, for vegetable oils to truly be a renewable alternative to petroleum derived solvents, they must be sustainably sourced.
  • the disclosure relates to microbial oil and derivatives thereof for use as a solvent.
  • the disclosure teaches methods of producing a solvent derived from a microbial oil.
  • the disclosure relates to home care compositions comprising a solvent derived from a microbial oil.
  • Process aids are substances which are used in the production of a consumer product. They may be present in the finished product in trace amounts, but are not required to be disclosed to the consumer as an ingredient. Triglycerides, for example, soybean oil, olive oil, linseed oil, corn oil, coconut oil, hydrogenated castor oil, palm oil, and hydrogenated soybean oil, are considered safe biological substances for use as process aids (EPA’s Safer Choice Criteria for Processing Aids and Additives, available on the world wide web at epa.gov/saferchoice/safer-choice-criteria-processing-aids-and-additives).
  • the disclosure relates to microbial oil and derivatives thereof for use as a process aid.
  • the disclosure teaches methods of producing a process aid derived from a microbial oil.
  • the disclosure relates to home care compositions comprising a process aid derived from a microbial oil.
  • Humectants attract water and thus are often found in personal care compositions, such as lotions and hair products, as moisturizers. They are also found in everyday home care compositions.
  • An example of a humectant that may be derived from the microbial oil described herein is glycerin.
  • softening agents can reduce the buildup of static electricity, in general the term is broad and applies to any substance that increases the softness of another substance.
  • An example of a softening agent that may be derived from the microbial oil described herein are fatty amines. Fatty amines are largely used as softening agents in the detergent industry.
  • the disclosure relates to microbial oil and derivatives thereof for use as a softening agent.
  • the disclosure teaches methods of producing a softening agent, derived from a microbial oil.
  • the disclosure relates to home care compositions comprising a softening agent derived from a microbial oil.
  • Rheology modifiers also referred to as thickeners or viscosity modifiers, help to control the viscosity of a substance. They may also increase the suspendability of soluble ingredients and stability of a product.
  • Naturally occurring rheology modifiers include, for example, pectin, gelatin, and collagen.
  • Rheology modifiers that can be derived from naturally occurring fats and oils, and the microbial oil described herein, include, but are not limited to, caprylic/capric triglycerides, oleic acid, glycol stearate, and lauryl alcohol.
  • Foam suppressors also known as anti -foaming agents, are substances that help prevent the formation of a foam.
  • Common anti-foaming agents include, for example, cetostearyl alcohol, insoluble oils, stearates, ether and glycols.
  • the disclosure teaches methods of producing a foam suppressor derived from a microbial oil.
  • the disclosure relates to home care compositions comprising a. foam suppressor derived from a microbial oil.
  • Foam boosters/stabilizers are substances that help prevent the formation of a foam.
  • Common anti-foaming agents include, for example, cetostearyl alcohol, insoluble oils, stearates, ether and glycols.
  • the disclosure teaches methods of producing a foam suppressor derived from a microbial oil.
  • the disclosure relates to home care compositions comprising a. foam suppressor derived from a microbial oil.
  • Foam boosters/stabilizers are substances that help prevent the formation of
  • Foam boosters also known as stabilizers or suds enhancers are commonly used to prolong the life of the foam head generated during the washing or cleaning process. Consumers tend to associate better product performance with the presence of higher levels of foam or suds and by foam that lasts for extended periods of time.
  • foam boosters typically provide other beneficial properties, for example, as mild surface-active agents, they enhance the cleaning performance of hand dish detergents, and greatly impact the aesthetic appeal of the detergent composition through viscosity modification and emolliency.
  • Examples of common foam boosters in home care compositions include, but are not limited to, amine oxides, betaines, sultaines, and alkanolamides.
  • An embodiment of the present disclosure relates to home care compositions comprising a microbial oil, or derivative thereof, and a cleaning agent.
  • a cleaning agent is any substance used to remove dirt, dust, stains, and/or odor. They may also be classified as a disinfectant or anti-microbial, and may also be classified as a surfactant. Cleaning agents may comprise liquids, powders, sprays, or granules, for example, pumice soapstone, and talc.
  • the cleaning agent is an alkaline solution, acidic solution, neutral solution, degreaser, or scouring agent.
  • the alkaline solution is sodium hydroxide (also known as lye) or potassium hydroxide.
  • An embodiment of the present disclosure relates to home care compositions comprising a microbial oil, or derivative thereof, and a polymer.
  • Polymers are a broad category of substances composed of the same, or similar, repeating subunits (monomers), and may be natural or synthetic. Polymers are routinely used in many home care products.
  • it may act as a thickener, structuring agent, emulsifier, emollient, delivery (“carrier”) system (for example, to deliver an active ingredient), film former, or to waterproof.
  • carrier for example, to deliver an active ingredient
  • the choice of polymer in a home care product depends on the application, formulation, and desired result.
  • polymers with may be used in the compositions described herein include, but are not limited to, polyacrylates, MA-acrylate copolymers, polyolefin, cellulose ethers (such as cellulose gum, methylcellulose, hydroxyethylcellulose, hydroxypropyl methylcellulose, starch, and xanthan gum), polyether, ethoxylated triglycerides, MA/olefin copolymers, sty rene/acry late copolymers, anionic polysaccharides, polyols, ethoxylated sorbitan ester, alkylether sulfosuccinate ester, polyvinyllactam, polycarboxylates, polyester, resin, starch alkenylsuccinate ester, and quaternary ammonium.
  • polyacrylates such as cellulose gum, methylcellulose, hydroxyethylcellulose, hydroxypropyl methylcellulose, starch, and xanthan gum
  • polyether e
  • the home care composition such as a detergent
  • a water-soluble, shelf-stable polymer such as polyvinyl alcohol (PVA).
  • the disclosure relates to home care compositions comprising a microbial oil, or derivative thereof, and an essential oil .
  • oils examples include for example, amyris, bergamot, black pepper, cardamom, cedarwood, chamomile, clary sage, eucalyptus, geranium, ginger, grapefruit juniper, lavender, lemongrass, lemon, lime, may chang, neroli, nutmeg, palmarosa, patchouli, peppermint, petitgrain, rose, rosemary/, rosewood, sandalwood, scots pine, spearmint, sweet marjoram, orange, tea tree, vetiver, and ylang ylang.
  • compositions described herein may also comprise a fragrance oil.
  • fragrance oils any one of which may be used with the compositions described herein.
  • antioxidants can prevent free radicals from oxidizing other ingredients, such as proteins, sugars, and lipids.
  • oxidation of the double bonds of lipids can produce shorter chain fatty acids, aldehydes, and ketones, which yield odors and discoloration.
  • Antioxidants in home care compositions may increase the shelf life of that product.
  • an antioxidant may also be classified as a biologically active ingredient.
  • the microbial oil and/or derivatives thereof may further function as a biologically active ingredient.
  • the disclosure relates to home care compositions comprising microbial oil and/or derivative thereof, wherein the microbial oil or derivative thereof functions as a biologically active ingredient.
  • the microbial oil and/or derivatives thereof described herein may also function as a replacement for other ingredients in home care compositions.
  • the oleaginous microorganisms described herein may be tailored to produce more or less of a particular hydrocarbon, for example C12 (lauric acid).
  • Exemplary feedstocks of corn stillage syrup, corn thin stillage, corn whole stillage, and corn stillage pre-blend were used in the fermentation of an exemplary oleaginous yeast, Rhodosporidium toruloides.
  • EXAMPLE 2 Media formulation, fermentation, and lipid extraction
  • yeast strains were propagated at 30°C, 200rpm, for 28 hours in yeast extract-peptone-dextrose (YPD) medium composed of 10 g/L yeast extract, 20 g/L peptone, and 20 g/L dextrose. Cultures were washed of residual nutrients before inoculating 100 mL of the exemplary feedstock to a starting OD600 of 1.0.
  • YPD yeast extract-peptone-dextrose
  • Fermentations were run in 250 mL baffled flasks within an orbital shaker incubator at. 200 rpm and 30°C. During harvest, cultures were centrifuged at 4700g for 10 minutes to pellet, resuspended in 20 mL deionized water, and centrifuged again to yield a washed, wet cell pellet.
  • the insoluble matter of the diluted corn stillage syrup feedstock could not be separated from the biomass to obtain a pure wet cell pellet, but the biomass could be separated from the thin stillage insoluble matter using 250 g/L sorbitol for a density gradient. Collected and washed cultures were resuspended in 45 mL 250 g/L sorbitol then centrifuged at 4700xg for 10 minutes. The top layer that formed was the desired biomass, whereas the insoluble matter collected at the bottom. The biomass layer was isolated and washed in 45 mL deionized water to obtain the wet cell pellet.
  • Biomass was dried to a constant mass in a vacuum oven. Dry cell weight (DCW ) was then measured, with correction for insoluble matter as needed.
  • Dried biomass was lysed with 8 mL 4M HC1 at 55°C, mild agitation for two hours and extracted with 8 mL chloroform/methanol mixture (2:1 v/v) at room temperature, 350 rpm for three hours. The mixture was centrifuged at 4700g for 10 minutes. The lower layer of chloroform with extracted lipids was isolated and re-extracted using 4 mL chloroform at room temperature, 350 rpm for 30 minutes. Chloroform was evaporated to finalize the lipid extraction. Oil titer was then calculated, with correction for contributions from insoluble matter as needed. Lipid content was determined by dividing oil titer by dry cell weight.
  • the exemplary feedstock employed was a 30% corn stillage syrup-based feedstock, comprising 30% v/v com stillage syrup, with insoluble components removed via centrifugation, diluted in deionized water.
  • a strain of R., toruloides was tested in a fed-batch fermentation format on two different exemplary feedstocks of the disclosure: 30% stillage and 40% stillage.
  • the 30% and 40% stillage feedstocks were formulated with 30% and 40% corn stillage syrup, respectively, diluted in deionized water.
  • the strain was also grown on defined media as a control.
  • the carbon source for this fed batch fermentation was pure glycerol.
  • the cultures were periodically sampled to measure residual glycerol concentration (via HPLC) and then fed with a bolus of concentrated glycerol (800 g/L) to replenish carbon to 60 g/L.
  • strains A, B, and C Three exemplary strains of R. toruloides (strains A, B, and C) were grown on yeast peptone (YP) media (20 g/L peptone, 10 g/L yeast extract) with added arabinose, glucose, glycerol, sucrose, and xylose combined to determine the ability and preference of this species to consume different carbon sources.
  • the carbon sources were added to equal initial concentrations of 12 g/L each, with a total carbon content of 60 g/L within the sample. The consumption of these carbon sources was measured via HPLC over time. The results of the analysis demonstrated that all three tested strains of R. toruloides could use any of the five carbon sources as fuel. All five carbon sources were consumed by R.
  • toruloides strain A with the general trend of preference in terms of consumption being: Glucose > Sucrose > Xylose/Tructose > Glycerol > Arabinose.
  • a 100g sample of crude microbial oil produced by the oleaginous microorganism A. toruloides was analyzed for general physical chemical characterization; fatty acid content, triglyceride content, diglyceride content, monoglyceride content, slip melting point, color; and contaminant (3-MCPD, GEs) levels. These analyses were carried out in comparison to standard Colombian palm oil and hybrid palm oil samples over the course of 70 days. Samples were stored in the dark, at cold temperatures, and at atmospheric nitrogen conditions.
  • crude microbial oil has similar amounts of free fatty acids, triglycerides, and monoglyceride as those found in crude palm oil and crude hybrid oil. Specific triglycerides were also measured and shown below.
  • Whole microbial oil may be used in home care items, for example as a replacement for any mineral oil or vegetable-derived oil. Additionally, it may be used as luxury soft oil in formulations of home care compositions.
  • microbial oil sample showed similarity to both palm oil and hybrid palm oil along different parameters of faty acid and triglyceride content.
  • microbial oil comprised approximately 1.2% w/w palmitic-palmitic-palmitic triglycerides, approximately 22,53% w/w palmitic-oleic-palmitic triglycerides, approximately 20.78% w/w oleic-oleic- palmitic triglycerides, approximately 1.53% w/w stearic-stearic-oleic triglycerides, and approximately 4.29% w/w stearic-oleic-oleic triglycerides.
  • Fractionation is another means of processing the microbial oil described herein for use in home care compositions. Fractionation may be used to physically separate room temperature oil into saturated and unsaturated components. As shown in FIG. 3, the primary fraction of microbial oil results in microbial stearin and microbial olein. A secondary fraction of microbial olein results in microbial soft mid-fraction and microbial super olein. A tertiary fractionation of the soft mid-fraction results in a microbial hard mid-fraction and microbial mid-olein. A tertiary' fractionation of the microbial super olein results in microbial mid-olein and microbial top olein.
  • FIG. 4A is a photograph of a fractionation of crude microbial oil (left) and crude palm oil (right). The top olein layer is liquid, and the bottom stearin layer is solid.
  • FIG. 4B is a photograph of a complete fractionation of crude microbial oil
  • FIG. 4C is a photograph of an incomplete fractionation of crude microbial oil.
  • the aqueous phase was separated by aspirating the upper olein phase into a pre-weighed scintillation vial.
  • the aqueous phase was heated - with its solidified stearin layer interspersed atop - until all fatty materials melted. This heated aqueous phase was centrifuged (4700 rpm, 1 min, 40°C) and the stearin fraction was also aspirated into a pre-weighed scintillation vial.
  • the iodine value (IV) for each fraction was calculated, which is expressed as the number of grams of iodine absorbed by 100 g of the oil sample.
  • the microbial olein fraction had an iodine value of between 80.9 and 81.5 and the microbial stearin fraction had an iodine value of approximately 22.4.
  • Crude microbial oil had an iodine value of between 62.6 and 62.9 (Table 7).
  • the crude palm oil olein fraction had an IV of 53 and the stearin fraction had an IV of 40.
  • Table 7 TV’s for an exemplary fractionated microbial oil of the disclosure.
  • FIG. 5 is a bar graph of the fatty acid profile of crude microbial oil, microbial olein layer, microbial midfraction, and microbial stearin layer.
  • FIG. 6 is a bar graph of the saturated profiles of crude microbial oil, microbial olein layer, microbial mid-fraction, and microbial stearin layer.
  • Microbial olein has a greater percentage of monounsaturated fatty acids compared to microbial stearin, which has a greater percentage of saturated fatty acids.
  • the microbial stearin fractions shown are solid at room temperature (slip melting point > 25 °C), whereas the olein fractions are liquid at room temperature. In some instances, microbial fractionation gives rise to three layers: a stearin, olein, and mid-fraction. In some instances, the microbial oil may be re-fractioned to generate double stearin, or double olein, for example. Thus, the microbial oil of the present disclosure may be fractioned similar to other plant- derived oils, such as palm oil.
  • fractionated microbial olein and fractionated microbial stearin may replace rice bran oil and shea butter, respectively in home care compositions. Fractioned olein may also replace vegetable oils high in oleic acids, such as tea seed oil.
  • Esterification is the general name for a reaction that generates esters, a compound derived from an acid.
  • the disclosure relates to esters derived from fatty acids produced by oleaginous yeast, wherein the esters are used in a home care composition.
  • Oil samples were converted into fatty acid methyl esters (FAMEs) and then analyzed using gas chromatography-mass spectrometry (GC-MS).
  • GC-MS gas chromatography-mass spectrometry
  • a method of using commercial aqueous concentrated HC1 (cone. HCI; 35%, w/w) as an acid catalyst was employed for preparation of fatty acid methyl esters (FAMEs) from microbial oil and palm oil for GC-MS.
  • FAME preparation was conducted according to the following exemplary protocol.
  • HCI Commercial concentrated HCI (35%, w/w; 9.7 ml) was diluted with 41.5 ml of methanol to make 50 ml of 8.0% (w/v) HCI.
  • This HCI reagent contained 85% (v/v) methanol and 15% (v/v) water that was derived from cone. HCI and was stored in a refrigerator.
  • a lipid sample was placed in a screw-capped glass test tube (16.5 x 105 mm) and dissolved in 0.20 ml of toluene. To the lipid solution, 1.50 ml of methanol and 0.30 ml of the 8.0% HCI solution were added in this order. The final HCI concentration was 1.2% (w/v) or 0.39 M, which corresponded to 0.06 ml of concentrated HCI in a total volume of 2 ml. The tube was vortexed and then incubated at 45°C overnight (14 h or longer) for mild methanolysis/methylation or heated at 100°C for 1 h for rapid reaction.
  • Fatty acids that were assayed but not detected in any sample include C4, C6, C13, C15, C 15: 1, C18:2 tt, C18:2 5,9, C18:2 tc, C18:3, C 18:3 etc, C18:3 ttt, C18:3 ttc+tct, C20:4 n6ARA, C22, and C24.
  • Table 8 Faty add composition of microbial oil samples
  • Fatty' acids that were assayed but not detected in any sample include C-4, C6, C13, C15, C15: 1, C18:2 tt, C18:2 5,9, C18:2 tc, C18:3, C18:3 etc, C18:3 ttt, CI 8:3 ttc+tct, C20:4 n6ARA, C22, and C24.
  • Table 9 Fatty acid composition breakdown
  • Table 10 shows the w/w percentage of saturate, trans, mono-unsaturated, poly- unsaturated, and unknown fatty acids in each sample.
  • the fatty acid compositions were determined via fatty acid methyl ester analysis with a GC-SSL/FID (7890A, Agilent) instrument. The methods employed were using AOCS Ce la-13 and AOCS C22-66.
  • FIG. 7A-7C show the chromatograms for the crude microbial oil (FIG, 7A), palm oil (FIG. 7B), and hybrid palm oil (FIG. 7C), respectively.
  • FIG. 7D shows a bar graph of representative compositions of microbial oil and palm oil.
  • esters derived from palm oil and used in home care items may be substituted for esters derived from oleaginous yeast.
  • Methods of producing esters from fatty acids are well known in the art. See, for example, Milinsk, M. C. et al., Comparative analysis of eight esterification methods in the quantitative determination of vegetable oil fatty acid methyl esters (FAME), J. Braz. Chem. Soc., 2008, vol.19, n.8.
  • One example use of the microbial oils described herein is esterification of a specific fatty acid produced from an oleaginous yeast, and use of the resultant ester as an ingredient, in a home care composition.
  • oleaginous yeast produced approximately 9% stearic acid. Esterification of stearic acid produced by the oleaginous yeast described herein can produce stearate esters for use as emollients and thickeners in home care items. For example, a reaction with ethylhexyl alcohol can produce Ethylhexyl Stearate (also known as Octyl Stearate).
  • reactions with other alcohols can produce Butyl Stearate, Cetyl Stearate, Isocetyl Stearate, Isopropyl Stearate, Myristyl Stearate, and Isobutyl Stearate, and Octyldodecyl Stearoyl Stearate.
  • Stearate esters may be used in home care compositions such as, for example, detergents, soaps, and smooth surface cleaners.
  • oleaginous yeast produced approximately 28.7% palmitic acid. Esterification of palmitic acid produced by the oleaginous yeast described herein can produce palmitate esters. For example, a reaction with ethylhexyl alcohol can produce ethylhexyl palmitate (also known as Octyl Palmitate), which may act as an emollient in a composition. Similarly, Isopropyl Palmitate is the ester of isopropyl alcohol and palmitic acid, and can function as an emollient, emulsifier, stabilizer, film former, spreader, and a solvent in a composition.
  • Cetyl Palmitate is the ester of cetyl alcohol and palmitic acid, and can function as an emollient in a composition.
  • Isostearyl Palmitate is the ester of isostearyl alcohol and palmitic acid, and can work as an emollient.
  • Palmitates used in home care products and ranges of their concentrations in various products see Final Report on the Safety Assessment of Octyl Palmitate, Cetyl Palmitate and Isopropyl Palmitate, Journal of the American College of Toxicology, 1990 : 1(2): 13-35.
  • the following microbial oil derivatives are produced for inclusion in home care products described herein: isostearyl palmitate, polyglyceryl -4 dipalmitate, sorbitan palmitate, polyglyceryl-10 dioleate, polyglyceryl-4 oleate, retinyl palmitate, ascorbyl palmitate, sucrose palmitate, ethyl palmate, methyl ester sulfonate, and esterquats.
  • Methyl ester sulfonate is an anionic surfactant.
  • esterquats are quaternary ammonium compounds having two long C16-C18 fatty acid chains with two weak ester linkages and are used in some embodiments in home care compositions herein, e.g., fabric conditioning agents. Esterquats may replace the use of dialkyl dimethyl ammonium salts and are more biodegradable.
  • Hydrolysis is the process whereby triglycerides in fats and oils are split (“fat splitting” or “oil splitting”) into glycerol and fatty acids. It is usually carried out using great amounts of high-pressure steam (“steam hydrolysis”) but may also be performed using catalysts (for example, the tungstated zirconia and solid acid composite SAC-13 (Hydrolysis of Triglycerides Using Solid Acid Catalysts, Ngaosuwan, K, et al., Ind. Eng. Chem. Res., 2009 48 (10), 4757- 4767)). The reaction proceeds in a step-wise fashion wherein fatty acids on triglycerides are displaced one at time, generating diglycerides, then monoglycerides, and finally free fatty acids and glycerin.
  • catalysts for example, the tungstated zirconia and solid acid composite SAC-13 (Hydrolysis of Triglycerides Using Solid Acid Catalysts, N
  • FIG. 8 A Shown in FIG. 8 A is a flow diagram of an example method to produce purified fatty acids from microbial oil or fractions thereof.
  • the crude microbial oil may first be deaerated to remove un-dissolved gasses.
  • the fatty acids are produced by steam hydrolysis, wherein the temperature is raised up to 260 degrees Celsius at. a pressure of 60 bar.
  • Glycerine may be collected and further purified for various uses, and the crude fatty acids are subsequently purified by distillation.
  • Fatty acids may be further modified to produce, for example, conjugated fatty acids, dimer acids, fatty acids ethoxylates, and fatty acid esters.
  • fatty acids derived from oleaginous microorganisms that may be used in home care composition include, but are not limited to, stearic acid, oleic acid, palmitic acid, and myristic acid.
  • Fatty alcohols may be produced via a methyl ester route or a wax ester route (FIG. SB).
  • FAMEs produced by transesterification may be hydrogenated to produce crude fatty alcohols, which are then refined, polished, and purified.
  • wax ester route also known as the Lurgi process
  • fatty acids produced from hydrolysis (“splitting”) are further modified via esterification to produce wax esters, which may then be hydrogenated to produce fatty alcohols. Direct hydrogenation of fatty acids is also possible and produces fatty alcohols.
  • Fatty alcohols may be further modified to produce, for example, fatty alcohol ethoxylates, and fatty alcohol sulfates.
  • fatty' alcohols derived from oleaginous microorganisms that may be used in home care compositions include, but are not limited to, cetearyl alcohol, cetyl alcohol, isostearyl alcohol, and myristyl alcohol.
  • Saponification is the process whereby triglycerides or free fatty acids used as feedstock are converted to fatty acids salts (soaps), glycerol, and free fatty acids in the presence of a base.
  • the base may be for example, sodium hydroxide, or potassium hydroxide.
  • Saponification may be achieved via a hot or cold process.
  • the cold process uses the heat generated from the combination of the fatty acids in the melted oils and fats with sodium hydroxide (base). This process takes longer, and an additional curing phase is needed for the soap to harder.
  • the hot process uses heat to speed up the saponification process, and generally no additional curing step is required before use of the soap. Methods of saponification are well known in the art.
  • the triglycerides or free fatty acids described herein may be used in a saponification reaction to produce salts, glycerin, and free fatty acids.
  • sodium stearate is produced by saponification of stearic acid, and it is one of the most commonly used commercial surfactants in soap.
  • Sodium oleate is produced by the saponification of oleic acid.
  • Saponification of palmitic acid produces sodium palmitate.
  • Potassium stearate is the potassium salt of stearic acid.
  • Metal salts may also be produced, for example, zinc stearate and magnesium myristate.
  • saponification of the triglycerides disclosed herein may produce a number of salts and glycerin for use in home care compositions.
  • the sterol composition was analyzed using the method of Johnsson et al., “Sidechain autoxidation of stigmasterol and analysis of a mixture of phytosterol oxidation products by chromatographic and spectroscopic methods,” Journal of the American Oil Chemists' Society 2003;80(8):777-83, incorporated by reference herein in its entirety, with the HPLC- DAD chromatogram results shown in FIG. 9. The other methods that were employed are indicated in Table 1 1.
  • the sterol composition of the microbial oil sample showed an atypical sterols chromatographic profile differentiating it from the palm oil and hybrid palm oil samples and warranting further investigation. In this illustrative sample, the unexpected sterol composition acts as a unique fingerprint for the microbial oil sample.
  • the microbial oil sample does not contain significant levels of unsaponifiable lipids, or tocopherols. Specifically, microbial oil has approximately 122 ppm of squalene, compared to 389 ppm and 260 ppm in palm oil and hybrid palm oil respectively. Microbial oil also contained less than 10 ppm of tocopherols, whereas palm oil and hybrid palm oil contained 869 ppm and 761 ppm respectively.
  • EXAMPLE 12 Compositional analysis of exemplary microbial oil for use in home care products
  • Microbial oil was prepared using R. toruloides fermented on glycerol feed, lysed with acid, and extracted with heptane solvent. The composition of the oil is shown below in Table 12 A.
  • Table 12B Triglyceride profiles of the oil samples including selected positional isomers
  • Solid fat content was determined using method I for non-stabilizing fats according to AOCS Cd 16-93 Direct, Parallel: Method I. This is a direct and parallel method meaning the NMR is calibrated using 3 samples of kno wn solid fat content and the different temperatures are run one after the other using the same sample tubes. The samples are conditioned by melting them at 80°C for 15 minutes and then 60°C for 5 minutes to clear thermal history. The sample is then left at 0°C for 1 hour to allow the solid fat crystals to form. It is then left at the selected temperature to equilibrate for 30 minutes and following this the solid fat content percentage is measured using NMR.
  • EXAMPLE 13 Analysis of microbial oil compositions following different stages of processing
  • Microbial oil from R. loruloides was prepared and extracted as described in the foregoing examples. Crude microbial oil was then compared to the same oil following consecutive steps of refinement, bleaching, and deodorizing. The results of the analyses is provided in Tables 13-18 below for crude (unrefined) microbial oil (“Crude Oil”), refined microbial oil (“Refined Oil”), refined and bleached microbial oil (“Refined & Bleached Oil”), and refined, bleached, and deodorized microbial oil (“RBD Oil”). Most analyses were performed with standard AOCS and ISO methodologies. After refining, 8-10% of the mass of the crude oil was recovered as soapstock, a by-product of the refining process. Spent clay was obtained as a by-product of bleaching.
  • Tables 13A-13C include the results of processing the crude oil with an antioxidant, and are visually shown in FIG. HA, while Tables 14A-14B include the results of processing the crude oil without an antioxidant, and are shown in FIG. 11B.
  • “NR” indicates that no measurement was taken for that sample parameter.
  • the crude oil can be processed to produce a very light-colored oil using standard RBD processes. Faty acid profile was generally maintained among all samples, demonstrating that the microbial oil was stable throughout processing. Adding an antioxidant before processing did not appear to significantly affect the stability of the oil during the RBD process, however, the addition of an antioxidant may affect shelf-life under various conditions. As will be understood by one skilled in the art, bleaching conditions, especially dosage, can be modified based on the requirement of color of the final product.
  • Table 13A Basic oil parameters of microbial oil in different stages of refinement with an antioxidant
  • Table 13B Fatty add composition of microbial oil in different stages of refinement with an antioxidant
  • Table 13C Diglyceride, nmnoglyceride, and phospholipid composition of microbial oil in different stages of refinement with an antioxidant
  • Table 14A Basic oil parameters of microbial oil in different stages of refinement without an antioxidant
  • Table 14B Fatty acid composition of microbial oil in different stages of refinement without an antioxidant
  • Table 14C Diglyceride, mono glyceride, and phospholipid composition of microbial oil io different stages of refinement without an antioxidant
  • FIG. 14A-14E show illustrative El spectra for sterols extracted from the crude palm oil spike-in preparation.
  • Table 16 Total sterol content.
  • Table 17 Sterol profiles.
  • Sample 2 exemplary microbial oil of the disclosure obtained from R. toruloides; strong acid (H2SO4) treatment with solvent extraction of lipids.
  • Sample 3 exemplary microbial oil of the disclosure obtained from R. toruloides; strong acid (HC1) treatment with solvent extraction of lipids.
  • Sample 4 exemplary microbial oil of the disclosure obtained from R. toruloides; weak acid (H3PO4) treatment with solvent extraction of lipids.
  • Sample 5 exemplary microbial oil of the disclosure obtained from R. toruloides; acid- free extraction of lipids.
  • Sample 6 exemplary microbial oil of the disclosure obtained from R. toruloides; acid- free extraction of lipids. Carotenoid analysis materials and methods
  • UV/Vis analysis For each sample, an initial overall UV/Vis absorbance spectrum was collected between 200 and 600 nm wavelengths. This overall spectrum shows the total overlapping absorbance of all of the sample’s carotenoids, which allows for estimation of the total carotenoid content within the sample. UV/Vis spectra were recorded with a Jasco V-530 spectrophotometer in benzene. (E 1% 1cm : 2500)
  • HPLC-DAD high performance liquid chromatography diode array detector
  • Sample 1 The overall UV/Vis absorbance spectrum for Sample I, agricultural palm oil, is shown in FIG. 15A with the absorbance at individual wavelengths identified in Table 18.
  • the overall UV/Vis spectrum shows the expected distribution centered around 450 nm.
  • the total carotenoid content roughly estimated using the absorbance at 459 nm, was determined to be approximately 478 ppm
  • Table 18 Sample 1, UV/Vis Abs at specific wavelengths.
  • Sample 2 The overall UV/Vis absorbance spectrum for Sample 2, strong acid-extracted microbial oil, is shown in FIG. 16A.
  • the overall UV/Vis spectrum shows essentially no absorbance in the 300-500 nm range, likely because of carotenoid degradation due to the strong acid treatment.
  • the HPLC -DAD chromatogram reporting absorbance at 450 nm is shown in FIG. 16B with no identifiable peaks.
  • Sample 3 The overall UV/Vis absorbance spectrum for Sample 3, strong acid-extracted microbial oil, is shown in FIG. 17A.
  • the overall UV/Vis spectrum show's essentially no absorbance in the 300-500 nm range, likely because of carotenoid degradation due to the strong acid treatment.
  • the HPLC-DAD chromatogram reporting absorbance at 450 nm is shown in FIG. 17B with no identifiable peaks.
  • Sample 4 The overall UV/Vis absorbance spectrum for Sample 4, weak acid-extracted microbial oil, is shown in FIG. ISA. The total carotenoid content, roughly estimated using the absorption at 496 nm, was determined to be approximately 169 ppm.
  • the HPLC- DAD chromatogram reporting absorbance at 450 nm is shown in FIG. 18B with individual peaks identified in Table 20.
  • the sample also contained ⁇ - carotene and derivatives thereof.
  • Table 20 Sample 4, HPLC peak identification.
  • Sample 5 The overall UV/Vis absorbance spectrum for Sample 5, acid-free extracted microbial oil, is shown in FIG. 19A with the absorbance at individual wavelengths identified in Table 21.
  • the overall UV/Vis spectrum shows a peak around 475 nm.
  • the total carotenoid content roughly estimated using the absorbance at 496 nm, was determined to be approximately 471 ppm.
  • Table 21 Sample 5, UV/Vis Abs at specific wavelengths.
  • FIG, 19B with individual peaks identified in Table 22.
  • this sample contained torulene, possible derivatives of torulene, ⁇ -carotene and ⁇ -carotene derivatives.
  • Sample 6 The overall UV/Vis absorbance spectrum for Sample 6, acid-free extracted microbial oil, is shown in FIG. 20A with the absorbance at individual wavelengths identified in Table 23. The overall UV/Vis spectrum shows a peak around 475 nm. The total carotenoid content, roughly estimated using the absorbance at 496 nm, was determined to be approximately 802 ppm.
  • Table 23 Sample 6, UV/Vis Abs at specific wavelengths.
  • FIG. 20B with individual peaks identified in Table 24. As with samples 4 and 5, this sample contained torulene, possible derivatives of torulene, P-carotene and ⁇ -carotene derivatives.
  • exemplary microbial oils of the disclosure comprise torulenes and/or torukmhodins, as well as ⁇ -carotene and derivatives thereof. This is in contrast to agricultural palm oil, which contains predominantly ⁇ - and ⁇ -carotenes and derivatives thereof.
  • Crude microbial oil was obtained from culturing an oleaginous microorganism, e.g,, R. tondoides. See, e.g., WO2021154863A1.
  • a jacketed filter was used for solid-liquid separation.
  • the filter temperature was also controlled by a heater/chiller (USA Lab Recirculating Heater Chiller RHC-7L) that flowed a solution of glycol into the jacket of the filter.
  • the filter temperature was set to the desired crystallization temperature and the filter was allowed to stabilize at that temperature.
  • a 1 pm filter was placed in the filter.
  • a vacuum of less than 50 torr was applied to the filtration system which facilitated the separation.
  • the mixture of crystals and liquid was poured into the filter, and the liquid was allowed through the filter paper, while the solids were retained.
  • the solid fraction was collected from the filter paper and placed in a separate container.
  • TAG profiles in different samples of oil were estimated by first weighing out 10 mg of each oil to be analyzed. All the oil samples were dissolved in 1 mL. of chloroform and vortexed to guarantee a completely homogenized solution. Oil samples were then set at room temperature on an Agilent autosampler (7693 A model) to be injected in a GC 8890 model coupled to an Agilent® 5975 mass selective detector, equipped with a split/splitless injector (split ratio 1 : 100) and set at a working temperature of 350°C.
  • the experimental chromatography conditions were as follow: the initial oven temperature of 300°C was held for 1 minute and raised to 355°C at a. rate of l°C/min and then held at this temperature for 14 minutes for a total run time of 70 minutes.
  • Helium was used as a carrier gas and the system was delivering a pressure at the top of the column of 23.234 psi and a flow of 1.3 mL/mm.
  • TAG analysis was performed by calculating the correction factor (F) that corrects for losses of TAGs during injection and column separation.
  • F was estimated following the indications described in the AOCS Official Method Ce 5-86. Peaks representing individual TAGs of interest were manually integrated using MassHunter Qualitative Analysis software (Agilent Technologies, Santa Clara, CA). Each integrated peak was then corrected applying the corresponding correction factor and the individual TAG abundance was expressed as percentage of the total area of all TAGs present in the chromatogram.
  • the oil samples (100 ⁇ L) were estenfied in 2 mL glass vials at 85°C for 1 h. At the end of the esterification reaction, samples were extracted with 500 ⁇ L of hexane containing ISTD to collect all the products of the FAME reaction. The samples were set at room temperature for 20 minutes to promote separation of the phases and 200 ⁇ L of the top phase were transferred to the GC vial for injection into an Agilent GC 7890B model equipped with a Flame Ionization Detector (FID).
  • FID Flame Ionization Detector
  • the FAME, samples were injected with the PAL 3 Sampler Robot (Model Pal RSI 120 from CTC Analytics, Switzerland) into a split/splitless injector at 250°C connected to a DB-FAST FAME capillary column 20 m long with an internal diameter (i.d) ::: 0.2 pm (Agilent Technologies, Santa Clara, CA).
  • the chromatographic conditions were as follow: the initial oven temperature of 50°C was held for 0.5 minute and raised to 194°C at a rate of 30°C/min and then held at this temperature for 3.5 minutes. This was followed by a further increase to 240°C at a rate of 5°C/min and held for 1 minute for a total run time of 19 minutes.
  • the system used helium as carrier gas and delivered a pressure at the top of the column of 20 psi and a flow' of 0.72476 mL/min.
  • FAME quantification analysis was performed using MassHunter Quantitative Analysis Software (Agilent Technologies®, USA) that allowed automatic peak integration, accelerating the quantification process of the FAME data collected for each sample.
  • the oil sample was initially held at 80°C for 3 min to remove any previous crystalline structure, cooled at 5°C/min to -80°C, held at this temperature for 5 min to fully crystallize, and finally heated from ⁇ 80°C to 80°C at a heating rate of 10°C/min.
  • Table 25 Process conditions for solvent fraetionation and resulting solid fraction melting point.
  • Table 26 FAME profile for solid fractions resulting from different solvent conditions.
  • Table 27 Comparison of solid and liquid fractions from the same solvent fractionation conditions.
  • EXAMP LE 18 Illustrative dry fractionations of microbial oils of the disclosure
  • FIG. 33A-36C show the results of TAG analysis of the solid fraction resulting from dry fractionation conditions 1-4, respectively .
  • FIG. 37A-37B show the results of FAME analysis of the solid fraction resulting from dry fractionation condition 5.
  • the microbial oil fractions resulting from these illustrative dry fractionation conditions differed in significant ways from the original RBD microbial oil.
  • Table 28 provides process conditions and melting points for the solid fractions resulting from these conditions.
  • Table 29 provides fatty’ acid profiles for the resulting solid fractions in comparison to the original RBD microbial oil, and the crude oil from which it was derived.
  • Table 30 provides an overall summary of the TAG profiles for the solid fractions from three of these conditions in comparison to two representative crude microbial oils.
  • Table 31 shows a more detailed breakdown of the TAG profile for the samples included in Table 27.
  • Table 28 Process conditions and melting point for dry conditions
  • Table 31 TAG Profiles of solid fractions obtained from different dry fractionation conditions.
  • EXAMPLE 19 Illustrative double solvent-based fractionation of a microbial oil of the disclosure.
  • a microbial oil was fractionated using solvent-based fractionation, e.g., as disclosed in the Examples supra.
  • the solvent was acetone.
  • the solvent to oil ratio was 4: 1.
  • the solid fraction from the first round was fractionated again, with a 6:1 solvent to oil ratio.
  • the crystallization temperature was 6°C, and the crystallization time was 1 hr.
  • FIG. 3SA-38B show the DSC curves from the solid and liquid fractions from the second round of fractionation in comparison to the curve for the original microbial oil. These figures demonstrate a significant upward shift in melting point for the solid fraction compared to the original oil. In addition, these chromatograms demonstrate a simplification of the peak structure in the DSC curve for the solid fraction, signifying the distillation of a more purified saturated/mono-unsaturated fatty acid composition within the solid fraction compared to the original oil sample.
  • Table 32 shows the TAG saturation profile of the original oil compared to the liquid and solid fractions from the second fractionation, as well as the percent change in composition between the solid fraction compared to the original oil.
  • Table 32 TAG saturation in original oil and liquid and solid fractions.
  • EXAMPLE 20 Properties and triglyceride profiles of illustrative crude and microbial oils of the disclosure.
  • Table 35 Illustrative Triglyceride Profiles of RED Microbial Oils
  • Table 36 Illustrative TAG Saturation Profiles of RBD Microbial Oils
  • EXAMPLE 21 Home care products that may be produced using microbial oil and/or derivatives
  • any home care composition comprising an oil or derivative thereof (e.g., as a primary surfactant, secondary surfactant, cleaning agent, process aid, enzyme stabilizer, anti-foaming agent, suds reducer, solvent, stabilizer, softener, softening agent, anti-static agent, emulsifier, foam stabilizer, humectant, and/or foam booster) may be substituted for a microbial oil or derivative thereof.
  • an oil or derivative thereof e.g., as a primary surfactant, secondary surfactant, cleaning agent, process aid, enzyme stabilizer, anti-foaming agent, suds reducer, solvent, stabilizer, softener, softening agent, anti-static agent, emulsifier, foam stabilizer, humectant, and/or foam booster
  • an oil or derivative thereof e.g., as a primary surfactant, secondary surfactant, cleaning agent, process aid, enzyme stabilizer, anti-foaming agent, suds reducer, solvent, stabilizer, soften
  • the microbial oils and derivatives thereof described herein are a good match of palm oil/hybrid palm oil and their derivatives along a number of different parameters, demonstrating their suitability’ for use as an environmentally friendly alternative to plant-derived palm oil and palm oil derivatives for use in home care compositions.
  • a refined, bleached, and/or deodorized (RBD) microbial oil produced by an oleaginous yeast wherein the microbial oil comprises ergosterol and does not comprise campesterol, ⁇ -sitosterol, or stigmasterol.
  • microbial oil of embodiment 1 wherein the oil is fractionable into two fractions, wherein the two fractions are microbial olein and microbial stearin, wherein each fraction comprises at least 10% of the microbial oil’s original mass, and wherein the iodine value (IV) of the fractions differs by at least 10.
  • the microbial oil of embodiment 7, wherein the fatty acid profile comprises: greater than 20% w/w saturated fatty acids; greater than 35% w/w mono-unsaturated fatty acids; and less than 25% w/w polyunsaturated fatty acids.
  • the microbial oil of embodiment 7, wherein the saturated fatty acids have chain lengths between 16 and 18 carbons long.
  • the microbial oil of embodiment 7, wherein the oi l comprises ergosterol, at least 50 ppm ergosterol, or at least 100 ppm ergosterol,
  • the microbial oil of embodiment 7, wherein the oil does not contain a phytosterol or chlorophyll.
  • the microbial oil of embodiment 7, wherein the oil has one or more characteristics similar to plant-derived palm oil selected from the group consisting of iodine value, slip melting point, and overall saturation level.
  • the microbial oil of embodiment 7, wherein the oil comprises 20-80% C18 unsaturated fatty acid.
  • the microbial oil of embodiment 7, wherein the oil comprises a saponification value similar to that of plant-derived palm oil.
  • the microbial oil of embodiment 7, wherein the oil comprises a saponification value of 150-210.
  • the oil comprises an iodine value similar to that of plant-derived palm oil.
  • the microbial oil of embodiment 7, wherein the oil comprises a saturated fatty acid composition similar to that of plant-derived palm oil.
  • the microbial oil of embodiment 7, wherein the oil comprises an unsaturated fatty acid composition of at most 80%.
  • the oil comprises at least one pigment selected from the group consisting of ⁇ -carotene, torulene and torulorhodin.
  • the microbial oil of embodiment 7, wherein the oleaginous yeast is a recombinant yeast.
  • the microbial oil of embodiment 7, wherein the oleaginous yeast is of the genus Yarrowia, Candida, Rhodotorula, Rhode sporidium, Metschnikowia, Cryptococcus, Trichosporon, or Lipomyces.
  • the microbial oil of embodiment 7, wherein the oleaginous yeast is of the genus Rhodosporidium .
  • the microbial oil of embodiment 7, wherein the oleaginous yeast is of the species Rhodosporidium toruloides.
  • the microbial oil of embodiment 7, wherein the oil is fractionable.
  • the microbial oil of embodiment 7, wherein the oil may be fractionated into microbial olein and microbial stearin.
  • the microbial oil of embodiment 7, wherein the oil may be fractionated into microbial olein and microbial stearin, and wherein the IV of the fractions differs by at least 30.
  • the microbial oil of embodiment 7, wherein the oil comprises at least 10% w/w C16 saturated faty acid.
  • the microbial oil of embodiment 7, wherein the oil comprises at least 20% w/w C18 unsaturated fatty acid.
  • the microbial oil of embodiment 7, wherein the oil comprises less than 5% combined C8, C10, C12, C14, and C15 saturated fatty acids.
  • the microbial oil of embodiment 48, wherein said palmitic-oleic-palmitic triglyceride content is between about 15% and 30% w/w.
  • the microbial oil of embodiment 48 further comprising a palmitic-linoleic-palmitic, palmitic-oleic-stearic, palmitic-linoleic-oleic, oleic-stearic-oleic, and/or oleic-oleic-oleic triglyceride content of at least 1% w/w and less than 20% w/w.
  • the microbial oil of embodiment 48 further comprising a stearic-stearic-oleic triglyceride content of less than 10% w/w and a stearic-oleic-oleic triglyceride content of less than 10% w/w.
  • the microbial oil of embodiment 48 wherein greater than 30% of said triglycerides have one unsaturated sidechain, and wherein greater than 30% of said triglycerides have two unsaturated sidechains.
  • the microbial oil of embodiment 48 wherein between 10% and 15% of palmitic and/or stearic fatty acids are located at the sn-2 position of triglyceride molecules.
  • the microbial oil of embodiment 7, wherein the oil comprises the following amounts of fatty acids relative to the total fatty acids: less than about 25% stearic acid; between about 25% and 70% oleic acid; and between about 2% and 20% linoleic acid.
  • the microbial oil of embodiment 7, wherein the oil has been refined.
  • the microbial oil of embodiment 58, wherein the oil has been chemically and/or physically refined.
  • the microbial oil of embodiment 58, wherein the oil is bleached or deodorized.
  • the derivative of embodiment 62, wherein the derivative is a fraction, and wherein the fraction is microbial stearin, microbial olein, microbial soft mid-fraction, microbial super olein, microbial hard mid-fraction, microbial olein, and/or microbial top olein.
  • the derivative of embodiment 62, wherein the derivative is a triglyceride, diglyceride, monoglyceride, free fatty acid, fatty acid salt, glycerin, ester, fatty alcohol, fatty amine, derivative thereof, or combination thereof.
  • the derivative of embodiment 62 wherein the derivative is selected from the list consisting of: C16-18 fatty acids; sodium salts of C12- 18 fatty acids; MEA salts of C12- 18 fatty acids; sodium C12-C15 alkyl sulfates; MEA C12-C15 alkyl ether sulfates; C10- C16 alkyl dimethyl amine oxide; ethoxylated C12-C16 alcohols; D-glucopyranose, oligomeric, C10-C16 alkylglycosides; sodium C14-C17 alcohol sulfate; C16-18 glycerides; sodium C14-C17 sec-alkyl sulfonates; C8-C10 alkyl polyglucosides; methyl ester sulfonates; and esterquats.
  • the derivative of embodiment 62 wherein the derivative is selected from the list consisting of: sodium lauryl sulfate; sodium laureth sulfate; sodium lauryl ether sulfate; sodium oleate; MEA laureth sulfate; MEA lauryl sulfate; laureth-6; laureth-9; glycerin; D-glucopyranose, oligomeric, decyl octyl glycoside; hydrogenated castor oil; coconut fatty acid; canola-amidoethyl hydroxy ethylammonium methyl sulfate; dipalmethyl hydroxyethylammonium methosulfate; dihydrogenated palmoylethyl hydroxethylmonium methyl sulfate; di (palm carboxyethyl) hydroxyethyl methyl ammonium methyl sulfate; lauramine oxide; capryloyl methyl glucamide;
  • a home care composition comprising: the microbial oil of any one of embodiments 1-6, and/or a microbial oil derivative of any one of embodiments 62-66, wherein the microbial oil is derived from an oleaginous yeast.
  • the composition of embodiment 67, wherein the microbial oil derivative functions as a surfactant in said home care composition
  • the composition of embodiment 69, wherein the surfactant is a primary surfactant or a secondary' surfactant in said home care composition.
  • composition of embodiment 69 wherein the surfactant is an emulsifier, detergent, wetting agent, cleaning agent, foaming agent, thickening agent, emollient, solubilizer, conditioning agent, co-surfactant or dispersant in said home care composition.
  • the composition of embodiment 67 wherein the microbial oil or derivative thereof functions as a biologically active ingredient in said home care composition.
  • the composition of embodiment 67 further comprising a cleaning agent, a polymer, a stabilizer, an emulsifier, a thickener, a builder, a solvent, an enzyme, a fragrance, a preservative, a pH adjuster, a disinfecting agent, a dye, a foam enhancer, a biologically active ingredient, or combinations thereof.
  • composition of embodiment 67 wherein the composition is a solid, liquid, powder, spray, gel, pod, sheet, wipe or foam.
  • the composition of embodiment 67, wherein the composition is a laundry detergent.
  • the composition of embodiment 80, wherein the laundry detergent is a po wdered laundry detergent, liquid laundry detergent, baby laundry detergent, concentrated laundry detergent, or laundry pod.
  • the composition of embodiment 67, wherein the composition is a fabric stain remover.
  • the composition of embodiment 67, wherein the composition is a fabric softener.
  • the composition of embodiment 67, wherein the composition is an anti-static spray.
  • the composition of embodiment 67, wherein the composition is a dryer sheet.
  • the composition of embodiment 67, wherein the composition is a dish detergent.
  • composition of embodiment 67 wherein the composition is an all-purpose cleaner.
  • the composition of embodiment 67, wherein the composition is a bathroom cleaner.
  • the composition of embodiment 67, wherein the composition is a multi-surface cleaner.
  • the composition of embodiment 67, wherein the composition is a glass cleaner,
  • the composition of embodiment 67, wherein the composition is a toilet bowl cleaner.
  • a home care composition comprising an oil and/or derivative thereof, wherein said oil and/or derivative thereof consists of a microbial oil and/or derivative produced by an oleaginous yeast.
  • the composition of embodiment 92, wherein the microbial oil comprises a fatty acid profile of at least 30% saturation level.
  • composition of embodiment 92 wherein the microbial oil derivative is selected from the list consisting of: C16-18 fatty acids; sodium salts of C12-18 fatty acids; MEA salts of C12-18 fatty acids; sodium C12-C15 alkyl sulfates; MEA C12-C15 alkyl ether sulfates; C10-C16 alkyl dimethyl amine oxide, ethoxylated C12-C16 alcohols, D- glucopyranose, oligomeric, C10-C16 alkylglycosides; sodium C14-C17 alcohol sulfate; C16-18 glycerides; sodium C14-C17 sec-alkyl sulfonates; C8-C10 alkyl poly glucosides; methyl ester sulfonates; and esterquats.
  • the microbial oil derivative is selected from the list consisting of: C16-18 fatty acids; sodium salts of C12-18 fatty acids; MEA salts of
  • composition of embodiment 92 wherein the microbial oil derivative functions as a surfactant, emulsifier, wetting agent, ester, solvent, process aid, humectant, quaternary ammonium compound, antistatic agent, softening agent, rheology modifier, thickener, foam suppressor, anti-foaming agent, foam booster, stabilizer, or cleaning agent in said home care composition
  • the composition of embodiment 92, wherein the microbial oil derivative functions as a surfactant in said home care composition
  • the composition of embodiment 100, wherein the surfactant is a primary surfactant or a secondary surfactant in said home care composition.
  • composition of embodiment 100 wherein the surfactant is an emulsifier, detergent, wetting agent, cleaning agent, foaming agent, thickening agent, emollient, solubilizer, conditioning agent, co-surfactant or dispersant in said home care composition.
  • the composition of embodiment 92 wherein the microbial oil or derivati ve thereof functions as a biologically active ingredient in said home care composition.
  • composition of embodiment 92 further comprising a cleaning agent, a polymer, a stabilizer, an emulsifier, a thickener, a builder, a solvent, an enzyme, a fragrance, a preservative, a pH adjuster, a disinfecting agent, a dye, a foam enhancer, a biologically active ingredient, or combinations thereof.
  • the enzyme is a protease, amylase, lipase, lyase, mannanase, cellulase, or pectinase.
  • composition of embodiment 104 wherein the cleaning agent is an alkaline solution, acidic solution, neutral solution, degreaser, scouring agent, or combinations thereof.07.
  • the composition of embodiment 104, wherein the biologically active ingredient is an antibiotic, antimicrobial, antifungal, or antiviral agent.
  • the composition of embodiment 92, wherein the oleaginous yeast is Rhodosporidiiim toruloides.
  • the composition of embodiment 92, wherein the composition does not comprise palm oil or palm kernel oil or derivatives thereof.
  • the composition of embodiment 92, wherein the composition is a solid, liquid, powder, spray, gel, pod, sheet, wipe or foam.
  • the composition of embodiment 92, wherein the composition is a laundry detergent. 12.
  • the composition of embodiment 111, wherein the laundry detergent is a powdered laundry detergent, liquid laundry detergent, baby laundry detergent, concentrated laundry detergent, or laundry pod. 13.
  • the composition of embodiment 92, wherein the composition is a fabric stain remover.
  • the composition of embodiment 92, wherein the composition is a fabric softener.
  • the composition of embodiment 92, wherein the composition is an anti-static spray.
  • the composition of embodiment 92, wherein the composition is a dryer sheet.
  • the composition of embodiment 92, wherein the composition is a dish detergent.
  • the composition of embodiment 92, wherein the composition is an all-purpose cleaner.
  • the composition of embodiment 92, wherein the composition is a bathroom cleaner.20.
  • the composition of embodiment 92, wherein the composition is a multi-surface cleaner.
  • composition of embodiment 92 wherein the composition is a glass cieaner.
  • the composition of embodiment 92, wherein the composition is a toilet bowl cleaner.
  • the composition of embodiment 92, wherein the oleaginous yeast is Rhodo sporidium toruloides.
  • a method for producing a home care composition comprising: obtaining a microbial oil, and/or a derivative thereof wherein the microbial oil and/or derivative thereof is derived from an oleaginous yeast, and producing a home care composition.
  • the method of embodiment 124, wherein the microbial oil comprises a fatty acid profile of at least 30% saturation level.
  • the microbial oil comprises a fatty acid profile of at least 20% palmitic acid, at least 5% stearic acid, and at least 30% oleic acid.
  • the method of embodiment 124, wherein the microbial oil comprises at least one of ergosterol, ⁇ -carotene, torulene, and torularhodin.
  • the method of embodiment 124, wherein the microbial oil derivative is a triglyceride, diglyceride, monoglyceride, free fatty acid, fatty acid salt, glycerin, ester, fatty alcohol, fatty amine, derivative thereof, or combination thereof.
  • the method of embodiment 124 wherein the microbial oil derivative functions as a surfactant, emulsifier, wetting agent, ester, solvent, process aid, humectant, quaternary ammonium compound, antistatic agent, softening agent, rheology modifier, thickener, foam suppressor, anti -foaming agent, foam booster, stabilizer, or cleaning agent in said home care composition.
  • the oleaginous yeast is Rhodospondium toruloides.
  • the composition does not comprise palm oil or palm kernel oil or derivatives thereof.
  • composition comprises a cleaning agent, a polymer, a stabilizer, an emulsifier, a thickener, a builder, a solvent, an enzyme, a fragrance, a preservative, a pH adjuster, a disinfecting agent, a dye, a foam enhancer, a biologically active ingredient, or combinations thereof.
  • a home care composition produced by embodiment 124 wherein the home care composition is a laundry detergent, fabric stain remover, fabric softener, anti-static spray, dryer sheet, dish detergent, all-purpose cleaner, bathroom cleaner, multi-surface cleaner, glass cleaner, or toilet bowl cleaner.
  • the method of embodiment 124, wherein the derivative is a triglyceride, diglyceride, monoglyceride, free fatty acid, fatty' acid salt, glycerin, ester, fatty’ alcohol, fatty amine, derivative thereof, or combination thereof.
  • the microbial oil derivative is selected from the list consisting of C16-18 fatty acids; sodium salts of C12-18 fatty acids; MEA salts of C12-18 fatty acids; sodium C12-C15 alkyl sulfates; MEA C12-CT5 alkyl ether sulfates; C10-C16 alkyl dimethyl amine oxide; ethoxylated C12-C16 alcohols; D-glucopyranose, oligomeric, C10-C16 alkylglycosides; sodium C14-C17 alcohol sulfate; C16-18 glycerides; sodium C14-C17 sec-alkyl sulfonates; C8-C10 alkyl polyglucosides; methyl ester sulfonates; and esterquats.
  • the microbial oil derivative is selected from the list consisting of: sodium lauryl sulfate; sodium laureth sulfate; sodium lauryl ether sulfate; sodium oleate; MEA laureth sulfate; AIEA lauryl sulfate; laureth-6; laureth-9; glycerin; D-glucopyranose, oligomeric, decyl octyl glycoside; hydrogenated castor oil; coconut fatty' acid; canola-amidoethyl hydroxy ethyl ammonium methyl sulfate; dipalmethyl hydroxy ethyl ammonium methosulfate; dihydrogenated palmoylethyl hydroxethylmonium methyl sulfate; di (palm carboxyethyl) hydroxyethyl methyl ammonium methyl sulfate; lauramine oxide; capryloyl
  • the method of embodiment 138 wherein the modifying comprises fractionation, interesterification, transesterification, hydrogenation, steam hydrolysis, distillation, saponification, amination, ethyoxylation, sulfonation, oxidation, quatermzation, or combinations thereof.
  • the method of embodiment 138, wherein the crude microbial oil extracted from the whole cell or lysed microbial biomass is as described in any one of embodiments 7-61.
  • the method of embodiment 138, wherein the method further comprises at least one of physically refining, chemically refining, deodorizing, and bleaching the microbial oil.
  • the method of embodiment 138, wherein the whole cell or lysed microbial biomass is produced by Rhodosporidium toruloides.
  • microbial oil derivative is a triglyceride, diglyceride, monoglyceride, free fatty acid, fatty acid salt, glycerin, ester, fatty alcohol, fatty amine, derivative thereof, or combination thereof.
  • the microbial oil derivative is selected from the list consisting of: C16-18 fatty acids; sodium salts of C12-18 fatty acids; ME A salts of C12-18 fatty acids; sodium C12-C15 alkyl sulfates; MEA C12-C15 alkyl ether sulfates; C10-C16 alkyl dimethyl amine oxide; ethoxylated C12-C16 alcohols; D-glucopyranose, oligomeric, C10-C16 alkylglycosides; sodium C14-C17 alcohol sulfate; C16-18 glycerides; sodium C14-C17 sec-alkyl sulfonates; C8-C10 alkyl polyglucosides; methyl ester sulfonates; and esterquats.
  • the microbial oil derivative is selected from the list consisting of: sodium lauryl sulfate; sodium laureth sulfate; sodium lauryl ether sulfate; sodium oleate; MEA laureth sulfate; AIEA lauryl sulfate; laureth-6; laureth-9; glycerin; D-glucopyranose, oligomeric, decyl octyl glycoside; hydrogenated castor oil; coconut fatty acid; canola-amidoethyl hydroxyethylammonium methyl sulfate; drpalmethyl hydroxyethyl ammonium methosulfate; dihydrogenated palmoylethyl hydroxethylmonium methyl sulfate; di (palm carboxyethyl) hydroxyethyl methyl ammonium methyl sulfate; lauramine oxide; capryloyl
  • the method of embodiment 138, wherein the derivative is isostearyl palmitate, The method of embodiment 138, wherein the derivative is polyglyceryl-4 dipalmitate.
  • the method of embodiment 138, wherein the derivative is sorbitan palmitate.
  • the method of embodiment 138, wherein the derivative is poly glyceryl- 10 dioleate.
  • the method of embodiment 138, wherein the derivative is polyglyceryl-4 oleate.
  • the method of embodiment 138, wherein the derivative is retinyl palmitate.
  • the method of embodiment 138, wherein the derivative is ascorbyl palmitate.
  • the method of embodiment 138, wherein the derivative is sucrose palmitate. 155.
  • the method of embodiment 138, wherein the derivative is ethyl palmate.
  • a polyglyceryl- 10 dioleate produced by the method of embodiment 150 is produced by the method of embodiment 150.

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Abstract

La présente divulgation concerne des compositions de soins à domicile comprenant une huile microbienne et/ou un dérivé de celle-ci. Ces lipides peuvent servir d'alternatives à l'huile de palme et être transformés et/ou dérivés par n'importe quel nombre de moyens connus dans l'art. L'huile microbienne ou son dérivé peuvent être utilisés dans diverses compositions de soins à domicile. La présente divulgation concerne également des procédés de production de dérivés à partir d'huile microbienne et de production de compositions de soins à domicile comprenant une huile microbienne et/ou un dérivé de celle-ci.
PCT/US2023/063528 2022-03-01 2023-03-01 Compositions de soins à domicile comprenant de l'huile produite par voie microbienne et leurs dérivés Ceased WO2023168301A2 (fr)

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US4110498A (en) * 1976-03-08 1978-08-29 The Procter & Gamble Company Fabric treatment compositions
US7666826B2 (en) * 2002-11-27 2010-02-23 Ecolab Inc. Foam dispenser for use in foaming cleaning composition
US7666828B2 (en) * 2008-01-22 2010-02-23 Stepan Company Sulfonated estolides and other derivatives of fatty acids, methods of making them, and compositions and processes employing them
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