CA2194796A1 - Cold water-dispersible compositions of fat-soluble active substances - Google Patents
Cold water-dispersible compositions of fat-soluble active substancesInfo
- Publication number
- CA2194796A1 CA2194796A1 CA002194796A CA2194796A CA2194796A1 CA 2194796 A1 CA2194796 A1 CA 2194796A1 CA 002194796 A CA002194796 A CA 002194796A CA 2194796 A CA2194796 A CA 2194796A CA 2194796 A1 CA2194796 A1 CA 2194796A1
- Authority
- CA
- Canada
- Prior art keywords
- fat
- active substances
- soluble active
- compositions
- soluble
- 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.)
- Abandoned
Links
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/174—Vitamins
-
- 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
- A23J3/30—Working-up of proteins for foodstuffs by hydrolysis
- A23J3/32—Working-up of proteins for foodstuffs by hydrolysis using chemical agents
- A23J3/34—Working-up of proteins for foodstuffs by hydrolysis using chemical agents using enzymes
- A23J3/346—Working-up of proteins for foodstuffs by hydrolysis using chemical agents using enzymes of vegetable proteins
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/66—Proteins
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/15—Vitamins
- A23L33/155—Vitamins A or D
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- 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
- A23L5/43—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives
- A23L5/44—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives using carotenoids or xanthophylls
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
- A23P10/00—Shaping or working of foodstuffs characterised by the products
- A23P10/40—Shaping or working of foodstuffs characterised by the products free-flowing powder or instant powder, i.e. powder which is reconstituted rapidly when liquid is added
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1658—Proteins, e.g. albumin, gelatin
Abstract
Partially decomposed soy protein is used as protecting colloid for fat-soluble active substances.
Description
BASF Aktiengesellschaft 930536 O.Z. 0050/45031 Coldwater-dispersible compositions of fat-soluble active sub-stances 5 The present invention relates to the use of partially degraded soybean proteins as protective colloids for fat-soluble active substances.
The invention further relates to compositions containing fat-10 soluble active substances and partially degraded soybean proteins and to the use of such compositions.
Fat-soluble active substances such as vitamins and carotenoids play an important part in human and An;m~l nutrition, whether as 15 essential substances such as the vitamins or proteins, or else, specifically in the case of carotenoids, as natural or nature-identical colorants which confer a characteristic color on many human or ~n;m~l foodstuffs.
20 It is common to these fat-soluble active substances that in their pure form they can be handled only with difficulty, if at all, because they are oxidation-sensitive substances. Furthermore, a fine dispersion of the active substance is advantageous for optimal absorbability or coloring action. In addition, it is 25 often desirable for the active substances to be dispersible in water. This is why these substances are frequently supplied in the form of emulsions or dry powders, in which case the active substances are embedded, either in pure form or as solution in a physiologically tolerated oil, finely dispersed in a protective 30 colloid.
The sensitivity of oil-soluble vitamins and carotenoids to oxygen makes great demands on the matrix in which the substances are embedded. The protective colloid envelope must, in order effec-35 tively to prevent oxidative decomposition processes, represent agood barrier to oxygen. This is why gelatin is frequently used, having excellent stabilizing properties.
According to EP-A 0 347 7~1, fish gelatin is also suitable as 40 protective colloid for fat-soluble substances.
However, the disadvantage of gelatins is that they have strong adhesive properties. On use of gelatin-containing products the drying methods conventional for liquid systems, such as spray 45 drying or spray fluidized bed drying, may lead to stringing or caking.
BASF Aktiengesellschaft 930536 O.Z. 0050/45031 21 ~796 In other protective colloids which are frequently used, such as gum arabic, starch, dextrins, pectin or tragacanth, it is often possible to embed only relatively low concentrations of fat-soluble substances. Furthermore, in the past as a consequence of 5 failed harvests, gum arabic in particular has not always been available or available in adequate quality.
Synthetic colloids such as polyvinylpyrrolidone or partially syn-thetic polymers such as cellulose derivatives likewise have a 10 limited emulsifying capacity and are not always acceptable, espe-cially in the foodstuffs sector.
It is furthermore known to use natural vegetable proteins such as soybean proteins as protective colloids for fat-soluble sub-15 stances. However, products of this type likewise have a number ofdisadvantages related to the properties typical of proteins.
Those which should be particularly mentioned here are: a tendency to flocculate, which is often pronounced, on exposure to heat or in the presence of salts, and not always adequate emulsifying ca-20 pacity. In addition, the products produced in this way often haveinadequate coldwater dispersibility. Furthermore, vegetable pro-teins may greatly increase the viscosity of liquid water-contain-ing systems, which may restrict the production or processing of such products.
The use of partially hydrolyzed soybean proteins as substitute for protein-based foaming agents in foodstuffs is disclosed in US-A 3 932 672 and US-A 4 015 019. Partially hydrolyzed soybean proteins can also be used for protein supplementation of soft 30 drinks (H.S. Olsen and J. Adler-Nissen, Zeitschrift fur Lebens-mitteltechnologie und Verfahrenstechnik, 31 (1980) 259-360).
US-A 4 293 574 discloses the production of mayonnaise-like food-stuffs using specific alcohol-denatured and partially hydrolyzed 35 soybean proteins as substitute for eggs.
It is an object of the present invention to find suitable protec-tive colloids for fat-soluble active substances such as vitamins or carotenoids, and compositions thereof.
We have found that this object is achieved, using partially degraded soybean proteins as protective colloid, and compositions of fat-soluble active substances.
45 The object of the present invention was to find suitable protec-tive colloids for fat-soluble active substances which do not involve technical disadvantages for processing and make it BASF AXtienge~ellschaft 930536 O.Z. 0050/45031 - 2 1 9$796 possible to produce in a simple way stable, coldwater-dispersible compositions of fat-soluble active substances.
Used according to the invention as protective colloids for fat-5 soluble active substances are partially degraded soybean proteins which preferably have a degree of degradation ("DH": "degree of hydrolysis") of 0.1 to 5%, particularly preferably 0.2 to 3%. The degree of degradation "DH" is defined as follows:
Number of cleaved peptide linkages DH = x 100%
Total number of peptide linkages The degree of degradation can be determined by the pH-stat method 15 as described by C.F. Jacobsen et al. in Methods of Biochemical Analysis, Vol. IV, pp. 171-210, Interscience Publishers Inc., New York 1957.
The partial degradation is, as a rule, carried out enzymatically, 20 suitable enzymes being proteases from plants, microorganisms, fungi or ~n;~l S. The partial degradation is preferably carried out with the vegetable protease bromelain.
The soybean proteins usually employed are commercial soybean pro-25 tein isolates and concentrates with protein contents of from 70 to 90% by weight, where the remaining 10 to 30~ by weight repre-sent other more or less undefined plant constituents. The soybean protein isolates are incubated with the enzyme in aqueous medium, preferably at from 50 to 70 C and at a pH of from 7 to 9. The 30 suitable protein to enzyme ratio for the desired degree of degra-dation can be determined in the individual case by laboratory tests which are simple for the skilled worker.
The aqueous soybean protein hydrolysate solutions are, as a rule, 35 produced in such a way that the protein content is from 6 to 10%
by weight.
Suitable fat-soluble active substances according to the invention are vitamins A, D, E and K, derivatives thereof such as vitamin A
gO palmitate or vitamin E acetate, as well as carotenoids, for example ~-carotene, apocarotenal, ethyl apocarotenoate, canthaxan-thin, zeaxanthin, astaxanthin, lycopene, citranaxanthin or mix-tures of said substances.
~ BASF AXtiengesellschaft 930536 O.Z. 0050/45031 21 ~47~6 The fat-soluble active substances can be added to the composi-tions according to the invention either in pure form or as mix-ture with physiologically tolerated oils such as sesame oil, corn - oil, cotton seed oil, soybean oil or peanut oil.
In addition to the fat-soluble active substances and the par-tially degraded soybean proteins, the compositions according to the invention may also contain conventional auxiliaries, for example sugars and sugar alcohols, starch or starch derivatives, lO stabilizers such as t-butyl-hydroxytoluene, as well as emulsi-fiers such as ascorbyl palmitate or lecithin.
The compositions can be produced in a conventional manner by emulsifying the fat-soluble active substances either in pure form 15 or mixed with physiologically tolerated oils or fats in the aqueous phase containing protective colloid. The emulsification can take place with the aid of conventional stirrers, rotor-sta-tor dispersers and other suitable mixers. It is advisable to carry out the emulsification at 40 to 70 C.
The compositions according to the invention can be either liquid or solid, and solid compositions are preferred. Solid composi-tions can be produced in a simple manner by spray drying or spray fluidized bed drying.
The compositions according to the invention contain the fat-soluble active substances in amounts of from 2 to 40, preferably 10 to 20, % of the total weight of active substance and protec-tive colloid.
The content of active substance in the compositions depends on the particular use and can be adjusted appropriately.
The compositions according to the invention are outstandingly 35 suitable for use in livestock nutrition, as additive to food-stuffs or, because of their good coldwater dispersibility, as addition to drinking water. Carotenoid-containing compositions are furthermore suitable as foodstuff colorants, especially for soft drinks. The compositions may also be added to other food-40 stuffs, for example baking mixes or blancmange powders.
The compositions are likewise outstandingly suitable for pro-ducing products for supplementing foodstuffs with vitamins.
~ BASF Aktiengesellschaft 930536 O.Z. 0050/45031 Examples In the following Examples 1, 2, 4 and 5, commercial soybean pro-tein isolates with a protein content of 85% by weight were used.
5 A concentrate with a protein content of 65% by weight was used in Example 3.
The bromelain which was used is a commercial enzyme (from Merck, 2m-Ansom-U/mg).
The emulsions were each spray dried in a Minor spray dryer from ~iro, the tower inlet temperature being 140 C and the tower outlet temperature being 90 C.
15 The pH was adjusted in each case with 1 M aqueous NaOH.
Example 1 600 ml of water and 45 g of soybean protein isolate were placed 20 in a 2 l beaker and heated to 60 C with stirring. The pH was then adjusted to 9.0, 0.46 g of bromelain was added and the mixture was stirred at 60 C for 30 minutes. The pH was then readjusted to 9Ø The DH was calculated on the basis of the consumption of sodium hydroxide solution to be 5. The mixture was boiled using 25 an immersion heater for 2 minutes, again cooled to 60 C, and the evaporated water was replaced. Then 80 g of glucose syrup (80%) and 5.0 g of ascorbyl palmitate were added and mixed with the mixture by brief agitation with an Ultraturrax (2000 rpm). Then 55 g of vitamin A acetate (stabilized, 2.1 million IU/g) were 30 emulsified in, and the emulsion was treated further with the Ultraturrax (9000 rpm) for 30 minutes, keeping the temperature of the emulsion at from 55 C to 65 C by occasional cooling with a water bath t20 C). The emulsion was then spray dried.
35 The resulting powder has a vitamin A acetate content of 0.63 million IU/g.
Example 2 40 As in Example 1, 45 g of soybean protein isolate were partially degraded in 600 ml of water with 0.19 g of bromelain, 80 g of glucose syrup (80%) and 5 g of ascorbyl palmitate were added, and then 60 g of D/L-alpha-tocopherol were emulsified in. The degree of degradation of the soybean protein was determined to be 2.9%.
45 The emulsion was further processed and spray dried as in Example 1.
~ BASF Aktiengesellschaft 930536 O.Z. 0050/45031 The powder had a tocopherol content of 33% by weight.
Example 3 5 300 ml of water and 34 g of soybean protein concentrate (protein content 65%) were placed in a 1 l beaker and heated to 60 C while stirring with a magnetic stirrer. The pH was then adjusted to 8.0, 0.05 g of bromelain was added and the mixture was stirred at 60 C for 30 minutes. The pH was then readjusted to 8.0, the mix-10 ture was subsequently boiled for 2 minutes, 90 g of glucose syrup(80%) and 3.5 g of ascorbyl palmitate were added, and brief mix-ing was carried out with an Ultraturrax (2000 rpm). The degree of degradation of the protein was 1.6%.
15 27 g of a 30% by weight dispersion of ethyl apo-8'-carotenoate in a medium chain-length triglyceride ("Miglyol-810") in a 100 ml round-bottom flask were stabilized with tocopherol and dissolved by stirring with a paddle stirrer in an oil bath at 180 C. The hot oily solution was emulsified in the aqueous phase and dispersed 20 with the Ultraturrax at 9000 rpm for 20 minutes, keeping the tem-perature of the emulsion at about 60 C by cooling with an ice bath. The emulsion was dried in a spray dryer.
The ethyl apo-8'-carotenoate content in the dry powder was 5%.
Example 4 As in Example 1, 20 g of soybean protein isolate were partially degraded in 280 ml of water in a 1 l beaker with 0.002 g of 30 bromelain, 110 g of glucose syrup (80%) and 2.6 g of ascorbyl palmitate were added, and brief mixing was carried out with an Ultraturrax (2000 rpm). The degree of degradation of the protein was 0.1%.
35 21.7 g of a 20% strength dispersion of citranaxanthin in a medium chain-length triglyceride ("Miglyol 810") in a 100 ml round-bottom flask were stabilized with tocopherol and dissolved by stirring at 180 C. The hot oily solution was emulsified in the aqueous phase and dispersed with the Ultraturrax at 9000 rpm for 40 20 minutes, keeping the temperature of the emulsion at about 60 C
by cooling with an ice bath.
The citranaxanthin content in the dry powder was 3.0'~.
' BASF Aktiengesellschaft 930536 O.Z. 0050/45031 ~ ~ 7 21 947q~
Example 5 As in Example 1, 20 g of soybean protein isolate were partially degraded in 280 ml of water in a 1 1 beaker with 0.05 g of brome-5 lain. The degree of degradation was 2.2%. After addition of 110 gof glucose syrup (80%) and 2.6 g of ascorbyl palmitate, the mix-ture was briefly mixed with an Ultraturrax (2000 rpm).
21.6 g of a 20% strength dispersion of ~carotene in peanut oil in 10 a 100 ml round-bottom flask were stabilized with tocopherol and dissolved by stirring with a paddle stirrer in an oil bath at 1~80 C. The hot oily solution was cautiously emulsified in the aqueous phase and dispersed with the Ultraturrax at 9000 rpm for 20 minutes, keeping the temperature of the emulsion at about 60 C
15 by cooling with an ice bath. The emulsion was dried in a spray dryer.
The ~-carotene content in the dry powder was 2.9%.
20 Orangeade beverages and multivitamin syrups produced with a ~-carotene-containing composition according to the invention had a brighter color and greater clarity than those produced using gel-atin or natural soybean protein.
The invention further relates to compositions containing fat-10 soluble active substances and partially degraded soybean proteins and to the use of such compositions.
Fat-soluble active substances such as vitamins and carotenoids play an important part in human and An;m~l nutrition, whether as 15 essential substances such as the vitamins or proteins, or else, specifically in the case of carotenoids, as natural or nature-identical colorants which confer a characteristic color on many human or ~n;m~l foodstuffs.
20 It is common to these fat-soluble active substances that in their pure form they can be handled only with difficulty, if at all, because they are oxidation-sensitive substances. Furthermore, a fine dispersion of the active substance is advantageous for optimal absorbability or coloring action. In addition, it is 25 often desirable for the active substances to be dispersible in water. This is why these substances are frequently supplied in the form of emulsions or dry powders, in which case the active substances are embedded, either in pure form or as solution in a physiologically tolerated oil, finely dispersed in a protective 30 colloid.
The sensitivity of oil-soluble vitamins and carotenoids to oxygen makes great demands on the matrix in which the substances are embedded. The protective colloid envelope must, in order effec-35 tively to prevent oxidative decomposition processes, represent agood barrier to oxygen. This is why gelatin is frequently used, having excellent stabilizing properties.
According to EP-A 0 347 7~1, fish gelatin is also suitable as 40 protective colloid for fat-soluble substances.
However, the disadvantage of gelatins is that they have strong adhesive properties. On use of gelatin-containing products the drying methods conventional for liquid systems, such as spray 45 drying or spray fluidized bed drying, may lead to stringing or caking.
BASF Aktiengesellschaft 930536 O.Z. 0050/45031 21 ~796 In other protective colloids which are frequently used, such as gum arabic, starch, dextrins, pectin or tragacanth, it is often possible to embed only relatively low concentrations of fat-soluble substances. Furthermore, in the past as a consequence of 5 failed harvests, gum arabic in particular has not always been available or available in adequate quality.
Synthetic colloids such as polyvinylpyrrolidone or partially syn-thetic polymers such as cellulose derivatives likewise have a 10 limited emulsifying capacity and are not always acceptable, espe-cially in the foodstuffs sector.
It is furthermore known to use natural vegetable proteins such as soybean proteins as protective colloids for fat-soluble sub-15 stances. However, products of this type likewise have a number ofdisadvantages related to the properties typical of proteins.
Those which should be particularly mentioned here are: a tendency to flocculate, which is often pronounced, on exposure to heat or in the presence of salts, and not always adequate emulsifying ca-20 pacity. In addition, the products produced in this way often haveinadequate coldwater dispersibility. Furthermore, vegetable pro-teins may greatly increase the viscosity of liquid water-contain-ing systems, which may restrict the production or processing of such products.
The use of partially hydrolyzed soybean proteins as substitute for protein-based foaming agents in foodstuffs is disclosed in US-A 3 932 672 and US-A 4 015 019. Partially hydrolyzed soybean proteins can also be used for protein supplementation of soft 30 drinks (H.S. Olsen and J. Adler-Nissen, Zeitschrift fur Lebens-mitteltechnologie und Verfahrenstechnik, 31 (1980) 259-360).
US-A 4 293 574 discloses the production of mayonnaise-like food-stuffs using specific alcohol-denatured and partially hydrolyzed 35 soybean proteins as substitute for eggs.
It is an object of the present invention to find suitable protec-tive colloids for fat-soluble active substances such as vitamins or carotenoids, and compositions thereof.
We have found that this object is achieved, using partially degraded soybean proteins as protective colloid, and compositions of fat-soluble active substances.
45 The object of the present invention was to find suitable protec-tive colloids for fat-soluble active substances which do not involve technical disadvantages for processing and make it BASF AXtienge~ellschaft 930536 O.Z. 0050/45031 - 2 1 9$796 possible to produce in a simple way stable, coldwater-dispersible compositions of fat-soluble active substances.
Used according to the invention as protective colloids for fat-5 soluble active substances are partially degraded soybean proteins which preferably have a degree of degradation ("DH": "degree of hydrolysis") of 0.1 to 5%, particularly preferably 0.2 to 3%. The degree of degradation "DH" is defined as follows:
Number of cleaved peptide linkages DH = x 100%
Total number of peptide linkages The degree of degradation can be determined by the pH-stat method 15 as described by C.F. Jacobsen et al. in Methods of Biochemical Analysis, Vol. IV, pp. 171-210, Interscience Publishers Inc., New York 1957.
The partial degradation is, as a rule, carried out enzymatically, 20 suitable enzymes being proteases from plants, microorganisms, fungi or ~n;~l S. The partial degradation is preferably carried out with the vegetable protease bromelain.
The soybean proteins usually employed are commercial soybean pro-25 tein isolates and concentrates with protein contents of from 70 to 90% by weight, where the remaining 10 to 30~ by weight repre-sent other more or less undefined plant constituents. The soybean protein isolates are incubated with the enzyme in aqueous medium, preferably at from 50 to 70 C and at a pH of from 7 to 9. The 30 suitable protein to enzyme ratio for the desired degree of degra-dation can be determined in the individual case by laboratory tests which are simple for the skilled worker.
The aqueous soybean protein hydrolysate solutions are, as a rule, 35 produced in such a way that the protein content is from 6 to 10%
by weight.
Suitable fat-soluble active substances according to the invention are vitamins A, D, E and K, derivatives thereof such as vitamin A
gO palmitate or vitamin E acetate, as well as carotenoids, for example ~-carotene, apocarotenal, ethyl apocarotenoate, canthaxan-thin, zeaxanthin, astaxanthin, lycopene, citranaxanthin or mix-tures of said substances.
~ BASF AXtiengesellschaft 930536 O.Z. 0050/45031 21 ~47~6 The fat-soluble active substances can be added to the composi-tions according to the invention either in pure form or as mix-ture with physiologically tolerated oils such as sesame oil, corn - oil, cotton seed oil, soybean oil or peanut oil.
In addition to the fat-soluble active substances and the par-tially degraded soybean proteins, the compositions according to the invention may also contain conventional auxiliaries, for example sugars and sugar alcohols, starch or starch derivatives, lO stabilizers such as t-butyl-hydroxytoluene, as well as emulsi-fiers such as ascorbyl palmitate or lecithin.
The compositions can be produced in a conventional manner by emulsifying the fat-soluble active substances either in pure form 15 or mixed with physiologically tolerated oils or fats in the aqueous phase containing protective colloid. The emulsification can take place with the aid of conventional stirrers, rotor-sta-tor dispersers and other suitable mixers. It is advisable to carry out the emulsification at 40 to 70 C.
The compositions according to the invention can be either liquid or solid, and solid compositions are preferred. Solid composi-tions can be produced in a simple manner by spray drying or spray fluidized bed drying.
The compositions according to the invention contain the fat-soluble active substances in amounts of from 2 to 40, preferably 10 to 20, % of the total weight of active substance and protec-tive colloid.
The content of active substance in the compositions depends on the particular use and can be adjusted appropriately.
The compositions according to the invention are outstandingly 35 suitable for use in livestock nutrition, as additive to food-stuffs or, because of their good coldwater dispersibility, as addition to drinking water. Carotenoid-containing compositions are furthermore suitable as foodstuff colorants, especially for soft drinks. The compositions may also be added to other food-40 stuffs, for example baking mixes or blancmange powders.
The compositions are likewise outstandingly suitable for pro-ducing products for supplementing foodstuffs with vitamins.
~ BASF Aktiengesellschaft 930536 O.Z. 0050/45031 Examples In the following Examples 1, 2, 4 and 5, commercial soybean pro-tein isolates with a protein content of 85% by weight were used.
5 A concentrate with a protein content of 65% by weight was used in Example 3.
The bromelain which was used is a commercial enzyme (from Merck, 2m-Ansom-U/mg).
The emulsions were each spray dried in a Minor spray dryer from ~iro, the tower inlet temperature being 140 C and the tower outlet temperature being 90 C.
15 The pH was adjusted in each case with 1 M aqueous NaOH.
Example 1 600 ml of water and 45 g of soybean protein isolate were placed 20 in a 2 l beaker and heated to 60 C with stirring. The pH was then adjusted to 9.0, 0.46 g of bromelain was added and the mixture was stirred at 60 C for 30 minutes. The pH was then readjusted to 9Ø The DH was calculated on the basis of the consumption of sodium hydroxide solution to be 5. The mixture was boiled using 25 an immersion heater for 2 minutes, again cooled to 60 C, and the evaporated water was replaced. Then 80 g of glucose syrup (80%) and 5.0 g of ascorbyl palmitate were added and mixed with the mixture by brief agitation with an Ultraturrax (2000 rpm). Then 55 g of vitamin A acetate (stabilized, 2.1 million IU/g) were 30 emulsified in, and the emulsion was treated further with the Ultraturrax (9000 rpm) for 30 minutes, keeping the temperature of the emulsion at from 55 C to 65 C by occasional cooling with a water bath t20 C). The emulsion was then spray dried.
35 The resulting powder has a vitamin A acetate content of 0.63 million IU/g.
Example 2 40 As in Example 1, 45 g of soybean protein isolate were partially degraded in 600 ml of water with 0.19 g of bromelain, 80 g of glucose syrup (80%) and 5 g of ascorbyl palmitate were added, and then 60 g of D/L-alpha-tocopherol were emulsified in. The degree of degradation of the soybean protein was determined to be 2.9%.
45 The emulsion was further processed and spray dried as in Example 1.
~ BASF Aktiengesellschaft 930536 O.Z. 0050/45031 The powder had a tocopherol content of 33% by weight.
Example 3 5 300 ml of water and 34 g of soybean protein concentrate (protein content 65%) were placed in a 1 l beaker and heated to 60 C while stirring with a magnetic stirrer. The pH was then adjusted to 8.0, 0.05 g of bromelain was added and the mixture was stirred at 60 C for 30 minutes. The pH was then readjusted to 8.0, the mix-10 ture was subsequently boiled for 2 minutes, 90 g of glucose syrup(80%) and 3.5 g of ascorbyl palmitate were added, and brief mix-ing was carried out with an Ultraturrax (2000 rpm). The degree of degradation of the protein was 1.6%.
15 27 g of a 30% by weight dispersion of ethyl apo-8'-carotenoate in a medium chain-length triglyceride ("Miglyol-810") in a 100 ml round-bottom flask were stabilized with tocopherol and dissolved by stirring with a paddle stirrer in an oil bath at 180 C. The hot oily solution was emulsified in the aqueous phase and dispersed 20 with the Ultraturrax at 9000 rpm for 20 minutes, keeping the tem-perature of the emulsion at about 60 C by cooling with an ice bath. The emulsion was dried in a spray dryer.
The ethyl apo-8'-carotenoate content in the dry powder was 5%.
Example 4 As in Example 1, 20 g of soybean protein isolate were partially degraded in 280 ml of water in a 1 l beaker with 0.002 g of 30 bromelain, 110 g of glucose syrup (80%) and 2.6 g of ascorbyl palmitate were added, and brief mixing was carried out with an Ultraturrax (2000 rpm). The degree of degradation of the protein was 0.1%.
35 21.7 g of a 20% strength dispersion of citranaxanthin in a medium chain-length triglyceride ("Miglyol 810") in a 100 ml round-bottom flask were stabilized with tocopherol and dissolved by stirring at 180 C. The hot oily solution was emulsified in the aqueous phase and dispersed with the Ultraturrax at 9000 rpm for 40 20 minutes, keeping the temperature of the emulsion at about 60 C
by cooling with an ice bath.
The citranaxanthin content in the dry powder was 3.0'~.
' BASF Aktiengesellschaft 930536 O.Z. 0050/45031 ~ ~ 7 21 947q~
Example 5 As in Example 1, 20 g of soybean protein isolate were partially degraded in 280 ml of water in a 1 1 beaker with 0.05 g of brome-5 lain. The degree of degradation was 2.2%. After addition of 110 gof glucose syrup (80%) and 2.6 g of ascorbyl palmitate, the mix-ture was briefly mixed with an Ultraturrax (2000 rpm).
21.6 g of a 20% strength dispersion of ~carotene in peanut oil in 10 a 100 ml round-bottom flask were stabilized with tocopherol and dissolved by stirring with a paddle stirrer in an oil bath at 1~80 C. The hot oily solution was cautiously emulsified in the aqueous phase and dispersed with the Ultraturrax at 9000 rpm for 20 minutes, keeping the temperature of the emulsion at about 60 C
15 by cooling with an ice bath. The emulsion was dried in a spray dryer.
The ~-carotene content in the dry powder was 2.9%.
20 Orangeade beverages and multivitamin syrups produced with a ~-carotene-containing composition according to the invention had a brighter color and greater clarity than those produced using gel-atin or natural soybean protein.
Claims (9)
1. The use of partially degraded soybean proteins as protective colloids for fat-soluble active substances.
2. The use as claimed in claim 1, wherein the partially degraded soybean proteins have a degree of degradation of from 0.1 to 5%.
3. A coldwater-dispersible composition containing fat-soluble active substances as essential ingredients and partially degraded soybean proteins as protective colloid.
4. A composition as claimed in claim 3, which is in solid form.
5. A composition as claimed in claim 3 or 4, containing as fat-soluble active substances vitamins A, D, E or K or a carotenoid or mixtures of these active substances.
6. A composition as claimed in any of claims 3 to 5, containing from 2 to 40% by weight of a fat-soluble active substance based on the total amount of active substance and protective colloid.
7. The use of the compositions as claimed in any of claims 3 to 6 in livestock nutrition.
8. The use of the compositions as claimed in any of claims 3 to 6 as additives in human foodstuffs.
9. The use of the compositions as claimed in any of claims 3 to 6 for human dietary supplementation.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4424085.6 | 1994-07-11 | ||
| DE4424085A DE4424085A1 (en) | 1994-07-11 | 1994-07-11 | Preparations of fat-soluble active ingredients dispersible in cold water |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2194796A1 true CA2194796A1 (en) | 1996-01-25 |
Family
ID=6522640
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002194796A Abandoned CA2194796A1 (en) | 1994-07-11 | 1995-07-03 | Cold water-dispersible compositions of fat-soluble active substances |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0768826A1 (en) |
| JP (1) | JPH10502626A (en) |
| CN (1) | CN1152857A (en) |
| AU (1) | AU2926495A (en) |
| CA (1) | CA2194796A1 (en) |
| DE (1) | DE4424085A1 (en) |
| WO (1) | WO1996001570A1 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6264986B1 (en) | 1996-10-14 | 2001-07-24 | Basf Aktiengesellschaft | Stable emulsions and dry powders of mixtures of fat-soluble vitamins, their preparation and use |
| US6639113B2 (en) | 2000-12-21 | 2003-10-28 | Basf Aktiengesellschaft | Production of dry powders of one or more oxygenated carotenoids |
| US7070812B2 (en) | 2001-01-31 | 2006-07-04 | Basf Aktiengesellschaft | Process for producing dry powders of one or more carotenoids |
| US9357796B2 (en) | 2005-06-30 | 2016-06-07 | Basf Se | Carotenoid-containing aqueous suspensions and powders, methods of producing the same and uses thereof |
| US10206965B2 (en) | 2001-11-26 | 2019-02-19 | Lycored Natural Products Industries Ltd. | Carotenoid formulation |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2774261B1 (en) * | 1998-02-02 | 2000-03-31 | Rhodia Chimie Sa | COMPOSITION FOR FOOD USE IN THE FORM OF A DRY EMULSION, MANUFACTURING METHOD THEREOF AND USE THEREOF |
| DE19951615A1 (en) * | 1999-10-26 | 2001-05-03 | Basf Ag | Process for the stabilization of liquid, aqueous preparations of fat-soluble substances |
| IL134701A0 (en) * | 2000-02-23 | 2001-04-30 | J P M E D Ltd | Homogeneous solid matrix containing vegetable proteins |
| US20080241320A1 (en) * | 2007-03-30 | 2008-10-02 | Dsm Ip Assets B.V. | Protective hydrocolloid for active ingredients |
| FR2953409B1 (en) * | 2009-12-09 | 2011-12-23 | Adisseo France Sas | PARTICLES OF ACTIVE STABLE LIPOSOLUBLE PRINCIPLES |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4167587A (en) * | 1977-06-22 | 1979-09-11 | Danforth Richard C | Compositions and process for colored liquid food or drink |
| JPS6042317A (en) * | 1983-08-18 | 1985-03-06 | Nisshin Oil Mills Ltd:The | Cosmetics |
| DE3702030A1 (en) * | 1987-01-24 | 1988-08-04 | Basf Ag | POWDERED, WATER-DISPERSIBLE CAROTINOID PREPARATIONS AND METHOD FOR THE PRODUCTION THEREOF |
| EP0298419B1 (en) * | 1987-07-06 | 1992-05-20 | Katayama Chemical Works Co., Ltd. | A protein partial degradation product, process for preparing it and its use |
| US5082672A (en) * | 1989-06-21 | 1992-01-21 | The United States Of American As Represented By The Secretary Of Agriculture | Enzymatic deamidation of food proteins for improved food use |
| EP0410236B1 (en) * | 1989-07-25 | 1993-10-27 | F. Hoffmann-La Roche Ag | Process for the production of carotinoid preparations |
| US5053240A (en) * | 1989-10-24 | 1991-10-01 | Kalamazoo Holdings, Inc. | Norbixin adducts with water-soluble or water-dispersible proteins or branched-chain or cyclic polysaccharides |
-
1994
- 1994-07-11 DE DE4424085A patent/DE4424085A1/en not_active Withdrawn
-
1995
- 1995-07-03 WO PCT/EP1995/002559 patent/WO1996001570A1/en not_active Application Discontinuation
- 1995-07-03 CN CN95194123A patent/CN1152857A/en active Pending
- 1995-07-03 AU AU29264/95A patent/AU2926495A/en not_active Abandoned
- 1995-07-03 JP JP8504092A patent/JPH10502626A/en active Pending
- 1995-07-03 EP EP95924961A patent/EP0768826A1/en not_active Withdrawn
- 1995-07-03 CA CA002194796A patent/CA2194796A1/en not_active Abandoned
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6264986B1 (en) | 1996-10-14 | 2001-07-24 | Basf Aktiengesellschaft | Stable emulsions and dry powders of mixtures of fat-soluble vitamins, their preparation and use |
| US7279180B2 (en) | 1996-10-14 | 2007-10-09 | Basf Aktiengesellschaft | Stable emulsions and dry powders of mixtures of fat-soluble vitamins, their preparation and use |
| US6639113B2 (en) | 2000-12-21 | 2003-10-28 | Basf Aktiengesellschaft | Production of dry powders of one or more oxygenated carotenoids |
| US7070812B2 (en) | 2001-01-31 | 2006-07-04 | Basf Aktiengesellschaft | Process for producing dry powders of one or more carotenoids |
| US10206965B2 (en) | 2001-11-26 | 2019-02-19 | Lycored Natural Products Industries Ltd. | Carotenoid formulation |
| US9357796B2 (en) | 2005-06-30 | 2016-06-07 | Basf Se | Carotenoid-containing aqueous suspensions and powders, methods of producing the same and uses thereof |
| US11337925B2 (en) | 2005-06-30 | 2022-05-24 | Basf Se | Preparation in the form of a powder containing at least one carotenoid, at least one modified starch, and sucrose |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1152857A (en) | 1997-06-25 |
| JPH10502626A (en) | 1998-03-10 |
| AU2926495A (en) | 1996-02-09 |
| DE4424085A1 (en) | 1996-01-18 |
| EP0768826A1 (en) | 1997-04-23 |
| WO1996001570A1 (en) | 1996-01-25 |
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