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WO2010127415A1 - Emulsifiant de type eau dans l'huile - Google Patents

Emulsifiant de type eau dans l'huile Download PDF

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Publication number
WO2010127415A1
WO2010127415A1 PCT/AU2010/000626 AU2010000626W WO2010127415A1 WO 2010127415 A1 WO2010127415 A1 WO 2010127415A1 AU 2010000626 W AU2010000626 W AU 2010000626W WO 2010127415 A1 WO2010127415 A1 WO 2010127415A1
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WO
WIPO (PCT)
Prior art keywords
composition
proteins
lupin
water
protein
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.)
Ceased
Application number
PCT/AU2010/000626
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English (en)
Inventor
Catherine Gail Fryirs
Geoffrey Reayburn Paterson
Sherry Elaine Duckworth
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.)
George Weston Foods Ltd
Original Assignee
George Weston Foods Ltd
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
Priority claimed from AU2009902033A external-priority patent/AU2009902033A0/en
Application filed by George Weston Foods Ltd filed Critical George Weston Foods Ltd
Publication of WO2010127415A1 publication Critical patent/WO2010127415A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
    • A23J1/00—Obtaining protein compositions for foodstuffs; Bulk opening of eggs and separation of yolks from whites
    • A23J1/14—Obtaining protein compositions for foodstuffs; Bulk opening of eggs and separation of yolks from whites from leguminous or other vegetable seeds; from press-cake or oil-bearing seeds
    • A23J1/148—Obtaining protein compositions for foodstuffs; Bulk opening of eggs and separation of yolks from whites from leguminous or other vegetable seeds; from press-cake or oil-bearing seeds by treatment involving enzymes or microorganisms
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
    • A23J3/00—Working-up of proteins for foodstuffs
    • A23J3/14—Vegetable proteins
    • 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
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/10—Foods or foodstuffs containing additives; Preparation or treatment thereof containing emulsifiers

Definitions

  • the invention relates to protein extracts, concentrates and isolates, especially those obtainable from plant sources that are useful in the manufacture of foods and food products, especially as emulsifiers, gelling agents, foaming agents, creaming agents, whipping agents and the like.
  • Vegetable and plant proteins have been used for some time in the manufacture of food products. In some applications these sources of proteins are used for nothing more than to increase the nutritive quality of food products. For example, soy protein may be added to meat products to increase protein content.
  • the protein sources are added to modify a quality or characteristic of a food product, or otherwise to provide a quality or characteristic to a mixture of ingredients which then leads to the formation of a food product.
  • protein sources that are used as emulsifiers, gelling agents, thickeners, whipping agents, creaming agents and whitening agents.
  • Vegetable protein isolates have been described for use in stabilising water-in-oil emulsions. These are essentially colloidal dispersions where water forms a discrete phase and oil forms a continuous phase. Depending on factors including relative amount of oil to water, the type of oil, the amount of solids, polysaccharides, pH, ionic strength and type and concentration of salt, these water-in-oil emulsions may be provided in the form of a liquid, a semi liquid in the form of a gel or paste, or a solid. Examples of water-in-oil emulsions that are liquids and solids include dressings (vinegar in oil), butter and coffee whitener respectively.
  • Most protein isolates that are useful for stabilising water-in-oil emulsions work by unfolding at the interface of the oil and water phases to provide the requisite degree of hydrophobicity for stabilising the emulsion.
  • the hydrophilic portions of the proteins are understood to at least partially dissolve into the discrete phase, leaving the more hydrophobic portions to dissolve into the continuous phase.
  • the degree of unfolding and surface hydrophobicity may be enhanced by thermal denaturation of the protein prior to emulsification, by chemical modification of the protein or by enzymatic modification of the protein.
  • the latter are understood to increase an entangled network of protein molecules at the interface of the oil and water phases.
  • thermal denaturation of lupin proteins is the most effective modification for improving foaming properties (foaming properties being similar to emulsifying properties) of lupin proteins.
  • the invention seeks to improve or at least to minimise one or more of the above problems or limitations and in one embodiment provides a composition useful as an emulsifier for stabilising a water-in-oil emulsion to form a food product, the composition including:
  • composition useful as an emulsifier for stabilising a water-in-oil emulsion to form a food product, the composition including:
  • a food product including oil or fat, water and a composition useful as an emulsifier for stabilising a water-in-oil emulsion according to the invention.
  • the food product is provided in the form of a water-in- oil emulsion such as a salad dressing or like product, a butter or like product, or a coffee whitener or like product.
  • the food product is provided in the form of a foaming agent, a creaming agent, or a whipping agent.
  • the present invention also relates to a process for producing a composition useful as an emulsifier for stabilising a water-in-oil emulsion, the process including:
  • Figure 1 Size exclusion profile of the composition of the invention.
  • Figure 2 Matrix Assisted Laser Desorption/lonisation-Time Of Flight (MALDI-TOF) profile of the composition of the invention.
  • Figure 3 Typical effect of different ratios of oil to water on the emulsion activity of the composition.
  • Figure 4 Typical effect of different ratios of water to oil on the emulsion activity of the composition.
  • Figure 5 Typical effect of pH on emulsion activity of the water-in-oil emulsifier.
  • lupin protein extracts, concentrates or isolates that predominantly consist of proteins having a low molecular weight are useful for stabilising water-in-oil emulsions.
  • compositions of the invention described herein are capable of stabilising water-in-oil emulsions across a wide range of oil to water ratios, pH, type and concentration of salt and temperature conditions.
  • the compositions of the present invention are particularly useful for stabilising water-in-oil emulsions over a wide pH and temperature range. Due to the stability of the emulsifier over a wide pH range, the emulsifier is less likely to precipitate or to cause other components of an emulsion to precipitate, coalesce or flocculate. This is particularly useful when pH-altering additives, such as flavours, are added to a water-in-oil emulsion containing the lupin protein isolate.
  • pH-altering additives such as flavours
  • a single emulsifier can be used to make a number of foods with different flavours and the stability of the emulsifier makes it possible to retain mouth-feel and/or other organoleptic properties in different flavour versions of the same product.
  • the stability of the emulsifiers over a wide range of temperatures means that it is possible to use the emulsifiers to derive foams that can be treated with heat without destroying the foam structure.
  • compositions of the invention described herein are that they do not require additional thermal denaturation or chemical or enzymatic modification.
  • composition useful as an emulsifier for stabilising a water-in-oil emulsion to form a food product the composition including:
  • proteins having a lower molecular weight may be provided in a low relative abundance.
  • An emulsion is generally understood as a mixture of two or more immiscible liquids, e.g. oil and water, in which one liquid forms a discrete phase and another a continuous phase. Liquids are said to be immiscible if they are not able to mix, in any proportions, to form a homogenous solution. Generally, a solution is homogenous if the liquids that make up the solution are uniformly dispersed throughout the solution.
  • compositions of the present invention are capable of stabilising mixtures of aqueous solutions and oils by forming a suspension of the aqueous phase in the oil phase (i.e. the aqueous phase forms a discrete phase and the oil phase forms a continuous phase), thereby preventing or minimising phase separation of the oil phase from the aqueous phase and increasing the homogeneity of the mixture. This results in an even distribution of the aqueous phase throughout the mixture. Phase separation may occur by as settling or synersis of the aqueous phase out of the oil phase. Minimising can mean any of reducing, diminishing, lessening, curtailing or decreasing phase separation.
  • a water-in-oil emulsion is generally understood as meaning an emulsion wherein water forms the discrete phase and oil forms the continuous phase.
  • An emulsifier is generally understood as meaning a substance which stabilizes an emulsion by increasing its kinetic stability.
  • the emulsifier minimises phase separation so that the relevant discrete and continuous phases forming the emulsion are maintained.
  • the composition includes lupin protein whereby about 75 to 98 % of the dry weight of the composition is lupin protein.
  • the composition includes lupin proteins in an amount of about 80 to 98 % or 85 to 98 %, or 90 to 98 %.
  • composition useful as an emulsifier for stabilising a water-in-oil emulsion to form a food product the composition including:
  • the protein may be obtained from a range of sources. Preferably it is obtained from lupin. Preferably about 60 to 70 % of the lupin proteins have a molecular weight of no more than about 30 kDa.
  • useful water-in-oil emulsifiers can be provided by removing attached and/or entrapped fibre from lupin proteins.
  • An example of attached fibre is O- and N- linked carbohydrates.
  • most if not all of the proteins are provided without having sugars or carbohydrates or fibre attached to them and/or entrapped within them. It will be clear that not all attached and/or entrapped fibre may be removed and that some residual fibre may remain.
  • the residual fibre, carbohydrates and/or sugars may be present due to, for example, incomplete digestion of the attached fibre during the preparation of the protein composition (discussed in more detail below).
  • it will also be clear that it is desirable to remove as much attached and/or entrapped carbohydrate as possible from the protein, thereby producing a protein composition having no or very little attached and/or entrapped sugars, carbohydrates and/or fibre. Therefore, in the context of the present invention, "substantially free” refers to compositions that have no attached and/or entrapped fibre, or if the fibre is present, it is only present incidentally e.g. by incomplete digestion.
  • about 30 to 35 % of the proteins may have a molecular weight from about 17 to 20 kDa.
  • about 30 to 35 % of the proteins may have a molecular weight from about 12 to 15 kDa.
  • about 30 to 35% of the proteins may have a molecular weight from about 8 to 11 kDa.
  • the relative abundance of the molecular weight ranges of lupin proteins in the composition are as shown in Table 5.
  • Table 5 discloses the relative abundance of protein species having the defined molecular weight ranges in the composition of the invention. This data is derived from size exclusion chromatography data as described in Figure 1.
  • Table 6 discloses the relative abundance of protein species in a sample of the composition that has been treated to enable MALDI TOF analysis.
  • Figure 2 describes the relative abundance of molecular ions in the MALDI TOF treated sample.
  • the proteins may include ⁇ -conglutin and fragments thereof.
  • the fibre is soluble fibre.
  • the soluble fibre is determined by AOAC Official Method 985.29 Total Dietary Fiber in Foods in AOAC Official Methods of Analysis 2005.
  • composition of the invention has an ANS hydrophobicity score of about 0.7 to 1.0 at pH 7.4.
  • An ANS hydrophobicity value or score is a measure of the hydrophobicity of a given protein- containing composition.
  • the value represents the degree of binding of ANS dye to hydrophobic regions of proteins.
  • the ANS value is influenced by the solubility of the composition in the given solvent in which the ANS hydrophobicity assay is conducted.
  • the ANS value for the composition of the invention is higher at more neutral pH partially reflecting the solubility and ionic charges present on the composition at acidic pH. It will be understood that the ANS value is a measure of hydrophobicity of the composition of the invention as it exists after the treatment that is provided to the composition in the ANS assay steps as in Example 3.
  • the ANS hydrophobicity assay is also described in Howe A et at. 2008 Pharma. Res. 25: 1487.
  • composition is generally soluble in an aqueous solution having a pH of about 2 to 9.
  • the composition may be applied as a liquid or as a powder.
  • composition of the invention does not include a fermentation product such as lactic acid, or lecithin.
  • the process includes the following steps:
  • the lupin protein-containing slurry may be formed from milling of de-hulled lupins to form a slurry. Prior to milling, the de-hulled lupins may have been steeped in water. The water may be heated to temperatures of no more than about 70 0 C. In certain embodiments the lupins have not been de-oiled with an organic solvent such as hexane for removing lupin oils or fats, although in other embodiments de-oiling is possible.
  • an organic solvent such as hexane for removing lupin oils or fats
  • the lupin protein-containing slurry generally has a pH in the range of 8 to 9, preferably about 8.4.
  • the adjustment of the pH may be provided by an alkali, NaOH being one example.
  • a protein-containing supernatant and fibre-containing pellet is formed.
  • the protein-containing supernatant may then be separated from the fibre-containing pellet. This can be done by, for example, decanting the supernatant from the pellet.
  • the lupins are of genus Lupinus. Particularly preferred species are Angustifolius, Luteus, Mutabils and other low alkaloid varieties of species including Albus. In one embodiment the lupin is not a pea, especially not a member of genus Pisum.
  • the inventors believe that the protein- containing supernatant is a mixture of higher and lower molecular weight proteins and residual lupin fibre, the latter remaining after alkaline treatment.
  • the inventors recognised that by treating this fibre component of the protein-containing supernatant, it then becomes possible to separate the lower molecular weight proteins from the higher molecular weight proteins. From this, the inventors were able to observe that the composition having lower molecular weight proteins is useful as a water-in-oil 5 emulsifier, something that could not be observed when the lower molecular weight proteins are in composition with the higher molecular weight proteins.
  • the treatment according to the invention involves the use of fibre-hydrolysing enzymes.
  • the fibre-hydrolysing enzyme is a carbohydrase.
  • the I carbohydrase may be a pectinase, cellulase or hemicellulase.
  • the fibre-hydrolysing enzyme is a carbohydrase.
  • the I carbohydrase may be a pectinase, cellulase or hemicellulase.
  • the fibre-hydrolysing enzyme is a carbohydrase.
  • the I carbohydrase may be a pectinase, cellulase or hemicellulase.
  • the fibre-hydrolysing enzyme is a carbohydrase.
  • the I carbohydrase may be a pectinase, cellulase or hemicellulase.
  • carbohydrase is an enzymatic composition of cellulase and pectinase.
  • glycans may be desirable to split the glycans to remove as much carbohydrate as possible from the protein, thereby producing a protein composition having no or very little attached and/or entrapped sugars, carbohydrates and/or fibre.
  • the carbohydrase treatment digests soluble fibre.
  • the fibre may or may not be attached to protein prior to digestion.
  • the quantity of enzyme used is dependent on the specific activity of the enzyme at the pH and temperature of the incubation period.
  • the treatment might be designed to be completed in one hour with the 25 enzymic reaction being carried out at a pH range of from about 6 to 8.
  • the enzymic reaction is completed when the protein-containing supernatant becomes less turbid.
  • the pH can be changed to, for example, between 7 and 8, preferably 7.5.
  • the heat treatment can be carried out at, for example, about 90 0 C for about 5 minutes.
  • the inventors have found that the decrease in specific gravity of the soluble protein fraction enables better separation of protein fractions through a clarifier which uses centrifugal force to separate the insoluble from the soluble protein fractions.
  • the lower molecular weight proteins in the enzyme-treated, protein-containing supernatant are separated from the higher molecular weight proteins. This can be achieved by adjusting the pH of the supernatant to the isoelectric point of the higher molecular weight proteins in the supernatant to precipitate the higher molecular weight proteins.
  • the pH range may be from about 5 to 6, preferably about 5.5.
  • the lower molecular weight proteins can be recovered by any technique for recovering lower molecular weight proteins of less than about 30 kDa including centrifugation and/or membrane filtration.
  • the recovered proteins can also be further treated by, for example, adjusting the pH, washing and/or spray drying.
  • a food product or ingredient for formation of a food product including water, and oil and/or fat and an emulsifier composition of the invention, as previously discussed.
  • the food product may be provided in the form of a water-in-oil emulsion, or it may be homogenised to create an emulsion. In the latter embodiments the emulsion may be stabilised by a composition as described above.
  • Particularly useful oils for use in a food product or ingredient of the invention are those that are edible e.g. animal and plant oils.
  • Examples of food products or ingredients according to the invention include dressings (vinegar in oil), butter, coffee whitener and the like.
  • the composition may be applied in the form of a liquid or a powder for formation of a food product or ingredient for forming a food product.
  • Example 1 Chemical analysis data of the major components of the water-in-oil composition
  • Table 1 Chemical analysis data of the major components of the composition according to the current invention showing the range of values
  • DSB refers to composition calculated on a dry solids basis.
  • a sample water-in-oil emulsifier composition according to the invention was analysed and found to be composed of the following:
  • DSB refers to composition calculated on a dry soli s asis.
  • Example 2 Molecular level analysis data for the protein component of the wa term-oil composition
  • Cysteine analysis was performed using performic acid oxidation followed by 24hr acid hydrolysis with 6 mol/kg HCI at 110 0 C.
  • For tryptophan analysis samples underwent 24 hr base hydrolysis in 5 mol/kg NaOH at 110 0 C. After hydrolysis all amino acids were analysed using the Waters AccQTag Ultra chemistry. Samples were analysed in duplicate and results are expressed as an average.
  • Table 4 Typical amino acid composition for serum albumin, soy protein and lupin protein
  • Example 2.2 Size exclusion chromatographic analysis of the protein component of the composition
  • a Phenomenex BIOSEP-SEC 4000 column was used for the analysis.
  • a running time of 10 min was used (flow rate 2 mL/min) instead of the Standard 35 min run (0.5 mL/min).
  • the eluent used was aqueous acetonitrile (ACN) buffer (0.05 % trifluoroactic acid (TFA)in water and 0.05 % in ACN).
  • the proteins were detected at a wavelength of 214 nm.
  • Example 2.3 MALDI-TOF analysis data of protein component of water-in-oil emulsifier composition
  • Samples were dissolved in 60 ⁇ m ACN/H 2 O (50:50 v/v) containing 0.05 % v/v TFA for 1 hour.
  • Sample preparation was carried out according to the dried droplet method using sinapinic acid (SA) as matrix (Kussmann, M., E. Nordhoff, H. Rahbek-Nielsen, S. Haebel, M. Rossel-Larsen, L. Jakobsen, J. Gobom, E. Mirgorodskaya, A. Kroll- Kristensen, L. Palm and P. Roepstorff, 1997, MALDI-MS sample preparation techniques designed for various peptide and protein analytes, J. Mass Spectrom. 32:593).
  • SA sinapinic acid
  • the matrix solution was prepared by dissolving SA in ACN/H 2 O (50:50 v/v) with 0.05 % v/v TFA at a concentration of 10 mg/mL.
  • a sample/ matrix solution mixture (1 :10 v/v) was deposited (2 ⁇ L) on to a 96-sample MALDI probe tip, and dried at room temperature.
  • MALDI-TOF mass spectrometric experiments were carried out on a Voyager DE-PRO TOF mass spectrometer (Applied Biosystems, Foster City, CA, USA) equipped with UV nitrogen laser (337 nm).
  • the instrument was used with the following parameters: laser intensity 2500, mass range 50-100 kDa, acceleration voltage 25 kV, grid voltage 93 %, guide wire 0.2 %, delay time 850 ns. Spectra were obtained in positive linear ion mode and were averaged from 50 laser shots to improve the S/N level. All the samples were automatically accumulated in a random pattern over the sample spot to provide the final spectrum. Human transferrin (79 549 Da) was used as the external standards for mass assignment.
  • Table 6 MALDI-TOF analysis data of the molecular size ranges for the protein component of the composition
  • Example 3 Physical characterisation of the water-in-oil emulsifier composition
  • Example 3.1 Solubility of water-in-oil emulsifier composition
  • Solubility (%) (Solids in Supernatant x 100)/Total solids
  • solubilities determined for the samples shown in Tables 7 and 8 are exemplary of the compositions according to the invention defined herein. Solubility is dependent on processing steps for manufacture of the composition including for example the parameters for drying. Accordingly, the composition of the invention may have solubilities outside the ranges generally shown in Tables 7 and 8.
  • Example 3.2 Determination of hydrophobicity value for water-in-oil emulsifier composition
  • the principle of the method is measuring the binding of a fluorescent dye (ANS) to the hydrophobic regions of the proteins.
  • the resulting values are inversely proportional to hydrophobicity thus a lower value indicates a greater hydrophobicity.
  • Buffer 1 0.1 mol/kg phosphate buffer from KH 2 PO 4 and Na 2 HPO 4 , pH 7.4.
  • ANS is dissolved, use nitrogen flow to degas the solution.
  • Spectrophotometer JASCO FP-920 Fluorescence Spectrophotometer Excitation wavelength: 370 nm Measuring wavelength: 480 nm
  • Table 11 Typical values for ANS Hydrophobicity for protein components of lupin, soy, dairy and beef sera (at pH 7.4)
  • the water-in-oil emulsifier is less hydrophobic than soy protein but more hydrophobic than sodium caseinate and bovine serum albumin.
  • EA (%) (emulsified layer (top) (cm) x 100)/ Total layer (cm)
  • Table 13 Typical effect of re-hydration medium for protein on emulsion activity
  • the highest emulsion activity for a 3.6 % concentration of water- in-oil composition occurs when the ratio of oil to water is 3:5.
  • the water-in-oil emulsifier retains good emulsion activity over a wide pH range.
  • Table 14 Typical effect of freezing and thawing on emulsion activity
  • the water-in-oil emulsifier does not lose emulsion activity after repeated freezing and thawing.
  • Example 7 Enhancement of the functional performance of the base water-in-oil emulsifier
  • the following methods can be used to improve performance of the water-in-oil emulsifier.
  • Proteases which break the protein, peptide or amino acid linkages e.g.: exo-proteases can be used to change the protein structure of the water-in-oil emulsifier.
  • the composition of the invention is one that has not been digested with an endopeptidase or related protease.
  • Heating to temperatures greater than 90 0 C can change the agglomeration of the proteins and alter the performance characteristics of the water-in-oil emulsifier.
  • Spray drying parameters including spray nozzle size, feed inlet pressures and instantising processes can affect the aggregation and hence solubility and performance of the water-in-oil emulsifier.
  • Chemical agents that change the covalent and non-covalent bonds between amino acids in the proteins can change the structure of the protein.
  • the conformational change influences the surface characteristics of the proteins.
  • Examples of chemical agents include carboxylic anhydrides, ionic salts and redox reagents.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Microbiology (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • General Preparation And Processing Of Foods (AREA)

Abstract

La présente invention concerne des extraits, des concentrés et des isolats protéiques, en particulier ceux pouvant être obtenus à partir de sources végétales qui sont utiles dans la fabrication d'aliments et de produits alimentaires, en particulier comme émulsifiants, agents de crémage et équivalents. En particulier, la présente invention concerne une composition utile comme émulsifiant destinée à stabiliser une émulsion de type eau dans l'huile afin de former un produit alimentaire, la composition comprenant des protéines de lupin en une quantité d'environ 75 à 98 % en poids sec de la composition, environ 60 à 70 % des protéines de lupin ayant un poids moléculaire inférieur à 30 kDa. La présente invention concerne également des procédés de production de cette composition.
PCT/AU2010/000626 2009-05-08 2010-05-07 Emulsifiant de type eau dans l'huile Ceased WO2010127415A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AU2009902033 2009-05-08
AU2009902033A AU2009902033A0 (en) 2009-05-08 Water-in-oil emulsifier

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WO2010127415A1 true WO2010127415A1 (fr) 2010-11-11

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014001031A1 (fr) 2012-06-27 2014-01-03 Unilever N.V. Émulsion eau dans huile comestible et son procédé de fabrication
US20220256878A1 (en) * 2019-06-18 2022-08-18 Corn Products Development, Inc Pulse protein emulsifiers

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060159805A1 (en) * 2003-07-15 2006-07-20 Elger Funda Powderous formulations of fat-soluble active ingredients
US20060257453A1 (en) * 2003-04-03 2006-11-16 Funda Elger Powderous formulations of fat-soluble active ingredients
US20080206439A1 (en) * 2003-07-01 2008-08-28 George Weston Foods Limited Process for the Production of Lupin Extracts
US20080241343A1 (en) * 2007-03-28 2008-10-02 California Natural Products Lupin food product base and processes
WO2008131008A2 (fr) * 2007-04-16 2008-10-30 Solae, Llc Compositions d'hydrolysat de protéine ayant des caractéristiques sensorielles et des propriétés physiques améliorées
WO2008143507A2 (fr) * 2007-05-21 2008-11-27 Nizo Food Research B.V. Produits d'encapsulation à base de protéine réticulée par oxydation

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060257453A1 (en) * 2003-04-03 2006-11-16 Funda Elger Powderous formulations of fat-soluble active ingredients
US20080206439A1 (en) * 2003-07-01 2008-08-28 George Weston Foods Limited Process for the Production of Lupin Extracts
US20060159805A1 (en) * 2003-07-15 2006-07-20 Elger Funda Powderous formulations of fat-soluble active ingredients
US20080241343A1 (en) * 2007-03-28 2008-10-02 California Natural Products Lupin food product base and processes
WO2008131008A2 (fr) * 2007-04-16 2008-10-30 Solae, Llc Compositions d'hydrolysat de protéine ayant des caractéristiques sensorielles et des propriétés physiques améliorées
US20080305212A1 (en) * 2007-04-16 2008-12-11 Solae, Llc Protein Hydrolysate Compositions Having Improved Sensory Characteristics and Physical Properties
WO2008143507A2 (fr) * 2007-05-21 2008-11-27 Nizo Food Research B.V. Produits d'encapsulation à base de protéine réticulée par oxydation

Non-Patent Citations (1)

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Title
MANRIQUE J. ET AL.: "The influence of isolation procedures on the yield and functional properties of the protein from Lupinus Leguminosae", PHD THESIS, 1977 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014001031A1 (fr) 2012-06-27 2014-01-03 Unilever N.V. Émulsion eau dans huile comestible et son procédé de fabrication
US20220256878A1 (en) * 2019-06-18 2022-08-18 Corn Products Development, Inc Pulse protein emulsifiers

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