WO2003040275A1 - Graisses et huiles riches en esters d'acides gras isoprenoides lineaires et leur procede de production - Google Patents

Graisses et huiles riches en esters d'acides gras isoprenoides lineaires et leur procede de production Download PDF

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Publication number
WO2003040275A1
WO2003040275A1 PCT/JP2002/011607 JP0211607W WO03040275A1 WO 2003040275 A1 WO2003040275 A1 WO 2003040275A1 JP 0211607 W JP0211607 W JP 0211607W WO 03040275 A1 WO03040275 A1 WO 03040275A1
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fatty acid
fats
oil
isoprenoid
oils
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PCT/JP2002/011607
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English (en)
Japanese (ja)
Inventor
Gou Shinohara
Chiemi Satou
Seiichi Shirasawa
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The Nisshin Oillio,Ltd.
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Priority to JP2003542315A priority Critical patent/JPWO2003040275A1/ja
Publication of WO2003040275A1 publication Critical patent/WO2003040275A1/fr

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    • 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
    • C12P7/62—Carboxylic acid esters
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • 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
    • C12P7/6454—Glycerides by esterification

Definitions

  • the present invention relates to fats and oils containing a large amount of chain isoprenoid fatty acid esters and a process for producing the same, and also relates to chain isoprenoid fatty acid esters obtained by isolating from the fats and oils containing a large amount of chain isoprenoid fatty acid esters. And its manufacturing method.
  • Isoprenoids are a general term for a group of natural organic compounds whose constituent units are isoprene (C5H8). Monoterpenes (C10), sesquiterpenes (C15), diterpenes (C20), Evening terpenes such as terpenes (C25) and triterpenes (C30), various steroids derived from squalene of C30, carotenoids of C40 ⁇ various polyprenols ranging from C30 to C120, and the molecular weight It is said that there are more than about 20,000 types of isoprenoids that exist in nature, up to 100,000 natural rubbers.
  • chlorophyll which has an isoprenoid in part of its structure, and bisubimine K1, K2, and complex isoprenoids such as ubiquinone and menaquinone are also naturally present in a wide variety of forms, such as in photosynthesis and electron transport. It is responsible for important biological functions in the body.
  • prenylated protein modified with a phenylesyl group (C 15) or geranylgeranyl group (C 20) plays an essential role in the cancer gene product Ras and G proteins important for signal transduction.
  • the physiological functions of isoprenoids have been elucidated.
  • An object of the present invention is to provide an oil or fat containing a high content of chain isoprenoid fatty acid esters and a method for producing the same.
  • the present inventors have conducted intensive studies to achieve the above object, and as a result, using a carboxylic acid ester hydrolytic enzyme, a chain isoprenoid alcohol, a fatty acid, a fatty acid methyl ester, a fatty acid ethyl ester, From one or more of the group consisting of monoglycerides, diglycerides, and triglycerides and fats and oils containing these, it is possible to easily obtain fats and oils high in the chain isoprenoid fatty acid ester represented by the following general formula (II). They have found that they can do this and have completed the present invention.
  • the present invention is characterized by being obtained by treating the following components (A) and (B) as raw materials with a carboxylic acid ester hydrolase, and selecting from linear isoprenoid fatty acid esters.
  • Fats or oils containing more than one kind of fats and oils more than ordinary fats and oils preferably obtained by treating with carboxylesterase and / or triacyl "lycerol lipase as carboxylic ester hydrolase.
  • the present invention relates to a method for producing fats and oils containing one or more kinds selected from chain isoprenoid fatty acid esters in comparison with ordinary fats and oils.
  • n any one integer selected from 1 to 14.
  • (B) One or more of the group consisting of fatty acids, fatty acid methyl esters, fatty acid ethyl esters, monoglycerides, diglycerides, and triglycerides, and fats and oils containing these.
  • oils and fats to be used are preferably vegetable oils which contain a small amount of chain isoprenoid fatty acid esters, and if edible, can be used as they are as edible oils.
  • linear isoprenoid alcohols examples include geraniol, fuarnesol, geranylgeranol, geranylfurnesol, fuarnesyl fuarnesol, geranylgeranyl fuarnesol geranyl fuarnesyl fuarnesol, and fuarnesol. It is preferable to use one or two or more selected from the group consisting of nesyl phenyl nesyl phenyls, phthals and dihydro phthals. As the fatty acid used, a fatty acid having 2 to 30 carbon atoms is preferable.
  • the fatty acid residue has 2 carbon atoms. It is preferably ⁇ 30.
  • the fats and oils containing high content of chain isoprenoid fatty acid esters obtained in this way may be subjected to concentration and Z or purification treatment in order to further increase the concentration thereof, whereby the chain isoprenoid fatty acid ester having a higher concentration is obtained. Fats and oils with a high content can be suitably obtained. Further, by further isolation, chain-like isoprenoid fatty acid esters can be obtained very easily and inexpensively.
  • the present invention relates to a method for producing a fatty acid / fat having a high content of linear isoprenoid fatty acid esters, which comprises treating the above components (A) and (B) as raw materials with a carboxylic ester hydrolase.
  • the present invention relates to a chain isoprenoid fatty acid ester-rich fat or oil obtained by treating the following components (A) and (B) as raw materials with a carboxylic ester hydrolase.
  • n any one integer selected from 1 to 14.
  • (B) One or more of the group consisting of fatty acids, fatty acid methyl esters, fatty acid ethyl esters, monoglycerides, diglycerides, and triglycerides, and fats and oils containing these.
  • chain isoprenoid fatty acid ester refers to a substance having a structure resulting from dehydration condensation from a chain of isoprenoid alcohol and a fatty acid.
  • the chain isoprenoid alcohol generally refers to one having a chain structure in which a plurality of isoprene units having 5 carbon atoms are bonded and having a hydroxyl group.
  • the ester form refers to an ester form which can be formed from a hydroxyl group of a chain isoprenoid alcohol and a carboxyl group of a fatty acid.
  • the carboxylate hydrolase used in the present invention may be of any origin, such as animals, plants, and microorganisms, and may be extracted and purified from the tissue or culture solution by a conventional method, and may be prepared. It is convenient to use commercially available products. In addition, any of these enzymes which are immobilized, those which are not immobilized, and those which are not immobilized can be suitably used, but immobilized enzymes are preferred from the viewpoint of ease of use.
  • carboxylic ester hydrolase used in the present invention carboxyesterase and / or triacylglycerol lipase are preferable.
  • Carboxylesterases are generally enzymes that hydrolyze fatty acid monoesters into alcohols and fatty acids.
  • Triacylglycerol lipase is an enzyme that generally catalyzes the hydrolysis of fats (triglycerides) into fatty acids and glycerol. It is.
  • the carboxylesterase and / or triacylglycerol lipase used in the present invention may be of any origin such as animals, plants, and microorganisms, and is not limited to the following.
  • Carboxylesterase and / or triacylglycerol lipase derived from malt, castor seed, etc. Aspenole: Zoles Niger, A sperg 111 usiiiger), Candy Evening, Candidacy 1 indracea, Candy Da An Evening — Cutica (C and idaantarctica), Rhizopus delemar (R hizopusde 1 emar), Rhizopus jyanicas (R hizopusj avanicus) Pannare force Alcal igenes esp.
  • the chain isoprenoid alcohol used as a raw material of the present invention is not particularly limited as long as it is represented by the following general formula (I).
  • n any one integer selected from 1 to 14.
  • the raw material of the present invention is not particularly limited as long as it is one or more of fatty acids, fatty acid methyl esters, fatty acid ethyl esters, monoglycerides, diglycerides, triglycerides, and fats and oils containing these.
  • the fats and oils may be any of crude oils, unrefined fats and oils in the middle of refining, refined fats and oils, for example, soybean oil, rapeseed oil, cottonseed oil, castor oil, safflower oil, sesame oil, orip oil, Vegetable oils such as linseed oil, rice oil, palm oil, cocoa butter, and kapok oil; animal fats and oils such as lard, beef tallow, fish oil, etc., but there is no particular limitation.
  • MCT, MLC Ts diglyceride, monoglyceride II, structural fats and oils with designed fatty acid structures, and the like.
  • vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, castor oil, safflower oil, sesame oil, olive oil, linseed oil, rice oil, palm oil, cocoa butter, and kapok oil are preferred, and most preferred.
  • vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, castor oil, safflower oil, sesame oil, olive oil, linseed oil, rice oil, Vegetable oils such as palm oil, cocoa butter and kapok oil are preferred.
  • the fatty acid used as a raw material of the present invention is not particularly limited as long as it is a fatty acid having a carbon number in the range of 2 to 30; for example, acetic acid, butyric acid, caproic acid, caprylic acid, Strength acid, pendecanoic acid, lauric acid, tridecanoic acid, myristic acid, pendecanoic acid, normitic acid, margaric acid, stearic acid, nonadecanoic acid, arakidic acid, behenic acid, lignoceric acid, serotinic acid, montanic acid, Straight-chain saturated fatty acids such as melicic acid, succinic acid, lindelic acid, pedic acid, olemic oleic acid, oleic acid, elaidic acid, paxenic acid, cis vaccenic acid, petroselinic acid, gadoleic acid, eicosenoic acid, L-force Monounsaturated fatty acids such as acid,
  • Branched fatty acids such as butyric acid, isovaleric acid, isoacids, antiisoic acids, etc., hydroxy fatty acids such as polyhydroxy acids, / 5-hydroxy acids, mycolic acid, polyhydroxy acids, epoxy fatty acids, keto fatty acids, cyclic fatty acids, etc.
  • linear fatty acids are preferable from the viewpoint of natural abundance and the like, and linear unsaturated fatty acids are more preferable.
  • palmitooleic acid and o Mono-unsaturated fatty acids such as innoic acid, noxenoic acid, and erlic acid, n-6 unsaturated fatty acids such as linoleic acid, arlinolenic acid, bishomo-arenolenic acid, and arachidonic acid; hy-linolenic acid, stearidonic acid; N-3 unsaturated fatty acids such as eicosatetraenoic acid, eicosapenic acid, docosapenic acid, and docosahexanoic acid; conjugated linoleic acid; conjugated S-fatty acid such as hyi-eleostearic acid; preferable.
  • Examples of the fatty acid residue constituting the fatty acid methyl ester used as a raw material of the present invention include the fatty acid residues mentioned in the description of the fatty acid.
  • Examples of the fatty acid residue constituting the fatty acid ethyl ester used as a raw material of the present invention include the fatty acid residues described in the description of the fatty acid.
  • the monoglyceride used as a raw material in the present invention may be any of 1-monoglyceride and 2-monoglyceride.
  • examples of the moon fatty acid residue constituting the monoglyceride include the fatty acid residues mentioned in the description of the fatty acid.
  • the diglyceride used as a raw material of the present invention may be any of 1,2-diglyceride and 1,3-diglyceride.
  • the fatty acid residues constituting the diglyceride at this time include the fatty acid residues mentioned in the description of the fatty acid, and the combination thereof is not particularly limited.
  • Examples of the fatty acid residue constituting the triglyceride used as a raw material of the present invention include the fatty acid residues mentioned in the description of the fatty acid, and the combination thereof is not particularly limited.
  • the chain isoprenoid fatty acid ester-rich fats and oils described so far can be mis- and / or purified, if necessary, to obtain a further high-content fat and oil.
  • concentration and / or purification in general, for example, fractional distillation, fractional sublimation, zone melting, solvent extraction, various adsorption methods, foam separation method, membrane separation method, molecular sieve And a method using chromatography.
  • the oil-and-fat having a high content of chain isoprenoid fatty acid esters of the present invention is characterized by being obtained by treating the above components (A) and (B) as raw materials with a carboxylic ester hydrolase. This is because, for example, the chain obtained by the chemical synthesis method from the component (A) and the component (B) can be obtained by the chemical synthesis method directly from the oil and fat containing high chain isoprenoid fatty acid esters.
  • the isoprenoid fatty acid ester-rich fats and oils are mixed with each other in component (A) or component (B)
  • a non-selective reaction between the two forms a side reaction product, which is not preferable because it may be difficult to suitably obtain the desired linear isoprenide lunar fatty acid esters.
  • undesirable side reaction products are contained as fats and oils, and a step of producing fats and oils again is required to remove these side reaction products.
  • component (A) and component (B) are selected in the reaction process.
  • the components (A) and (B) do not undergo oxidative deterioration, etc., so that they can be used in the same manner as ordinary fats and oils.
  • fats and oils obtained through such a process cannot be used as edible oils in particular, but the fats and oils high in the chain isoprenoid fatty acid esters of the present invention are To get From using enzyme, excellent in safety, preferable particularly when Ru is used as edible oil.
  • the content of the chain isoprenoid fatty acid ester in the oil and fat having a high content of the chain isoprenoid fatty acid ester of the present invention is not particularly limited.However, for example, in consideration of practical use such as edible, medical and cosmetic use, and cosmetic use. When put, it is preferable that the fats and oils are refined, and in such a case, the content is, for example, 0.0001 to 50% by mass, preferably 0.0005 to 45% by mass.
  • chain isoprenoid fatty acid esters are concentrated and / or purified as required, they may be concentrated and / or purified as necessary, and are not particularly limited. For example, 0.01 to 90% by mass, Preferably 0.0
  • the present invention provides a method for producing a chain-type isoprenoid fatty acid ester-rich fat or oil, comprising treating the following components (A) and (B) as raw materials with a carboxylic ester hydrolase. About the method.
  • n any one integer selected from 1 to 14.
  • (B) One or more of the group consisting of fatty acids, fatty acid methyl esters, fatty acid ethyl esters, monoglycerides, diglycerides, and triglycerides, and fats and oils containing these.
  • the raw material component (A) is as described above, and is not particularly limited as long as it is represented by the general formula (I). Geraniol, farnesol, geranylgeranol, geranyl fuarnesol, Arnesyl arnesol, geranyl geranyl arnesol, geranyl arnesyl arnesol, arnesilfa Renesyl arnesol, phytol and dihydrophytol are preferred, and geranylgeradiol is particularly preferred.
  • the raw material component (B) is not particularly limited as long as it is a fatty acid, a fatty acid methyl ester, a fatty acid ethyl ester, a monoglyceride, a diglyceride, a triglyceride, or an oil or fat containing them, and is a crude oil or an unrefined oil. Any of fats and oils, fats and oils in the middle of purification, refined fats and the like may be used, but from the viewpoint of reactivity, triglycerides are particularly preferred, and for example, fats and oils having high triglyceride content are preferred.
  • the fat or oil having a high triglyceride content is not necessarily specified because it may be selected according to the properties of the required fat and the like.
  • the triglyceride content is 90% by mass or more, preferably 95% by mass or more. Is preferably 97% by mass or more.
  • these triglycerides are mainly used, the reactivity is very high, and the desired product can be obtained in a yield of nearly 100%, which is very preferable.
  • chain isoprenoid fatty acid ester-rich fats and oils of the present invention one or more selected from chain isoprenoid alcohols, and fatty acids, fatty acid methyl esters, fatty acid ethyl esters, monoglycerides, diglycerides, triglycerides
  • the mixing ratio of one or more selected from the following can be set arbitrarily because it depends on the form of the target final product, the reaction efficiency, etc.
  • one or more selected from linear isoprenoid alcohols one or more selected from fatty acids, fatty acid methyl esters, fatty acid ethyl esters, monoglycerides, diglycerides, and triglycerides (mass: mass ), For example, 10:;! ⁇ 1: 1 000 000, preferably 5: 1 to 1: 1 000 000, more preferably 2: 1 to 1: 1 000 000.
  • geranylgeranol is used as the raw material component (A), and triglyceride and an oil having a triglyceride content of 90% or more are used as the raw material component (B).
  • the mixing ratio is as follows: geranylgeranol: triglyceride (mass: mass), for example, 1: 1 to: L: 100000, preferably 1: 1 to L : 1 000 000, more preferably 1: 1 to 1: 1 000 000.
  • a hydrophobic organic solvent is preferable as the solvent used in the production of the present invention.
  • Examples include ethyl, propyl acetate, butyl acetate, benzene, toluene, xylene and the like, and particularly preferred are hexane, heptane, octane and isooctane.
  • the amount of the enzyme to be used depends on the type of the enzyme, the reactivity, the content of additives such as the immobilizing agent, etc., and is not specified unconditionally. However, the amount is not limited to the following. 0.01 to 100 times (mass), preferably 0.01 to 100 times (mass), more preferably 0.1 to 25 times (mass) If this happens, the reaction will proceed efficiently.
  • the time required for the reaction depends on the degree of progress of the reaction and the amount of the target product, and is not unequivocally defined, but is, for example, 0.5 to 72 hours, preferably 1 to 48 hours, more preferably 1 to 48 hours. If it is 24 hours, it can be balanced with the manufacturing cost.
  • the temperature depends on the degree of progress of the reaction and the amount of the target product, and is not generally defined, but is, for example, 20 to 80 ° C, preferably 25 to 75 ° C, and more preferably 3 to 75 ° C.
  • the temperature is 0 to 70 ° C, the reaction proceeds efficiently.
  • the chain isoprenoid fatty acid ester contained in the chain isoprenoid fatty acid ester-rich fats and oils described above can be obtained as almost a chain isoprenoid fatty acid ester by isolation. It can. That is, the present invention relates to a chain isoprenoid fatty acid ester obtained by isolating from the above-mentioned chain isoprenoid fatty acid ester-rich oil or fat. Isolation methods for this purpose are generally difficult to specify, but include, for example, fractional distillation, fractional sublimation, zone melting, solvent extraction, various adsorption methods, foam separation, membrane separation, separation using molecular sieves, There is a method using chromatography.
  • chromatography is preferred, and adsorption chromatography is more preferred.
  • a method utilizing liquid chromatography is preferred because the linear isoprenoid fatty acid esters in the present invention can be isolated in good yield without decomposing.
  • Specific examples of liquid chromatography include normal-phase liquid chromatography, reversed-phase liquid chromatography, thin-layer chromatography, paper chromatography, and high-performance liquid chromatography (HPLC).
  • HPLC high-performance liquid chromatography
  • any method can be used.
  • normal phase liquid chromatography, reverse phase liquid chromatography, and high performance liquid chromatography (HPLC) are preferable in consideration of the separation ability, the throughput, the number of steps, and the like.
  • normal phase liquid chromatography refers to, for example, the following method. That is, for example, a column was prepared using silica gel as a stationary phase, a mixture of hexane-monoethyl acetate, a mixture of chloroform and methyl alcohol as a mobile phase, and the reaction mixture obtained by the above production method was prepared. The compound is supplied at a load ratio of 0.1 to 5% (wt (mass) / v (volume)), and is subjected to a continuous elution method using a single mobile phase or a stepwise elution method in which the solvent polarity is gradually increased. This is a method to elute the fraction.
  • Reverse phase liquid chromatography refers to, for example, the following method. That is, for example, a column was prepared in which silicic acid (ODS) to which octane decylsilane was bonded was used as a stationary phase, a mixture of water and methanol, a mixture of water and acetonitrile, and a mixture of water and acetone.
  • ODS silicic acid
  • the reaction mixture obtained by the production method is supplied at a load ratio of 0.1 to 5% (wt (mass) / V (volume)), and is continuously eluted with a single solvent or stepwise elution with a stepwise decrease in solvent polarity Is a method for eluting a predetermined fraction.
  • HPLC High-performance liquid chromatography
  • the linear isoprenoid fatty acid esters of the present invention can be highly isolated, and can be obtained in a state in which more impurities are removed. Therefore, it is preferable.
  • the chain-form isoprenoid fatty acid esters obtained as described above are preferable because they can be obtained inexpensively and in large quantities easily, as compared with those obtained by a method such as chemical synthesis.
  • the fats and oils are very inexpensive.
  • the solvent mainly used is an inexpensive solvent such as hexane. Preferred.
  • the use of chemicals is minimal, which is preferable in terms of safety.
  • the chain isoprenide S fatty acid esters obtained as described above can be used as they are, but one or more of them may be added to or contained in other fats and oils according to the purpose. Can also.
  • the chain isoprenoid fatty acid esters are highly isolated, so that unnecessary ones in fats and oils are more removed, This is preferable because it does not add unnecessary color or smell. In this case, it is also preferable in that the content can be easily controlled.
  • the fats and oils thus obtained can also be suitably used.
  • the oil is refined through a generally performed oil / fat refining step, so that it can be used as a normal oil / fat.
  • the chain isoprenoid fatty acid esters obtained by the above method may be used for foods, pharmaceuticals and the like.
  • the present invention relates to fats and oils containing a large amount of chain isoprenoid fatty acid esters and a method for producing the same, and a chain isoprenoid fatty acid ester obtained by isolating from the fats and oils containing a large amount of chain isoprenoid fatty acid esters. And its manufacturing method.
  • ADVANTAGE OF THE INVENTION According to this invention, fats and oils which contain many chain isoprenoid fatty acid esters very simply can be provided.
  • chain isoprenoid fatty acid esters obtained by isolation from these fats and oils can be safely used in forms such as pharmaceuticals, foods and drinks, and external preparations for skin.
  • Geraniol manufactured by Wako Pure Chemical Industries, Ltd.
  • arnesol manufactured by Sigma
  • geranylgeraniol manufactured by Sigma
  • phytol used as a raw material in the following examples
  • Geranylgeraniol 10 Omg and tristearin 90 Omg were dissolved in 1 g of isooctane, Novosam 435 (manufactured by Novo) was added to 1% of the total amount, and the mixture was stirred at 60 ° C for 3 hours. . After confirming that the reaction reached equilibrium by GC, lipase was removed by filtration from the reaction solution diluted with 10 times the amount of hexane, and hexane was distilled off by vacuum distillation to produce a crude reaction. I got something. Purification by silica gel column chromatography gave 187 mg of geranylgeranyl stearate. Example 9 Geranylgeranyl Oleate
  • the mixing ratio required for the reaction between the linear isoprenoid alcohols, fatty acids, triglycerides, etc., and the fats and oils containing these are particularly 1: 1 to 1: 10000 in order to efficiently react.
  • any of the chain isoprenoid alcohols can be used.
  • the use of geranylgeranol was effective. It was found that geranylgeranyl fatty acid ester-rich fats and oils could be efficiently obtained.
  • Each of the chain isoprenoid fatty acid esters obtained in the same manner as in Examples 9, 18, and 19 was added to each of the purified soybean oil and the purified rapeseed oil so as to have a mass ratio of 1000 ppm and 1000 Oppm, respectively.
  • a total of 12 types of chain isoprenide fatty acid ester-containing fats and oils were prepared. All of the fats and oils had good taste, flavor and the like, and could be used in the same manner as the fats and oils to which the chain isoprenoid fatty acid ester was not particularly added.
  • Example 24 Fats and oils containing a high content of chained isoprenoid fatty acid esters
  • Three kinds of chain isoprenoid fatty acid esters obtained in the same manner as in Examples 7, 8, and 22 were added to each of the purified soybean oil and the fat and oil of Example 1 in a mass ratio of 10 ppm, 100 ppm, 1000 ppm, Addition and dissolution were carried out at a rate of 10000 ppm to prepare a total of eight kinds of fats and oils containing the above three kinds of chain isoprenide fatty acid esters in high content. All fats and oils have good taste and flavor, and the above three types of chain-like soprenoid fatty acids! : Can be used with refined soybean oil to which no stell is particularly added and the fat and oil of Example 1.
  • chain isoprenoid fatty acid ester-rich fats and oils can be obtained simply and efficiently. In particular, it is very safe in terms of the use of enzymes and can be used as edible fats and oils.
  • chain isoprenoid fatty acid esters can be isolated from these fats and oils, and these can be used as novel pharmaceuticals and foods.

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Abstract

L'invention se rapporte à des graisses et des huiles riches en esters d'acides gras isoprénoïdes linéaires, caractérisées en ce que leur procédé de production consiste à : utiliser des matières premières telles que (A) un ou plusieurs éléments sélectionnés dans le groupe comprenant des alcools isoprénoïdes linéaires et (B) un ou plusieurs éléments sélectionnés dans le groupe comprenant des acides gras, des esters méthyliques d'acides gras, des esters éthyliques d'acides gras, des monoglycérides, des diglycérides et des triglycérides ou une huile ou une graisse contenant une ou plusieurs de ces substances ; et à soumettre le mélange des composants (A) et (B) à un traitement faisant appel à de l'hydrolase d'ester carboxylique.
PCT/JP2002/011607 2001-11-07 2002-11-07 Graisses et huiles riches en esters d'acides gras isoprenoides lineaires et leur procede de production WO2003040275A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6356293A (ja) * 1986-08-27 1988-03-10 Agency Of Ind Science & Technol 脂肪酸エステルの合成法
JPS63133991A (ja) * 1986-11-26 1988-06-06 Kao Corp エステル化方法
EP0274798A2 (fr) * 1986-12-19 1988-07-20 Unilever N.V. Procédé de préparation d'esters
JPH01174391A (ja) * 1987-12-28 1989-07-10 Sapporo Breweries Ltd 脂肪酸エステル製造方法

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JPS63133991A (ja) * 1986-11-26 1988-06-06 Kao Corp エステル化方法
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JPH01174391A (ja) * 1987-12-28 1989-07-10 Sapporo Breweries Ltd 脂肪酸エステル製造方法

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