JP2000302777A - Production of vitamins - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain sterol-fatty acid esters and specific vitamins without practically applying an organic solvent by making an esterase act on a mixture comprising specific vitamins, sterols, fatty acids or the like to selectively form the sterol-fatty acid esters. SOLUTION: By making an esterase (e.g. a lipase) act on a mixture comprising vitamins (e.g. tocopherols) each having at least one hydroxyl group, sterols, fatty acids and/or their esters or the like to selectively produce the sterol-fatty acid esters, followed by separating them from the vitamins, the sterol-fatty acid esters and the vitamins each having at least one hydroxyl group are obtained. The mixture is preferably a fraction obtained by distilling scum and/or recovery (especially scum) obtained in an oil and fat production process. The above reaction is carried out at about 10-80 deg.C in a system showing a pH value of about 2-10 and having a moisture content of about 0-80%. The above separation process is preferably distillation or the like.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to sterol-fatty acid esters or vitamins, in particular tocopherols,
The present invention relates to a method for producing tocotrienols.

[0002]

BACKGROUND OF THE INVENTION Natural fats and oils, especially vegetable fats and oils, contain vitamins (vitamin A, vitamin D, tocopherol,
Tocotrienols) and sterols are contained in a large amount, and a considerable amount is distributed to so-called scum, which is a by-product of the deodorization treatment step, in the production of vegetable oils and fats.

Conventionally, in the method for separating and recovering tocopherols and sterols from scum, first, fatty acids and fatty acid esters (mainly glycerides) in scum are converted into fatty acid methyl in the presence of a chemical catalyst. afterwards,
(1) Crystallize and separate sterols in an organic solvent, (2) Distill off fatty acid methyl by distillation, and crystallize and separate sterols contained in the distillation residue in an organic solvent, or And (3) recovering sterols and tocopherols as distillation fractions (hereinafter sometimes simply referred to as fractions) from the distillation residue obtained by distilling the fatty acid methyl, and crystallizing the sterols in an organic solvent. After the separation of sterols, such as separation of sterols, the tocopherols and sterols are separated and recovered by concentrating the tocopherols by high-vacuum distillation and separating and purifying them by ion exchange chromatography or the like.

Recently, Japanese Unexamined Patent Publication No. 7-2827 discloses that scum is heated at 150 ° C. to 250 ° C. to synthesize esters of fatty acids and sterols present in the scum (hereinafter referred to as sterol-fatty acid esters). It is described that tocopherols are recovered by distillation and then sterols are recovered after decomposing sterol-fatty acid esters in the distillation residue.

[0005] However, in this method, the scum is reduced to 150 ° C or less.
Since heating must be performed at 250 ° C., it is an energy-consuming reaction, and tocopherols are denatured by the reaction due to heating, and tocopherols-by-products such as fatty acid esters are produced. Absent.

[0006]

Therefore, sterol-fatty acid esters are selectively produced in a scum which is energy-saving and contains various impurities without using an organic solvent. There is a need for a method for separating vitamins and sterol-fatty acid esters.

[0007]

SUMMARY OF THE INVENTION The present invention has been made to solve the above-mentioned problems, and the present invention solves the above-mentioned problems.

[0008] That is, the present invention provides an esterase which acts on a mixture containing vitamins having hydroxyl groups, sterols, fatty acids and / or fatty acid esters,
The present invention relates to a method for producing sterol-fatty acid esters, comprising: a step of selectively producing sterol-fatty acid esters; and a step of separating the obtained sterol-fatty acid esters.

In a preferred embodiment, the separation step in the production method is distillation, solvent fractionation, membrane separation or ion exchange chromatography, or a step of separating them by a combination thereof.

[0010] In a preferred embodiment, the mixture used in the production method is a scum and / or a recovered product obtained in a fat / oil production step.

[0011] In a more preferred embodiment, the mixture used in the production method is a fraction obtained by distilling scum.

The present invention also provides a process for selectively synthesizing sterol-fatty acid esters by reacting esterase on a mixture containing vitamins having hydroxyl groups, sterols, fatty acids and / or fatty acid esters. And a step of separating the obtained fatty acid esters and vitamins having a hydroxyl group; and a method of producing vitamins having a hydroxyl group.

In a preferred embodiment, the separation step of the production method is distillation, solvent fractionation, membrane separation or ion exchange chromatography, or a step of separating them by a combination thereof.

In a more preferred embodiment, the vitamins having a hydroxyl group are tocopherols and / or tocotrienols.

[0015]

DETAILED DESCRIPTION OF THE INVENTION The vitamins having a hydroxyl group used in the present invention include vitamin B1 (thiamine), vitamin B2 (riboflavin), vitamin B6 (pyridoxal, pyridoxine, pyridoxamine), biotin, pantothenic acid, vitamin A, Vitamin C, Vitamin E (α
-, Β-, γ-, δ-tocopherol and α-, β-,
γ-, δ-tocotrinol) and the like. When referring to vitamins, not only a mixture of vitamins but also a case of only one type of vitamin is included.

Sterols are substances having a hydroxyl group in the steroid skeleton, and include cholesterol, brassicasterol, campesterol, stigmasterol, β-sitosterol, ergosterol and the like. The term sterols includes not only a mixture of sterols but also a case of only one type of sterol.

The fatty acid is not particularly limited, and may be a free acid or a salt. Among them, saturated or unsaturated, straight-chain or branched fatty acids having about 6 to 24 carbon atoms are preferred. The term "fatty acids" includes not only a mixture of fatty acids but also a case of only one type of fatty acid.

Fatty acid esters are esters of fatty acids and alcohols, and the alcohols may include not only monohydric alcohols but also polyhydric alcohols. Therefore, it may be a fatty acid ester of glycerol (monoglyceride, diglyceride, triglyceride). The term "fatty acid esters" includes not only a mixture of fatty acid esters but also a case of only one fatty acid ester.

Esterase is a general term for enzymes that decompose esters, and includes lipases and microorganisms that produce esterases. As the esterase, any enzyme may be used as long as it can selectively synthesize sterol-fatty acid esters from sterols and fatty acids even in the presence of vitamins having a hydroxyl group. For example, the enzyme may be of any origin. In the case of lipase, it is preferable that the lipase is non-specific to the position of the ester bond of triglyceride.
-It may be specific. Commercially available lipase can also be used. The form of the enzyme may be a free form, an immobilized form, or a microbial cell holding the enzyme or an immobilized cell form thereof. The immobilized lipase or the immobilized bacterial cells are more preferable because they can be collected and reused. Further, thermostable and thermophilic lipases are also preferably used.

The vitamins, sterols, fatty acids and / or fatty acid esters can be present in the mixture in any proportion. In the mixture, about 1 to 80% by weight of vitamins, about 1 to 60% by weight of sterols, and about 1 to 90% by weight of fatty acids and / or fatty acid esters may be contained. An appropriate amount of esterase may be selected according to the content of sterols, fatty acids and / or fatty acid esters.

The reaction is carried out under suitable conditions, for example at about 10 ° C.
The reaction can be performed in a system containing 〜80 ° C., about pH 2-10, and about 0-80% water. It is not necessary to add an organic solvent. If added, alcohols such as methanol and ethanol, and organic solvents such as acetone and hexane are used.

In the present invention, as a starting material, a by-product (scum) obtained in a deodorizing step, which is one of the steps for producing fats and oils, and a recovered material in a deoxidizing step are preferable. Here, the recovered product is a recovered product of distillation deoxidation (distillate)
And recovered products in alkali deoxidation (so-called dark oil)
Say. The scum and the recovered product include vitamins having a hydroxyl group, sterols, fatty acids and / or fatty acid esters, and the present invention relates to the scum and the sterols in the recovered product as sterol-fatty acid. It is effective to convert the sterol-fatty acid esters and vitamins efficiently into esters.

Incidentally, Japanese Patent Publication No. 5-33712 discloses that
Examples have been reported in which sterol-fatty acid esters were produced using lipase. However, in this reaction, the reaction substrates are only sterols and fatty acids, whereas the present invention is particularly effective when compounds having other hydroxyl groups (here, mainly vitamins) are present. In the presence of compounds containing various hydroxyl groups, it was first revealed that the synthesis of sterol-fatty acid esters proceeded efficiently, but that vitamins did not react with fatty acids and / or fatty acid esters at all or hardly. Things.

The method for producing the sterol-fatty acid esters of the present invention will now be described with reference to scum and recovered products as examples.
A method for separating vitamins, particularly tocopherols, will be described.

Scum and collected products are by-products in the process of producing edible fats and oils. The scum and the collected product of the vegetable oil are preferable because the scum and the collected product of the vegetable oil contain a large amount of vitamins, particularly, tocopherols, tocotrienols, and sterols. Vegetable oils and fats include soybean oil, rice bran oil, palm oil, safflower oil, corn oil, rapeseed oil, cottonseed oil, olive oil, peanut oil and the like.
Among these scums and collected products, vitamins (particularly, tocopherols, tocotrienols), sterols (brassicasterol, campesterol, stigmasterol, β-sitosterol, etc.), free fatty acids, fatty acid esters ( Triglycerides, diglycerides, monoglycerides), and other hydrocarbons.

When an esterase (preferably a lipase) is added to the scum or the recovered product, if necessary, with water, and the mixture is reacted with stirring, sterols and fatty acids are selectively reacted to form sterol-fatty acid ester. Kind is generated.

Before adding the lipase to the scum, the scum should be about 0.005 to 0.5 mmHg, preferably about 0.05 mmHg.
Under a vacuum of 5 to 0.1 mmHg, about 150 ° C. to 250
C., preferably at about 220 ° C. to 240 ° C., removes odorous substances, glycerides, hydrocarbons, and high-boiling substances contained in the scum, and the next esterification reaction proceeds smoothly. About 70-90% of the sterols contained are converted to sterol-fatty acid esters. Further, sterol-fatty acid esters can be efficiently recovered.

After completion of the esterification reaction, about 0.005 to
0.5 mmHg, preferably about 0.05-0.1 mmH
under vacuum of about 100 ° C. to 270 ° C., preferably about 1 ° C.
Distill at 500-240 ° C. Vitamins, unreacted fatty acids, and unreacted sterols are recovered in a fraction, and the synthesized sterol-fatty acid esters can be recovered from the distillation residue.

In the fraction, vitamins, unreacted fatty acids,
If unreacted sterols remain, esterification can be carried out by further adding esterase (lipase) and, if necessary, water. Vitamins, unreacted fatty acids, and unreacted sterols are recovered, and then sterol-
Fatty acid esters can also be recovered.

[0030] Vitamins are recovered from the distillate. Vitamins, unreacted fatty acids, unreacted sterols and the like contained in the fraction are separated, for example, by distillation. When the vitamins are tocopherols or tocotrienols, first, about 0.005 mmHg to 0.5 m
By distilling at about 140 ° C. to 230 ° C., preferably about 160 ° C. to 200 ° C. under a vacuum condition of mHg, first,
Fatty acids are recovered as a fraction. Then, raise the temperature slightly to about 170 ° C to 260 ° C, preferably about 180 ° C.
By distilling at ~ 255 ° C, vitamins (tocopherols, tocotrienols) are recovered as a fraction. The mixed sterol-fatty acid esters,
Collected as residue. The distillation conditions can be changed by the degree of vacuum and the temperature.

The distillation method and apparatus are not limited. For example, a falling film distillation apparatus, a centrifugal molecular distillation apparatus, a precision distillation apparatus, and the like are used.

After completion of the esterification reaction, not only the distillation operation but also the separation operation such as distillation operation, solvent fractionation, ion exchange chromatography, membrane separation, etc., alone or in combination, may be used to obtain sterol-fatty acid esters, vitamins Can be separated and recovered. The solvent fractionation can be performed using an organic solvent such as methanol and ethanol. Ion exchange chromatography generally uses a column, and can be performed using an organic solvent such as hexane, methanol, or ethanol.

For example, esterification reaction-distillation-ion exchange chromatography-distillation, esterification reaction-distillation-
Any appropriate combination of solvent fractionation-ion exchange chromatography, esterification reaction-ion exchange chromatography-distillation, etc. may be performed.

[0034]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below based on embodiments, but the present invention is not limited to these embodiments. (Example 1) Soybean oil scum was used as a raw material. The soybean oil scum had the following composition: The unit is% by weight. Free fatty acids 36.0% Sterols 12.7% Tocopherols 11.8% (acid value: 71.9)

To a reaction mixture of 4 g of the soybean oil scum and 1 g of water, 200 U of lipase was added per 1 g of the reaction mixture, and the mixture was shaken at 35 ° C. for 20 hours at 500 rpm.
Reacted. In addition, 1 U of lipase refers to the amount of enzyme that releases 1 μmol of fatty acids from olive oil in one minute.
After completion of the reaction, the oil content was recovered by centrifugation, and the total content of tocopherols and tocotrienols was measured by gas chromatography using tricaproin as an internal standard, and the result was taken as the weight of tocopherols. The esterification rate is
From the total sterol content before and after the reaction, it was determined by the following equation.

[0036]

(Equation 1)

The results are shown in Table 1. In Table 1,
LIPOSAM is a lipase manufactured by Showa Denko KK
da is a lipase from Candida cylindracea (hereinafter referred to as Can
dida lipase) and sold by Meito Sangyo Co., Ltd.

[0038]

[Table 1]

From these results, it was found that tocopherols were not esterified at all by Candida lipase, and only sterols were selectively esterified. When sterols are esterified with fatty acids, the acid value should decrease, but an increase in the acid value was observed in this reaction. This phenomenon is considered to be due to the fact that fatty acids (including monoglycerides) contained in the scum were hydrolyzed by lipase to release fatty acids.

Example 2 The soybean oil scum used in Example 1 was reduced to 0.2 mmH using a falling film distillation apparatus.
g, distilled at 240 ° C., and the fractions were collected to obtain distilled soybean oil scum. 17.7% by weight of high-boiling substances were removed as distillation residue. The distilled soybean oil scum had the following composition: The unit is% by weight. Free fatty acids 41.5% Sterols 16.6% Tocopherols 14.5% (acid value: 83.1)

The results of the enzyme treatment of the distilled soybean oil scum and the raw material soybean oil scum were compared. The reaction conditions were the same as in Example 1. Table 2 shows the results.

[0042]

[Table 2]

From these results, it is found that the use of distilled soybean oil scum as a raw material, although slightly, makes it easier to esterify sterols and a higher esterification rate than undistilled scum (raw material scum). Can be achieved, indicating that distilled soybean oil scum contributes to the improvement of reactivity. It was also found that even when distilled soybean oil scum was used, the tocopherols contained therein were not esterified at all by Candida lipase. Furthermore, since high-boiling impurities having a large molecular weight are removed in advance, it is advantageous for purification of sterol-fatty acid esters synthesized by an enzymatic reaction.

Example 3 The effect of moisture on the synthesis of sterol-fatty acid esters in scum was examined. The distilled soybean oil scum obtained in Example 2 and water were mixed so that the total amount of water was 5 g, and Candida lipase was added to 100 g.
After adding 0 U, the reaction was carried out at 35 ° C. for 20 hours with stirring at 500 rpm. Table 3 shows the results.

[0045]

[Table 3]

From these results, it was shown that the amount of water had little effect on the esterification reaction of sterols, and that even if the amount of water changed, the tocopherols were not esterified by Candida lipase.

Example 4 The effect of temperature on the synthesis of sterol-fatty acid esters in scum was examined. 4 g of distilled soybean oil scum of Example 2, 1 g of water, Cand
1000 U of ida lipase was added and mixed, and reacted at the temperature shown in Table 4 for 3.5 hours and 23 hours with stirring at 500 rpm. Table 4 shows the results.

[0048]

[Table 4]

The esterification rate of the sterols at the beginning of the reaction (3.5 hours) depends on the temperature, but when the equilibrium state is reached (24 hours), the esterification rate reaches the maximum value at 30 to 35 ° C. Indicated. This result indicates that when the reaction is performed at 40 ° C. or higher, the enzyme is gradually deactivated. It was also found that tocopherols were not esterified by Candida lipase even when the temperature was changed.

Example 5 The effects of the amount of enzyme and the reaction time on the esterification reaction of sterols in scum by Candida lipase were examined. Candida lipase was added to 4 g of the distilled soybean oil scum obtained in Example 2 and 1 g of water at 50 U, 200 U, and 800 U per 1 g of the reaction mixture, and reacted at 35 ° C. with stirring.
Table 5 shows the results.

[0051]

[Table 5]

From these results, it was found that when the amount of the enzyme was increased, the esterification rate of sterols was increased, and the time required to reach the equilibrium state was shortened. However, it was found that the esterification rate of sterols finally reached does not depend on the amount of enzyme. Also, even if the amount of enzyme is changed,
Further, no change in the amount of tocopherol was observed even when the reaction time was extended.

Example 6 Using 10 kg of soybean oil scum used in Example 1 as a starting material, tocopherols and sterol-fatty acid esters were separated and purified. Table 6 shows the material balance in this purification operation.

[0054]

[Table 6]

First, the raw soybean oil scum was distilled at 240 ° C. and 0.2 mmHg using a falling thin film distillation apparatus to obtain 8.23 kg of distilled soybean oil scum (fraction-1). The contents of sterols and tocopherols in the distilled soybean oil scum were 13.3% by weight and 13.7% by weight, respectively. Distilled soybean oil scum (fraction-1) was reacted with 20% by weight of water and 50 U of Candida lipase per 1 g of the reaction mixture while stirring at 35 ° C. for 24 hours. By this enzyme treatment, the content of free sterols was reduced from 13.3% to 2.5% (esterification rate: 81.2%), but the content of tocopherols was reduced by
Few were recognized. In addition, the stirring efficiency was improved by increasing the reaction scale, and the reaction efficiency was improved as compared with the case of the small scale.

The oil was recovered from the enzyme reaction solution, dehydrated, and distilled at 0.2 mmHg and 250 ° C. to recover a fraction-2. Since this fraction still contained free sterols, the enzyme treatment was performed again under the same conditions as described above. As a result, there was almost no loss of tocopherols, and the content of free sterols could be reduced to 0.5% by weight (the esterification rate of sterols was 81.%).
5%).

The oil was recovered from the reaction solution subjected to the second enzyme treatment, dehydrated, and then distilled at 0.2 mmHg and 160 ° C. to recover a fraction 3-1. Then, the temperature was raised to 200 ° C. to collect the fraction 3-2, and the degree of vacuum was further increased to 0.04 mm.
After collecting fraction 3-3 at 230 ° C. in Hg, the temperature was finally raised to 255 ° C. to collect fraction 3-4. The residue in this series of distillation steps was designated as residue-3. Fraction 3-3
Was recovered, and the content of free sterols and the content of tocopherols in fraction 3-3 were 2.9% by weight and 65.3% by weight, respectively. In addition, 52.5% of the tocopherols contained in the first soybean oil scum could be recovered in the fraction 3-3.

The fraction 3-2 and the fraction 3-4 contained 17.1% and 23.8% of tocopherol, respectively. Assuming an actual industrial production process, these fractions can be mixed with the fraction of the next enzymatic treatment and distilled, so that the loss of tocopherols is reduced to fraction 3
-1 and the amount of the residue. Therefore, in the purification of tocopherols from soybean oil scum, by introducing an enzymatic reaction step, the organic solvent is not used at all, and only in combination with the distillation method, the tocopherols can be obtained in a high yield of at least 80% or more. Can be increased to 65% by weight or more.

Next, in the above step, the amount of free fatty acids in the fraction (total 1.84 kg) obtained by mixing the residue 2 and the residue 3 was determined.
The amounts of free sterols and tocopherols are 1.1%, 1.2%, and 2.2% by weight, respectively.
Met. This fraction is subjected to thin layer chromatography (TL
C) According to the analysis, a single spot was detected at the developed position of the sterol-fatty acid esters. The developing solvent was hexane: ethyl acetate: acetic acid = 90: 10: 1 (volume), and was detected by a sulfuric acid coloring method. Further, this fraction was analyzed by gas chromatography after methylating fatty acids in the presence of sodium methylate. As a result, only fatty acid methyls and sterols could be detected at a molar ratio of 1: 1. From this, it was presumed that the mixed fraction of the residue 2 and the residue 3 contained a sterol-fatty acid ester having a purity of at least 90% or more.

Example 7 200 g of distilled soybean oil scum obtained in Example 2 was distilled again at 0.2 mmHg and 200 ° C. to obtain deoxidized soybean oil scum (hereinafter referred to as deoxidized scum).
Was recovered as a distillation residue. The composition of the deoxidized scum was as follows. Free fatty acids 1.4% by weight Sterols 31.8% by weight Tocopherols 27.3% by weight Monoglycerides 0.4% by weight (acid value 2.8)

Monoolein glyceride, oleic acid, water and lipase having the composition shown in Table 7 were added to the deoxidized scum to prepare reaction mixtures of reaction systems 1 to 5.

[0062]

[Table 7]

The reaction mixture was reacted with stirring at 35 ° C. for 24 hours, and the acid value, monoglyceride content, sterol content, and tocopherol content before and after the reaction were measured. The results are shown in Table 8

[0064]

[Table 8]

Although the reaction system 1 contained almost no free fatty acids, the sterols were efficiently esterified. In addition, since the monoglyceride was hydrolyzed by the reaction, it was suggested that the fatty acids generated by the hydrolysis were used as substrates for the esterification reaction with sterols. The esterification rate of sterols was found to increase as the amount of free fatty acids in the reaction system increased, but this seems to be related to the fluidity of the reaction mixture.

[0066]

According to the present invention, when lipase is used as a catalyst, the esterification reaction between sterols and fatty acids proceeds selectively even when vitamins having a hydroxyl group are present. In particular, it has been clarified for the first time that this enzymatic reaction proceeds efficiently even in scum generated in the deodorization step of vegetable oil and the like. Sterols, which previously made it difficult to separate vitamins, can be removed without using any organic solvent, which is useful for recovering vitamins, especially tocopherols, with high safety and high yield. .

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[Procedure amendment]

[Submission date] April 5, 2000 (200.4.5)

[Procedure amendment 1]

[Document name to be amended] Statement

[Correction target item name] 0028

[Correction method] Change

[Correction contents]

After completion of the esterification reaction, about 0.005 to
0.5 mmHg, preferably about 0.05-0.1 mmH
under vacuum of about 100 ° C. to 270 ° C., preferably about 1 ° C.
Distilled at 50 ° C. to 240 ° C.. Vitamins, unreacted fatty acids, and unreacted sterols are recovered in a fraction, and the synthesized sterol-fatty acid esters can be recovered from the distillation residue.

[Procedure amendment 2]

[Document name to be amended] Statement

[Correction target item name] 0029

[Correction method] Change

[Correction contents]

[0029] recovered fractions, vitamins, fatty acids unreacted If <br/> if the sterols, etc. is contained unreacted, a further esterases (lipase), water as needed After the reaction, vitamins, unreacted fatty acids, and unreacted sterols are recovered in a distillation fraction (fraction), and then the sterol-fatty acid ester is removed from the residue. Can also be collected.

[Procedure amendment 3]

[Document name to be amended] Statement

[Correction target item name] 0049

[Correction method] Change

[Correction contents]

The esterification rate of the sterols at the beginning of the reaction (3.5 hours) depends on the temperature, but when the equilibrium state is reached (23 hours) , the esterification rate reaches the maximum value at 30 to 35 ° C. Indicated. This result indicates that when the reaction is performed at 40 ° C. or higher, the enzyme is gradually deactivated. It was also found that tocopherols were not esterified by Candida lipase even when the temperature was changed.

Continuation of the front page (72) Inventor Seiichi Nakai 5-7-17 Kami Minami, Hirano-ku, Osaka-shi, Osaka Inside the Yatsushiro Osaka Plant (72) Inventor Shoji Suenaga 5-5-Kaminami, Hirano-ku, Osaka, Osaka No. 17 Inside Yatsushiro Osaka Plant Co., Ltd. (72) Inventor Yuji Shimada 4-6-113 Kitatanabe, Higashisumiyoshi-ku, Osaka-shi, Osaka (72) Inventor Takeo Sugihara 6-87 Senmon, Itami-shi, Hyogo Person Yoshio Tominaga 2-7-2 Utajima, Nishiyodogawa-ku, Osaka-shi, Osaka F-term (reference) 4C055 AA01 BA02 BA05 BA06 CA03 CA06 CA16 CA42 DA06 DA16 4C062 FF15 FF24 4C063 AA01 BB02 CC62 DD29 EE01 4C091 AA02 BB01 BB01 BB01 BB01 BB01 BB01 BB01 EE HH01 JJ03 KK01 LL01 MM03 NN01 PA02 PA05 PB05 QQ01

Claims (7)

[Claims] Claims: 1. A step of reacting a mixture containing a hydroxyl group-containing vitamin, a sterol, a fatty acid and / or a fatty acid ester with an esterase to selectively produce a sterol-fatty acid ester; Separating the obtained sterol-fatty acid esters. 2. The sterol-fatty acid esters according to claim 1, wherein the separation step is distillation, solvent fractionation, membrane separation or ion exchange chromatography, or a combination thereof. Production method. 3. The method according to claim 1, wherein the mixture is a scum and / or a recovered product obtained in a process for producing fats and oils. 4. The process according to claim 1, wherein the mixture is a fraction obtained by distilling scum. 5. A process for selectively synthesizing sterol-fatty acid esters by reacting esterase on a mixture containing vitamins having hydroxyl groups, sterols, fatty acids and / or fatty acid esters; Separating the obtained sterol fatty acid esters and vitamins having a hydroxyl group. 6. The method according to claim 5, wherein the separation step is distillation, solvent fractionation, membrane separation, or ion exchange chromatography, or a step of separating them by a combination thereof. Production method. 7. The method for producing a hydroxyl group-containing vitamin according to claim 5, wherein the vitamin is a tocopherol and / or a tocotrienol.