JP3192410B1 - Method for producing sterol fatty acid ester for food - Google Patents

Abstract

Abstract: PROBLEM TO BE SOLVED: To provide a raw material treatment condition, a synthesis reaction condition, and a subsequent purification step for producing a safe and inexpensive food-grade sterol fatty acid ester from deodorized scum oil.
An inexpensive sterol fatty acid ester that is configured to be usable as a general food material, health food material or pharmaceutical material, has excellent functional quality such as color, smell and taste, and contains almost no trans-type fatty acid, and is excellent in safety. And a method for producing the same. SOLUTION: Deodorized scum oil is used as a raw material, and fatty acid esters such as triacylglycerol contained in the deodorized scum oil are decomposed in advance by a hydrolysis reaction using a chemical catalyst, and the generated fatty acids are removed by molecular distillation. Obtain a fraction containing sterols. Subsequently, starting from a sterol-containing fraction to which any fat or oil containing triacylglycerol as a main component is added as a raw material, sterol fatty acid esters are synthesized under strictly controlled reaction conditions using an enzyme having lipolytic activity as a catalyst. Performs a reaction, and further performs several stages of purification treatment to obtain appropriate quality as a food, and contains almost no degraded fatty acids such as trans-type fatty acids, and is a safe and inexpensive food-grade sterol fatty acid ester. Is produced enzymatically.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a method for producing sterol fatty acid esters for foods from deodorized scum oil at low cost.

[0002]

2. Description of the Related Art In the process of refining vegetable oils such as soybean oil and rapeseed oil, many sterols including β-sitosterol are obtained as a part of unsaponifiable substances. It is known to have a cholesterol lowering effect. Also, recently, it has been revealed that β-sitosterol, a saturated form of β-sitosterol, has a stronger plasma cholesterol lowering effect than β-sitosterol, and has been receiving more and more attention.

[0003] However, the above-mentioned free sterols and free stanols are insoluble in the micellar phase in the digestive tract, and thus cannot be said to be an appropriate intake form for obtaining their physiological effects. In contrast, ingestion as a sterol fatty acid ester has been proposed to improve fat solubility, and recently,
Attempts have also been made to add it to various foods such as margarine containing plant sterols as sterol fatty acid esters.

However, sterol fatty acid esters have heretofore been mainly used as a cholesteric liquid crystal and a hydrophilic base material for pharmaceutical cosmetics. Therefore, a chemical synthesis method using an acid catalyst or a base catalyst has been used as a method for producing the same. However, in general, in chemical synthesis, the reaction conditions are severe, so that there are problems such as easy deterioration of quality and easy generation of by-products, and the purification process after the synthesis reaction becomes very complicated. Inevitably, when used for foods or pharmaceuticals, there is a problem that there is a concern that by-products or reaction catalysts may be mixed.

[0005] Therefore, use of enzymes has been studied to avoid the above-mentioned problems.

[0006] Such enzymes include cholesterol esterase and lipase. Both are classified as one of the carboxylate hydrolases, and cholesterol esterase is defined as an enzyme that produces free sterols and free fatty acids from cholesterol fatty acid esters by a hydrolysis reaction. Lipase (mainly triacylglycerol lipase) is defined as an enzyme that produces glycerol and free fatty acids from glycerol fatty acid esters by a hydrolysis reaction.

However, in many cases, cholesterol esterase activity and lipase activity are found in the same enzyme (D. Lombardo et al., Biochem. Biophys. Acta, 6
11, (1980), 147-), cholesterol esterases and lipases have also been shown to catalyze the degradation of triacylglycerols (WEMomsen et al., Bioche
m. Biophys. Acta, 486, (1977), 103-). At present, there are many examples in which cholesterol esterase or lipase cannot be clearly classified.

By the way, it is known that the above-mentioned enzyme usually catalyzes a hydrolysis reaction of a carboxylic acid ester while catalyzing an ester synthesis reaction.

Lawrence A. et al. Have shown that cholesterol oleate can be synthesized from free cholesterol and free oleic acid by a sterol ester hydrolase from canine pancreatic juice, known as cholesterol esterase (Biochem. Biophys. Acta,
231, (1971), 558-560).

Similarly, D. Lombardo et al. Have shown that cholesterol esterase derived from human pancreatic juice catalyzes the synthesis reaction of cholesterol fatty acid esters (Biochimie et al, 1980, 62, 427-432).

Have also confirmed that lipase can synthesize cholesterol fatty acid esters (Japanese Patent Application No. 60-45128).

As described above, it has been shown that cholesterol fatty acid esters can be synthesized by using enzymes in the above-mentioned chemical synthesis.

However, the conventional method for producing a cholesterol fatty acid ester using the above enzyme has the following problems.

(1) All of the above examples merely show the synthesis reaction of sterol fatty acid esters, and are not intended to produce sterol fatty acid esters as general food materials, health food materials or pharmaceutical materials. Absent. In other words, in consideration of the synthetic reaction conditions, and the quality in terms of color, smell, taste, and other sensory aspects that are important for use as a general food material, health food material, or pharmaceutical material in the subsequent purification method, and further, safety is considered I haven't.

(2) Since sterols used as raw materials for sterol ester fatty acid esters are made of pure products having a high degree of purification, the sterol fatty acid esters after synthesis become expensive and are used in foods and the like. Is cost prohibitive.

(3) The deodorized scum oil generated in the step of deodorizing vegetable oils contains a high concentration of unsaponifiable substances such as sterols, fatty acids, and the like. To obtain a sterol fatty acid ester. However, it is known that the deodorized scum contains peroxides and trans-type fatty acids as products of deteriorated fatty acids. Of these, trans-fatty acids have been found to be produced mainly in the partial hydrogenation step of fats and oils and in the deodorization step at high temperatures, but when humans ingest a large amount of this trans-fatty acid, coronary artery There have been reports of an increased risk of developing heart disease. In particular, there has been an interest in trans-fatty acid contents in various foods mainly in Europe and the United States. In recent years, products having reduced trans-fatty acids have come to be found in margarine and the like. In other words, when synthesizing a sterol fatty acid ester from the deodorized scum oil itself as a raw material, if an enzyme or a chemical catalyst that catalyzes the esterification reaction is used, a sterol fatty acid ester containing trans-type fatty acids or other deteriorated fatty acids is used. Is not preferred from the viewpoint of safety.

[0017]

Therefore, the present invention provides a sterol fatty acid ester for foods which is suitable for foods, can be produced at low cost, and contains almost no degraded fatty acids such as trans fatty acids. It is intended to provide a manufacturing method.

[0018]

The feature of the present invention is to produce a safe and inexpensive food-grade sterol fatty acid ester containing almost no degraded fatty acids such as trans-type fatty acids from deodorized scum oil. is there.

That is, the outline of the present invention will be described with reference to FIG. (Step 100), fatty acid esters such as triacylglycerol contained in the deodorized scum oil are previously decomposed by a hydrolysis reaction using a chemical catalyst (Step 101) (Step 110),
The generated fatty acids (steps 112 and 113) are removed by molecular distillation (step 111) to obtain a sterol-containing fraction (step 120).

Subsequently, a strictly controlled reaction is carried out using an enzyme having lipolytic activity as a catalyst, using a sterol-containing fraction to which an oil or fat mainly containing triacylglycerol is added as a raw material (step 122). A sterol fatty acid ester (step 130) is synthesized under the conditions (step 121), and several steps of purification (steps 131 and 1) are performed to obtain appropriate quality as food.
41, 151) to provide safe and inexpensive food-grade sterol fatty acid esters containing almost no degraded fatty acids such as trans-fatty acids (step 160)
Is produced enzymatically.

Here, the invention of claim 1 according to the present invention is characterized in that a fraction containing sterol and triacylglycerol are used.
Add an enzyme with lipolytic activity to the fat
To produce sterol fatty acid esters,
The sterol fatty acid ester is further subjected to a predetermined purification step.
To produce sterol fatty acid esters for food
The sterol raw material used is deodorized scum oil generated in the step of deodorizing vegetable oils and fats, and the hydrolysis reaction of fatty acid esters in the deodorized scum oil is carried out to obtain the first molecular steam.
Fatty acids are mainly removed by distillation to collect a sterol-containing fraction, and the collected sterol-containing fraction is added with an oil or fat mainly composed of triacylglycerol. enzymatic conducted synthesis reaction a certain time in a system temperature and moisture content is controlled to the sterol fatty acid esters with, further, the removal of the first of mainly unreacted as a purification step by a second molecular distillation process sterols and fatty acids In the second purification step, the coloring matter component is mainly removed by the adsorbent treatment, and in the third purification step, the odor component is mainly removed by the steam distillation treatment, and the purification temperature is controlled to produce the trans fatty acid. Sterol for food, which suppresses, has excellent physical properties for food, and is excellent in sensory and safety aspects Characterized in that to obtain a fatty acid ester.

According to a second aspect of the present invention, in the first aspect of the invention, the hydrolysis reaction liberates degraded fatty acids such as trans fatty acids and oxidized fatty acids in the deodorized scum oil.
It is characterized in that it is performed to make it in a form easily removed as an acid .

The invention of claim 3 is characterized in that, in the invention of claim 1, soybean deodorized scum oil generated in a step of refining soybean oil is used as a sterol raw material.

Further, the invention of claim 4 is characterized in that, in the invention of claim 1, when the hydrolysis reaction of the fatty acid esters in the deodorized scum oil is carried out, the hydrolysis reaction is carried out by an acid or alkali catalyst. And

Further, the invention of claim 5 is characterized in that, in the invention of claim 1, when the fatty acid is mainly removed by the first molecular distillation treatment and the fraction containing sterol is recovered, it is 13.3 Pa or less. , At 100 to 200 ° C.

The invention of claim 6 is characterized in that, in the invention of claim 1, when fatty acids are mainly removed by the first molecular distillation treatment and a sterol-containing fraction is recovered, it is 13.3 Pa or less. The sterol-containing fraction was collected as a residual fraction by treating at 100 to 200 ° C., and the obtained sterol-containing fraction was further reduced to 13.3 Pa or less by 170.
It is characterized in that a fraction containing sterol is collected as a distillate fraction by treating at ~ 250 ° C.

Further, the invention of claim 7 is the invention of claim 1, wherein, birds fractions containing recovered sterols
When a synthetic reaction of a sterol fatty acid ester by an enzyme having lipolytic activity is carried out in a system in which temperature and moisture content are controlled for a certain period of time using a material to which an oil or fat containing acylglycerol as a main component is added as a raw material, An enzyme having activity of decomposing sterol fatty acid esters is used as the enzyme having activity.

Further, the invention of claim 8 is the invention of claim 1, wherein, birds fractions containing recovered sterols
When a synthetic reaction of a sterol fatty acid ester by an enzyme having lipolytic activity is carried out in a system in which temperature and moisture content are controlled for a certain period of time using a material to which an oil or fat containing acylglycerol as a main component is added as a raw material, An enzyme having an activity of decomposing a sterol fatty acid ester derived from the genus Pseudomonas is used as the enzyme having the activity.

According to the ninth aspect of the present invention, there is provided the method of the seventh or eighth aspect.
In the described invention, the enzyme having lipolytic activity is cholesterol esterase.

[0030] The invention of claim 10 is the invention according to claim 1, wherein the fraction containing the collected sterol is added to the fraction containing sterol .
When a synthetic reaction of a sterol fatty acid ester by an enzyme having lipolytic activity is carried out in a system in which temperature and moisture content are controlled for a certain period of time, using a raw material to which fats and oils mainly containing liacylglycerol are added as a raw material, An enzyme having a decomposing activity of triacylglycerol is used as the enzyme having a decomposing activity.

[0031] In the eleventh aspect of the present invention, in the first aspect of the present invention, the fraction containing the collected sterols may be treated .
When a synthetic reaction of a sterol fatty acid ester by an enzyme having lipolytic activity is carried out in a system in which temperature and moisture content are controlled for a certain period of time, using a raw material to which fats and oils mainly containing liacylglycerol are added as a raw material, It is characterized in that an enzyme having a decomposing activity of triacylglycerol derived from the genus Candida is used as the enzyme having a decomposing activity.

[0032] The invention of claim 12 is characterized in that, in the invention of claim 10 or 11, the enzyme having lipolytic activity is lipase.

The invention of claim 13 is the invention of claim 1, wherein the fraction containing the collected sterols is added to the fraction .
When a synthetic reaction of a sterol fatty acid ester by an enzyme having lipolytic activity is carried out for a certain period of time in a system in which temperature and moisture content are controlled, starting from a raw material to which fats and oils mainly containing liacylglycerol are added, 0.1 to 50% by weight based on acyl glycerol-based fat or oil
Characterized in that the reaction is performed within a range of 30 to 60 ° C. within 48 hours in the presence of water.

[0034] The invention of claim 14 is the invention according to claim 1, wherein the first purification step is a second molecular distillation.
When mainly removing unreacted sterols and fatty acids by the treatment , the treatment is carried out at 13.3 Pa or less at 100 to 250 ° C.

According to a fifteenth aspect of the present invention, in the invention according to the first aspect, when the dye component is mainly removed by the adsorbent treatment as the second purification step, the adsorbent is used as an adsorbent with respect to the weight of the raw material to be treated. It is characterized in that it is treated at a temperature of 100 ° C. or less using a single substance of activated clay, silica gel or activated carbon of 0.1 to 50%, or a mixture of two or more kinds.

Further, the invention of claim 16 is the invention of claim 1, wherein the removal of odor components mainly by steam distillation as the third purification step is performed at 13.3 kPa.
Hereinafter, the treatment is performed at 50 to 150 ° C.

The invention of claim 17 is the invention of claim 1 wherein the sterol fatty acid ester content in the sterol fatty acid ester obtained as a product is 90% by weight.
The trans fatty acid content in the constituent fatty acids of the sterol fatty acid ester is 2% or less, the peroxide value is 10 or less, the acid value is 1 or less, and the color is 6 or less (Gardner Method) and is almost odorless sensory.

The invention of claim 18 is the invention of claim 1, wherein soybean oil is used as the fat and oil containing triacylglycerol as a main component, which is added to the recovered sterol-containing fraction. The sterol fatty acid ester obtained as a product has a melting point of 20 to 40 ° C., and the content of trans fatty acid in the constituent fatty acids of the sterol fatty acid ester is 2% or less.

The invention of claim 19 is the invention according to claim 1, wherein rapeseed oil is used as a fat and oil containing triacylglycerol as a main component to be added to the recovered sterol-containing fraction. The sterol fatty acid ester obtained as above has a melting point of 20 to 40 ° C., and the content of trans fatty acid in the constituent fatty acids of the sterol fatty acid ester is 2% or less.

According to a twentieth aspect of the present invention, in the first aspect of the invention, olive oil is used as an oil containing triacylglycerol as a main component, which is added to the recovered sterol-containing fraction. The sterol fatty acid ester obtained as above has a melting point of 25 to 45 ° C. and a trans fatty acid content in the constituent fatty acids of the sterol fatty acid ester of 1% or less.

The invention of claim 21 is characterized in that, in the invention of claim 1, palm oil is used as a fat and oil containing triacylglycerol as a main component to be added to the recovered sterol-containing fraction. The sterol fatty acid ester obtained as a product has a melting point of 40 to 100 ° C., and the content of trans fatty acid in the constituent fatty acids of the sterol fatty acid ester is 1% or less.

According to a twenty-second aspect of the present invention, in the first aspect of the invention, palm oil is used as an oil containing triacylglycerol as a main component and added to the recovered sterol-containing fraction, The sterol fatty acid ester obtained as a product has a melting point of 40 to 100 ° C. and the trans fatty acid content in the constituent fatty acids of the sterol fatty acid ester is 1% or less. There is a feature.

According to a twenty-third aspect of the present invention, in the first aspect of the invention, fish oil is used as an oil containing triacylglycerol as a main component to be added to the recovered sterol-containing fraction. The sterol fatty acid ester obtained as above has a melting point of −10 to 20 ° C. and a trans fatty acid content in the constituent fatty acids of the sterol fatty acid ester of 2% or less.

Hereinafter, the present invention will be described in detail with reference to FIG.

First, the step relating to the decomposition of the deodorized scum oil in step 100 will be described.

In the present invention, as the deodorized scum oil used as a raw material, any deodorized scum oil derived from any vegetable oil can be used as long as it is generated in the step of deodorizing vegetable oils and fats. And rapeseed deodorized scum oil, palm deodorized scum oil and the like. In addition, deodorized scum oil derived from sunflower oil, rice bran oil, corn oil, safflower oil and the like can also be used. In these deodorized scum oils, including free sterols and free fatty acids, triacylglycerol, diacylglycerol,
Monoacylglycerol, tocopherol, carotene,
Contains wax and the like.

Of these, free sterols include β-sitosterol, campesterol, brassicasterol, stigmasterol, cholesterol, etc., while free fatty acids or triacylglycerol, diacylglycerol, monoacylglycerol are included. Fatty acids that are bound to include linoleic acid, oleic acid, palmitic acid, stearic acid, α-linolenic acid, myristic acid, and the like. Among these fatty acids, it is considered that trans-fatty acids are high in linoleic acid and the like having a relatively large amount of unsaturated bonds, and trans-fatty acid content in soybean deodorized scum oil containing a large amount of linoleic acid is high.

Since the deodorized scum oil as described above usually contains a pigment component and other solid substances in many cases, when used directly for the synthesis of sterol fatty acid esters, the deodorized scum oil does not have a decolorizing or deodorizing property. Difficulty is likely to occur in the purification process.

Therefore, in the present invention, fatty acid esters such as triacylglycerol contained in the deodorized scum oil in advance are hydrolyzed (step 101), and the fatty acids generated thereafter (step 110) are subjected to molecular distillation ( step 110). No.
(1) Molecular distillation treatment) The sterol-containing fraction obtained after removal by (Step 111) (Step 12)
0) is used as a substrate for the sterol fatty acid ester synthesis reaction.

Thus, fatty acid esters such as triacylglycerol are converted into free fatty acids in advance (step 11).
0), facilitates removal of degraded trans fatty acids and oxidized fatty acids by molecular distillation (step 111).

The catalyst used for hydrolyzing fatty acid esters such as triacylglycerol contained in the deodorized scum oil in advance includes chemical catalysts such as acids and alkalis, and those usable in foods. Any of these may be used, for example, hydrochloric acid, sulfuric acid and the like as the acid, and sodium hydroxide, potassium hydroxide and the like as the alkali.

In general, an enzyme having lipolytic activity such as lipase can be used for the hydrolysis of fatty acid esters, as described above, in addition to the chemical catalyst. When a lipase or the like is used in the hydrolysis of the fatty acid ester of the present invention, the synthesis reaction of the sterol fatty acid ester proceeds simultaneously with the decomposition of the triacylglycerols. Therefore, the lipase or the like is used in the hydrolysis of the fatty acid ester in the present invention. It is not appropriate to use an enzyme having lipolytic activity.

The concentration of the catalyst, the reaction temperature, and the reaction time in the hydrolysis reaction of the fatty acid ester (step 101) can be arbitrarily set, but an excessive reaction causes deterioration of each component in the deodorized scum oil, and causes coloration and the like. It is desirable to terminate the reaction at 150 ° C. or lower within several hours, since this may cause an undesirable phenomenon.

After the completion of the reaction, neutralization is carried out with a suitable acid or alkali, followed by washing with water to remove the chemical catalyst and the formed glycerin and salts. After washing with water, dewatering is performed by heating at a temperature of about 60 to 120 ° C. for a predetermined time under reduced pressure after separating oil and water (Step 110).

Deodorizing scum after the above dehydration treatment (Step 1)
10) performs fractionation by molecular distillation (step 1)
11). An object of the present invention is to remove trans fatty acids and fatty acid peroxides (steps 112 and 113) which are present as deteriorated fatty acids.
The mixture is treated at 100 to 200 ° C. at 3.3 Pa or less to remove fatty acids as a distillate fraction and obtain a sterol-containing fraction as a residual fraction (step 120).

In order to remove the coloring matter components and other solids contained in the deodorized scum oil, the remaining fraction (step 120) obtained by the above-mentioned molecular distillation treatment (step 111) was again subjected to 13.3 Pa. Hereinafter, processing at 170-250 ° C,
The fraction containing sterol as the distillate fraction (Step 1)
20) can be obtained. As a result, in the subsequent purification step, in particular, the decolorization and deodorization steps can be easily performed, and the obtained product can be obtained with excellent color, smell, taste and the like.

Next, the steps relating to the synthesis of the sterol fatty acid ester in steps 121, 122 and 130 will be described. This produces a sterol fatty acid ester (step 130).

The sterol-containing fraction (fraction of step 120) obtained by the decomposition and distillation of the above-mentioned deodorized scum oil is used as one raw material, and an oil or fat mainly containing any triacylglycerol (step 122) is used. A sterol fatty acid ester synthesis reaction is performed as the other raw material.

The fats and oils containing triacylglycerol as a main component include soybean oil, rapeseed oil, olive oil, palm oil,
Sunflower oil, safflower oil, corn oil, cottonseed oil, sesame oil, rice bran oil, coconut oil, peanut oil, tallow, lard, chicken fat,
Fish oils and the like may be mentioned, and these oils and fats may be used alone or as a mixture of two or more kinds. In the present invention, a sterol fatty acid ester having a desired specific melting point can be obtained by employing an arbitrary fat or oil.

In recent years, it has been known that physiological activities are found in specific fatty acids. In the present invention, fats and oils containing a large amount of desired fatty acids can be selected by focusing on the physiological functions of fatty acids. .

The amount of the fat or oil to be added is preferably 50 to 500% by weight, more preferably 100 to 300% by weight, based on the sterol-containing fraction.

In the synthesis reaction of sterol fatty acid ester,
And an enzyme having lipolytic activity used as a catalyst
Lipase and cholesterol esterase
It is. These are of microbial, animal and plant origin
But microbial sources include pseudo
Monas (Pseudomonas) Genus, Alcaligenes (Alcalig en
es) Genus, Candida (Candida) Genus, mucor (Muco
rGenus, Rhizopus (Rhizopus) Genus, Geotricum (Geotr
icum) Genus-derived enzymes with lipolytic activity
Animal-derived lipolysis from porcine pancreas
Enzymes having an activity.

The enzymes used in the present invention include:
Enzyme with proteolytic activity of the sterol fatty acid ester is an enzyme having a degrading activity (cholesterol esterase), or triacylglycerol (lipase), Examples of the former Pseudomonas (Pseudomonas)
Examples of the latter include enzymes derived from the genus Alcaligenes and Candida .
Genus and the like. Many enzymes having both sterol fatty acid ester decomposing activity and triacylglycerol decomposing activity are also known, and in the present invention, any enzyme having lipolytic activity capable of catalyzing a sterol fatty acid ester synthesis reaction can be used. It is not constrained by enzymatic taxonomic definitions.

When a sterol fatty acid ester synthesis reaction is carried out under a high temperature condition, a heat-resistant enzyme having lipolytic activity may be used. In addition, the enzyme may be purified or crudely purified, and when an enzyme having lipolytic activity derived from a microorganism is used, the culture solution may be used even if the cells themselves are used. May be used.
Further, the enzyme may be a free enzyme or an enzyme immobilized by various carriers such as celite.

The conditions for the synthesis of the sterol fatty acid ester by the enzyme having lipolytic activity used in the present invention include not only the quality in terms of color, smell and taste but also the quality suitable for food in consideration of safety. There is a need for strict control in order to obtain a product having a low cost. The synthesis reaction conditions are described below.

The amount of the enzyme used is not more than 50,000 units, more preferably not more than 10,000 units per gram of sterol contained in the raw material to be treated.
The amount should be not more than 00 units (1 unit is the amount of enzyme that releases 1 micromol of fatty acid per minute from olive oil). Prevents deterioration due to heat treatment during the manufacturing process,
In order to obtain a product at lower cost, it is desirable to reduce the amount of the enzyme used as much as possible, and it is preferable that the amount be 5,000 units or less per gram of sterol contained in the raw material to be treated. Furthermore, the amount of enzyme used can be reduced by adding the enzyme stepwise during the synthesis reaction.

In the present invention, when water is not present at all or is present in a very small amount, there is a very high possibility that triacylglycerol or a small amount of diacylglycerol or monoacylglycerol will remain. Since it becomes difficult to remove in the process,
It is desirable to carry out the enzymatic reaction by adding water of at least%. By performing an enzymatic reaction in the presence of 0.1% or more of water, triacylglycerol and coexisting diacylglycerol, monoacylglycerol, etc. undergo a hydrolysis reaction, and are decomposed into free fatty acids and glycerin, and the fatty acids generated by the decomposition Is also a substrate for the ester synthesis reaction of sterol fatty acid esters.

The efficiency of the synthesis reaction itself can be enhanced by increasing the amount of water added. On the other hand, the added water must be removed in the purification step after the synthesis of the sterol fatty acid ester. It is necessary to minimize the amount of water used for compression, and it is desirable that the amount of water is not more than 300% by weight based on the sterol fraction as a raw material.

The temperature and the time are preferably low and in a short time in order to minimize thermal degradation during the reaction, and usually at 30 to 60 ° C. and within 48 hours. When the treatment is performed at a low temperature, an enzyme having a lipolytic activity that easily exhibits an activity at a low temperature may be used.

On the other hand, since the sterols used as raw materials have a very high melting point, they have very poor solubility with fatty acids as the other substrate, and the sterol fatty acid ester synthesis reaction efficiency is low. There is. In order to solve this problem, it is also possible to carry out the synthesis reaction at a higher temperature, using an enzyme having a thermostable lipolytic activity, 50 ~
The reaction is preferably performed at 90 ° C within 24 hours. At this time, since the thermal degradation during the reaction proceeds more intensely and the enzyme may be deactivated during the reaction, vitamin E is added to prevent the thermal degradation and oxidative degradation of the sterol fatty acid ester. Or a substance having an antioxidant effect such as tea or polyphenols, and also a substance that prevents enzyme inactivation such as salts such as bile salts and saccharides and proteins to prevent enzyme inactivation. Good.

In the present reaction, the reaction is usually carried out with stirring in order to increase the efficiency of the synthesis reaction. However, in some cases, a static reaction is also possible. When a static reaction is performed, an emulsifier or the like may be added. In addition, the use of an organic solvent such as hexane can increase the reaction efficiency, but in that case, the solvent must be removed and the production cost may be increased.

After the sterol fatty acid ester synthesis reaction, the enzyme is inactivated, dehydrated, and the enzyme protein is removed.
The enzyme inactivation treatment can be achieved by stirring at 60 to 100 ° C. for about 30 to 120 minutes. The dehydration treatment is performed by treating at 60 to 120 ° C. for a certain period of time under reduced pressure. For removal of the enzyme protein, a normal filter paper, filter cloth, or filtration filter can be used.If the removal of the enzyme protein is insufficient at that time, in a subsequent step,
It is necessary to remove the enzyme protein more completely because it tends to cause quality deterioration such as coloring due to heating.Before filtration, filter aids such as diatomaceous earth and clay are added in advance,
Filtration after stirring can be carried out efficiently. The above is the process regarding the synthesis of the sterol fatty acid ester.

Next, a method for purifying sterol fatty acid esters will be described.

In the present invention, in order to obtain a sterol fatty acid ester having a suitable quality as a food such as color, smell, taste, etc. and excellent in safety, at a low cost, the above-mentioned purification after the synthesis reaction is carefully performed. It must be made.
In particular, temperature treatment must be strictly performed because treatment at high temperatures may newly generate trans-type fatty acids and peroxides.

First, as a first purification step, a molecular distillation treatment is performed.
(Second molecular distillation treatment) Sterols and fatty acids mainly unreacted by (Step 131) (Step 13)
2) is removed. The sterol fatty acid ester (reaction product) after the enzyme protein removal treatment contains unreacted sterols, fatty acids and other trace components, which must be removed.

In the present invention, first, a molecular distillation treatment (step 131) is performed to efficiently remove sterols, fatty acids (step 132) and the like. In this case, the product sterol fatty acid ester is obtained as a residual fraction (step 140), and unreacted sterols, fatty acids and some odor components are removed as a distillate fraction (step 132). Examples of the apparatus for performing molecular distillation include a falling film type, a centrifugal type, and other short-path distillation apparatuses, and the like, which can achieve a desired degree of vacuum and temperature, and are capable of achieving a desired free sterol, free fatty acid, and the like. Any distillation apparatus may be used as long as it can remove a trace component of the above.

The molecular distillation conditions are as follows: 133 Pa or less;
300 ° C is desirable, preferably 13.3Pa or less, 100-250
C is good. The molecular distillation operation may be repeated a plurality of times. It should be noted that odor components that cannot be completely removed by the steam distillation treatment (step 151), which is the third purification step, can be removed by this step. On the other hand, a slight heating odor may be generated by this step. For this reason, in order to obtain a product from which odor components are efficiently removed, it is necessary to perform a molecular distillation treatment before the steam distillation treatment (step 151).

Subsequently, a second purification step (step 1)
As 41), mainly the dye component (step 142) is removed. The sterol fatty acid ester after molecular distillation (step 140) contains a dye component derived from raw materials, a dye component generated by heating during molecular distillation, an odor component, and the like.

In the present invention, the dye component (step 142)
Adsorbent treatment (step 14)
Perform 1). As the adsorbent used in this case, activated clay, acid clay, activated carbon,
Silica, silica magnesia, or the like is used, and it is preferable to use any of activated clay, activated carbon, and silica. These may be used alone or as a mixture of two or more. These adsorbents are
It is preferable to add 0.1 to 50% by weight, more preferably 1 to 20%.
% By weight. Further, in order to perform decolorization more efficiently, the above-mentioned adsorbent may be treated in a non-polar solvent such as hexane. The solvent used is 0.1
The weight is preferably 50 to 50 times, more preferably 0.1 to 50 times.
It is good to weigh 5 to 20 times. When a non-polar solvent is not used, the adsorbent is added and the mixture is stirred at 40 to 150 ° C. for a certain time. Although it can be carried out at normal pressure, it is more preferred to carry out under reduced pressure in order to suppress the deterioration of the processing raw material and to efficiently decolorize. The pressure is preferably lower, and the pressure is preferably 13.3 kPa or less. For removal of the adsorbent after the adsorbent treatment, ordinary filter paper, filter cloth, or a filter can be used.However, by adding a filter aid such as diatomaceous earth in advance before filtration, stirring, and then filtering efficiently, Can be implemented. When a non-polar solvent is used, the raw material to be treated is dissolved in the non-polar solvent in advance, and then the adsorbent is added to the solution to reduce the amount of the solution.
Stir at 0 ° C. for a certain time. The adsorbent is removed as described above, and then the non-polar solvent is removed by a distillation method. When the pigment component is more completely removed or when the color of the processing raw material is poor, the above-described adsorbent treatment may be repeated several times. When repeated, any adsorbent is added again after filtration of the adsorbent, and the same treatment is performed. When a non-polar solvent is used, after the addition of the adsorbent, stirring, and filtration, the adsorbent is added again without removing the solvent,
The same processing is performed. Solvent removal is performed after the final filtration.

Before performing the above adsorbent treatment,
By performing an acid treatment, an alkali treatment, or the like, a decolorized product can be obtained more effectively. In this case, the processing raw material may be dissolved in a nonpolar solvent such as hexane to form a micellar state, and an acid treatment, an alkali treatment, or the like may be performed. still,
Since there is a possibility that odor components may be generated or adhered at the same time in this step, the above adsorbent treatment (step 14)
1) needs to be performed after the molecular distillation treatment (step 131) and before the steam distillation post-treatment (step 151).

The sterol fatty acid ester (step 150) from which the pigment component (step 142) has been removed in this way
Finally, as a third purification step, odor components (step 152) and the like are removed by steam distillation treatment (step 151). In order to use the decolorized sterol fatty acid ester as food, it is necessary to remove odor components derived from raw materials and odor components generated in the above-described steps. In the case where the decolorization treatment is performed using an organic solvent, the organic solvent may remain even after the solvent removal treatment, so that they must be completely removed. Therefore, the above-mentioned odor components and residual solvent can be almost completely removed by the steam distillation treatment. As a device for performing steam distillation,
A continuous type, a semi-continuous type, or a batch type can be used, but any type of device may be used. The steam distillation conditions are desirably 13.3 kPa or less and 50 to 200 ° C., preferably 1330 Pa or less and 50 to 150 ° C. The steam distillation operation may be repeated several times.

It is known that trans-fatty acids are remarkably produced by carrying out steam distillation at a high temperature for the purpose of deodorization.
It is important to perform the steam distillation at least at 200 ° C. or less, preferably at 150 ° C. or less. As described above, in order to completely remove odor components that cannot be completely removed by steam distillation (step 151) alone, steam distillation processing (step 151) and molecular distillation processing (step 13) are performed.
It is necessary to carry out 1) together, and in that case, it is important to perform a molecular distillation process (step 131) before the steam distillation process (step 151).

The sterol fatty acid ester (step 160) finally obtained according to the present invention comprises:
It is almost tasteless, odorless, colorless or pale yellow, and contains little or no trans-fatty acid, is excellent in safety, and has appropriate quality as a general food, health food, or pharmaceutical material. is there.

This sterol fatty acid ester is expected to have a cholesterol-lowering effect, and its addition to general foods such as margarine and dressing as a functional material has been studied. According to the present invention, a product having a desired melting point can be obtained. Therefore, application to a wider range of foods is expected.

Further, sterol fatty acid esters containing a large amount of arbitrary fatty acids are expected to be used in health foods and pharmaceuticals in the future as a new material having a high physiological activity intended for the functionality of fatty acids. It is.

[0086]

DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, embodiments of the present invention will be described, but the present invention is not limited to these embodiments.

[0087]

Example 1 Soybean deodorized scum oil (sterol content 12.3)
%) 0.2N ethanolic potassium hydroxide (KOH) 1 in 200g
0 ml was added, and the mixture was stirred at 60 ° C. for 2 hours to decompose fatty acid esters such as triacylglycerol. Then, neutralized with 0.4N hydrochloric acid, washed with water to remove ethanol, KCl, KOH and glycerin, under reduced pressure,
A dehydration treatment was performed at 80 ° C. Subsequently, molecular centrifugation was performed by a centrifugal molecular distillation apparatus at a degree of vacuum of 1.5 Pa and an evaporating surface temperature of 170 ° C. to remove fatty acids mainly as a distillate fraction, and collect 28 g of a sterol-containing residual fraction.

Next, the collected fraction containing the above sterols
25 g of soybean refined oil mixed with 25 g of water 25 ml
A suspension of 1.0 g of an enzyme powder (50,000 units / g) having lipolytic activity derived from the genus Pseudomonas was added to the mixture, and a sterol fatty acid ester synthesis reaction was carried out with stirring at 40 ° C. for 24 hours. After that, the mixture was heated to 80 ° C and stirred for 30 minutes to perform enzyme inactivation treatment.After washing with hot water, dehydration treatment was performed at 80 ° C under reduced pressure, and 1 g of diatomaceous earth was added and stirred to remove enzyme proteins. Filtration was performed for

Subsequently, as a second purification step, using a centrifugal molecular distillation apparatus, the degree of vacuum was 1.5 Pa, and the evaporation surface temperature was 230.
The unreacted fatty acid and sterol were removed as a distillate fraction by performing a molecular distillation treatment at ℃. Next, as a second purification step, 10% of activated clay was added to the remaining fraction containing the sterol fatty acid ester, and the mixture was stirred at 80 ° C. under reduced pressure for 30 minutes, and then the dye component was adsorbed by filtration. Activated clay was removed. Finally, as a third purification step, using a batch-type steam distillation apparatus, a vacuum degree of 500 Pa, a distillation temperature of 150 ° C.,
Steam distillation treatment was carried out for one hour in distillation time, and finally 34 g of sterol fatty acid ester from which odor components had been removed could be obtained.

The obtained sterol fatty acid ester was almost tasteless, odorless and pale yellow, had a melting point of 30.1 ° C. and a trans fatty acid content in the constituent fatty acids of 1.2%. The analysis results are shown in Table 1.

[0091]

Example 2 A product obtained by hydrolyzing with ethanolic potassium hydroxide in the same manner as in Example 1 was subjected to molecular distillation at a degree of vacuum of 1.5 Pa and an evaporation surface temperature of 170 ° C. by a centrifugal molecular distillation apparatus. The fatty acid is mainly removed as a distillate fraction, and the remaining fraction containing the collected sterols is further subjected to molecular distillation at a vacuum degree of 1.5 Pa and an evaporation surface temperature of 230 ° C.
22 g of a fraction containing sterol was collected as a distillate fraction.

Next, a mixture of 20 g of the collected sterol-containing fraction and 40 g of refined soybean oil was mixed with 20 ml of water in 0.4 ml of an enzyme powder having lipolytic activity derived from the genus Alcaligenes (90,000 units / g). g was suspended, and a sterol fatty acid ester synthesis reaction was carried out with stirring at 40 ° C. for 24 hours, followed by enzyme inactivation treatment, hot water washing, dehydration treatment, and enzyme protein removal treatment as in Example 1. .

Subsequently, in the same manner as in Example 1, a molecular distillation treatment was performed as a second purification step, an adsorbent treatment was performed as a second purification step, and a steam distillation treatment was performed as a third purification step. 29 g of the ester could be obtained.

The sterol fatty acid ester obtained was almost tasteless, odorless and almost colorless, and had a melting point of 31.5 ° C. The trans fatty acid content in the constituent fatty acids is 1.3
%Met. The analysis results are shown in Table 1.

[0095]

Example 3 A mixture of 25 g of a sterol-containing fraction collected by the same procedure as in Example 1 and 50 g of rapeseed refined oil was mixed with 25 ml of water to determine the lipolytic activity derived from the genus Mucor. A suspension of 0.5 g of an enzyme powder (80,000 units / g) was added, and a sterol fatty acid ester synthesis reaction was carried out with stirring at 40 ° C. for 24 hours. Dehydration treatment and enzyme protein removal treatment were performed.

Subsequently, in the same manner as in Example 1, a molecular distillation treatment was performed as a second purification step, an adsorbent treatment was performed as a second purification step, and a steam distillation treatment was performed as a third purification step. 35 g of the ester could be obtained. The obtained sterol fatty acid ester was almost tasteless, odorless and pale yellow, and had a melting point of 31.2 ° C. The trans fatty acid content in the constituent fatty acids was 1.0%. The analysis results are shown in Table 1.

[0097]

EXAMPLE 4 A mixture of 25 g of a sterol-containing fraction and 50 g of refined olive oil collected by the same procedure as in Example 1 was added to 25 ml of water and the lipolytic activity derived from the genus Candida was added to 25 ml of water. A suspension of 0.2 g of an enzyme powder (360,000 units / g) having a sterol was added, and a sterol fatty acid ester synthesis reaction was carried out with stirring at 40 ° C. for 24 hours. , Dehydration treatment and enzyme protein removal treatment.

Subsequently, in the same manner as in Example 1, a molecular distillation treatment was performed as a second purification step, an adsorbent treatment was performed as a second purification step, and a steam distillation treatment was performed as a third purification step. 36 g of the ester could be obtained. The obtained sterol fatty acid ester was almost tasteless, odorless and pale yellow, and had a melting point of 34.7 ° C. The trans fatty acid content in the constituent fatty acids was 0.4%. The analysis results are shown in Table 1.

[0099]

Example 5 Rhizopus with respect a mixture of fractions 25g and palm refined oil 50g including sterols recovered by performing the same procedure as in Example 1, a heat resistance to water 25ml (Rhiz
opus ) Enzyme powder with lipolytic activity (60,000
Unit / g) A suspension of 0.5 g was added, and a sterol fatty acid ester synthesis reaction was carried out with stirring at 60 ° C. for 12 hours. As in Example 1, enzyme inactivation treatment, hot water washing, dehydration treatment,
An enzyme protein removal treatment was performed.

Subsequently, in the same manner as in Example 1, a molecular distillation treatment was performed as a second purification step, an adsorbent treatment was performed as a second purification step, and a steam distillation treatment was performed as a third purification step. 32 g of the ester could be obtained. The obtained sterol fatty acid ester was almost tasteless, odorless and pale yellow, and had a melting point of 68.5 ° C. The trans fatty acid content in the constituent fatty acids was 0.2%. The results of the analysis are shown in Table 1.

[0101]

Example 6 A mixture of 25 g of a sterol-containing fraction collected by the same procedure as in Example 1 and 50 g of purified tuna oil was mixed with 25 ml of water to determine the lipolytic activity derived from the genus Mucor. 0.5g of enzyme powder (80,000 units / g)
The suspension was added, and a sterol fatty acid ester synthesis reaction was carried out with stirring at 40 ° C. for 24 hours. As in Example 1, enzyme inactivation treatment, hot water washing, dehydration treatment, and enzyme protein removal treatment were carried out.

Subsequently, as in Example 1, a molecular distillation treatment was performed as a second purification step, an adsorbent treatment was performed as a second purification step, and a steam distillation treatment was performed as a third purification step to obtain a sterol fatty acid. 35 g of the ester could be obtained. The obtained sterol fatty acid ester was almost tasteless, odorless and pale yellow, and had a melting point of 15.1 ° C. The trans fatty acid content in the constituent fatty acids was 1.8%. The analysis results are shown in Table 1.

[0103]

Comparative Example 1 To 200 g of soybean deodorized scum oil (sterol content: 12.3%) used in Example 1, 4.0 g of an enzyme powder (50,000 units / g) having lipolytic activity derived from the genus Pseudomonas was suspended. Add turbid, add 40
After performing a synthesis reaction of sterol fatty acid ester while stirring at 48 ° C, washing with hot water, and then performing a dehydration treatment at 100 ° C,
Filtration was performed to remove the enzyme protein.

Subsequently, a molecular distillation treatment was performed using a centrifugal molecular distillation apparatus at a degree of vacuum of 1.5 Pa and an evaporation surface temperature of 230 ° C.
43 g of sterol fatty acid ester could be obtained. The obtained sterol fatty acid ester had a very strong bitter taste and a strong off-flavor, and had a brown color. The melting point is 29.8 ° C,
The trans fatty acid content in the constituent fatty acids was 4.8%. The sterol fatty acid ester content was 59.2%. The analysis results are shown in Table 2.

[0105]

Comparative Example 2 To 200 g of soybean deodorized scum oil (sterol content: 12.3%) used in Example 1, 0.6 g of enzyme powder (90,000 units / g) having lipolytic activity derived from the genus Alcaligenes was suspended. Add turbid, add 40
Perform a sterol fatty acid ester synthesis reaction while stirring at 24 ° C for 24 hours, wash with hot water, and then perform a dehydration treatment at 100 ° C.
Filtration was performed to remove the enzyme protein.

Subsequently, a molecular distillation treatment was carried out using a centrifugal molecular distillation apparatus at a degree of vacuum of 1.5 Pa and an evaporating surface temperature of 230 ° C.
Unreacted fatty acids and sterols are removed as a distillate fraction, and then, using a batch steam distillation apparatus, a vacuum of 1 k
Steam distillation was performed at Pa, a distillation temperature of 250 ° C., and a distillation time of 2 hours to obtain 41 g of a sterol fatty acid ester. The obtained sterol fatty acid ester had weak bitterness and burnt odor, and exhibited a deep yellow color. Melting point 30.5 ℃
The trans fatty acid content in the constituent fatty acids was 7.5%. The sterol fatty acid ester content was 58.9%. The analysis results are shown in Table 2.

[0107]

Comparative Example 3 Deodorized scum was subjected to hydrolysis of fatty acid esters and molecular distillation in the same manner as in Example 1.
Subsequently, the dehydrated product obtained by performing the sterol fatty acid ester synthesis reaction was subjected to molecular distillation treatment at a degree of vacuum of 1.5 Pa and an evaporating surface temperature of 230 ° C. using a centrifugal molecular distillation apparatus, and unreacted fatty acid was obtained. Then, sterols were removed as a distillate fraction, and then steam distillation was performed using a batch-type steam distillation apparatus at a degree of vacuum of 500 Pa, a distillation temperature of 150 ° C., and a distillation time of 1 hour. Finally, 10% of activated clay was added, and the mixture was stirred under reduced pressure at 80 ° C. for 30 minutes, and then filtered to obtain 35 g of sterol fatty acid ester. The obtained sterol fatty acid ester was pale yellow, and bitterness and off-flavor were felt. The melting point was 30.6 ° C., and the trans fatty acid content in the constituent fatty acids was 1.7%. The sterol fatty acid ester content was 95.2%. The analysis results are shown in Table 2.

[0108]

[Table 1]

[0109]

[Table 2]

[0110]

As described above, in the present invention, first, deodorized scum oil generated as a distillate containing volatile components in a deodorizing step, which is one of the refining steps for vegetable oils, is used as a raw material. Fatty acid esters such as triacylglycerol contained in the oil are decomposed in advance by a hydrolysis reaction using a chemical catalyst, and the produced fatty acids are converted into a first fatty acid .
It was the removed by molecular distillation to obtain a fraction containing the sterols. Subsequently, starting from a sterol-containing fraction to which any fat or oil containing triacylglycerol as a main component is added as a raw material, sterol fatty acid esters are synthesized under strictly controlled reaction conditions using an enzyme having lipolytic activity as a catalyst. Performs a reaction, and further performs several stages of purification treatment to obtain appropriate quality as a food, and contains almost no degraded fatty acids such as trans-type fatty acids, and is a safe and inexpensive food-grade sterol fatty acid ester. Is produced enzymatically.

[Brief description of the drawings]

FIG. 1 is an overall configuration diagram showing an outline of the present invention.

────────────────────────────────────────────────── ─── Continuing on the front page (72) Inventor Shoji Kaneko 95-7 Minoki-cho, Fukuyama-shi, Hiroshima Ikeda Food Research Inc. (72) Inventor Fumi 95-7 Minoki-cho, Fukuyama-shi, Hiroshima Ikeda Food Research Inc. (56) References JP-A-62-296894 (JP, A) JP-A-53-106710 (JP, A) JP-A-61-204197 (JP, A) JP-A-2000-302777 (JP, A) 1979-489 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) C07J 1/00-75/00 WPI (DIALOG)

Claims (23)

(57) [Claims] (1)Fractions containing sterols and triacylglycols
Yeast having lipolytic activity in fats and oils based on cerol
To form sterol fatty acid esters.
Further refine the sterol fatty acid ester
Manufacturing process to produce sterol fatty acid esters for food
In the method Sterol Generated in the process of deodorizing vegetable oils as raw materials
Hydrolysis of fatty acid esters in deodorized scum oil
IFirst molecular distillation treatment Mainly to remove fatty acids
To collect the sterol-containing fractions, and to collect the collected sterol-containing fractions.Triacylglycero
Oils and fats containingWith the addition of
Sterol fatty acid ester by an enzyme having lipolytic activity
Tell synthesis reaction in a system with controlled temperature and moisture content
For a certain time,further,  As the first purification stepSecond molecular distillation treatmentWith the Lord
To remove unreacted sterols and fatty acids.
The components are removed, and the third purification step is mainly performed by steam distillation.
Removal of odor components and control of purification temperature
Suppresses the production of sense-type fatty acids, has excellent physical properties for foods, and has
Good sterol fatty acid esters for food
Of sterol fatty acid esters for foods characterized by the following
Method. 2. The hydrolysis reaction liberates degraded fatty acids such as trans fatty acids and oxidized fatty acids in deodorized scum oil.
2. The method for producing a sterol fatty acid ester for food according to claim 1, wherein the method is carried out to make the form easy to remove as an acid . 3. The method for producing a sterol fatty acid ester for food according to claim 1, wherein soybean deodorized scum oil generated in the step of refining soybean oil is used as a sterol raw material. 4. The method for producing a sterol fatty acid ester for food according to claim 1, wherein the hydrolysis reaction of the fatty acid ester in the deodorized scum oil is carried out by an acid or alkali catalyst. . 5. The method according to claim 1, wherein the fatty acid is mainly removed by the first molecular distillation treatment , and the fraction containing sterol is collected at 13.3 Pa or less at 100 to 200 ° C. 2. The method for producing a sterol fatty acid ester for food according to 1 above. 6. A method for removing a sterol-containing fraction by mainly removing fatty acids by a first molecular distillation treatment , and treating the sterol-containing fraction at 13.3 Pa or less at 100 to 200 ° C. to obtain a sterol as a residual fraction. The fraction containing the obtained sterols was further collected to 13.3 Pa or less, 170
The method for producing a sterol fatty acid ester for food according to claim 1, wherein a fraction containing sterol is collected as a distillate fraction by treating at ~ 250 ° C. 7. The collected sterol-containing fraction is separated into
When a synthetic reaction of a sterol fatty acid ester by an enzyme having lipolytic activity is carried out in a system in which temperature and moisture content are controlled for a certain period of time using a material to which an oil or fat containing acylglycerol as a main component is added as a raw material, The method for producing a sterol fatty acid ester for food according to claim 1, wherein an enzyme having a sterol fatty acid ester decomposing activity is used as the enzyme having an activity. 8. bird fractions containing recovered sterols
When a synthetic reaction of a sterol fatty acid ester by an enzyme having lipolytic activity is carried out in a system in which temperature and moisture content are controlled for a certain period of time using a material to which an oil or fat containing acylglycerol as a main component is added as a raw material, 2. The method for producing a sterol fatty acid ester for food according to claim 1, wherein an enzyme having an activity of decomposing a sterol fatty acid ester derived from the genus Pseudomonas is used as the enzyme having an activity. 9. The method according to claim 7, wherein the enzyme having lipolytic activity is cholesterol esterase.
Or a method for producing a sterol fatty acid ester for food according to 8 above. 10. preparative fractions containing the recovered sterols
When a synthetic reaction of a sterol fatty acid ester by an enzyme having lipolytic activity is carried out in a system in which temperature and moisture content are controlled for a certain period of time, using a raw material to which fats and oils mainly containing liacylglycerol are added as a raw material, The method for producing a sterol fatty acid ester for food according to claim 1, wherein an enzyme having a decomposing activity of triacylglycerol is used as the enzyme having a decomposing activity. 11. preparative fractions containing the recovered sterols
When a synthetic reaction of a sterol fatty acid ester by an enzyme having lipolytic activity is carried out in a system in which temperature and moisture content are controlled for a certain period of time, using a raw material to which fats and oils mainly containing liacylglycerol are added as a raw material, The method for producing a sterol fatty acid ester for food according to claim 1, wherein an enzyme having a decomposing activity of triacylglycerol derived from the genus Candida is used as the enzyme having a decomposing activity. 12. The method for producing a sterol fatty acid ester for food according to claim 10, wherein the enzyme having lipolytic activity is lipase. 13. preparative fractions containing the recovered sterols
When a synthetic reaction of a sterol fatty acid ester by an enzyme having lipolytic activity is carried out for a certain period of time in a system in which temperature and moisture content are controlled, starting from a raw material to which fats and oils mainly containing liacylglycerol are added, 0.1 to 50% by weight based on acyl glycerol-based fat or oil
The method for producing a sterol fatty acid ester for food according to claim 1, wherein the reaction is carried out within a range of 30 to 60 ° C within 48 hours in the presence of water. 14. A second molecular distillation as a first purification step .
2. The method for producing a sterol fatty acid ester for food according to claim 1, wherein the treatment is performed at 100 to 250 [deg.] C. at 13.3 Pa or less when mainly removing unreacted sterols and fatty acids. 15. In the second purification step, when mainly removing pigment components by treatment with an adsorbent, the adsorbent may be any one of activated clay, silica gel and activated carbon in an amount of 0.1 to 50% based on the weight of the raw material to be treated. The method for producing a sterol fatty acid ester for food according to claim 1, wherein the treatment is carried out at 100 ° C or lower using a single substance or a mixture of two or more kinds. 16. The sterol fatty acid ester for food according to claim 1, wherein when the odor component is mainly removed by steam distillation as a third purification step, the sterol fatty acid ester for food is treated at a temperature of 50 to 150 ° C. at 1330 Pa or less. Manufacturing method. 17. The sterol fatty acid ester content of the sterol fatty acid ester obtained as a product is 90% by weight.
The trans fatty acid content in the constituent fatty acids of the sterol fatty acid ester is 2% or less, the peroxide value is 10 or less, the acid value is 1 or less, and the color is 6 or less (Gardner 2. The method for producing a sterol fatty acid ester for foods according to claim 1, wherein the sterol fatty acid ester is food-free. 18. A soybean oil as a fat or oil containing triacylglycerol as a main component to be added to the recovered sterol-containing fraction, wherein the sterol fatty acid ester obtained as a product has a melting point of 20 to 40 ° C. The method for producing a sterol fatty acid ester for food according to claim 1, wherein the trans fatty acid content in the constituent fatty acids of the sterol fatty acid ester is 2% or less. 19. Rapeseed oil is used as a fat and oil containing triacylglycerol as a main component to be added to the recovered sterol-containing fraction, and the sterol fatty acid ester obtained as a product has a melting point of 20 to 40 ° C. The method for producing a sterol fatty acid ester for food according to claim 1, wherein the content of trans fatty acid in the constituent fatty acids of the sterol fatty acid ester is 2% or less. 20. Use of olive oil as a fat or oil mainly containing triacylglycerol to be added to the recovered sterol-containing fraction, wherein the sterol fatty acid ester obtained as a product has a melting point of 25 to 45 ° C. The trans fatty acid content in the constituent fatty acids of the sterol fatty acid ester is 1% or less.
A method for producing the sterol fatty acid ester for food according to the above. 21. A palm oil is used as a fat and oil containing triacylglycerol as a main component to be added to the collected sterol-containing fraction, and the sterol fatty acid ester obtained as a product has a melting point of 40 to 100 ° C. 2. The trans-fatty acid content in the constituent fatty acids of the sterol fatty acid ester is 1% or less.
A method for producing the sterol fatty acid ester for food according to the above. 22. A palm oil is used as a fat or oil containing triacylglycerol as a main component to be added to the collected sterol-containing fraction, and an enzyme having heat-resistant lipolytic activity is used. The sterol fatty acid for food according to claim 1, wherein the sterol fatty acid ester obtained as a product has a melting point of 40 to 100 ° C and the content of trans fatty acid in the constituent fatty acids of the sterol fatty acid ester is 1% or less. Method for producing ester. 23. A fish oil is used as a fat or oil containing triacylglycerol as a main component to be added to the recovered sterol-containing fraction, and the sterol fatty acid ester obtained as a product has a melting point of -10 to 20 ° C. The method for producing a sterol fatty acid ester for food according to claim 1, wherein the trans fatty acid content in the constituent fatty acids of the sterol fatty acid ester is 2% or less.