JP3276696B2 - Fat composition and emulsified fat composition - Google Patents

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 good taste, and an emulsified oil / fat composition which is obtained by using the oil / fat and which is suitably applied to a flavorful and refreshing food, particularly a confectionery material. About.

[0002]

2. Description of the Related Art Polyglycerin is a polymer of glycerin, a viscous, hygroscopic, sweet liquid and 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 modifier in the food field. In Japan, its use as a food additive "glycerin fatty acid ester" has been approved since June 1981. Overseas, in the 1960s, many researchers conducted studies on metabolism and safety, and FAO / W
HO (United Nations Food and Agriculture Organization / World Health Organization)
It has been confirmed that this is a highly safe emulsifier.

[0003] Methods for producing polyglycerin fatty acid esters include a direct esterification method, a transesterification method and an enzymatic method. In general, the direct esterification method using an alkali catalyst of a fatty acid and polyglycerin is industrially used. It has been implemented. On the other hand, the enzymatic method is not generally practiced, and Okumura et al. Report that diglycerin oleate can be synthesized in a series of studies on esterification of alcohols using lipase as an enzyme. (Biochim, Biophy. Acta, 575, 156 (1979)).

Emulsifier manufacturers have been studying polyglycerin esters using lipase. The above report relates to an esterification reaction using polyglycerin and a fatty acid as starting materials. There is no report on the transesterification used. Lipase is also known as a hydrolase of fats and oils, particularly triglycerides.In recent years, it has been recognized that it catalyzes not only hydrolysis but also esterification, and many application examples have been reported.

[0005]

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

[0006]

Means for Solving the Problems The present inventors have intensively studied the use of lipase in the transesterification of fats and oils, but as a result of further study focusing on the transesterification activity of lipase. It has been found that a transesterification reaction is possible even between polyglycerin and fats and oils.

[0007] The present invention has been made based on the above findings, the mixture consisting of oil and polyglycerol, obtained by performing the transesterification with lipase trig
Lyceride 30-80% by weight, diglyceride 10-30 weight
%, Less than 4% by weight of monoglyceride and polyglycerin
It is intended to provide a novel oil / fat composition containing 10 to 45% by weight of an ester . The present onset Ming, the mixture consisting of oil and polyglycerol, obtained by performing the transesterification with lipase, 30-80 fold triglycerides
%, Diglyceride 10 to 30% by weight, monoglyceride
4% by weight or less and polyglycerol ester 10 to 45 weight
A grease comprising a fat composition containing an amount%, obtained by emulsifying the water, is to provide a novel emulsified oil composition.

First, the first invention will be described. The polyglycerin used in the present invention refers to a polymerization degree of 2-1.
5, preferably 2 to 10 dehydration condensates of glycerin, and all linear or cyclic polyglycerins are applicable. Specific examples include diglycerin, triglycerin, tetraaglycerin, pentaglycerin, hexaglycerin, heptaglycerin, octaglycerin, nonaglycerin, decaglycerin, pentadecaglycerin and the like. As polyglycerin, those obtained by dehydration condensation of glycerin, recovery of glycerin from a distillation residue, or synthesis 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 edible purposes, specifically, vegetable oils such as coconut oil, soybean oil, rapeseed oil, palm oil, palm kernel oil, sunflower oil, safflower oil, olive oil, rice oil, cottonseed oil, castor oil, milk oil, Animal oils such as beef tallow, lard, fish oil, and castor oil containing hydroxy acids. Further, these hydrogenated oils, fractionated oils and the like can also be mentioned.

The fat and oil composition of the present invention is obtained by mixing the above-mentioned fat and oil with polyglycerin in a molar equivalent of 10 to 1, preferably 8 to 2, with respect to 1 polyglycerin,
It is produced by adding lipase thereto and reacting it under a mild condition of 30 ° C to 70 ° C. As the lipase used in the present invention, either a lipase having 1,3-position specificity or a lipase having no 1,3-position specificity can be used. Specifically, examples of the lipase having 1,3-position specificity include enzymes derived from microorganisms such as Rhizopus, such as Rhizopus delemar, Aspergillus, such as Aspergillus niger, Mucor, such as Mucor-Mehi, and Alkagens. And animal-derived enzymes such as pancreatin. As a lipase having no 1,3-position specificity, an enzyme derived from a microorganism of the genus Candida can be used.

[0011] The form of addition of the lipase in producing the oil / fat composition of the present invention is not particularly limited, but it is preferable to use immobilized lipase from the viewpoint of efficiency and economy. The lipase may be immobilized on an insoluble carrier by physical adsorption, ionic bonding, or the like. As the insoluble carrier, diatomaceous earth, ion exchange resin, activated carbon, alumina,
Chitosan and the like can be mentioned. In the present invention,
Particularly, diatomaceous earth and ion exchange resin are suitable.

The amount of lipase to be added is optional, but may be 0.001 to 100% by weight based on triglyceride (oil or fat).
Preferably, it may be 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, e.g., hexane, isooctane, it may be mentioned acetone, t- butyl alcohol, in particular, negative impact on hexane Enzymatically active Is not preferred.

Furthermore, Oite the present invention, in order to prevent the formation of free fatty acids resulting from the hydrolysis of fats and oils by lipase, reactants may dehydration prior to the reaction, it is desirable to dry. As another method, a desiccant such as molecular sieve may be added to the reaction system to adsorb and remove water in the reaction system during the reaction. Still further, in the present invention, a monovalent lower alcohol such as methanol, ethanol, propanol, isopropanol and butanol may be added to the reaction system to remove water.

[0014] The oil or fat composition of the present invention obtained by the above, triglyceride 3 0-80 wt%, diglycerides 1
0 - 30 wt%, preferably 15 to 30 wt%, Monogu <br/> Riseri de 4 wt% or less, polyglycerol ester 10 ~
It contains 45 % by weight , preferably 20 to 45 % by weight.

The polyglycerin ester is a fatty acid ester of polyglycerin obtained by subjecting a mixture of fat and oil and polyglycerin to a transesterification reaction with lipase. Since fatty acids are supplied by fats and oils,
Fatty acid esters of prior SL polyglycerol varies depending fat used in the reaction, for example, the palmitic acid ester of polyglycerol, the stearic acid ester of polyglycerol oleic acid ester of the poly glycerin. The above fat and oil composition is suitably used as a fat and oil of an emulsified fat and oil composition by bleaching and deodorizing in a usual fat and oil refining process.

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

Examples of the fats and oils other than the fats and oils of the first invention include the above-mentioned animal and vegetable fats and oils used for ordinary foods, hydrogenated oils and fractionated oils thereof. Examples of the water used in the present invention include water, milk, and the like that are generally used.

The fat and oil content and the water content are 10 to 9
It is used in a proportion of 90 to 10% by weight of water with respect to 0% by weight. In addition, in the emulsified fat / oil composition of the present invention, components contained in a general emulsified fat / oil composition other than the above fat / oil and water may be appropriately contained. For example, fruit paste, jam, granular solids, dietary fiber, starch, and protein may be mentioned, and 30% by weight in the emulsified oil / fat composition of the present invention.
Used in the following proportions:

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

[0020]

The present invention will be described below in more detail with reference to examples. Example 1 500 g of high oleic sunflower oil (US SVO,
To a mixture of 80 g of TRISUN 80) and 80 g of diglycerin (K-COL-II manufactured by Kashima Chemical Co., Ltd.), 15 g of lipase [lipase PL powder derived from alkaligenes (manufactured by Meito Sangyo Co., Ltd.)] was added, and 40 g A transesterification reaction was performed at 15 ° C. for 15 hours. By the above reaction, formation of various esters (reaction products) was recognized, and as a result of the iatroscan analysis, as shown in the chart of FIG. 1, triglyceride (TG), diglyceride (DG), diglycerin monoester (DGM) And diglycerin diester (DGD) peaks. The following equipment and developing solvent were used for the above 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 above reaction product (oil / 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 and the like were contained. The obtained reaction product was separated from the enzyme powder by filter paper filtration. bleaching,
Deodorization was carried out in accordance with a usual fat and oil refining method. Bleaching was performed at a clay of 3% at a temperature of 85 ° C. under reduced pressure for 30 minutes. Deodorization is performed by blowing steam for 190 minutes at a temperature of 190 ° C., and stopping the blowing of steam when the temperature is lowered after the deodorization is completed.
A bleached and deodorized oil / fat composition was obtained. From the above, the smell of the obtained oil and fat composition is almost in a state,
Partially unreacted diglycerin came out as a fraction (prepared 450 g, fraction 1 g).

Example 2 The oil and fat composition 1 obtained in Example 1 was subjected to 60 ° C.
Of warm water was added at a ratio of 3 and gently stirred with a spatula. Emulsification occurred simply by this operation alone, and a white emulsified oil / fat composition was obtained. The emulsified oil / fat composition exhibited yogurt-like characteristic physical properties, had good melting in the mouth, and had a good flavor.

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

[0024] Instead of the fat compositions prepared in Comparative Examples 1-2 Example 1, except for using the following emulsifier 2% by weight and high-oleic sunflower oil 28% by weight of the mixture, Example 3 Similarly water-oil A type emulsion composition was obtained. Comparative Example 1 used a commercially available oleic acid ester of distilled monoglyceride, and Comparative Example 2 used a commercially available diglycerin monooleate. The emulsion stability of the obtained emulsified oil / fat composition was evaluated. Table 1 shows the results.

[0025]

[Table 1]

Example 4 A whipped cream having the composition shown in Table 2 was prepared by a conventional method. At this time, preliminary emulsification was performed at 70 ° C. and a homomixer at 500 rpm for 3 minutes, sterilization was performed at 80 ° C., and primary homogenization was performed at 3 ° C.
0 kg / cm ² , secondary homogenization was performed at 70 kg / cm ² , and aging was performed at 5 ° C. for 5 days. The obtained whipped cream was evaluated for overrun and shape retention by the following methods.
Overrun was measured every minute with a whipper in a 5 ° C. water bath. The shape retention was observed by squeezing the whipped cream to form an artificial flower, leaving it to stand at 5 ° C (immediately after production), and leaving it to stand at 10 ° C. Table 3 shows the results.

[0027]

[Table 2]

Comparative Examples 3 and 4 Whipped cream was prepared 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 instead of the oil and fat composition prepared in Example 1. I got In Comparative Example 3, a commercially available monooleate was used, and in Comparative Example 4, a commercially available diglycerin monooleate was used. The overrun and the shape retention of the obtained whipped cream were evaluated in the same manner as in Example 4. Table 3 shows the results
Shown in

[0029]

[Table 3]

Example 5 To a mixture of rapeseed salad oil (500 g) and diglycerin (80 g) was added 20 g of Mucor-Mehi immobilized enzyme (manufactured by Lipozyme NOVO) as a lipase, followed by transesterification 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 binding fatty acids are mainly palmitic acid, stearic acid, oleic acid and linoleic acid) was obtained. The reaction product obtained, to obtain a purified in the same manner as in Example 1 fat composition.

Example 6 2% by weight of the oil / fat composition prepared in Example 5, 58% by weight of soybean hardened oil and 40% by weight of water were mixed to obtain a fat spread by a generally used method. About the obtained fat spread, creaming property and water absorption were evaluated by the following methods. For the creaming property, the specific volume (mg / g) was measured over time by whipping. The water absorption was measured by adding water colored with methylene blue at 25 ° C. dropwise while whipping with a mixer, and measuring the amount of water injected until the water became immiscible. Table 4 shows the results.

Comparative Examples 5 to 6 Fat spread was performed 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 instead of the oil and 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. About the obtained fat spread, the creaming property and the water absorption were evaluated in the same manner as in Example 6. Table 4 shows the results.

[0033]

[Table 4]

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

Example 8 Using the oil / fat composition prepared in Example 7, an ice cream was trial-produced according to the formulation shown in Table 5, and found to have foaming properties.
Excellent in shape retention.

[0036]

[Table 5]

COMPARATIVE EXAMPLE 7 A mixture of 500 g of soybean white squeezed oil and 50 g of decaglycerin was subjected to a transesterification reaction at 80 ° C. for 1 hour using 0.5 g of sodium methylate as a reaction catalyst to obtain a reaction product (triglyceride). 60% by weight, diglyceride 1
5% by weight, 25% by weight of decaglycerin fatty acid ester whose fatty acids to be bound are mainly oleic acid and linoleic acid). However, after the completion of the reaction, when water was added to perform hot water washing for catalyst removal, emulsification occurred,
The desired clear composition could not be obtained. Further, coloring occurred and decoloring was difficult.

[0038]

The novel 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 the drawings]

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

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI A23D 9/007 A23D 9/02 9/02 C12P 7/64 C12P 7/64 A23D 9/00 518 (56) References JP JP-A-58-21493 (JP, A) JP-A-63-287492 (JP, A) JP-A-3-103499 (JP, A) JP-A-3-43092 (JP, A) A) JP-A-2-268634 (JP, A) JP-A-59-173131 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) C11B 3/10 A23D 7/00 A23D 9 / 00 A23D 9/02 C12P 7/64 A23D 9/007

Claims (2)

(57) [Claims] 1. Triglyceride 30-80% by weight, diglyceride 1 obtained by subjecting a mixture comprising oil and fat and polyglycerin to a transesterification reaction with lipase.
0 to 30% by weight, monoglyceride 4% by weight or less and poly
A fat or oil composition comprising 10 to 45% by weight of a glycerin ester . 2. A mixture of fats and oils and polyglycerin, which is subjected to a transesterification reaction with lipase, to obtain 30 to 80% by weight of triglyceride and diglyceride 1.
0 to 30% by weight, monoglyceride 4% by weight or less and poly
Oil and fat group containing 10 to 45% by weight of glycerin ester
And grease containing Narubutsu, emulsified oil composition characterized in that it is obtained by emulsifying the water.