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WO2025196673A1 - Procédé de préparation d'une composition colorante à stabilité améliorée et procédé d'emballage et/ou de stockage de celle-ci - Google Patents

Procédé de préparation d'une composition colorante à stabilité améliorée et procédé d'emballage et/ou de stockage de celle-ci

Info

Publication number
WO2025196673A1
WO2025196673A1 PCT/IB2025/052900 IB2025052900W WO2025196673A1 WO 2025196673 A1 WO2025196673 A1 WO 2025196673A1 IB 2025052900 W IB2025052900 W IB 2025052900W WO 2025196673 A1 WO2025196673 A1 WO 2025196673A1
Authority
WO
WIPO (PCT)
Prior art keywords
lux
light
colorant composition
packaged
packaging component
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/IB2025/052900
Other languages
English (en)
Inventor
Mauricio BRAIA
Betina CARNEVALE
Bernardo LIBONATTI
Mariano DI RUBBO
Emilia MAZZA
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Michroma Corp
Original Assignee
Michroma Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Michroma Corp filed Critical Michroma Corp
Publication of WO2025196673A1 publication Critical patent/WO2025196673A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A23L5/40—Colouring or decolouring of foods
    • A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
    • A23L5/46—Addition of dyes or pigments, e.g. in combination with optical brighteners using dyes or pigments of microbial or algal origin
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
    • C09B23/005—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a COOH and/or a functional derivative thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0034—Mixtures of two or more pigments or dyes of the same type
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0083—Solutions of dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0092—Dyes in solid form
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0097—Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
    • C12R2001/00—Microorganisms ; Processes using microorganisms
    • C12R2001/645—Fungi ; Processes using fungi

Definitions

  • the present invention is generally related to forms of handling and storing colorant compositions to improve their stability.
  • the invention is related to forms of handling and storing colorant compositions comprising a red pigment to improve the stability of said pigment. More particularly, the invention is related to forms of handling and storing colorant compositions comprising a red pigment obtained from fungi of the Talaromyces genus, even more particularly from Talaromyces atroroseus, to improve the stability of said pigment.
  • the filamentous fungi of the Talaromyces genus are known to produce a variety of pigments, which are azaphilone compounds and include red, orange, and yellow pigments. These pigments, due to being obtained from a natural source, are excellent candidates for preparing natural colorants, which are increasingly being used in a variety of products as a substitute for traditional synthetic colorants.
  • Talaromyces are known to produce a family of red pigments derived from monascorubraminic acid, which incorporate amino acids into their structure, and may generally be referred to as monascus pigments.
  • the different pigments of this family differ between each other according to the incorporated amino acid and they exist as cis- or trans- forms due to a C-C double bond bridging the azaphilone core to the carboxyl group of the base monascorubraminic acid.
  • the cis- form is the main compound, while the trans- form is considered a byproduct.
  • the packaging component prevents or reduces the transmission of light having a wavelength between 290-800 nm.
  • the packaged colorant composition comprises less than 10%, preferably less than 5%, of a compound of Formula (II)
  • the packaged colorant composition maintains less than 10%, preferably less than 5% of the compound of Formula (II) over a 6-month storage period.
  • the packaging component reduces the transmission of light or a portion of the wavelength spectrum thereof by at least 50%, at least 60%, at least 70%, at least 80%, at least 90%, at least 95% or at least 98%.
  • the packaging component reduces the transmission of light below 500 lux, 400 lux, 200 lux, 100 lux, 75 lux, 50 lux, 25 lux, 10 lux or 5 lux.
  • a packaged colored end product comprising: i) a colored end product comprising the compound of Formula (I); and ii) a packaging component, wherein the packaging component prevents or reduces the transmission of light.
  • the packaging component prevents or reduces the transmission of light having a wavelength between 290-800 nm.
  • the colored end product is selected from a foodstuff, a pharmaceutical product, and a cosmetic product.
  • handling and storing the colorant composition or the colored end product under protection from light comprises packaging the colorant composition or the colored end product with a packaging component which prevents or reduces the transmission of light.
  • the packaging component prevents or reduces the transmission of light having a wavelength between 290-800 nm.
  • the packaging component reduces the transmission of light or a portion of the wavelength spectrum thereof by at least 50%, at least 60%, at least 70%, at least 80%, at least 90%, at least 95% or at least 98%.
  • the packaging component reduces the transmission of light below 500 lux, 400 lux, 200 lux, 100 lux, 75 lux, 50 lux, 25 lux, 10 lux or 5 lux.
  • the hue value of the colorant composition or the colored end product experiences a decrease not greater than 10% over a 6-month storage period.
  • a method for producing a colorant composition comprising the compound of Formula (I), the method comprising i) culturing a fungus of the Talaromyces genus in a culture broth in conditions such that the compound of Formula (I) is produced; ii) extracting the compound of Formula (I) produced in step i) from the culture broth, thus obtaining a colorant composition; and iii) packaging the colorant composition with a packaging component which prevents or reduces the transmission of light.
  • the fungus of the Talaromyces genus is
  • the packaging component prevents or reduces the transmission of light having a wavelength between 290-800 nm.
  • the packaging component reduces the transmission of light or a portion of the wavelength spectrum thereof by at least 50%, at least 60%, at least 70%, at least 80%, at least 90%, at least 95% or at least 98%.
  • the packaging component reduces the transmission of light below 500 lux, 400 lux, 200 lux, 100 lux, 75 lux, 50 lux, 25 lux, 10 lux or 5 lux.
  • FIG. 1 (A) UV-VIS spectrum of c/.s-TarE. (B) UV-VIS spectrum of /raw.s-TarE.
  • FIG. 2 HPLC chromatogram showing the transformation of c/.s-TarE to /raw.s-TarE due to exposure to light at 1000 MW/m 2 over 3 hours.
  • FIG. 3 TLC result for a sample being exposed to light at 1000 MW/m 2 over 3 hours.
  • the red stain (a) corresponds to c/.s-TarE
  • the purple stain (b) corresponds to /raw.s-TarE.
  • FIG. 4 Hue variation of a solution of c/.s-TarE over time due to light exposure.
  • the present invention is based on the surprising discovery made by the inventors that the generation of /ra/7.s-TarE during the production and storage of c/.s-TarE is due to or increased by the exposure of TarE to light, and that moreover, the generation of /ra/7.s-TarE has a significant impact on the color and thus the utility of the compound.
  • the production of /raw.s-TarE generates a perceptible color change in the colorant, shifting its hue towards purple while also decreasing its coloring power.
  • the compound of Formula (I) is the cis- form of N-glutamyl monascorubraminic acid and corresponds to the pigment of the family of monascorubraminic acids which is formed when glutamate is incorporated into the base cv.s-monascorubraminic acid structure.
  • N- glutamyl monascorubraminic acid may be referred to interchangeably as TarE.
  • the compound of Formula (I) may be referred to as cv.s-TarE herein.
  • the term “colorant composition” is to be understood as referring to a composition which may be readily used as a colorant, such as for coloring a product. More particularly, the term “packaged colorant composition” is to be understood as referring to a colorant composition that is contained within another tangible object, such as a packaged item intended for commercialization, distribution and/or storage.
  • the packaged colorant composition of the invention comprises the compound of Formula (I), and may comprise other colored components.
  • concentrations of colored components in the packaged colorant composition may be ascertained by HPLC with UV/Vis detection at 520 nm, by comparing the peak area observed for each compound, thus expressing the concentrations as percentages determined by relative peak area at 520 nm.
  • relative peak area at 520 nm absorbance it should be understood that the recited percentage for a specific component X corresponds to the value obtained by the following expression: wherein each peak area is obtained from subjecting the packaged colorant composition of the invention to a HPLC analysis in conditions upon which a proper separation of the colored components thereof may be achieved, detecting the compounds with UV/Vis detection at 520 nm.
  • concentrations of the colored components which may be present in the packaged colorant composition of the invention will be expressed as relative peak area at 520 nm, unless otherwise is specifically pointed out.
  • the packaged composition of the invention comprises TarE at a concentration of at least 70%, preferably from 70% to 80%.
  • other minor components exhibiting light absorption at 520 nm may be present in the composition, such as the compound of Formula (II) (also referred to throughout this description as /raw.s-TarE),.
  • the packaged colorant composition comprises less than
  • the packaged colorant composition maintains less than 10%, preferably less than 5% of the compound of Formula (II) over a 6-month storage period.
  • colored components which may be present in the packaged colorant composition of the invention as minor byproducts of the production of c/.s-TarE are, for instance, N-glutamyl monascorubramine, N-glutaminyl monascorubraminic acid, and compounds related thereto. These additional colored components taken together may be present in the packaged colorant composition in a concentration not higher than 10%, preferably not higher than 5%.
  • the packaged colorant composition may be in solid form (e.g., as a colored powder) or liquid form (e.g., as a colored solution or suspension). If the composition is in liquid form, it may further comprise a suitable carrier for the compound of Formula (I) to be dissolved or suspended in, and which allows for a proper coloring of the intended product. For instance, such a carrier may be water.
  • the packaged colorant composition may further comprise at least one additional colored compound other than the compound of Formula (I), to modify the color hue of the composition as needed.
  • at least one additional colored compound other than the compound of Formula (I) to modify the color hue of the composition as needed.
  • a colorant of a blue or yellow hue may be mixed with the packaged colorant composition herein to form additional colorants.
  • the packaging component of the packaged colorant composition of the invention may be any packaging means which is suitable for containing the colorant composition, as long as it properly prevents or reduces the transmission of light.
  • the packaging component may be selected from a container, a vial, a wrapper, a foil, a box, a bin, a box, a protective covering, a canister, a drum or a case.
  • the material of the packaging component may also be selected from any suitable material, including but not limited to plastic, glass, metal, paper, wood, cardboard, or foil.
  • the packaging component does not necessarily block the transmission of light completely, as long as it ensures that a properly low amount of /raw.s-TarE is generated during the storage of the packaged colorant composition.
  • the packaging component may prevent the transmission of light of a particular wavelength range, or may prevent the transmission of a particular percentage of the light the packaged colorant composition is exposed to.
  • the packaging component prevents the transmission of light having a wavelength between 290-800 nm.
  • the packaging component blocks at least 50% of the light, preferably at least 75% of the light, that the packaged colorant composition is exposed to, as measured by, for instance, the comparative light intensity measured by a suitable detector placed outside and inside the corresponding packaging component.
  • the packaging component reduces the transmission of light or a portion of the wavelength spectrum thereof by at least 50%, at least 60%, at least 70%, at least 80%, at least 90%, at least 95% or at least 98%. In yet another embodiment of the invention, the packaging component reduces the transmission of light below 500 lux, 400 lux, 200 lux, 100 lux, 75 lux, 50 lux, 25 lux, 10 lux or 5 lux.
  • the compound of Formula (I) is suitable for its use as a colorant in several industries. It is known that fungus of the Talaromyces genus do not generate mycotoxins such as citrinin, which is produced by fungus of the Monascus genus. This fact, combined with the fact that the packaged colorant composition according to the present invention is able to maintain low amounts of /raw.s-TarE during handling and storage, makes the packaged colorant composition of the present invention particularly suitable for industries related to products for human use and/or consumption, such as the food, pharmaceutical and cosmetic industries.
  • a packaged colored end product comprising: i) a colored end product comprising the compound of Formula (I); and ii) a packaging component, wherein the packaging component prevents or reduces the transmission of light.
  • colored end product is to be understood throughout this description as referring to a product colored by the presence of a compound of Formula (I) therein or by the application of the packaged colored composition of the invention thereto, which is ready for human use and/or consumption.
  • the colored end product may be any end product feasible to be colored by the compound of Formula (I).
  • the colored end product is selected from a foodstuff, a pharmaceutical product, and a cosmetic product.
  • the colored end product may further comprise additional components depending on the type of product and the use thereof.
  • the packaging component of the colored end product according to this aspect of the invention may share the same characteristics with the packaging component of the packaged colorant composition described above.
  • the packaged colored end product maintains less than 10%, or even less than 5%, of the compound of Formula (II) over a 6-month storage period.
  • the present inventors have surprisingly found that the generation of /raw.s-TarE in a colorant composition due to its exposure to light causes a shift in the color hue of the composition, since /raw.s-TarE has a purple color, different from the red color of cv.s-TarE.
  • color stability is to be understood as the capability of a colorant composition or a colored end product to maintain their color hue and coloring power unaltered in time. Since there is no suggestion whatsoever in the state of the art about the susceptibility of cv.s-TarE to light, and particularly that the exposure of cv.s-TarE to light could result in the trans- isomerization thereof, with /raw.s-TarE having a purple color, protecting a colorant composition or a colored end product comprising the compound of Formula (I) from light has the surprising effect of minimizing any color change during the handling and storage of said colorant composition or colored end product, thus improving their color stability.
  • the color stability of the colorant composition or colored end product may be measured by techniques known to the person of skill in the art, such as measuring the CIELAB parameters thereof with an appropriate spectrometer, which may then be used to calculate the hue value.
  • the isomerization of cv.s-TarE to /ra/v.s-TarE generates a decrease in the hue value of the colorant.
  • the hue value of the colorant composition or the colored end product experiences a decrease not greater than 10% over a 6-month storage period.
  • handling and storing the colorant composition or the colored end product under protection from light comprises packaging the colorant composition or the colored end product with a packaging component which prevents or reduces (i.e., significantly reduces) the transmission of light or certain wavelengths thereof.
  • the packaging component used to this end may be a container, a vial, a wrapper, a foil, a box, a bin, a box, a protective covering, a canister, a drum or a case.
  • the material of the packaging component may also be selected from any suitable material, including but not limited to plastic, glass, metal, paper, wood, cardboard, or foil.
  • c/.s-TarE is generated by culturing a fungus of the Talaromyces genus.
  • Step i) of the method may involve culturing any fungus species of the Talaromyces genus capable of producing cv.s-TarE.
  • the fungus of the Talaromyces genus cultured in step i) of the method may be selected from T.
  • albobiverticillius T. amestolkiae, T. apiculatus, T. assiutensis, T. atroroseus, T. aurantiacus, T. austrocalifomicus, T. bacillisporus, T. barcinensis, T. boninensis, T. brunneus, T. calidicanius, T. proliferationdicola, T. coalescens, T. convolutus, T. dendriticus, T. derxii, T. duclauxii, T. echinosporus, T. emodensis, T. erythromellis, T. euchlorocarpius, T. flavus, T.
  • T. galapagensis T. hachijoensis
  • T. helicus T. indigoticus
  • T. intermedins T. islandicus
  • T. lagunensis T. leycettanus
  • T. loliensis T. luteus
  • T. macrosporus T. malagensis, T. mameffei, T. mimosinus, T. minioluteus, T. muroii, T. palmae, T. panamensis, T. paucisporus, T. phialosporus, T. piceus, T. pinophilus, T. pittii, T. primulinus, T. proteolyticus, T. pseudostromaticus, T.
  • T. purpurogenus T. rademirici, T. radicus, T. ramulosus, T. retardatus, T. rotundus, T. ruber, T. rubicundus, T. rugulosus, T. ryukyuensis, T. sabulosus, T. siamensis, T. stipitatus, T. stollii, T. subinflatus, T. sublevisporus, T. tardifaciens, T. thermocitrinus, T. trachyspermus, T. ucrainicus, T. udagawae, T. unicus, T. variabilis, T. varians, T.
  • the fungus of the Talaromyces genus cultured in step i) of the method is T. atroroseus.
  • the extraction process of the produced compound of Formula (I) may comprise: (a) eliminating the biomass of the Talaromyces fungus used for fermentation; (b) eliminating soluble fermentation secondary products; and (c) precipitating the compound of Formula (I). These sub-steps may be carried out by simple precipitation/centrifugation processes, although the present invention also contemplates other means to isolate the compound of Formula (I).
  • the Talaromyces fungus used for fermentation may be eliminated by centrifugation of the fermentation broth after the fermentation process has been completed, separating the supernatant.
  • the supernatant may then be treated to induce the precipitation of soluble fermentation secondary products (such as proteins, peptides and sugars), for instance, by adding ethanol thereto, which may then be removed by centrifugation as well.
  • soluble fermentation secondary products such as proteins, peptides and sugars
  • the precipitation of the compound of Formula (I) may be achieved by acidification of the medium (for instance, with concentrated sulfuric acid) and an additional centrifugation to assist in the precipitation of the crystals. If necessary, the crystals of the compound of Formula (I) thus obtained may be subjected to a recrystallization to further improve the purity thereof.
  • Steps i) and ii) of the method described above may be carried out in metal reactors and piping when production is performed at an industrial scale and thus protected from light during its production and isolation.
  • Steps i) and ii) of the method described above may be carried out in light- protected containers, such as covered flasks and handling steps in reduced light or dark to protect the composition from light.
  • Step iii) of the method of this aspect of the invention involves packaging the colorant composition with a packaging component which prevents or reduces the transmission of light, so as to maintain the compound of Formula (I) protected from light to avoid the trans- isomerization thereof.
  • the packaging component used to this end be a container, a vial, a wrapper, a foil, a box, a bin, a box, a protective covering, a canister, a drum or a case.
  • the material of the packaging component may also be selected from any suitable material, including but not limited to plastic, glass, metal, paper, wood, cardboard, or foil.
  • step iii) of the method of this aspect of the invention minimizes the generation of /raw.s-TarE, since said generation is more likely to take place during storage of the colorant composition if it is not properly protected from light.
  • this feature of the invention has the surprising effect of minimizing the generation of /raw.s-TarE during the storage of the colorant composition comprising the compound of Formula (I) and protecting the desired red hue of the colorant composition.
  • T. atroroseus conidia were used to inoculate a broth prepared with the following composition per liter: 20 g of glucose, 3 g of sodium nitrate, 2 g of yeast extract, 0.5 g of potassium chloride, 0.5 g of magnesium sulfate heptahydrate, 0.5 g of dipotassium acid phosphate and 10 mg of ferrous sulfate heptahydrate.
  • the pH was adjusted to 5.
  • 50 mb of culture media were inoculated at 2x10 5 conidia per milliliter.
  • Flasks were incubated at 30°C and 200 rpm for 48 hours.
  • the seed culture was transferred at 1% to a 2L-bioreactor with color-producing broth with the following composition per liter: 30 g of starch, 10 g of glucose, 8.35 g of monosodium glutamate,! g of yeast extract, 5 g of magnesium sulfate,
  • the culture broth was centrifuged for 10 min at 3000 g to separate the supernatant. 3 volumes of ethanol were added followed by 16 hours incubation at 4°C to induce the precipitation of proteins, peptides, and sugars, which were removed by centrifugation. Concentrated sulfuric acid was added to lower the pH up to 2.5, and the sample was stored at 4°C for 16 hours before centrifugation for 10 min at 4.000 rpm to help precipitate the formed crystals. Potassium hydroxide was used to resuspend the crystals bringing the pH up to 5 or above. The final resuspension was dried by heat or spray drying to obtain cv.s-TarE.
  • a 0.1% solution of cv.s-TarE obtained in Example 1 was made by diluting 50 mg of the final powder in 50 ml of water. Aliquots of the solution were exposed to light at 1000 MW/m 2 inside a Solarbox 1500 (wavelength 290-800) for 30 minutes, 1 hour, 2 hours and 3 hours. Following exposure, the samples were subjected to HPLC and monitored at 520bnm to assess for the presence of the cis- double bond of cv.s-TarE and its transformation to the trans- form.
  • HPLC The following protocol describes the methodology used for identification, assay and purity evaluation of cv.s-TarE.
  • the samples were analyzed using a Thermo Scientific Vanquish Core HPLC system consisting of an autosampler organizer, column manager and heater, quaternary pump and PDA absorbance detector.
  • Enterprise Chromel eon 7.3 software was used for system control and data acquisition.
  • the column used was Column Poroshell 120 Phenyl-Hexyl 150 mm x 2.1 mm, 2.7 pm.
  • Instrumental conditions include: Flow: 0.35 mL/min; Detection: 520 nm; Column temperature: 50 °C; Autosampler temperature: 15 °C; Injection volume: 5 pL (loop volume 20 pL); Run time: 33 minutes; Needle wash solvent: MeOH:H2O (20:80). The gradient described in Table 1 was used.
  • the mobile phase and solvent solution consist of: Mobile Phase A: 0.1% formic acid, filter;
  • a solution of the colorant composition was prepared by diluting the colorant composition in a 50 mM dipotassium phosphate buffer having a pH of about 5.0 in order to obtain an absorbance of about 0.5.
  • the CIELAB parameters of the solution were measured using a spectrophotometer Lovibond PFX-Z that automatically calculates L*, a*, and b*.
  • the chroma value (C) was calculated from a* and b* using the equation [(a*)2+(b*)2] 1/2 .
  • the hue value (co) was calculated from a* and b* using the equation tan-l(b*/a*).
  • Coloring power was also examined for the same samples exposed to light for 4 hours or protected in the dark for an equivalent amount of time. Briefly, for each sample, a colorant solution was prepared with 5 mg of cv.s-TarE added to 5 mL distilled water. Color was measured using a spectrophotometer Lovibond PFX-z . A small volume of the colorant solution was added to a 5 mL cuvette with water, so the initial reading was about value of 0.3 AU. Small amounts of the colorant solution described above, or the 10% solution studied, were added in order to increase absorbance by 0.1 AU. These steps were repeated until 0.7 AU was reached, and all the volumes added were recorded.
  • a stability assay was conducted to evaluate the shelf life of the colorant powder by assessing its photolytic degradation under different light exposure conditions. The experiment aimed to determine the extent of degradation over time using spectrophotometric and chromatographic analyses.
  • the pigment was subjected to three different treatments, a) Complete light protection; b) exposed to natural light; and c) accelerated degradation using a SolarBox 1500E solarbox exposition at 480 W/m 2 (where 1 hour exposure is equal to 21 hours of natural sunlight).
  • the stability assay showed a conversion of c/.s-TarE to /raw.s-TarE over time when exposed to light (see Fig. 5C and Fig. 5D). This conversion explains the loss of coloring capacity and increase in Hue observed.
  • the results indicate that a decrease of 10% of c/.s-TarE corresponds to an increase of about 6% of /raw.s-TarE, which correlates with an increase of 10% of Hue and a decrease of 15% of coloring capacity.

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Abstract

La présente invention concerne une composition colorante comprenant de l'acide N-glutamyl monascorubraminique avec une génération réduite de la forme trans par protection du composé vis-à-vis de la lumière. L'invention concerne également des produits comprenant de l'acide N-glutamyl monascorubraminique qui sont particulièrement stables à la dégradation par protection de ceux-ci vis-à-vis de la lumière, ainsi que des procédés associés.
PCT/IB2025/052900 2024-03-20 2025-03-19 Procédé de préparation d'une composition colorante à stabilité améliorée et procédé d'emballage et/ou de stockage de celle-ci Pending WO2025196673A1 (fr)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018206590A1 (fr) * 2017-05-08 2018-11-15 Danmarks Tekniske Universitet Procédé de production d'une azaphilone dans talaromyces atroroseus
WO2024076937A2 (fr) * 2022-10-03 2024-04-11 Michroma Corporation Compositions de colorant et procédés de production

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018206590A1 (fr) * 2017-05-08 2018-11-15 Danmarks Tekniske Universitet Procédé de production d'une azaphilone dans talaromyces atroroseus
WO2024076937A2 (fr) * 2022-10-03 2024-04-11 Michroma Corporation Compositions de colorant et procédés de production

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