WO1995010626A1 - Procede pour la transformation enzymatique des triglycerides d'une matiere grasse, en particulier la matiere grasse laitiere - Google Patents
Procede pour la transformation enzymatique des triglycerides d'une matiere grasse, en particulier la matiere grasse laitiere Download PDFInfo
- Publication number
- WO1995010626A1 WO1995010626A1 PCT/FR1994/001192 FR9401192W WO9510626A1 WO 1995010626 A1 WO1995010626 A1 WO 1995010626A1 FR 9401192 W FR9401192 W FR 9401192W WO 9510626 A1 WO9510626 A1 WO 9510626A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- latex
- fat
- enzymatic
- triglycerides
- reaction system
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 31
- 230000002255 enzymatic effect Effects 0.000 title claims abstract description 28
- 150000003626 triacylglycerols Chemical class 0.000 title claims abstract description 24
- 230000009466 transformation Effects 0.000 title claims abstract description 16
- 235000013365 dairy product Nutrition 0.000 title abstract description 4
- 239000004816 latex Substances 0.000 claims abstract description 42
- 229920000126 latex Polymers 0.000 claims abstract description 42
- 239000000758 substrate Substances 0.000 claims abstract description 26
- 238000002360 preparation method Methods 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 22
- 229930195729 fatty acid Natural products 0.000 claims abstract description 22
- 239000000194 fatty acid Substances 0.000 claims abstract description 22
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 16
- 238000009884 interesterification Methods 0.000 claims abstract description 15
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 10
- 238000012546 transfer Methods 0.000 claims abstract description 9
- 125000002252 acyl group Chemical group 0.000 claims abstract description 7
- -1 fatty acid esters Chemical class 0.000 claims abstract description 6
- 210000002966 serum Anatomy 0.000 claims abstract description 4
- 241000219172 Caricaceae Species 0.000 claims abstract description 3
- 241000221017 Euphorbiaceae Species 0.000 claims abstract description 3
- 240000006432 Carica papaya Species 0.000 claims description 15
- 235000009467 Carica papaya Nutrition 0.000 claims description 15
- 235000021243 milk fat Nutrition 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 14
- 230000000694 effects Effects 0.000 claims description 13
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 claims description 13
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 claims description 12
- 102000004190 Enzymes Human genes 0.000 claims description 9
- 108090000790 Enzymes Proteins 0.000 claims description 9
- 235000013311 vegetables Nutrition 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000008346 aqueous phase Substances 0.000 claims description 4
- 239000012071 phase Substances 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 3
- 238000004108 freeze drying Methods 0.000 claims description 2
- 241000093828 Euphorbia characias subsp. characias Species 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 abstract description 8
- 235000013305 food Nutrition 0.000 abstract description 6
- 238000012545 processing Methods 0.000 abstract description 2
- 239000003925 fat Substances 0.000 description 18
- 235000019197 fats Nutrition 0.000 description 18
- 229940088598 enzyme Drugs 0.000 description 8
- 102000004882 Lipase Human genes 0.000 description 7
- 108090001060 Lipase Proteins 0.000 description 7
- 239000004367 Lipase Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 235000019421 lipase Nutrition 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 102000057234 Acyl transferases Human genes 0.000 description 5
- 108700016155 Acyl transferases Proteins 0.000 description 5
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 235000021391 short chain fatty acids Nutrition 0.000 description 4
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 4
- 229960002703 undecylenic acid Drugs 0.000 description 4
- 239000012510 hollow fiber Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000005924 transacylation reaction Methods 0.000 description 3
- ANLABNUUYWRCRP-UHFFFAOYSA-N 1-(4-nitrophenyl)cyclopentane-1-carbonitrile Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1(C#N)CCCC1 ANLABNUUYWRCRP-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 208000031968 Cadaver Diseases 0.000 description 2
- 241000221081 Euphorbia characias Species 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 210000000720 eyelash Anatomy 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 150000004666 short chain fatty acids Chemical class 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- DUXYWXYOBMKGIN-UHFFFAOYSA-N trimyristin Chemical compound CCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCC DUXYWXYOBMKGIN-UHFFFAOYSA-N 0.000 description 2
- XPQPWPZFBULGKT-UHFFFAOYSA-N undecanoic acid methyl ester Natural products CCCCCCCCCCC(=O)OC XPQPWPZFBULGKT-UHFFFAOYSA-N 0.000 description 2
- QDICJGWYEVKHJA-UHFFFAOYSA-N (1-butanoyloxy-3-hexadecanoyloxypropan-2-yl) octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)CCC)COC(=O)CCCCCCCCCCCCCCC QDICJGWYEVKHJA-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 241001133760 Acoelorraphe Species 0.000 description 1
- 244000099147 Ananas comosus Species 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- UDHXJZHVNHGCEC-UHFFFAOYSA-N Chlorophacinone Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)C(=O)C1C(=O)C2=CC=CC=C2C1=O UDHXJZHVNHGCEC-UHFFFAOYSA-N 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 102000004157 Hydrolases Human genes 0.000 description 1
- 108090000604 Hydrolases Proteins 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 108700014220 acyltransferase activity proteins Proteins 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 108010011222 cyclo(Arg-Pro) Proteins 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940079919 digestives enzyme preparation Drugs 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 239000003264 margarine Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000014594 pastries Nutrition 0.000 description 1
- 230000002797 proteolythic effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229940113164 trimyristin Drugs 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6458—Glycerides by transesterification, e.g. interesterification, ester interchange, alcoholysis or acidolysis
Definitions
- the present invention relates to a new process for the enzymatic transformation of the triglycerides of a fat, in particular milk fat.
- This process finds particular application for the modification of the rheological properties of milk fat as well as of its fractions known under the name of olein and stearin.
- this process can be used to form, from an olein of milk fat, a fat whose rheological behavior is close to that of a stearin.
- this process can be used in the food industry to recover various fats, by selectively exchanging or replacing some of the fatty acids constituting the triglycerides of these fats with fatty acids of other kinds. , so as to modify the rheological and / or nutritional properties of the treated fatty matter.
- this process makes it possible to replace part of the short-chain fatty acids with unsaturated fatty acids, the consumption of which is recommended for health.
- the transformation of fats by the enzymatic route, and in particular by transfer of acyls, interesterification, transesterification or intrainteresterification has been the subject of numerous studies.
- the methods described in the state of the art comprise the use of various enzymatic preparations, in a reaction system comprising said fatty material alone (transacylation or intrainteresterification) or in mixture with a co-substrate chosen from fatty acids (transesterification), fatty acid esters where another fat (interesterification).
- Interesterification methods are for example described in documents GB-1577933 and EP-0035883, and a transesterification method is for example described in document GB-2236 537.
- lipases which can be regioselective (that is to say which make it possible to transfer acids found in a specific position, in particular in position 1 and / or in position 3, on triglycerides) ?
- lipases capable of being used for the transformation of triglycerides can be of various origins, but all the illustrative examples use purified lipases of microbial origin.
- the enzymatic preparation is prepared according to a specific process comprising the dispersion, adsorption or binding of the enzyme in or on a support, in an aqueous medium, then drying of the mixture thus obtained at a controlled slow speed.
- plant latexes as well as their serum and coagulum, i.e. in fact unpurified vegetable enzyme preparations, can be successfully used for processing enzymatic of triglycerides of various fats, and in particular of milk fat.
- the originality of the present invention therefore lies in the fact that nothing suggested that enzymatic preparations based on plant latex, known for their proteolytic activity could manifest acyltransferase activity, in particular in the presence of a limited aqueous phase, similar to that of lipases, all the more so since until now no one has isolated latex lipase.
- the present application aims to cover a process for the enzymatic transformation of triglycerides of a main fatty matter by transfer of acyls, interesterification, transesterification or intrainteresterification, of the type comprising the use of a preparation enzymatic in a reaction system comprising said main fatty material alone or in admixture with a co-substrate chosen from fatty acids, fatty acid esters, or a secondary fatty material, characterized in that said enzymatic preparation comprises a vegetable latex, or a serum or coagulum thereof.
- the main fat capable of being treated by the process according to the invention can be of various types and origins.
- the main fat will be chosen from milk fat, its olein or its stearin.
- the nature and origin of the secondary fat that may be used can be varied.
- secondary fat mention may be made of: sunflower, palm, coconut, rapeseed, soybean oils, etc.
- the fatty acids or esters of fatty acids can be varied.
- fatty examples mention will be made of the total fatty acids of any edible or officinal or synthetic fatty substance such as undecylenic acid, for non-food uses, and as examples of fatty acid esters, mention will be made the ethyl, isopropyl or methyl esters of these acids depending on whether the objective is food or non-food.
- the plant latex capable of being used in the context of the present invention can come from various laticiferous plants. Preferably, it will be a latex of Euphorbiaceae or Caricaceae, and in particular a latex of Euphorbia characias or Carica papaya.
- the plant latexes and in particular the Carica papaya latex have a high regiospecificity for position 3 and / or a very strong typoselectivity for short chains ( from 4 to 10 carbon atoms), which is particularly interesting in the case of milk fat where it is sought to change the short chain fatty acids occupying mainly position 3.
- the abovementioned latex is in dry form, for example in the form of a powder, preferably obtained by lyophilization.
- dry form is meant a latex whose residual moisture content is less than or equal to about 15%, and preferably less than 10%.
- the enzymatic preparation containing the vegetable latex comes from an aqueous phase whose pH is between 5.5 and 9, so as to confer a pH corresponding to the aqueous phase of the reaction system, even if that -this is quantitatively limited.
- this enzyme preparation can be made magnetic, so as to facilitate its removal from the reaction system.
- the water activity (a w ) of the reaction system is between 0.1 and 0.6 and preferably close to 0.3, and when the temperature of the reaction system is between 10 and 90 ° C, preferably between 50 and # 70 C. in general, these ranges or values of the water activity of the reaction system corresponds to a water content of fat between 0.05 and 0.02% and preferably of the order of 0.1%.
- the activity of water is defined as the ratio of the water vapor pressure of a solution or a powder to the partial water vapor pressure of pure water at the same temperature.
- the measurements are made at 40 ° C. using a device of the type
- the molar ratio between the substrate, that is to say the main fat, and the co-substrate will be between 10: 1 and 1:10 and the amount of enzyme preparation used will be of the order of 0.5 to 10% by weight relative to the total weight of the substrate and of the co-substrate forming the fatty phase.
- the process according to the present invention will advantageously be carried out continuously on a fixed bed composed of the enzyme preparation alone or in admixture with a support.
- support By way of example of support, mention may be made of celluloses, celite, silicas, aluminas, hollow fibers, etc.
- the present application aims to cover the use of plant latexes as an enzymatic system allowing the transformation of the triglycerides of a fatty material by transfer of acyls, interesterification or transesterification or intrainteresterification.
- the percentages are expressed in molar percentages for the substrates and the co-substrates, and in percentage by weight for the enzymatic preparation.
- BT. triglyceride
- MGL milk fat
- the triglyceride fraction is separated at the end of the reaction by thin layer chromatography.
- fatty acid analysis of these triglycerides can then be carried out in a manner known per se, for example by gas chromatography:
- This experimental protocol makes it possible, in general, to measure the acyltransferase activity of a given latex by "opposing" the triglycerides of a given fat, as the case may be, to a free fatty acid, in particular undecynelic acid. , or its methyl ester.
- EXAMPLE 2 The influence of the temperature and of the substrate / co-substrate molar ratio on the interesterification of a milk fat catalyzed by the latex of Carica papaya of Example 1 was studied.
- the co-substrate used is methyl undecylenate.
- the molar ratio substrate / co-substrate was set at 1/1, then 1/2, and the temperature was varied from 25 to 70 ° C, the reaction time being set at 16 hours.
- the results obtained have been collated in Table I below. We see that we incorporate more Cll: l with the ratio 1/2 and that the optimal temperature is 60 * C.
- Example 2 The experimental protocol of Example 2 was reproduced, using as co-substrate undecylenic acid (Cll: 1 AG) in a substrate / co-substrate molar ratio equal to 1/2.
- Cll co-substrate undecylenic acid
- EXAMPLE 4 Examples 2 and 3 were reproduced using a less "raw" Carica papaya latex, namely the latex sold under the name SIGMA P3375.
- Examples 2 and 3 were reproduced, replacing the latex of Carica papaya with a lyophilized latex of Euphorbia characias harvested in the region of opponent.
- Dairy fat olein 19 is opposed to palm fatty acids, in 1/2, 1/1 and 2/1 molar ratios.
- the dropping point passes 19 to 34 * C, to the triglycerides obtained after neutralization.
- This example shows the many possibilities of industrial applications of the process according to the present invention, for example in the field of basic preparation for table margarine, pastries or other food products.
- the enzyme preparation used comprises a Carica papaya latex sold under the name SIGMA P3250 attached to hollow fibers sold by the company MERCK under the name DYNAGARD.
- the reaction is carried out in batch; the quantity of enzymatic preparation (fixed latex) being chosen so as to be sufficient to use 3% by weight of latex relative to the fatty phase.
- the triglycerides of milk fat were opposed to undecylenic acid.
- Table VI below shows that excellent results, comparable to those obtained with free latex, can be obtained with an enzymatic preparation comprising latex fixed on hollow fibers.
- olein 22 from milk fat was opposed to palm olein or palm stearin.
- the reaction was carried out in the presence of Carica papaya latex sold under the name SIGMA P3250 at 60 ° C., for a period of 6 hours 30 minutes.
- Oleine AG "Oleine” "MGLA stearin from palm to palm from palm to palm
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Edible Oils And Fats (AREA)
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU79959/94A AU7995994A (en) | 1993-10-14 | 1994-10-14 | Method for the enzymatic transformation of triglycerides in a fat, in particular dairy fat |
EP94931065A EP0723596A1 (fr) | 1993-10-14 | 1994-10-14 | Procede pour la transformation enzymatique des triglycerides d'une matiere grasse, en particulier la matiere grasse laitiere |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9312209A FR2711142B1 (fr) | 1993-10-14 | 1993-10-14 | Procédé pour la transformation enzymatique des triglycérides d'une matière grasse, en particulier la matière grasse laitière. |
FR93/12209 | 1993-10-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1995010626A1 true WO1995010626A1 (fr) | 1995-04-20 |
Family
ID=9451806
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR1994/001192 WO1995010626A1 (fr) | 1993-10-14 | 1994-10-14 | Procede pour la transformation enzymatique des triglycerides d'une matiere grasse, en particulier la matiere grasse laitiere |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0723596A1 (fr) |
AU (1) | AU7995994A (fr) |
CA (1) | CA2174208A1 (fr) |
FR (1) | FR2711142B1 (fr) |
WO (1) | WO1995010626A1 (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006029605A1 (fr) * | 2004-09-14 | 2006-03-23 | Toximed Gmbh | Procede et principe actif pour lutter contre les plasmodies |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3190753A (en) * | 1963-05-20 | 1965-06-22 | Carnation Co | Process for modifying milk fat |
FR2301267A1 (fr) * | 1975-02-20 | 1976-09-17 | Lek Tovarna Farmacevtskih | Obtention d'enz |
JPS57156482A (en) * | 1981-03-20 | 1982-09-27 | Koichi Ogawa | Concentrating and purifying method of tocopherol |
CA1136920A (fr) * | 1979-12-14 | 1982-12-07 | Masanobu Yamamoto | Procede de conservation du poisson |
-
1993
- 1993-10-14 FR FR9312209A patent/FR2711142B1/fr not_active Expired - Fee Related
-
1994
- 1994-10-14 EP EP94931065A patent/EP0723596A1/fr not_active Withdrawn
- 1994-10-14 CA CA002174208A patent/CA2174208A1/fr not_active Abandoned
- 1994-10-14 WO PCT/FR1994/001192 patent/WO1995010626A1/fr not_active Application Discontinuation
- 1994-10-14 AU AU79959/94A patent/AU7995994A/en not_active Abandoned
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3190753A (en) * | 1963-05-20 | 1965-06-22 | Carnation Co | Process for modifying milk fat |
FR2301267A1 (fr) * | 1975-02-20 | 1976-09-17 | Lek Tovarna Farmacevtskih | Obtention d'enz |
CA1136920A (fr) * | 1979-12-14 | 1982-12-07 | Masanobu Yamamoto | Procede de conservation du poisson |
JPS57156482A (en) * | 1981-03-20 | 1982-09-27 | Koichi Ogawa | Concentrating and purifying method of tocopherol |
Non-Patent Citations (3)
Title |
---|
C.R. ACAD. SCI., SER III, vol. 314, no. 8, 1992, pages 337 - 342 * |
CHEMICAL ABSTRACTS, vol. 117, no. 5, 3 August 1992, Columbus, Ohio, US; abstract no. 43208a, MOULIN,ANDRE ET AL.: "Purification of a lipase from the latex of Euphorbia characias using an apolar solvent extraction method." page 388; * |
CHEMICAL ABSTRACTS, vol. 98, no. 17, 25 April 1983, Columbus, Ohio, US; abstract no. 143683j, page 605; * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006029605A1 (fr) * | 2004-09-14 | 2006-03-23 | Toximed Gmbh | Procede et principe actif pour lutter contre les plasmodies |
Also Published As
Publication number | Publication date |
---|---|
CA2174208A1 (fr) | 1995-04-20 |
AU7995994A (en) | 1995-05-04 |
EP0723596A1 (fr) | 1996-07-31 |
FR2711142A1 (fr) | 1995-04-21 |
FR2711142B1 (fr) | 1996-01-05 |
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