JPH0928289A - Oil and fat composition for heat-cooking - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an oil and fat composition having suppressed bubbling without the sense of incompatiblity and capable of being cooked with a small amount of the composition without scorching by including specific amounts of phospholipid and an organic acid monoglyceride in an edible oil and fat respectively. SOLUTION: This edible oil contains 0.01-10wt.% phospholipid mixture comprising a phospholipid expressed by formula I having no N atom [A<1> is H or an 8-24C aliphatic acyl; R<1> is an 8-24C aliphatic acyl; X<1> is an inositol residue, a glycerol residue, an alkali (alkaline earth) metal or a trivalent metal; X<2> is H, an alkali (alkaline earth) metal or a trivalent metal] and a phospholipid of formula II having an N atom [A<2> is H or an 8-24C aliphatic acyl; R<2> is an 8-24C aliphatic acryl; X<3> is a choline residue, an ethanolamine residue, a serine residue or ammonium; X<4> is H, an alkali (alkaline earth) metal, a trivalent metal or ammonium] in a weight ratio of 1/(0.001-1) and 0.01-10wt.% organic acid monoglyceride.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to an oil and fat composition containing a phospholipid and an organic acid monoglyceride, which is preferably used as a cooking oil.

[0002]

BACKGROUND OF THE INVENTION Fats and oils are materials that give a good flavor as a heat medium for cooking, and also when cooking stir-fried foods, etc.
It is essential to prevent sticking (sticking) to cooking utensils due to heating. On the other hand, it is known that the dietary habits of modern Japanese people are westernized, and especially the amount of oil used is increasing, but in terms of recent changes in taste, health, dieting, etc. It is also required to reduce the intake of fats and oils. Therefore, even when cooking the above-mentioned stir-fried food, it is required to cook with as little oil as possible, but the problem of charring becomes conspicuous if the amount of oil is simply reduced to cook. As an oil for solving this problem and cooking without burning with a small amount of oil, an oil and fat for stir-frying, which is a mixture of oil and fat with lecithin (phospholipid), is commercially available. This oil / fat utilizes the fact that among various surfactants, lecithin has an excellent releasability effect, and that lecithin also has an effect of suppressing sputtering during cooking.

[0003]

However, according to the studies by the present inventors, although the oil containing lecithin has no problem of charring during cooking, there is a browning phenomenon due to high temperature heating, and the oil is colored and decomposed. There is a problem that an offensive odor is generated by objects. In addition, there is a problem that when cooked with stir-fried food, there is a lot of foaming during cooking and the appearance is unsatisfactory, and in some cases, the food adheres to the cooked food and gives a very bad impression. In general, foaming may be used as an index of oil deterioration, and in frying cooking, for example, the foaming may be used to determine the limit of oil use. From this, the phospholipid-blended oil gives the impression of deteriorated so-called old oil from its foaming. The present inventors have proposed an oil and fat composition in which the phospholipids that cause coloring and the generation of an offensive odor are reduced by heating against the drawbacks of the phospholipid-containing oil (JP-A-2-291228), No fundamental improvement to bubbling has been made. It is also an object of the present invention to provide an oil and fat for heating which is capable of improving the drawbacks of the above-mentioned oil containing lecithin, particularly foaming, and which can be sufficiently cooked in a small amount without burning without causing a feeling of discomfort.

[0004]

Means for Solving the Problems As a result of various studies to achieve the above-mentioned object, the present inventors have found that it is effective to use a specific amount of phospholipid and a specific amount of organic acid monoglyceride in oil and fat. This has led to the present invention. That is, the present invention is an oil and fat composition for cooking, which comprises 0.01 to 10% by weight of phospholipid and 0.01 to 10% by weight of organic acid monoglyceride in edible oil and fat. When used for stir-fry cooking, the oil / fat composition of the present invention has a good mold release property, so that a small amount can be sufficiently cooked without burning, and it is also free from foaming and has a good flavor.

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION First, the phospholipid contained in the oil and fat composition for cooking of the present invention will be described. Phospholipids are usually phosphatidylcholine (PC), phosphatidylethanolamine (PE), phosphatidylinositol (PI), phosphatidylglycerol (PG),
A mixture of phosphatidic acid (PA) and phosphatidylserine (PS), or a phosphoric acid compound such as a lyso form thereof. In the present invention, these usual compounds can be used, but the following formula (1) A phospholipid having no nitrogen atom and a phospholipid having a nitrogen atom represented by the following formula (2) are added to a phospholipid having a nitrogen atom for 1 part by weight of a phospholipid having no nitrogen atom. From 0.001 to lipid
It is preferably a phospholipid mixture containing 1 part by weight (preferably 0.005 to 0.5 part by weight).

[0006]

Embedded image

(In the formula, A ¹ is a hydrogen atom or has 8 to 8 carbon atoms.
24 represents a saturated or unsaturated aliphatic acyl group, R ¹ represents a saturated or unsaturated aliphatic acyl group having 8 to 24 carbon atoms, X ¹ represents an inositol residue, a glycerol residue, an alkali metal atom, It is selected from the group consisting of alkaline earth metal atoms and trivalent metal atoms, X ² is a hydrogen atom,
Selected from the group consisting of alkali metal atoms, alkaline earth metal atoms and trivalent metal atoms)

[0008]

Embedded image

(In the formula, A ² is a hydrogen atom or has 8 to 8 carbon atoms.
24 represents a saturated or unsaturated aliphatic acyl group, R ² represents a saturated or unsaturated aliphatic acyl group having 8 to 24 carbon atoms, X ³ represents a choline residue, an ethanolamine residue, a serine residue And X ⁴ is a hydrogen atom, an alkali metal atom, an alkaline earth metal atom, a trivalent metal atom, or an ammonium group.) The above nitrogen Examples of phospholipids having no atom include phosphatidic acid (PA), phosphatidylglycerol (PG), phosphatidylinositol (PI), and lyso forms thereof. Examples of phospholipids having a nitrogen atom include phosphatidylcholine (PC), phosphatidylethanolamine (PE),
Mention may be made of phosphatidylserine (PS) and their lyso forms. Phospholipids are lecithins obtained from soybeans or egg yolks and / or hydrolyses them,
It can be used by selecting from hydrogenation, transesterification, solvent fractionation, purification treatment, enzyme-treated lecithin and the like. In particular, as the above-mentioned phospholipid mixture, for example, natural lecithin typified by soybean lecithin is used as a raw material, and phosphatidylcholine and phosphatidylethanolamine (phospholipid having a nitrogen atom) are selected using phospholipase D and phospholipase A ₂ as catalysts. Phosphatidic acid and lysophosphatidic acid (phospholipids having no nitrogen atom) are simultaneously decomposed to reduce their contents, or phospholipase D, phospholipase D Those obtained by a method in which natural lecithin is similarly decomposed by using pholipase C as a catalyst to increase the content of phosphatidic acid are preferably used. In addition, phospholipase-catalyzed transphosphatidylation reduces the content of PC, PE, and PS (phospholipids having a nitrogen atom) in natural lecithin, and PI and P
Those obtained by utilizing the method of increasing the contents of G and PA (phospholipids having no nitrogen atom) can also be advantageously used. In addition, a phospholipid obtained by synthesis of a phosphoric acid ester obtained by phosphoric acid of monoglyceride or diglyceride can also be used. Phospholipids (particularly the above phospholipid mixture) are contained in edible fats and oils in an amount of 0.01 to 10% by weight.
(Preferably 0.1 to 7% by weight, more preferably 0.1 to 5
(% By weight) is added.

Next, the organic acid monoglyceride contained in the oil and fat composition for cooking of the present invention will be described. The organic acid monoglyceride (glycerin organic acid fatty acid monoester) used in the present invention is a compound obtained by esterifying a glycerin fatty acid monoester and an organic acid. Regarding the esterification reaction, a general esterification reaction method such as a method of esterifying a glycerin fatty acid monoester and an acid anhydride by heating, a method of directly esterifying a glycerin fatty acid monoester and an organic acid by heating, etc. Can be used. In the esterification in the production of these organic acid monoglycerides, one molecule of monoglyceride is esterified with two molecules of an organic acid, and if the organic acid is a dicarboxylic acid, one molecule of monoglyceride is esterified with one molecule of an organic acid. Various kinds of organic acid monoglyceride derivatives and polymers obtained by esterification are produced, and such organic acid monoglyceride derivatives and polymers obtained by esterification can also be used as the organic acid monoglyceride of the present invention. As the fatty acid constituting the organic acid monoglyceride, a fatty acid having 14 to 22 carbon atoms is preferable, and since it is used by dissolving in oil, oleic acid, linoleic acid, unsaturated fatty acid such as linoleic acid is 70% by weight with respect to the total fatty acid. %, Preferably 80% by weight or more. Examples of the organic acid constituting the organic acid monoglyceride include oxalic acid, succinic acid and other aliphatic saturated dicarboxylic acids; maleic acid, fumaric acid and other aliphatic unsaturated dicarboxylic acids; lactic acid, malic acid, tartaric acid, Examples thereof include oxycarboxylic acids such as diacetyltartaric acid and citric acid; and amino acids such as glycine and aspartic acid. The organic acid preferably has 10 or less carbon atoms (more preferably 4 to 8 carbon atoms). Specifically, citric acid, succinic acid, tartaric acid, and diacetyltartaric acid are preferable, and citric acid and succinic acid are particularly preferable. The organic acid monoglyceride used in the present invention is a compound obtained by esterifying a glycerin fatty acid monoester with an organic acid, and a part of the unreacted organic acid or glycerin fatty acid monoester (commercially available product) is also included in the present invention. However, preferably, after the esterification reaction, the unreacted organic acid is reduced by the method described below, and the acid value in the range of 30 to 120 is used as a flavor point. Is preferred. The ester produced by a general method was treated under reduced pressure with
Method of distilling off unreacted organic acid by steaming (1 to 5 hours) at about 100 to 180 ℃ Ester produced by a general method is washed with a large amount of water to remove unreacted organic acid with water. Method of removing to a layer Method of reacting glycerin fatty acid monoester with organic acid at a reaction molar ratio of 1: 1 or more Organic acid monoglyceride is 0.01 to 10% by weight in edible oil and fat.
(Preferably 0.1 to 7% by weight, more preferably 0.1 to 5
(% By weight) is added.

It is preferable to add a diglyceride mixture to the oil and fat composition for cooking according to the present invention for the purpose of improving the solubility of phospholipids and organic acid monoglycerides. The diglyceride mixture used in the present invention contains monoglyceride and triglyceride as components other than diglyceride, but the diglyceride content is 30% by weight from the viewpoint of improving solubility.
The above is preferable (preferably 50% by weight or more). Further, when the amount of monoglyceride in the diglyceride mixture is large, smoking tends to occur when heated, so the monoglyceride content is preferably 20% by weight or less (preferably 15% by weight or less). Further, the fatty acid residues constituting the diglyceride mixture are preferably fatty acid residues having 8 to 24 carbon atoms, and the content of unsaturated fatty acid residues in all the constituent fatty acid residues is 60.
It is preferably not less than 70% by weight, more preferably not less than 70% by weight, especially not less than 80% by weight. The diglyceride mixture used in the present invention has a high level of unsaturated fatty acid residues,
For example, safflower oil, olive oil, cottonseed oil, corn oil,
Rapeseed oil, soybean oil, palm oil, sunflower oil, sesame oil, lard, beef tallow, fish oil, milk fat, or one or more selected from fractionated oils thereof, randomized oils, hydrogenated oils, transesterified oils. A mixture of oil and fat and glycerin is transesterified in the presence of a hydroxide of an alkali metal and / or an alkaline earth metal, or a fatty acid having a high unsaturated fatty acid level derived from these oil and fat is esterified with glycerin. The oil and fat having a high diglyceride content obtained by the reaction can be obtained alone or by mixing with the above-mentioned raw material oil and fat. Excess monoglyceride produced in the reaction can be removed by molecular distillation or chromatography. Although these reactions can be performed by a chemical reaction using an alkali catalyst, etc., it is superior in terms of flavor and the like to perform them under mild enzymatic conditions using a 1,3-position selective lipase. preferable. Another method for increasing the diglyceride content in the diglyceride mixture is, for example, the use of a fractionated oil of natural edible fats and oils. The diglyceride mixture is 2 to 70 in edible oil and fat.
% By weight (preferably 5 to 60% by weight, more preferably 5 to 60% by weight)
50% by weight) is added. Further, the diglyceride mixture is preferably added in an amount of 0.5 to 100 parts by weight (more preferably 1 to 50 parts by weight) based on the total parts by weight of the phospholipid and the organic acid monoglyceride.

There is no particular limitation on the edible oil and fat that can be used in the present invention, and any one can be used as long as it can be used for ordinary cooking. For example, olive oil, rice bran oil, sesame oil, safflower oil, soybean oil, camellia oil, corn oil,
Examples thereof include vegetable oils and fats such as rapeseed oil, palm oil, sunflower oil and cottonseed oil, animal oils and fats such as lard, beef tallow, fish oil and butter fat, or hydrogenated oils thereof, fractionated oils and random transesterified oils. These oils may be used alone or in an appropriate mixture.

In the present invention, for the purpose of preventing charring when used in cooking, various emulsifiers such as sucrose fatty acid ester, sorbitan fatty acid ester, propylene glycol fatty acid ester and glycerin are added to the oil and fat composition of the present invention. A fatty acid ester, a polyglycerin fatty acid ester, etc. can be used together. In addition, various antioxidants, flavor imparting agents (flavors), nutritional enhancers, thickeners and the like can be added to the oil and fat composition of the present invention depending on the purpose.

[0014]

EXAMPLES The present invention will be described in more detail with reference to the following Examples, but it should not be construed that the present invention is limited thereto. (Preparation of phospholipids A, B and C) A mixture of phosphatidylcholine and phosphatidylethanolamine obtained by column fractionation of soybean lecithin was decomposed with phosphalipase D as a catalyst to give phospholipid mixtures as shown in the table below. Prepared. In Table 1 below, "PC" represents phosphatidylcholine, "PE" represents phosphatidylethanolamine, "PA" represents phosphatidic acid, and "LPA" represents lysophosphatidic acid.

[0015]

[Table 1]

In the above table, the contents of "PC", "PE" and "PA + LPA" are shown in Oil Chemistry, 35 (12),
P1018-1024, according to the method described in '86, P
The molecular weights of C, PE, PA, and LPA are 77
3, 728, 704, and 444.

(Preparation of Organic Acid Monoglyceride A and B) [Organic Acid Monoglyceride A] Glycerin Fatty Acid Ester (trade name: O-95R, manufactured by Kao Corporation, unsaturated fatty acid 90
% Or more) 1000 g (2.81 mol) and succinic anhydride (trade name;
280.9 g (2.81 mol) of RIKACID manufactured by Shin Nippon Rika Co., Ltd. was heated from 80 ° C. to 120 ° C. with stirring at 10 ° C./hour to obtain an esterification reaction product. This esterified product
Deodorization was carried out at 150 ° C./5 mmHg for 4 hours to obtain organic acid monoglyceride A. The acid value of this organic acid monoglyceride was 70. [Organic acid monoglyceride B] Glycerin fatty acid ester (trade name: O-95R, manufactured by Kao Corporation, unsaturated fatty acid 90
%) 1000 g (2.81 mol) and citric acid (citric acid anhydride, manufactured by Wako Pure Chemical Industries, Ltd.) 269.6 g (1.41 mol) at 80 ° C.
To 180 ° C. under reduced pressure of 50 mmHg, the temperature was raised with stirring at 20 ° C./hour to obtain organic acid monoglyceride B. The acid value of this organic acid monoglyceride was 80.

(Preparation of diglycerides A, B and C) A commercially available lipase preparation which is an immobilized 1,3-position selective lipase (trade name: Lipozyme 3A, manufactured by Novo Industry AS).
As a catalyst, fatty acids derived from vegetable oils listed in Table 2 below.
860 g and 140 g of glycerin were reacted at 40 ° C. After filtering off the lipase formulation, the final product is subjected to molecular distillation,
Purification was carried out by a conventional method to obtain diglyceride as shown in Table 2. The glyceride composition (%) is an analysis value by gas chromatography.

[0019]

[Table 2]

Examples 1 to 3 and Comparative Examples 1 to 3 Various phospholipids shown in Table 1, organic acid monoglycerides A and B, and various diglycerides shown in Table 2 were mixed with fats and oils,
Inventive fat composition 1 to 3 shown in Table 3, Comparative fat composition 4
~ 6 were prepared. Using these oil and fat compositions, a foaming test, a foam disappearance test, and fried rice cooking evaluation were performed.
Table 4 shows the evaluation results. The evaluation method is as follows. [Foaming test] Oil and fat composition with an iron frying pan (diameter 15c
m), heat on medium heat for 45 seconds, chopped onion 1
0 g was added, the foaming was observed, and relative evaluation was performed. [Foam disappearance test] Oil and fat composition with iron frying pan (diameter 15c
m), heat for 45 seconds on medium heat, wiener sausage 5
The book was fried for 2 minutes, taken out in a dish and left for 5 minutes, and the state of bubbles adhering to the surface was observed for relative evaluation. [Cooking evaluation of fried rice] Iron frying pan (diameter 24 cm)
Put 9 g of the oil and fat composition in, heat it over medium heat, and chop onion (10
g) and eggs (40 g) were fried, then chilled rice (300 g) was fried and seasoned with salt (1 g) and soy sauce (2.5 ml). During this cooking, foaming and charring during cooking were observed and relative evaluation was performed. Further, the flavor of the obtained fried rice was relatively evaluated.

[0021]

[Table 3]

[0022]

[Table 4]

Examples 4 to 6 and Comparative Examples 4 to 6 Various phospholipids shown in Table 1, organic acid monoglycerides A and B, and various diglycerides shown in Table 2 were mixed with fats and oils,
Inventive fat composition 7 to 9 shown in Table 5, Comparative fat composition 10
~ 12 were prepared. Using these oil and fat compositions, a foaming test, a foam disappearance test, and a yakisoba cooking evaluation were performed. Table 6 shows the evaluation results. For the foaming test and the foam disappearance test, relative evaluation was performed in the same manner as described above. Moreover, the cooking evaluation of yakisoba was performed as follows. [Cooking evaluation of yakisoba] Put 15 g of oil and fat composition in an iron frying pan (diameter 24 cm), pork (50 g), cabbage (50
g), bamboo shoots (25g), onions (25g), shiitake mushrooms (15
g), stir-fry Chinese buckwheat noodles (180 g), and finish with salt (3.5
g) was added to cook yakisoba. During this cooking, foaming and charring during cooking were observed and relative evaluation was performed.
Moreover, the obtained yakisoba flavor was relatively evaluated.

[0024]

[Table 5]

[0025]

[Table 6]

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Hideki Yokomichi 20 Higashi-Fukashiba, Kamisu-cho, Kashima-gun, Ibaraki Kao Corporation Stock Research Institute

Claims (4)

[Claims] 1. An oil and fat composition for cooking, which comprises 0.01 to 10% by weight of phospholipid and 0.01 to 10% by weight of organic acid monoglyceride in edible oil and fat. 2. A phospholipid having no nitrogen atom represented by the following formula (1) and a phospholipid having a nitrogen atom represented by the following formula (2) Lipid 1
0.001 to 1 of phospholipid having a nitrogen atom with respect to parts by weight
The oil-and-fat composition for cooking according to claim 1, which is a phospholipid mixture contained in a ratio of parts by weight. Embedded image (In the formula, A ¹ represents a hydrogen atom or a saturated or unsaturated aliphatic acyl group having 8 to 24 carbon atoms, and R ¹ has 8 to 24 carbon atoms.
Represents a saturated or unsaturated aliphatic acyl group, X ¹ is selected from the group consisting of an inositol residue, a glycerol residue, an alkali metal atom, an alkaline earth metal atom and a trivalent metal atom, and X 1 ² is selected from the group consisting of hydrogen atom, alkali metal atom, alkaline earth metal atom and trivalent metal atom) (In the formula, A ² represents a hydrogen atom or a saturated or unsaturated aliphatic acyl group having 8 to 24 carbon atoms, and R ² has 8 to 24 carbon atoms.
Represents a saturated or unsaturated aliphatic acyl group, X ³ is selected from the group consisting of choline residue, ethanolamine residue, serine residue and ammonium group, X ⁴ is a hydrogen atom, an alkali metal atom , Alkaline earth metal atoms, 3
Selected from the group consisting of valent metal atoms and ammonium groups) 3. The oil and fat composition for cooking according to claim 1, wherein the organic acid monoglyceride is succinic acid monoglyceride and / or citric acid monoglyceride. 4. Further, the diglyceride mixture is 2 to 70% by weight.
The oil-fat composition for heating and cooking according to any one of claims 1 to 3, which comprises.