EP0723596A1 - Verfahren zur enzymatischen umsetzung von triglyceriden aus fett, insbesondere milchfett - Google Patents

Verfahren zur enzymatischen umsetzung von triglyceriden aus fett, insbesondere milchfett

Info

Publication number
EP0723596A1
EP0723596A1 EP94931065A EP94931065A EP0723596A1 EP 0723596 A1 EP0723596 A1 EP 0723596A1 EP 94931065 A EP94931065 A EP 94931065A EP 94931065 A EP94931065 A EP 94931065A EP 0723596 A1 EP0723596 A1 EP 0723596A1
Authority
EP
European Patent Office
Prior art keywords
latex
fat
enzymatic
triglycerides
reaction system
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.)
Withdrawn
Application number
EP94931065A
Other languages
English (en)
French (fr)
Inventor
Jean Emile Graille
Didier Jean-Luc Montet
Catherine Lucette Ozenne
Gilles François LAMBERET
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Institut National de la Recherche Agronomique INRA
Centre de Cooperation Internationalel en Recherche Agronomique pour le Development CIRAD
Original Assignee
Institut National de la Recherche Agronomique INRA
Centre de Cooperation Internationalel en Recherche Agronomique pour le Development CIRAD
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Institut National de la Recherche Agronomique INRA, Centre de Cooperation Internationalel en Recherche Agronomique pour le Development CIRAD filed Critical Institut National de la Recherche Agronomique INRA
Publication of EP0723596A1 publication Critical patent/EP0723596A1/de
Withdrawn legal-status Critical Current

Links

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

Landscapes

  • 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)
EP94931065A 1993-10-14 1994-10-14 Verfahren zur enzymatischen umsetzung von triglyceriden aus fett, insbesondere milchfett Withdrawn EP0723596A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9312209 1993-10-14
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.
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

Publications (1)

Publication Number Publication Date
EP0723596A1 true EP0723596A1 (de) 1996-07-31

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP94931065A Withdrawn EP0723596A1 (de) 1993-10-14 1994-10-14 Verfahren zur enzymatischen umsetzung von triglyceriden aus fett, insbesondere milchfett

Country Status (5)

Country Link
EP (1) EP0723596A1 (de)
AU (1) AU7995994A (de)
CA (1) CA2174208A1 (de)
FR (1) FR2711142B1 (de)
WO (1) WO1995010626A1 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102004044428A1 (de) * 2004-09-14 2006-03-30 Toximed Gmbh Verfahren und pharmazeutischer Wirkstoff zur Bekämpfung von Plasmodien

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3190753A (en) * 1963-05-20 1965-06-22 Carnation Co Process for modifying milk fat
YU40433B (en) * 1975-02-20 1986-02-28 Lek Tovarna Farmacevtskih Process for obtaining pure, proteolytically active anzymes
CA1136920A (en) * 1979-12-14 1982-12-07 Masanobu Yamamoto Fish canning process
JPS57156482A (en) * 1981-03-20 1982-09-27 Koichi Ogawa Concentrating and purifying method of tocopherol

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9510626A1 *

Also Published As

Publication number Publication date
FR2711142B1 (fr) 1996-01-05
WO1995010626A1 (fr) 1995-04-20
FR2711142A1 (fr) 1995-04-21
AU7995994A (en) 1995-05-04
CA2174208A1 (en) 1995-04-20

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