JPH06220484A - Fat composition and emulsified fat composition - Google Patents

Abstract

PURPOSE:To obtain a new fat composition having a good flavor and to obtain a new emulsified fat composition having a good flavor and a good emulsion stability and preperid by using the former composition. CONSTITUTION:The fat composition is obtained by subjecting a mixture comprising a fat and polyglycerol to transesterification with a lipase. The emulsified fat composition is obtained by emulsifying the former composition in water.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an oil and fat composition having a good flavor, and an emulsified oil and fat composition obtained by using the oil and fat, which is suitable for foods having a good taste and a refreshing feeling, especially for confectionery materials. Regarding

[0002]

2. Description of the Related Art Polyglycerin is a polymer of glycerin, is a viscous, hygroscopic and sweet liquid, and is a kind of polyhydric alcohol. This fatty acid ester is obtained by esterifying some of the hydroxyl groups of polyglycerin with a fatty acid, exhibits high stability in an acidic region, and is widely used as an emulsifier and a viscosity adjusting agent in the food field. In Japan, it has been approved for use as a food additive "glycerin fatty acid ester" since June 1981, and overseas, in the 1960s, many researchers conducted research on metabolism and safety. W
Evaluated by HO (United Nations Food and Agriculture Organization / World Health Organization),
It has been confirmed to be a highly safe emulsifier.

As a method for producing a polyglycerol fatty acid ester, there are a direct esterification method, a method by transesterification and an enzyme method. Generally, a direct esterification method using an alkali catalyst of fatty acid and polyglycerin is industrially used. It has been implemented. On the other hand, the enzymatic method is not generally performed, and Okumura et al. Report that diglycerin oleate can be synthesized in a series of studies on esterification of alcohols by using lipase as an enzyme. (Biochim, Biophy. Acta, 575, 156 (1979)).

[0004] Further, emulsifier manufacturers are investigating polyglycerin esters using lipase, but the above report relates to the esterification reaction using polyglycerin and fatty acids as starting materials, and the enzyme of oils and fats and polyglycerin is used. There is no report on the transesterification used. Further, lipase is known as a hydrolase for fats and oils, especially triglyceride, but in recent years, it has been recognized that it catalyzes not only hydrolysis but also esterification reaction, and many application examples have been reported.

[0005]

The object of the present invention is obtained by transesterification of a mixture of fats and oils and polyglycerin using an enzyme under mild reaction conditions.
It is intended to provide a novel oil and fat composition having a good flavor, and a novel emulsified oil and fat composition having a good flavor and obtained by using the oil and fat composition and having stable emulsion.

[0006]

[Means for Solving the Problems] The present inventors have conducted extensive studies on the use of lipase in the transesterification reaction of fats and oils, and as a result of further studies focusing on the transesterification activity of lipase. It was found that transesterification is possible even between polyglycerin and fats and oils.

The present invention has been made on the basis of the above findings, and provides a novel oil and fat composition obtained by subjecting a mixture of oil and fat and polyglycerin to a transesterification reaction with lipase. Further, the present invention provides a novel emulsified oil / fat composition obtained by emulsifying an oil / fat and oil-containing oil / fat obtained by performing a transesterification reaction with lipase in a mixture of oil / fat and polyglycerin. It is a thing.

First, the first invention will be described. The polyglycerin used in the present invention has a polymerization degree of 2-1.
It is a dehydrated condensate of 5, preferably 2 to 10 glycerin, and is applicable to all linear or cyclic polyglycerin. Specific examples thereof include diglycerin, triglycerin, tetoaglycerin, pentaglycerin, hexaglycerin, heptaglycerin, octaglycerin, nonaglycerin, decaglycerin, pentadecaglycerin and the like. As the polyglycerin, in addition to dehydration condensation of glycerin, those obtained by recovering glycerin from a distillation residue or synthesizing from a glycerin-like compound can also be used.

The fats and oils used in the present invention include
Animal and vegetable resins used for normal edibles, specifically, palm oil, soybean oil, rapeseed oil, palm oil, palm kernel oil, sunflower oil, safflower oil, olive oil, rice oil, cottonseed oil, castor oil and other vegetable oils, milk fat, Examples include beef tallow, lard, animal oils such as fish oil, and castor oil containing hydroxy acid. Further, these hydrogenated oils, fractionated oils and the like can be mentioned.

In the oil / fat composition of the present invention, the above-mentioned oil / fat and polyglycerin are mixed in a molar equivalent of 1 to 10 parts, preferably 8 to 2 parts of polyglycerin,
It is produced by adding lipase to this and reacting it under mild conditions of 30 ° C to 70 ° C. As the lipase used in the present invention, both a lipase having 1,3 position specificity and a lipase having no 1,3 position specificity can be used. Specifically, examples of lipases having 1,3-position specificity include enzymes of the genus Rhizopus such as Rhizopus derema, genus Aspergillus such as Aspergillus niger, genus Mucor such as Mucor and Mihai, and genus Alcaligenes. , Animal-derived enzymes such as pancreatin can be used. As the lipase having no 1,3-position specificity, an enzyme originating from a microorganism belonging to the genus Candeda can be used.

There is no particular limitation on the form of addition of lipase when producing the oil / fat composition of the present invention, but immobilized lipase is preferably used in terms of efficiency and economy. The immobilization of the lipase may be performed by physical adsorption, ionic bond or the like on the insoluble carrier. As the insoluble carrier, diatomaceous earth, ion exchange resin, activated carbon, alumina,
Examples include chitosan. In the present invention,
Particularly, diatomaceous earth and ion exchange resins are preferable.

The amount of lipase added is arbitrary, but 0.001 to 100% by weight based on triglyceride (oil and fat),
It is preferably 0.1 to 50% by weight. Further, in the present invention, it is also possible to carry out by adding an organic solvent to the reaction system, and examples thereof include hexane, isooctane, acetone, t-butyl alcohol and the like. It is preferable because it is not given.

Further, in the present invention, in order to prevent the production of free fatty acids generated by the hydrolysis of fats and oils by lipase, it is desirable that the reaction raw materials are well dehydrated and dried before the reaction. As another method, it is also possible to add a desiccant such as molecular sieve to the reaction system to adsorb and remove water in the reaction system during the reaction. Furthermore, in the present invention, a monovalent lower alcohol such as methanol, ethanol, propanol, isopropanol, butanol may be added to the reaction system to remove water.

The oil and fat composition of the present invention obtained as described above contains 85% by weight or less of triglyceride, preferably 30 to 30% by weight.
80% by weight, 10% by weight or more of diglyceride, preferably 15 to 30% by weight, 5% by weight or less of monoglyceride, preferably 4% by weight or less, 10% by weight or more of polyglycerol ester, preferably 20 to 45% by weight Is.

The polyglycerol ester is a fatty acid ester of polyglycerol obtained by subjecting a mixture of oil and fat and polyglycerin to transesterification with lipase. Since fatty acids are supplied by fats and oils,
The fatty acid ester of polyglycerin varies depending on the fats and oils used in the reaction, and examples thereof include palmitic acid ester of polyglycerin, stearic acid ester of polyglycerin, and oleic acid ester of polyglycerin. The above oil / fat composition is suitably used as an oil / fat of an emulsified oil / fat composition by bleaching and deodorizing in the usual oil / fat purification step.

Next, the second invention will be described. The mixture of fats and oils and polyglycerin used in the present invention, the fats and oils containing fats and oils obtained by performing transesterification reaction with lipase, to the mixture of fats and oils and polyglycerin, transesterification reaction with lipase Oil and fat composition obtained by the following (hereinafter referred to as the oil and fat of the first invention)
Is an oil and fat containing 3% by weight or more in the whole oil and fat.

Examples of fats and oils other than the fats and oils of the first invention include animal and plant fats and oils commonly used for edible foods, hydrogenated oils and fractionated oils thereof. The water used in the present invention includes water, milk and the like commonly used.

The fats and oils and the water content are the same as the fats and oils 10 to 9.
It is used in a proportion of 90 to 10% by weight of water relative to 0% by weight. In addition, the emulsified oil and fat composition of the present invention may appropriately contain components other than the above-mentioned oil and fat content and water, which are contained in general emulsified oil and fat compositions. Examples thereof include fruit paste, jam, granular solid matter, dietary fiber, starch, and protein, and 30% by weight in the emulsified oil and fat composition of the present invention.
Used in the following proportions.

The emulsion oil / fat composition of the present invention may be an oil-in-water emulsion oil / fat composition or a water-in-oil emulsion oil / fat composition. The emulsification method may be a general method. The emulsified oil / fat composition obtained as described above is used for foods, particularly as a confectionery material.

[0020]

EXAMPLES The present invention will be specifically described below with reference to examples. Example 1 500 g of high oleic sunflower oil (manufactured by SVO USA,
TRISUN 80) and a mixture of 80 g of diglycerin (K-COL-II manufactured by Kashima Chemical Co., Ltd.), 15 g of lipase [lipase PL powder of Alcaligenes origin (manufactured by Meito Sangyo Co., Ltd.)] was added, and 40 The transesterification reaction was carried out at 15 ° C. for 15 hours. By the above reaction, formation of various esters (reaction products) was recognized, and as a result of iatroscan analysis, as shown in the chart of FIG. 1, triglyceride (TG), diglyceride (DG), diglycerin monoester (DGM) And the peaks of diglycerin diester (DGD) were confirmed. The following instruments and developing solvents were used for the above-mentioned iatrocan analysis. [Equipment; Iatrocan TH-10 (Yatron Co., Ltd.) Chromarod S-III developing solvent; benzene: chloroform: formic acid = 70: 30: 2]

The specific composition of the reaction product (oil and fat composition) is as follows: triglyceride 36% by weight, diglyceride 20
% By weight, and 43% by weight of diglycerin fatty acid ester. As diglycerin fatty acid ester, diglycerin oleate, diglycerin dioleate, diglycerin tetraoleate, etc. were contained. The obtained reaction product was separated from the enzyme powder by filter paper filtration. bleaching,
Deodorization was performed according to the usual oil and fat refining method. Bleaching was carried out at a temperature of 85 ° C. for 30 minutes under a reduced pressure of 3% clay. Deodorization is performed by blowing steam at a temperature of 190 ° C. for 40 minutes, and when deodorization is completed and the temperature is lowered, blowing steam is stopped.
A bleached and deodorized oil and fat composition was obtained. From the above, the obtained oil and fat composition has almost no odor,
Partly unreacted diglycerin came out as a distillate (preparation: 450 g, distillate: 1 g).

Example 2 The oil / fat composition 1 obtained in Example 1 was treated at 60 ° C.
The warm water of 3 was added at a ratio of 3, and the mixture was slowly stirred with a spatula. Emulsification easily occurred only by this operation, and a white emulsified oil / fat composition was obtained. The emulsified oil / fat composition had characteristic yogurt-like physical properties, melted in the mouth and had a good flavor.

Example 3 30% by weight of the oil / fat composition prepared in Example 1 was mixed with 55% by weight of water, 10% by weight of strawberry jam and 5% by weight of sugar,
The mixture was emulsified with a homogenizer to obtain an oil-in-water emulsion composition. The emulsion stability of the obtained emulsified oil and fat composition was evaluated.
The results are shown in Table 1.

Comparative Examples 1 to 2 An aggregate was prepared in the same manner as in Example 3 except that a mixture of 2% by weight of the following emulsifier and 28% by weight of high oleic sunflower oil was used instead of the oil and fat composition prepared in Example 1. A medium oil type emulsion composition was obtained. In Comparative Example 1, a commercially available oleic acid ester of distilled monoglyceride was used, and in Comparative Example 2, a commercially available diglycerin monooleate was used. The emulsion stability of the obtained emulsified oil and fat composition was evaluated. The results are shown in Table 1.

[0025]

[Table 1]

Example 4 A whipped cream having the composition shown in Table 2 was prepared by a conventional method. At that time, pre-emulsification was performed at 70 ° C. and 500 rpm for 3 minutes with a homomixer, sterilization was performed at 80 ° C., and primary homogenization was performed at 3
0 kg / cm ² , secondary homogenization was 70 kg / cm ² , and aging was performed at 5 ° C. for 5 days. The overrun and shape retention of the obtained whipped cream were evaluated by the following methods.
The overrun was measured every minute by a whipper in a water bath at 5 ° C. The shape-retaining property was observed by squeezing a whipped cream, artificially culturing the flowers, and allowing them to stand at 5 ° C. for observation (immediately after production), and then allowing them to stand at 10 ° C. for observation. The results are shown in Table 3.

[0027]

[Table 2]

Comparative Examples 3 to 4 Whipped cream was carried out in the same manner as in Example 4 except that a mixture of 2% by weight of the following emulsifier and 28% by weight of high oleic sunflower oil was used in place of the oil and fat composition prepared in Example 1. Got In Comparative Example 3, a commercially available monooleate was used, and in Comparative Example 4, a commercially available diglycerin monooleate was used. The obtained whipped cream was evaluated for overrun and shape retention in the same manner as in Example 4. The results are shown in Table 3.
Shown in.

[0029]

[Table 3]

Example 5 To a mixture of 500 g of rapeseed salad oil and 80 g of diglycerin, 20 g of immobilized enzyme of Mucor Mihai (Lipozyme NOVO) as a lipase was added, and transesterification reaction was carried out at 40 ° C. for 15 hours, A reaction product (55% by weight of triglyceride, 18% by weight of diglyceride, 4% by weight of monoglyceride, 20% by weight of diglycerin fatty acid ester whose fatty acid to be bound is mainly palmitic acid, stearic acid, oleic acid and linoleic acid) was obtained. The obtained reaction product was purified in the same manner as in Example 1 below to obtain an oil and fat composition.

Example 6 2% by weight of the oil / fat composition prepared in Example 5, 58% by weight of soybean hydrogenated oil, and 40% by weight of water were mixed to obtain a fat spread by a commonly used method. The obtained fat spread was evaluated for creaming property and water absorption by the following methods. For the creaming property, the specific volume (mg / g) was measured by whipping and aging. For water absorption, water colored with methylene blue at 25 ° C. was dropped while whipped with a mixer, and the amount of water injected until the water became immiscible was measured. The results are shown in Table 4.

Comparative Examples 5-6 Fat spreads were prepared in the same manner as in Example 6 except that a mixture of 5% by weight of the following emulsifier and 45% by weight of rapeseed salad oil was used in place of the oil / fat composition prepared in Example 5. Obtained. In Comparative Example 5, a commercially available monooleate was used, and in Comparative Example 6, a commercially available diglycerin monooleate was used. The obtained fat spread was evaluated for creaming property and water absorption in the same manner as in Example 6. The results are shown in Table 4.

[0033]

[Table 4]

Example 7 To a mixture of 500 g of soybean white squeezing oil and 50 g of decaglycerin (K-COL-IV700, Kashima Chemical Co., Ltd.) was added 30 g of Mucor Mehhi immobilized enzyme as a lipase at 40 ° C. A transesterification reaction was carried out for 15 hours to obtain a reaction product (70% by weight of triglyceride, 10% by weight of diglyceride, 20% by weight of decaglycerin fatty acid ester whose bound fatty acids are mainly oleic acid and linoleic acid). The obtained product was purified in the same manner as in Example 1 to obtain an oil and fat composition having almost no odor and a good flavor.

Example 8 Using the oil / fat composition prepared in Example 7, an ice cream having a formulation shown in Table 5 was produced as a trial product.
It was excellent in shape retention.

[0036]

[Table 5]

Comparative Example 7 A transesterification reaction was carried out at 80 ° C. for 1 hour using a mixture of 500 g of soybean white squeezing oil and 50 g of decaglycerin and 0.5 g of sodium methylate as a reaction catalyst to obtain a reaction product (triglyceride). 60% by weight, diglyceride 1
5% by weight, decaglycerin fatty acid ester whose bound fatty acid is mainly oleic acid and linoleic acid (25% by weight) was obtained. However, after the reaction was completed, when water was added for washing with hot water to remove the catalyst, emulsification occurred,
The intended clear composition could not be obtained. Further, coloring occurred and it was difficult to decolorize.

[0038]

The novel oil and fat composition of the present invention has a good flavor. Further, the novel emulsified oil / fat composition of the present invention obtained by emulsifying the above oil / fat composition of the present invention has a good flavor, stable emulsification, and a refreshing feeling.

[Brief description of drawings]

FIG. 1 is a chart showing the analysis results by an iatroscan analysis of the composition of an example of the oil and fat composition (reaction product) of the present invention.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification code Office reference number FI technical display location A23D 9/00 518 9/02 C12P 7/64 7432-4B

Claims (2)

[Claims] 1. An oil and fat composition obtained by subjecting a mixture of oil and fat and polyglycerin to a transesterification reaction with lipase. 2. An emulsified oil / fat composition, which is obtained by emulsifying an oil / fat containing an oil / fat obtained by subjecting a mixture of the oil / fat and polyglycerin to a transesterification reaction with lipase, and water.