JP2002201484A - Fat and oil composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a fat and oil composition having a high content of a vegetable sterol fatty acid ester having an inhibitory action on the absorption of cholesterol, its manufacturing method, and a food using the same. SOLUTION: The fat and oil composition comprises (A) >=18 wt.% vegetable sterol fatty acid ester and (B) a triglyceride.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an oil / fat composition having a high content of plant sterol fatty acid esters, a process for producing the same, and a food using the same. The present invention relates to a composition, a method for producing the composition, and a food using the composition.

[0002]

BACKGROUND OF THE INVENTION It has long been known that plant sterol has an effect of suppressing cholesterol absorption from the small intestine, and has been used as a plasma cholesterol concentration lowering agent. Cholesterol absorption requires that cholesterol be dissolved in bile acid micelles. However, the amount of cholesterol dissolved in bile acids is low, and most of them are in an emulsion state.

[0003] On the other hand, plant sterols are dissolved in bile acid micelles in an amount substantially equal to that of cholesterol. Therefore, when cholesterol and plant sterol coexist, the amount of cholesterol dissolved in bile acid micelles decreases. In addition, since the absorption rate of plant sterols from the small intestine is low and remains in the small intestinal lumen, the amount of cholesterol dissolved in bile acid micelles remains limited, and the absorption of cholesterol is suppressed. Therefore, for humans susceptible to dietary cholesterol, plant sterols have been used clinically as effective plasma cholesterol lowering agents.

[0004] This plant sterol is contained in vegetable fats and oils, soybeans, wheat and the like, and is consumed in daily meals.
The amount is negligible. In order to suppress cholesterol absorption, about 1-2 g of plant sterols are required daily, and it is difficult to consume such a large amount of plant sterols in a normal human diet.

[0005] On the other hand, there is also a method in which a plant sterol is converted to a plant sterol fatty acid ester to increase the solubility in fats and oils. Plant sterol fatty acid esters are hydrolyzed in the small intestine into free plant sterols and fatty acids, and thus have a cholesterol absorption inhibitory effect, similarly to plant sterols. Belgian Patent No. 756,648 discloses a salad oil to which 0.5 to 10% by weight of a plant sterol fatty acid ester is added, wherein the salad oil is prepared by a chemical transesterification reaction between a plant sterol and a fatty acid anhydride. It is disclosed that the sterol fatty acid ester is produced by a method of adding to fats and oils.
However, this method requires multiple steps of purification after preparing the plant sterol fatty acid ester, which is not preferable in terms of yield and cost. Also, in the above publication,
As for the method for preparing the plant sterol fatty acid ester, only a chemical method is mentioned, and the chemical method is not suitable for food.

Further, Japanese Patent Application Laid-Open No. 11-127779,
JP-A-11-146575 and JP-A-2000-
JP 102361 discloses a food containing a plant sterol fatty acid ester, but does not disclose a food containing a high content of plant sterol fatty acid ester (18% by weight or more).

Accordingly, an object of the present invention is to provide an oil / fat composition containing a high content of a plant sterol fatty acid ester having a cholesterol absorption inhibitory action, a method for producing the same, and a food using the same.

[0008]

SUMMARY OF THE INVENTION The present invention provides an oil / fat composition containing at least 18% by weight of a plant sterol fatty acid ester (A) and triglyceride (B). The present invention also provides a method for producing an oil / fat composition in which a mixture of a plant sterol, an oil / fat, and a fatty acid lower alcohol ester and / or a fatty acid is subjected to an esterification reaction in the absence of a solvent using a lipase or an alkali as a catalyst. It is. Further, the present invention provides a food containing 18% by weight or more of plant sterol fatty acid ester and triglyceride.

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION First, the fat and oil composition of the present invention will be described in detail. The oil / fat composition of the present invention contains at least 18% by weight of a plant sterol fatty acid ester (A) and triglyceride (B).

The above-mentioned plant sterol fatty acid ester (A)
There are no particular restrictions on the plant sterols that constitute
For example, plant sterols such as β-sitosterol, stigmasterol, campesterol, brassicasterol and the like, and plant stanols obtained by hydrogenating these plant sterols are mentioned, and one or two selected from these.
More than a species. In particular, as the plant sterol, β
One or two selected from sitosterol, β-sitostanol, campesterol and campestanol
More than one type is preferred.

The fatty acid constituting the plant sterol fatty acid ester (A) is not particularly limited, and is preferably a saturated fatty acid and / or unsaturated fatty acid having 4 to 24 carbon atoms. Preferred are saturated fatty acids and / or unsaturated fatty acids having 16 to 24 carbon atoms, and more preferred are unsaturated fatty acids having 16 to 24 carbon atoms.

The above plant sterol fatty acid ester (A)
Is 18% by weight or more, preferably 25 to 90% by weight, more preferably 30 to 85% by weight, and most preferably 35 to 80% by weight in the oil and fat composition of the present invention. When the content of the plant sterol fatty acid ester (A) in the oil / fat composition is less than 18% by weight, the amount of the plant sterol ester to be taken is undesirably reduced.

The above-mentioned triglyceride (B) is obtained by binding three molecules of fatty acid to one molecule of glycerin. The type of fatty acid is not particularly limited, but is preferably a saturated fatty acid having 4 to 24 carbon atoms and / or an unsaturated fatty acid, and among them, a saturated fatty acid having 16 to 24 carbon atoms and / or
Alternatively, unsaturated fatty acids are preferable, and unsaturated fatty acids having 16 to 24 carbon atoms are more preferable.

The content of the above triglyceride (B) is not particularly limited, but is preferably 1 to 5 in the oil and fat composition of the present invention.
0-80% by weight, more preferably 20-75% by weight, more preferably 25-70% by weight, most preferably 30-6% by weight.
5% by weight.

In the present invention, it is preferable that the fatty acid composition of the plant sterol fatty acid ester (A) and the fatty acid composition of the triglyceride (B) are substantially the same.

The oil / fat composition of the present invention comprises, in addition to the vegetable sterol fatty acid ester (A) and the triglyceride (B), a free vegetable sterol (C), a partial glyceride (D) and a free fatty acid. One or more selected ones may be contained.

The content of the free plant sterol (C) is not particularly limited, but is preferably 5% by weight or less, more preferably 3% by weight or less, and most preferably 1% by weight in the oil or fat composition of the present invention. % Or less. The content of the partial glyceride (D) is not particularly limited, but is preferably 1 to 20% by weight, more preferably 1 to 15% by weight, and still more preferably 1 to 10% by weight in the fat and oil composition of the present invention. %, Most preferably 1 to 5% by weight.

In the present invention, when the free plant sterol (C) is contained, the weight ratio A / C of the plant sterol fatty acid ester (A) to the free plant sterol (C) is preferably 6 or more. , More preferably 7 or more, more preferably 8 or more, and most preferably 9 or more. When the weight ratio A / C is less than 6, free plant sterols do not dissolve, and crystallization tends to occur.

In the present invention, when the partial glyceride (D) is contained, the weight ratio D / B of the partial glyceride (D) to the triglyceride (B) is preferably 4 or less, more preferably 3.5. Hereinafter, it is more preferably 3 or less. When the weight ratio D / B is more than 4, the partial glyceride (D) is concentrated, so that the production cost is high and not only impractical, but also the solidification property when used in oil and fat foods such as margarine becomes slow. easy.

In the present invention, the above partial glyceride (D) means monoglyceride and / or diglyceride. The weight ratio E / F between the diglyceride (E) and the monoglyceride (F) is preferably 5 or more, more preferably 6 or more. When the weight ratio E / F is less than 5, when the fat or oil composition is used as a cooking or frying fat or oil composition for heating during cooking, smoke is likely to be generated.

The content of the free fatty acid is not particularly limited, but is preferably 0.6% in the fat and oil composition of the present invention.
% By weight, more preferably 0.4% by weight or less, and most preferably 0.3% by weight or less.

The fat or oil composition of the present invention can be used as a raw material for various foods.

Next, a preferred embodiment of the method for producing an oil / fat composition of the present invention will be described. In the method for producing an oil / fat composition of the present invention, a mixture of a plant sterol, an oil / fat, a fatty acid lower alcohol ester and / or a fatty acid is subjected to an esterification reaction in the absence of a solvent using a lipase or an alkali as a catalyst.

As the above-mentioned plant sterols, the same ones as those exemplified as the plant sterols constituting the above-mentioned plant sterol fatty acid ester (A) are used.

As the above fats and oils, for example, fats and oils composed of a saturated fatty acid or an unsaturated fatty acid having a constituent fatty acid composition of 4 to 24 carbon atoms are used. Specifically, palm oil, palm olein, super olein, palm stearin, Palm-based fats such as palm middle melting point, soybean oil, rapeseed oil, cottonseed oil,
Liquid oils such as safflower oil, olive oil, sunflower oil, high oleic sunflower oil, rice bran oil, lauric fats such as palm kernel oil and coconut oil, animal fats such as tallow, lard, fish oil, milk fat, MCT Such as synthetic oils, these hardened oils,
The fractionated oil or transesterified oil can be used alone or in combination of two or more. Of these, vegetable oils and fats are preferably used in consideration of health. In particular,
When the fat or oil composition is used for margarine, fat spread or the like, it is preferable to use a fat or oil blend containing 30% by weight or more of a polyunsaturated fatty acid as the fat or oil.

The fatty acid portion of the fatty acid lower alcohol ester is preferably a saturated fatty acid having 4 to 24 carbon atoms and / or an unsaturated fatty acid, more preferably 16 carbon atoms.
To 24 saturated fatty acids and / or unsaturated fatty acids. On the other hand, the alcohol portion is preferably a lower alcohol having a boiling point of 100 ° C. or lower, such as ethanol or methanol, which is released when hydrolyzed.

The above fatty acid preferably has 4 carbon atoms.
To 24 saturated fatty acids and / or unsaturated fatty acids, and more preferably a saturated fatty acid and / or unsaturated fatty acid having 16 to 24 carbon atoms.

In the present invention, the mixing ratio of the mixture of the plant sterol, the oil and the fatty acid lower alcohol ester and / or the fatty acid before the esterification reaction is not particularly limited, but is preferably 10 to 70% by weight of the plant sterol. %, Oil and fat 10 to 90% by weight, fatty acid lower alcohol ester and / or fatty acid 5 to 60% by weight, more preferably plant sterol 20 to 60% by weight, oil and fat 20 to 80% by weight, fatty acid lower alcohol ester and / or fatty acid 10 The content is preferably set to 50% by weight.

In the present invention, the lipase used as a catalyst is not particularly limited, but it is preferable to use one having no regioselectivity. Specifically Alcaligenes
Genus, Chromobacterium, Pseudomonas, Humicola, etc.
Enzymes obtained from the genus s, Chromobacterium and Pseudomonas are more preferred, and enzymes obtained from the genus Alcaligenes are most preferred. These enzymes can be used as they are as enzyme powders, but they can also be used by immobilizing them on carriers such as diatomaceous earth, alumina, ion exchange resin, activated carbon, and ceramics.

When the above lipase is used as a catalyst, the water content of the reaction system of the esterification reaction is preferably 900 p.
pm or less, more preferably 500 ppm or less, because the hydrolysis of the reaction oil can be minimized and the loss in the deodorization step can be reduced. Further, the esterification reaction can be performed under normal pressure or reduced pressure conditions.

In the present invention, when an alkali is used as a catalyst, it is preferable to use sodium methylate. When sodium methylate is used as a catalyst, a mixture of plant sterols, fats and oils, fatty acid lower alcohol esters and / or fatty acids is heated at 80 to 100 ° C., preferably 900 ppm or less, more preferably 5 ppm or less.
After dehydration to a water content of 00 ppm or less, a catalyst is added,
The esterification reaction is preferably performed under normal pressure or reduced pressure. After completion of the esterification reaction, neutralization, washing with water and dehydration are performed with an acid such as citric acid or phosphoric acid.

In the present invention, the use of lipase as a catalyst is more efficient and economical than the use of alkali.

When the esterification reaction is carried out using the lipase or the alkali as a catalyst, it is preferable to carry out random transesterification. By performing the random transesterification, the plant sterols are randomly esterified with the constituent fatty acids of the fats and oils, so that the constituent fatty acid compositions of the plant sterol fatty acid esters and the constituent fatty acids of the fats and oils (triglyceride) become substantially the same. .

The oil composition thus obtained may be subjected to a solvent such as hexane or acetone or dry fractionation to remove free plant sterols.

Thereafter, the fat or oil composition is refined by the same method as the usual method for refining fat or oil. The usual method for purifying fats and oils here means bleaching, deodorization or deacidification.
By performing purification, the odor peculiar to plant sterols is eliminated, and the oil and fat composition of the present invention having a good flavor and color tone is obtained.

Next, the food of the present invention using the above-described fat or oil composition will be described. The food of the present invention contains 18% by weight or more, preferably 25% by weight of a plant sterol fatty acid ester by using the above-mentioned oil or fat composition of the present invention.
% By weight or more, more preferably 30% by weight or more,
It preferably contains 5 to 80% by weight, more preferably 10 to 70% by weight of triglyceride.

[0037] In addition to the above-mentioned plant sterol fatty acid ester and the above-mentioned triglyceride, the food of the present invention includes, for example,
Glucose, fructose, sucrose, maltose, enzymatic saccharified starch syrup, lactose,
Reduced starch saccharified product, isomerized liquid sugar, sucrose-bound starch syrup, oligosaccharide, reduced sugar polydextrose, sorbitol, reduced lactose, trehalose, xylose, xylitol, maltitol, erythritol, mannitol, fructooligosaccharide, soybean oligosaccharide, galacto-oligosaccharide, Nutrate oligosaccharides, raffinose, lactulose, palatinose oligosaccharides, saccharides such as stevia and aspartame, phosphates (hexametaphosphate, diphosphoric acid, monophosphate), alkali metal salts of citric acid (potassium, sodium, etc.) Guar gum, xanthan gum, tamarind gum, carrageenan, alginate, furcellulan, locust bean gum, pectin, curdlan, starch, modified starch, crystalline cellulose, gelatin, dextrin, agar, dextran and other stabilizers, α-la Eggs such as whey proteins such as toalbumin, β-lactoglobulin, and serum albumin, casein, other milk proteins, low-density lipoprotein, high-density lipoprotein, phosvitin, rivetin, phosphoglycoprotein, ovalbumin, conalbumin, and ovomucoid Proteins, wheat proteins such as gliadin, glutenin, prolamin, glutelin, other proteins such as animal and vegetable proteins, salt, rock salt, sea salt, inorganic salts such as potassium chloride,
Acidulants such as acetic acid, lactic acid, gluconic acid, etc., coloring agents such as β-carotene, caramel, red yeast rice pigment, antioxidants such as tocopherol and tea extract, eggs such as whole egg, egg yolk, egg white, enzyme-treated egg , Cereals such as strong flour, medium flour, flour, legumes such as soybean powder, water, flavors, dairy products, seasonings, pH adjusters, enzymes, food preservatives, shelf life improvers, fruit, fruit juice, coffee, nuts Food materials and food additives such as pastes, spices, cacao mass, cocoa powder, cereals, beans, vegetables, meat, fish and shellfish may be contained.

The food of the present invention is a mixture of the above-mentioned fat or oil composition alone or with other edible fats and oils, and specifically, for example, for confectionery, baking, and western confectionery. Shortening, margarine, kneading fat, roll-in fat; whipping cream fat; mayonnaise fat; chocolate fat; anhydrous cream fat; cooking fat; frying fat, spray fat, and the like. And using such oils and fats, bread, sweet buns, pies, danish, shreds, donuts, cakes, crackers, cookies, biscuits, waffles, scones,
Snacks, whipped cream, milk replacement composition, dessert, ice cream, beverage, mayonnaise, dressing, chocolate, anhydrous cream, candy, gum, rice cracker, sand cream, filling cream, salad, retort food, roux, fried food, frozen Foods such as foods can be manufactured.

Next, the specific composition of the food will be described. However, fats and oils contain triglycerides, partial glycerides, plant sterol fatty acid esters, plant sterols and the like.

1. Water-in-oil emulsion (margarine, fat spread) ・ Oil phase / water phase (weight ratio) 95/5 to 30/70 ・ Content of plant sterol fatty acid ester in water-in-oil emulsion 18 to 70% by weight・ Melting point of fats and oils in oil phase 20-50 ° C

2. Shortening-Content of vegetable sterol fatty acid ester in shortening 18-80% by weight-Melting point of fats and oils in oil phase 20-50C

3. Oil for frying, oil for cooking, oil for spraying ・ Fat oil, oil for cooking, or content of vegetable sterol fatty acid ester in oil for spraying 18 to 80% by weight ・ Antioxidant 0 to 500 ppm ・ Defoamer 0 500 ppm

4. Fat for chocolate, fat for anhydrous cream ・ Content of vegetable sterol fatty acid ester in fat for chocolate or fat for anhydrous cream 18-80% by weight ・ Melting point of fat in oil phase 15-40 ° C

5. Acidified oil-in-water emulsified food (mayonnaise,
Dressing) ・ Oil phase / water phase (weight ratio) 80/20 to 20/80 ・ Content of vegetable sterol fatty acid ester in acidic oil-in-water-type emulsified food 18 to 70% by weight ・ Melting point of oils and fats in oil phase 20 ° C. Less than

6 Whipped cream ・ Oil phase / water phase (weight ratio) 60/40 to 20/80 ・ Content of plant sterol fatty acid ester in whipped cream 18 to 50% by weight ・ Melting point of fat or oil in oil phase 25 to 35 ° C.

7. Bread ・ Fat 10-40% by weight ・ Plant sterol fatty acid ester 18-35% by weight ・ Flour 20-50% by weight ・ Saccharide 5-25% by weight ・ Salt 0.1-0.5% by weight ・ Protein 3-15% by weight %

8. Baked confectionery ・ Oil 10-40% by weight ・ Plant sterol fatty acid ester 18-35% by weight ・ Flour 20-40% by weight ・ Saccharide 5-25% by weight ・ Salt 0.1-0.5% by weight ・ Protein 3-10 weight%

9. Chocolate-Fat content 25-60% by weight-Plant sterol fatty acid ester content 18-50
% By weight-0-50% by weight of cacao mass-0-30% by weight of cocoa powder-0-30% by weight of milk powder-10-60% by weight of carbohydrate-0-5% by weight of emulsifier-0-3% by weight of fragrance

10. Anhydrous cream ・ Fat 25-60% by weight ・ Content of plant sterol fatty acid ester 18-50
% By weight-Sugar 10-60% by weight-Taste powder 0-30% by weight-Milk powder 0-30% by weight

11. Candy ・ Fat and fat content 1 to 45% by weight ・ Plant sterol fatty acid ester content 18 to 40
% By weight ・ Saccharides, taste components 40-90% by weight

12. Roux (for curry, for stew, for bean sprouts, etc.)-Oil content 25-60% by weight-Plant sterol fatty acid ester content 18-50
Weight% ・ Flour 0-40% by weight ・ Seasoning 10-60% by weight

[0052]

EXAMPLES Hereinafter, the present invention will be described specifically with reference to Examples, but the present invention is not limited to these Examples.

[Examples 1 to 4] A commercially available lipase which is a lipase having no regioselectivity (Lipase QL, trade name: Lipase QL)
(Alcaligenes genus, manufactured by Meito Sangyo Co., Ltd.) as a catalyst, a mixture (800) of fats and oils, fatty acid lower alcohol esters, and plant sterols in the formulation shown in Table 1 below.
g) was subjected to an esterification reaction at 65 ° C. by adjusting the water content of the reaction system. Table 1 below shows the total composition before the esterification reaction.
It was shown to. Table 2 below shows the total composition of the plant sterols 1 to 3 used in the esterification reaction and the composition of the plant sterol portion of each of the plant sterols 1 to 3. Then, after filtering the lipase, bleaching (temperature 85
℃, 1% by weight of clay is added to the reaction product,
Treat under the following reduced pressure for 30 minutes), 200 ° C, 399P
a Dewatering by performing steam distillation under reduced pressure of 60 minutes or less,
Unreacted fatty acid ethyl was removed to obtain the oil / fat composition of the present invention. Table 3 below shows the total composition and the ratio of the specific components of the obtained oil and fat composition of the present invention. Table 4 below shows the constituent fatty acid compositions of the specific components of the oil and fat composition. As is clear from the description in Table 4 below, the fatty acid compositions of Examples 1 to 4 have substantially the same constituent fatty acid composition of triglyceride, diglyceride and plant sterol fatty acid ester. Table 5 below shows the evaluation of the flavor and color tone of the oil / fat composition.

[0054]

[Table 1]

[0055]

[Table 2]

[0056]

[Table 3]

[0057]

[Table 4]

[0058]

[Table 5]

Example 5 (Preparation of Margarine) 20% by weight of hydrogenated soybean oil (melting point 45 ° C.), 15% by weight of palm oil, oil and fat composition 50 of Example 1
By weight, 13.3% by weight of water, 1% by weight of salt, 0.5% by weight of skim milk powder and 0.2% by weight of flavor were emulsified and quenched plasticizing to prepare margarine. This margarine contains 20.5% by weight of plant sterol fatty acid ester,
It contained 0.8% by weight of free plant sterols. The obtained margarine did not contain an emulsifier, but did not separate water during quenching plasticization or during storage (4 months). Also, since no emulsifier was added, the flavor was very good. In addition, the obtained margarine,
2.4.9.1- of Reference Oil and Fat Analysis Method (Japan Oil Chemical Association)
When measured according to 1996 (thin layer chromatography-gas chromatography), it contained 13.1% by weight of plant sterols (in terms of free form).

Example 6 (Preparation of fat spread) Hardened fish oil (melting point 45 ° C.)
17.6% by weight, 28.4% by weight of the oil and fat composition of Example 2, 52.3% by weight of water, 1% by weight of salt, 0.5% of skim milk powder
The fat spread was prepared by emulsifying and quenching plasticizing of 0.2% by weight and 0.2% by weight of the flavor. This fat spread contains 18.1 plant sterol fatty acid esters.
% Of free plant sterols by weight. The obtained fat spread did not contain an emulsifier, but did not separate water during quenching plasticization or storage (3 months). Also, since no emulsifier was added, the flavor was very good. Further, the obtained fat spread was measured according to 2.4.9.1-1996 (thin layer chromatography-gas chromatography) of the standard fats and oils analysis method (Japan Oil Chemicals Association),
It contained 11.4% by weight of plant sterols (in terms of free form).

Example 7 (Preparation of Mayonnaise) 8.5% by weight of egg yolk, 9.5% by weight of vinegar having a concentration of 5% by weight, and 3.2% by weight of a seasoning spice are mixed to prepare an aqueous phase. The oil and fat composition 7 of Example 3
After adding 8.8% by weight, stirring and preliminary emulsification, finishing emulsification was performed by a colloid mill to obtain mayonnaise. This mayonnaise contains 5 plant sterol fatty acid esters.
It contained 9.6% by weight and 2.0% by weight of free plant sterols. The obtained mayonnaise is in storage (3 months)
Had no water separation. The flavor was also very good. When the obtained mayonnaise was measured in accordance with 2.4.9.1-1996 (thin layer chromatography-gas chromatography) of the standard method for analyzing fats and oils (Japan Oil Chemistry Association), plant sterol (free form) was obtained. (Equivalent to 38.4% by weight).

Example 8 (Preparation of Soft Chocolate) 50 parts by weight of sugar, 5 parts by weight of cacao mass, 15 parts by weight of whole milk powder, 30 parts by weight of the oil and fat composition of Example 3, 0.3 part by weight of lecithin, vanillin 0.
In the composition consisting of 04 parts by weight, roll according to the usual method,
Conching treatment was performed to obtain soft chocolate. This soft chocolate contains 22.6% by weight of plant sterol fatty acid ester and 0.8% by weight of free plant sterol.
Contained. The obtained soft chocolate had no bloom and had a very good flavor. Moreover, when the obtained soft chocolate was measured according to 2.4.9.1-1996 (thin layer chromatography-gas chromatography) of the standard fats and oils analysis method (Japan Oil Chemistry Association), the plant sterol (free) was determined. (In terms of type) was contained at 14.5% by weight.

Example 9 (Preparation of an anhydrous cream) 70% by weight of the oil and fat composition of Example 3, 29% by weight of rapeseed hardened oil (melting point: 23 ° C.), and 1% by weight of rapeseed hardened oil (melting point: 60 ° C.) Were mixed and quenched and plasticized to prepare an oil / fat mixture. 35% by weight of the fat / oil mixture, 45% by weight of sugar, 10% by weight of taste powder, 1 powdered milk
0% by weight was mixed to obtain an anhydrous cream. This anhydrous cream contained 18.5% by weight of plant sterol fatty acid ester and 0.6% by weight of free plant sterol. The obtained anhydrous cream had a very good flavor. Moreover, when the obtained anhydrous cream was measured according to 2.4.9.1-1996 (thin layer chromatography-gas chromatography) of the standard fats and oils analysis method (Japan Oil Chemistry Association), it was found that plant sterol (free) was obtained. 11.9)
% By weight.

Example 10 (Preparation of Sand Cream) 70 parts by weight of the oil / fat composition of Example 2, 30 parts by weight of rapeseed oil (melting point: 36 ° C.), and 0.1 part by weight of monoglyceride were mixed and quenched and plasticized. A fat mixture was prepared. The fat mixture was whipped to a specific gravity of 0.3. Then add 100 parts by weight of syrup,
Further whipping was performed to obtain a sand cream having a specific gravity of 0.65. This sand cream contains 22.2% by weight of plant sterol fatty acid ester and 0.5% of free plant sterol.
% By weight. The obtained sand cream had a very good flavor. Further, the obtained sand cream was subjected to 2.4.9.
When measured according to 1-196 (thin layer chromatography-gas chromatography), it contained 14.1% by weight of plant sterol (in terms of free form).

[Example 11] (Preparation of hard candy) Oil composition 10 of Example 3
A fat composition was prepared in advance by adding 23 parts by weight of decaglycerin monostearate of HLB13, 14 parts by weight of glycerin fatty acid ester of HLB3, and 4 parts by weight of sucrose fatty acid ester of HLB16 to 0 parts by weight.
35 parts by weight of the oil or fat composition to which this emulsifier was added, 35 parts by weight of sugar, 8.5 parts by weight of starch syrup, 1.5 parts by weight of skim milk powder, and 40 parts by weight of water were mixed to obtain an oil-in-water emulsion. Is boiled down to 140 ° C, the water content is 1.9% by weight
Then, the water was blown off, cooled and molded to obtain a hard candy. This hard candy contained 19.4% by weight of plant sterol fatty acid ester and 0.7% by weight of free plant sterol. The obtained hard candy did not exude the oil during storage and had a good flavor. Further, the obtained hard candy was subjected to the standard oil and fat analysis method (Japan Oil Chemistry Association), 2.4.9.1-1.
996 (thin layer chromatography-gas chromatography)
As a result, it was found to contain 12.5% by weight of plant sterol (in terms of free form).

[Example 12] (Preparation of whipped cream) First, 49.5% by weight of water was heated to 60 ° C and, with stirring, 4.9% by weight of skim milk powder and 0.1% by weight of sodium tripolyphosphate And an aqueous phase in which 0.2% by weight of sucrose fatty acid ester was dissolved. On the other hand, an oily phase was prepared by dissolving soy lecithin 0.2 wt% and glycerin fatty acid ester 0.1 wt% in soy hardened oil (melting point 36 ° C.) 15 wt%, the fat and oil composition of Example 3 30 wt%. The oil phase was added to the above aqueous phase, and the mixture was stirred with stirring to prepare a preliminary emulsion. After the pre-emulsification, the mixture was homogenized at a pressure of 5 MPa, and then sterilized with a VTIS sterilizer (UHT sterilizer manufactured by Alfa Laval) at 142 ° C. for 4 seconds, and again sterilized at 5 MPa.
After homogenization at a pressure of MPa, the mixture was cooled to 5 ° C. Thereafter, aging was performed for 24 hours in a refrigerator to obtain whipped cream. This whipped cream contained 22.7% by weight of plant sterol fatty acid ester and 0.8% by weight of free plant sterol. The obtained whipped cream was excellent in all of overrun, emulsion stability, heat-resistant shape retention, flavor, mouth-drying, and artificialness. When the obtained whipped cream was measured according to 2.4.9.1-1996 (thin layer chromatography-gas chromatography) of the standard method for analyzing fats and oils (Japan Oil Chemistry Association), plant sterols (free (In terms of mold) was contained at 14.7% by weight.

[Example 13] (Preparation of whipped cream) First, 49.5% by weight of water was heated to 60 ° C and, with stirring, 4.9% by weight of skim milk powder and 0.1% by weight of sodium tripolyphosphate And an aqueous phase in which 0.2% by weight of sucrose fatty acid ester was dissolved. On the other hand, an oily phase prepared by dissolving 0.2% by weight of soybean lecithin and 0.1% by weight of glycerin fatty acid ester in 15% by weight of butter oil and 30% by weight of the oil / fat composition of Example 2 was prepared. The oily phase was added and mixed and stirred to prepare a pre-emulsion. After pre-emulsification, the mixture was homogenized at a pressure of 5 MPa, sterilized with a VTIS sterilizer (UHT sterilizer manufactured by Alfa Laval) at 142 ° C. for 4 seconds, homogenized again at a pressure of 5 MPa, and cooled to 5 ° C. Thereafter, aging was performed for 24 hours in a refrigerator to obtain whipped cream. This whipped cream contains one plant sterol fatty acid ester.
It contained 9.1% by weight and 0.4% by weight of free plant sterols. The obtained whipped cream was excellent in all of overrun, emulsion stability, heat-resistant shape retention, flavor, mouth-drying, and artificialness. Further, the obtained whipped cream was subjected to 2.4.
When measured according to 9.1-1996 (thin layer chromatography-gas chromatography), it contained 12.1% by weight of plant sterols (in terms of free form).

[Example 14] (Preparation of milk replacement composition) 64.2% by weight of water was heated to 60 ° C, and while stirring, 10% by weight of skim milk powder, 0.1% by weight of sodium hexametaphosphate, citrate An oil phase in which 0.3% by weight of sorbitan monostearate was dissolved in 25% by weight of the oil and fat composition of Example 3 was added to an aqueous phase in which 0.1% by weight of sodium citrate and 0.3% by weight of sucrose fatty acid ester were dissolved. The mixture was mixed and stirred to prepare a preliminary emulsion. After pre-emulsification, homogenized at a pressure of 5 MPa, sterilized with a VTIS sterilizer (UHT sterilizer manufactured by Alfa Laval) at 142 ° C. for 4 seconds, homogenized again at a pressure of 15 MPa, and cooled to 5 ° C., a milk substitute composition I got This milk replacement composition contained 18.9% by weight of plant sterol fatty acid ester and 0.7% by weight of free plant sterol. The resulting milk replacer composition had good flavor and emulsion stability. When the obtained milk substitute composition was measured in accordance with 2.4.9.1-1996 (thin layer chromatography-gas chromatography) of the standard method for analyzing fats and oils (Japan Oil Chemistry Association), plant sterols were obtained. (Free conversion) 12.2
% By weight.

[Example 15] (Preparation of fats and oils for frying) 50% by weight of the vegetable sterol-containing fats and oils composition of Example 1 and rapeseed oil 50 having an iodine value of 111.0.
% By weight, and 100 ppm of tocopherol was added to obtain a fat and oil for frying. This frying fat contained 20.4% by weight of plant sterol fatty acid ester and 0.7% by weight of free plant sterol. The oxidation stability of the obtained frying fat was good. Moreover, when the obtained fats and oils for frying were measured according to 2.4.9.1-1996 (thin layer chromatography-gas chromatography) of the standard fats and oils analysis method (Japan Oil Chemicals Association), the plant sterol ( 13.2% by weight (in terms of free form).

[Example 16] (Preparation of fats and oils for frying) 100% by weight of the sterol-containing fat and oil composition of Example 4 was added to 100 pp of tocopherol.
m was added to obtain a fat and oil for frying. This fat for frying contains 28.5% by weight of plant sterol fatty acid ester,
It contained 0.6% by weight of free plant sterols. The oxidation stability of the obtained frying fat was good. Moreover, when the obtained fats and oils for frying were measured according to 2.4.9.1-1996 (thin layer chromatography-gas chromatography) of the standard fats and oils analysis method (Japan Oil Chemicals Association), the plant sterol ( 18% by weight (in terms of free form).

[0071]

The oil and fat composition of the present invention contains a high content of a plant sterol having a cholesterol absorption inhibitory action,
It can be used as a raw material fat for foods. Further, the method for producing an oil / fat composition of the present invention can produce the above-mentioned oil / fat composition at a high yield and at low cost.

Continuing from the front page (72) Inventor Maruzen Shoji 7-35, Higashiogu, Arakawa-ku, Tokyo Asahi Denka Kako Kogyo Co., Ltd. (72) Inventor Toshiyuki Hirokawa 7-35, Higashiogu, Arakawa-ku, Tokyo Asahi Asahi Denka Kogyo Co., Ltd. F-term (reference) in Denka Kogyo Co., Ltd. 4H059 BA30 BA33 BA34 BB02 BB03 BB57 BC03 BC13 BC48 CA35 CA48

Claims (9)

[Claims] 1. An oil or fat composition comprising at least 18% by weight of a plant sterol fatty acid ester (A) and triglyceride (B). 2. The fat and oil composition according to claim 1, wherein the constituent fatty acid composition of the plant sterol fatty acid ester (A) and the constituent fatty acid composition of the triglyceride (B) are substantially the same. 3. It contains a free plant sterol (C),
The fat or oil composition according to claim 1 or 2, wherein the weight ratio A / C of the plant sterol fatty acid ester (A) and the free plant sterol (C) is 6 or more. 4. The fat or oil according to claim 1, comprising a partial glyceride (D), wherein the weight ratio D / B between the partial glyceride (D) and the triglyceride (B) is 4 or less. Composition. 5. The oil and fat composition according to claim 4, wherein the partial glyceride (D) comprises diglyceride (E) and monoglyceride (F), and the weight ratio E / F is 5 or more. 6. A method for producing an oil / fat composition in which a mixture of a plant sterol, an oil / fat, and a fatty acid lower alcohol ester and / or a fatty acid is subjected to an esterification reaction in the absence of a solvent using a lipase or an alkali as a catalyst. 7. The method according to claim 6, wherein the lipase is a lipase having no regioselectivity. 8. The method according to claim 6, wherein the water content of the reaction system in the esterification reaction is 900 ppm or less. 9. A food containing 18% by weight or more of plant sterol fatty acid ester and triglyceride.