CA2058038A1 - Process for the removal of cyclodextrin residues from fats and oils - Google Patents
Process for the removal of cyclodextrin residues from fats and oilsInfo
- Publication number
- CA2058038A1 CA2058038A1 CA002058038A CA2058038A CA2058038A1 CA 2058038 A1 CA2058038 A1 CA 2058038A1 CA 002058038 A CA002058038 A CA 002058038A CA 2058038 A CA2058038 A CA 2058038A CA 2058038 A1 CA2058038 A1 CA 2058038A1
- Authority
- CA
- Canada
- Prior art keywords
- cyclodextrin
- process according
- oils
- fats
- fat
- 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
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y302/00—Hydrolases acting on glycosyl compounds, i.e. glycosylases (3.2)
- C12Y302/01—Glycosidases, i.e. enzymes hydrolysing O- and S-glycosyl compounds (3.2.1)
- C12Y302/01001—Alpha-amylase (3.2.1.1)
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C15/00—Butter; Butter preparations; Making thereof
- A23C15/12—Butter preparations
- A23C15/14—Butter powder; Butter oil, i.e. melted butter, e.g. ghee ; Anhydrous butter
- A23C15/145—Removal of steroids, e.g. cholesterol or free acids; Fractionation of anhydrous milkfat by extraction with solvents other than solvent crystallisation or with supercritical gases or by distillation
-
- 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
- A23L5/20—Removal of unwanted matter, e.g. deodorisation or detoxification
- A23L5/25—Removal of unwanted matter, e.g. deodorisation or detoxification using enzymes
-
- 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
- A23L5/20—Removal of unwanted matter, e.g. deodorisation or detoxification
- A23L5/27—Removal of unwanted matter, e.g. deodorisation or detoxification by chemical treatment, by adsorption or by absorption
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/003—Refining fats or fatty oils by enzymes or microorganisms, living or dead
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Microbiology (AREA)
- Organic Chemistry (AREA)
- Nutrition Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Biochemistry (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- General Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Zoology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Fats And Perfumes (AREA)
- Edible Oils And Fats (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- General Preparation And Processing Of Foods (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
ABSTRACT
Process for the removal of cyclodextrin residues from fats and oils According to the present invention, there is provided a process for the removal of cyclodextrin residues from fats and oils, wherein the fats and oils are emulsified with water and the cyclodextrin is broken down enzymatically with the help of at least one .alpha.-amylase selected from hog pancreatic amylase and the .alpha.-amylases formed by micro-organisms of the group Aspergillus niger, Aspergillus oryzae, Bacillus polymyxa and Bacillus coagulans, as well as Flavo-bacterium and/or preferably of a CTGase selected from the CTGases formed by bacteria of the group Bacillus, Klebsiella, Micrococcus and alkalophilic bacteria.
Process for the removal of cyclodextrin residues from fats and oils According to the present invention, there is provided a process for the removal of cyclodextrin residues from fats and oils, wherein the fats and oils are emulsified with water and the cyclodextrin is broken down enzymatically with the help of at least one .alpha.-amylase selected from hog pancreatic amylase and the .alpha.-amylases formed by micro-organisms of the group Aspergillus niger, Aspergillus oryzae, Bacillus polymyxa and Bacillus coagulans, as well as Flavo-bacterium and/or preferably of a CTGase selected from the CTGases formed by bacteria of the group Bacillus, Klebsiella, Micrococcus and alkalophilic bacteria.
Description
2~8~
The present invention is concerned with a process for the removal of cyclodextrin residues :Erom fats and oils from which complexable, undesired su~stances, for example sterols, especially cholesterol, ~ree fatty acids, vitamins, colouring materials and other impurities have been removed with the help of cyclo-dextrin and which still have a certain residual content of cyclodextrin.
It is known that increased cholesterol levels in the blood serum of humans represent an increased risk ~ac~or for arteriosclerosis and for coronary heart disease. For this reason, the endeavours of the food-stuff industry are markedly to reduce the content of cholesterol and cholesterol esters in faL-rich food-stuffs of animal origin, an important problem therebybeing substantially to maintain the sensory and nutritional-physiological properties of the foodstuffs.
A relatively gentle process for the removal of cholesterol derivatives is the complexing of these substances with ~-cyclodextrin and separation of the complex formed.
According to EP-A 0 256 911, a liquefied fat mass is treated with a solid cyclodextrin, the cholesterol value being said to be reduced by up to 80%. However, for this purpose~ a repeated cyclodextrin treatment is necessary.
- 2 - ~ a ~ ~
From W. Schlenk and V.M. Sand (J.S.C.S., 84, 2312/1961), it i5 Icnown to complex free i~atty acids with cyclodextrin.
In the case of these processes 9 it is an important problem that a certain amount of the dissolved cyclo-dextrin remains behind in the fats and oils when the previously known ~ethods are employed for the separation thereof. Normally, cyclodextrins (, ~- and ~)~ which are annular oligosaccharides consisting of 6 to 8 glucose units, are not toxicological. Thus, tests for the acute toxicity in mice and rats have also given no indication of a toxic effect in the case of oral administration. Nevertheless, in many countries, cyclo-dextrins have hitherto not been permitted to be used as '~ood additives".
Therefore, it is an object of the present invention to provide a process for the removal of cyclo-dextrin residues from fats and oils which, without great technical expense, makes possible a substantial and selective removal of cyclodex-trin from the treated starting materials.
Thus, according to the present invention, there is provided a process for the removal of cyclodextrin residues from fats and oils, wherein fats and oils are emulsified with water and the cyclodextrin is broken down enzymatically with the help of at least one a-amylase selected from hog pancreatic amylase and the - 3 - ~0~ ~ 038 a-amyla~3es formed by micro-organisms of the group Aspergillus niger, Aspergillus oryzae, Bacillus polymyxa and Bacillus coagulans, as well as Flavobacterium and/or preferably of a CTGase selected from the CTGases formed by bacteria of the group Bacillus, Klebsiella, Micrococcus and alkalophilic bacteria.
Surprisingly, we have shown that, in this way, a practically complete breakdown of the cyclodextrin in fats and oils can be achieved in an economically acceptable way. This is surprising because cyclo-dextrins have been described as being potent inhibitors of the a- and ~-amylases (see R.J. Weselake and R.D. Hill, Cereal Chem., 60, 98/1983) and are substant-ially resistant to most - and ~-amylases. We have now found that a few types of -amylase, for example those from ~acillus polymyxa and Aspergillus oryzae, as well as hog pancreatic amylase~ are admittedly able to hydrolyse cyclodextrins but with low veloclties. There-fore, i~ was especially surprising and not foreseeable that this activity would suffice to break down the cyclodextrin in fat and oil emulsions relatively quickly and completely.
In the process according to the present invention, the starting material, consisting of fats and oils of animal or vegetable origin, for example butter fat, hog and ~eef fat, goose fat, fish oils, sunflower oils and the like, which, because of a treatment with cyclo-_ 4 _ ~5 ~ 03 ~
dextrin, still have a residual content of cyclodextrinsof, for example, 0.001 to 1.0% by weight, are subjected to an enzymatic treatment.
PreEerably, there are thereby used ~-amylases selecte~ from hog pancreatic amylase and the a-amylases formed by micro-organisms of the group Aspergillus niger, Aspergillus oryzae, ~acillus polymyxa and Bacillus coagulans, as well as Flavobacterium~ From the group of the CTGases (cyclodextrin trans-glycosylases = EC 2.4.1.19), those CTGases formed by bacteria of the group Bacillus (for example Bacillus macerans, Bacillus megateriuTn, Bacillus s~earothermophilus, Bacillus circulans and Bacillus ohbensis), Klebsiella (for example pneumoniae), Micrococcus (for example varians) and alkalophilic bacteria, for example Nos. 38-2 and 17-1, are especially preferred. The mentioned enzymes can also be expressed from host cells of other origin by methods of genetic manipulation. These ~-amylases and CTGases make possible a practically complete break-down of the cyclodeY~trin. The necessary amount ofenzyme thereby depends essentially upon the initial content of cyclodextrin in the fat or oil and, in the case of ~-amylase, is usually from 10 to 500 FAU per g of cyclodextrin to be removed (1 FAU = one fungal a-amylase unit breaks down 5.2 g of starch in one hourunder standard conditions (subs-trate: soluble starch, incubation time 7 to 20 minutes, temperature 37C, _ 5 _ 2 ~ 8 ~ ~ ~
p}l = 4.7)). In the case of the CTGases, these are preferably used in an amount of 0.5 to 20 U per g of cyclodextrin to be removed (1 unit = conversion of 1 ~mol of substrate per minute). It is also possible to use larger amounts of enzyme. However~ in general this is uneconomical because an improved effect is not obtained. According to a preferred embodiment of the process according to the present invention, mixtures of a-amylase and CTGase are used.
It is important for the present invention to use the fat or oil in the form of an oil-water emulsion.
For this purpose, the starting material~ possibly after liquefaction, is emulsified in water, preferably 0.1 to 5 kg of water thereby being added per kg of fat or oil.
The water can already contain the a-amylase and/or CTGase. However, the enzyme can also be added to the emulsion after the formation thereof. Before -the addition of the enzyme, the pH value of the water or of the emulsion is preferably adjusted to one which is favourable for the enzyme used and especially -to one which is optimal for the enzyme used. The adjustment of the pH value is preferably carried out with buffer substances and especially edible substances, for example citric acid, lactic acid and salts thereof.
Co-factors, for example divalent ions, such as calciu,n or magnesium ions, can possibly be added in trace amounts -to the emulsion. Furthermore, acceptors, for ~ 6 ~ 8038 example glucose, can also be admixed with the CTGases.
The treatment conditions, for example temperature and period of time, can be varied within certain limits but the fats and oils should be present in the liquid phase, i.e. the enzymatic decomposition should be carried out at a temperature between the melting point of the fat or oil in question and 70C. The temperature for the enzymatic decomposition is preferably from 25 to 55C, in which case treatment times of from 1 to 5 hours are usual.
With the help of the process according to the present invention, it is possible to carry out a substantial and selective removal of the cyclodextrin from the treated fat or oil in a technically especially simple manner, the content of residual cyclodextrin thereby being below a limit of detection of < 10 ppm~
The following Examples are given for the purpose of illustrating the present inven~ion:
Example 1.
1 kg of fish oil which has been pretreated with ~-cyclodextrin, with a residual content of ~-cyclo-dextrin of 150 ppm, was mixed with 1 kg of water and emulsified at 40C. The pH value of the emulsion was adjusted with citric acid to 5.5. Subsequently, 50 FAU
of an ~-amylase mixture from Aspergillus oryzae were added thereto in the form of the commercially available product Fungamyl 800 (Novo). After incubation for _ 7 _ ~0 ~ ~ 0 2 ~ours at 40C, ~-cyclodextrin could no longer be detec~ed (detection limit 10 ppm).
Ex ple 2.
1 kg of a butter oil pretreated with ~-cyclodextrin with a residual content of ~-cyclodextrin of 2500 ppm was emulsified in 1 kg of water at 50C. The pH value of the emulsion was adjusted to 6.2 with citric acid and incubated for 2 hours at 50C with 250 FAU of an a-amylase from Bacillus coagulans (non-purified prepar-ation). After this treatment, ~-cyclodextrin could no longer be detected (detection limit 10 ppm).
Example 3.
1 kg of bee~ tallow~with a resldual content of a-cyclodextrin of 200 ppm was emulsified in a 5 mmol/l solution of calcium sulphate at 40C and the pH value was adjusted to 6.5 with citric acid. Subsequently, 5 g of glucose and 20 U of a CTGase from Bacillus macerans were added to the emulsion. After incubation at 40C for 2.S hours~ a-cyclodextrin could no longer be detected (detection limit 10 ppm).
The present invention is concerned with a process for the removal of cyclodextrin residues :Erom fats and oils from which complexable, undesired su~stances, for example sterols, especially cholesterol, ~ree fatty acids, vitamins, colouring materials and other impurities have been removed with the help of cyclo-dextrin and which still have a certain residual content of cyclodextrin.
It is known that increased cholesterol levels in the blood serum of humans represent an increased risk ~ac~or for arteriosclerosis and for coronary heart disease. For this reason, the endeavours of the food-stuff industry are markedly to reduce the content of cholesterol and cholesterol esters in faL-rich food-stuffs of animal origin, an important problem therebybeing substantially to maintain the sensory and nutritional-physiological properties of the foodstuffs.
A relatively gentle process for the removal of cholesterol derivatives is the complexing of these substances with ~-cyclodextrin and separation of the complex formed.
According to EP-A 0 256 911, a liquefied fat mass is treated with a solid cyclodextrin, the cholesterol value being said to be reduced by up to 80%. However, for this purpose~ a repeated cyclodextrin treatment is necessary.
- 2 - ~ a ~ ~
From W. Schlenk and V.M. Sand (J.S.C.S., 84, 2312/1961), it i5 Icnown to complex free i~atty acids with cyclodextrin.
In the case of these processes 9 it is an important problem that a certain amount of the dissolved cyclo-dextrin remains behind in the fats and oils when the previously known ~ethods are employed for the separation thereof. Normally, cyclodextrins (, ~- and ~)~ which are annular oligosaccharides consisting of 6 to 8 glucose units, are not toxicological. Thus, tests for the acute toxicity in mice and rats have also given no indication of a toxic effect in the case of oral administration. Nevertheless, in many countries, cyclo-dextrins have hitherto not been permitted to be used as '~ood additives".
Therefore, it is an object of the present invention to provide a process for the removal of cyclo-dextrin residues from fats and oils which, without great technical expense, makes possible a substantial and selective removal of cyclodex-trin from the treated starting materials.
Thus, according to the present invention, there is provided a process for the removal of cyclodextrin residues from fats and oils, wherein fats and oils are emulsified with water and the cyclodextrin is broken down enzymatically with the help of at least one a-amylase selected from hog pancreatic amylase and the - 3 - ~0~ ~ 038 a-amyla~3es formed by micro-organisms of the group Aspergillus niger, Aspergillus oryzae, Bacillus polymyxa and Bacillus coagulans, as well as Flavobacterium and/or preferably of a CTGase selected from the CTGases formed by bacteria of the group Bacillus, Klebsiella, Micrococcus and alkalophilic bacteria.
Surprisingly, we have shown that, in this way, a practically complete breakdown of the cyclodextrin in fats and oils can be achieved in an economically acceptable way. This is surprising because cyclo-dextrins have been described as being potent inhibitors of the a- and ~-amylases (see R.J. Weselake and R.D. Hill, Cereal Chem., 60, 98/1983) and are substant-ially resistant to most - and ~-amylases. We have now found that a few types of -amylase, for example those from ~acillus polymyxa and Aspergillus oryzae, as well as hog pancreatic amylase~ are admittedly able to hydrolyse cyclodextrins but with low veloclties. There-fore, i~ was especially surprising and not foreseeable that this activity would suffice to break down the cyclodextrin in fat and oil emulsions relatively quickly and completely.
In the process according to the present invention, the starting material, consisting of fats and oils of animal or vegetable origin, for example butter fat, hog and ~eef fat, goose fat, fish oils, sunflower oils and the like, which, because of a treatment with cyclo-_ 4 _ ~5 ~ 03 ~
dextrin, still have a residual content of cyclodextrinsof, for example, 0.001 to 1.0% by weight, are subjected to an enzymatic treatment.
PreEerably, there are thereby used ~-amylases selecte~ from hog pancreatic amylase and the a-amylases formed by micro-organisms of the group Aspergillus niger, Aspergillus oryzae, ~acillus polymyxa and Bacillus coagulans, as well as Flavobacterium~ From the group of the CTGases (cyclodextrin trans-glycosylases = EC 2.4.1.19), those CTGases formed by bacteria of the group Bacillus (for example Bacillus macerans, Bacillus megateriuTn, Bacillus s~earothermophilus, Bacillus circulans and Bacillus ohbensis), Klebsiella (for example pneumoniae), Micrococcus (for example varians) and alkalophilic bacteria, for example Nos. 38-2 and 17-1, are especially preferred. The mentioned enzymes can also be expressed from host cells of other origin by methods of genetic manipulation. These ~-amylases and CTGases make possible a practically complete break-down of the cyclodeY~trin. The necessary amount ofenzyme thereby depends essentially upon the initial content of cyclodextrin in the fat or oil and, in the case of ~-amylase, is usually from 10 to 500 FAU per g of cyclodextrin to be removed (1 FAU = one fungal a-amylase unit breaks down 5.2 g of starch in one hourunder standard conditions (subs-trate: soluble starch, incubation time 7 to 20 minutes, temperature 37C, _ 5 _ 2 ~ 8 ~ ~ ~
p}l = 4.7)). In the case of the CTGases, these are preferably used in an amount of 0.5 to 20 U per g of cyclodextrin to be removed (1 unit = conversion of 1 ~mol of substrate per minute). It is also possible to use larger amounts of enzyme. However~ in general this is uneconomical because an improved effect is not obtained. According to a preferred embodiment of the process according to the present invention, mixtures of a-amylase and CTGase are used.
It is important for the present invention to use the fat or oil in the form of an oil-water emulsion.
For this purpose, the starting material~ possibly after liquefaction, is emulsified in water, preferably 0.1 to 5 kg of water thereby being added per kg of fat or oil.
The water can already contain the a-amylase and/or CTGase. However, the enzyme can also be added to the emulsion after the formation thereof. Before -the addition of the enzyme, the pH value of the water or of the emulsion is preferably adjusted to one which is favourable for the enzyme used and especially -to one which is optimal for the enzyme used. The adjustment of the pH value is preferably carried out with buffer substances and especially edible substances, for example citric acid, lactic acid and salts thereof.
Co-factors, for example divalent ions, such as calciu,n or magnesium ions, can possibly be added in trace amounts -to the emulsion. Furthermore, acceptors, for ~ 6 ~ 8038 example glucose, can also be admixed with the CTGases.
The treatment conditions, for example temperature and period of time, can be varied within certain limits but the fats and oils should be present in the liquid phase, i.e. the enzymatic decomposition should be carried out at a temperature between the melting point of the fat or oil in question and 70C. The temperature for the enzymatic decomposition is preferably from 25 to 55C, in which case treatment times of from 1 to 5 hours are usual.
With the help of the process according to the present invention, it is possible to carry out a substantial and selective removal of the cyclodextrin from the treated fat or oil in a technically especially simple manner, the content of residual cyclodextrin thereby being below a limit of detection of < 10 ppm~
The following Examples are given for the purpose of illustrating the present inven~ion:
Example 1.
1 kg of fish oil which has been pretreated with ~-cyclodextrin, with a residual content of ~-cyclo-dextrin of 150 ppm, was mixed with 1 kg of water and emulsified at 40C. The pH value of the emulsion was adjusted with citric acid to 5.5. Subsequently, 50 FAU
of an ~-amylase mixture from Aspergillus oryzae were added thereto in the form of the commercially available product Fungamyl 800 (Novo). After incubation for _ 7 _ ~0 ~ ~ 0 2 ~ours at 40C, ~-cyclodextrin could no longer be detec~ed (detection limit 10 ppm).
Ex ple 2.
1 kg of a butter oil pretreated with ~-cyclodextrin with a residual content of ~-cyclodextrin of 2500 ppm was emulsified in 1 kg of water at 50C. The pH value of the emulsion was adjusted to 6.2 with citric acid and incubated for 2 hours at 50C with 250 FAU of an a-amylase from Bacillus coagulans (non-purified prepar-ation). After this treatment, ~-cyclodextrin could no longer be detected (detection limit 10 ppm).
Example 3.
1 kg of bee~ tallow~with a resldual content of a-cyclodextrin of 200 ppm was emulsified in a 5 mmol/l solution of calcium sulphate at 40C and the pH value was adjusted to 6.5 with citric acid. Subsequently, 5 g of glucose and 20 U of a CTGase from Bacillus macerans were added to the emulsion. After incubation at 40C for 2.S hours~ a-cyclodextrin could no longer be detected (detection limit 10 ppm).
Claims (11)
1. A process according to claim 1 wherein CTGase is used in place of or together with the Flavobacterium and the CTGase is selected from those formed by bacteria of the group Bacillus, Klebsiella, Micrococcus and alkalophilic bacteria.
2. A process for the removal of cyclodextrin residues from fats and oils, wherein the fats and oils are emulsified with water and the cyclodextrin is broken down enzymatically with the help of at least one .alpha.-amylase selected from hog pancreatic amylase and the .alpha.-amylases formed by micro-organisms of the group Aspergillus niger, Aspergillus oryzae, Bacillus polymyxa and Bacillus coagulans, as well as Flavobacterium and/or preferably of a CTGase selected from the CTGases formed by bacteria of the group Bacillus, Klebsiella, Micrococcus and alkalophilic bacteria.
3. A process according to claim 1 wherein the .alpha.-amylase is used in an amount of from 10 to 500 FAU per g of cyclodextrin to be removed.
4. A process according to claim 2 wherein the .alpha.-amylase is used in an amount of from 10 to 500 FAU per g of cyclodextrin to be removed.
5. A process according to claim 2 wherein the CTGase is used in an amount of from 0.5 to 20 U per g of cyclodextrin to be removed.
6. A process according to claim 1, 2, 3, 4 or 5 wherein the enzymatic decomposition is carried out at a temperature between the melting point of the fat or oil and 70°C.
7. A process according to claim 1, 2, 3, 4 or 5 wherein the enzymatic decomposition is carried out at a temperature of from 25 to 55°C.
8. A process according to claim 1, 2, 3, 4 or 5 wherein 0.1 to 5 parts by weight of water are emulsified with 1 part by weight of fat or oil.
9. A process according to claim 1, 2, 3, 4 or 5 wherein 0.1 to 5 parts by weight of water are emulsified with 1 part by weight of fat or oil and wherein the enzymatic decomposition is carried out at a temperature between the melting point of the fat or oil and 70°C.
10. A process according to claim 1, 2, 3, 4 or 5 wherein 0.1 to 5 parts by weight of water are emulsified with 1 part by weight of fat or oil and wherein the enzymatic decomposition is carried out at a temperature of from 25 to 55°C.
11. Fats and oils, whenever freed from residues of cyclodextrin by the process according to claim 1, 2, 3, 4 or 5.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4041386A DE4041386A1 (en) | 1990-12-21 | 1990-12-21 | METHOD FOR REMOVING CYCLODEXTRINE RESIDUES FROM FATS AND OILS |
| DEP4041386.1 | 1990-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2058038A1 true CA2058038A1 (en) | 1992-06-22 |
Family
ID=6421169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002058038A Abandoned CA2058038A1 (en) | 1990-12-21 | 1991-12-18 | Process for the removal of cyclodextrin residues from fats and oils |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0492475B1 (en) |
| JP (1) | JPH04296396A (en) |
| AT (1) | ATE117357T1 (en) |
| AU (1) | AU640837B2 (en) |
| CA (1) | CA2058038A1 (en) |
| CZ (1) | CZ404691A3 (en) |
| DE (2) | DE4041386A1 (en) |
| DK (1) | DK0492475T3 (en) |
| ES (1) | ES2067840T3 (en) |
| HR (1) | HRP921073A2 (en) |
| HU (1) | HU208474B (en) |
| IE (1) | IE65633B1 (en) |
| NO (1) | NO915069L (en) |
| NZ (1) | NZ240920A (en) |
| PL (1) | PL165829B1 (en) |
| RU (1) | RU2086618C1 (en) |
| ZA (1) | ZA919676B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5571554A (en) * | 1993-09-16 | 1996-11-05 | Consortium Fur Elektrochemische | Process for reducing the content of triglycerides in egg yolk and in products containing egg yolk |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL9202130A (en) * | 1992-12-09 | 1994-07-01 | Nl Ind Eiprodukten Bv | Method for removing Beta cyclodextrin from egg yolk or egg yolk plasma. |
| CN101610824A (en) * | 2006-12-22 | 2009-12-23 | 丹尼斯科美国公司 | The de-emulsification of the aqueous lipid extracts that enzyme is auxiliary |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4001611C1 (en) * | 1990-01-20 | 1991-02-28 | Skw Trostberg Ag, 8223 Trostberg, De | |
| FR2657623B1 (en) * | 1990-01-29 | 1995-02-17 | Roquette Freres | PROCESS FOR RECOVERING LIPOPHILIC COMPOUNDS EXTRACTED FROM FAT MEDIA BY ACTION OF CYCLODEXTRIN. |
| DE4029287A1 (en) * | 1990-09-14 | 1992-03-19 | Sueddeutsche Kalkstickstoff | METHOD FOR PRODUCING CHOLESTERIN-REDUCED EGG YELLOW |
-
1990
- 1990-12-21 DE DE4041386A patent/DE4041386A1/en not_active Withdrawn
-
1991
- 1991-12-04 IE IE421491A patent/IE65633B1/en not_active IP Right Cessation
- 1991-12-09 ZA ZA919676A patent/ZA919676B/en unknown
- 1991-12-10 NZ NZ240920A patent/NZ240920A/en unknown
- 1991-12-11 AU AU89630/91A patent/AU640837B2/en not_active Ceased
- 1991-12-18 CA CA002058038A patent/CA2058038A1/en not_active Abandoned
- 1991-12-19 EP EP91121867A patent/EP0492475B1/en not_active Expired - Lifetime
- 1991-12-19 PL PL91292867A patent/PL165829B1/en unknown
- 1991-12-19 HU HU914055A patent/HU208474B/en not_active IP Right Cessation
- 1991-12-19 ES ES91121867T patent/ES2067840T3/en not_active Expired - Lifetime
- 1991-12-19 AT AT91121867T patent/ATE117357T1/en not_active IP Right Cessation
- 1991-12-19 JP JP3336465A patent/JPH04296396A/en active Pending
- 1991-12-19 DE DE59104331T patent/DE59104331D1/en not_active Expired - Fee Related
- 1991-12-19 DK DK91121867.5T patent/DK0492475T3/en active
- 1991-12-20 NO NO91915069A patent/NO915069L/en unknown
- 1991-12-20 RU SU915010432A patent/RU2086618C1/en active
- 1991-12-23 CZ CS914046A patent/CZ404691A3/en unknown
-
1992
- 1992-10-16 HR HRP921073AA patent/HRP921073A2/en not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5571554A (en) * | 1993-09-16 | 1996-11-05 | Consortium Fur Elektrochemische | Process for reducing the content of triglycerides in egg yolk and in products containing egg yolk |
Also Published As
| Publication number | Publication date |
|---|---|
| HRP921073A2 (en) | 1995-02-28 |
| HUT61163A (en) | 1992-12-28 |
| ATE117357T1 (en) | 1995-02-15 |
| PL292867A1 (en) | 1992-08-24 |
| PL165829B1 (en) | 1995-02-28 |
| CZ404691A3 (en) | 1993-01-13 |
| ZA919676B (en) | 1992-09-30 |
| IE65633B1 (en) | 1995-11-01 |
| DE4041386A1 (en) | 1992-06-25 |
| IE914214A1 (en) | 1992-07-01 |
| NO915069D0 (en) | 1991-12-20 |
| AU640837B2 (en) | 1993-09-02 |
| DE59104331D1 (en) | 1995-03-02 |
| EP0492475B1 (en) | 1995-01-18 |
| NZ240920A (en) | 1993-04-28 |
| DK0492475T3 (en) | 1995-05-29 |
| HU914055D0 (en) | 1992-03-30 |
| AU8963091A (en) | 1992-06-25 |
| RU2086618C1 (en) | 1997-08-10 |
| EP0492475A1 (en) | 1992-07-01 |
| ES2067840T3 (en) | 1995-04-01 |
| JPH04296396A (en) | 1992-10-20 |
| NO915069L (en) | 1992-06-22 |
| HU208474B (en) | 1993-11-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |