JP4724094B2 - Margarine and shortening with low trans fatty acid content - Google Patents

Description

  The present invention relates to margarine and shortening having a low trans fatty acid content and excellent stability.

  Conventionally, in margarine and shortening, hydrogenated fats and oils are generally blended with natural animal and vegetable fats and oils in order to obtain preferable hardness, good plasticity in a wide temperature range, creaming properties, and the like. The method of blending hydrogenated fats and oils is a typical method for increasing the melting point of margarine and shortening. However, hydrogenated fats and oils other than fully hydrogenated fats and oils, that is, partially hydrogenated fats and oils, are usually converted into constituent fatty acids. About 10 to 50% by weight of fatty acid is contained. On the other hand, there are almost no trans fatty acids in natural fats and oils, and the fats and oils derived from animals contain only less than 10% by weight. It has been suggested that trans fatty acids promote the increase of LDL cholesterol and neutral fat in the blood and cause cardiovascular disease. Therefore, margarine and shortening containing no or reduced trans fatty acids are desired.

  As a method for obtaining a plastic oil composition such as margarine or shortening that does not contain or reduce trans fatty acid, a method of appropriately mixing fractionated fats and oils obtained by fractionating natural fats and oils (Patent Document 1) is performed. However, in this method, it is difficult to freely set a preferable hardness, plasticity in a wide temperature range, and the like. For example, in order to obtain plasticity in a wide temperature range simply by blending high melting point oil such as extremely hardened oil and fractionated hard part oil with low melting point oil such as liquid oil and fractionated soft part oil, a large amount of high melting point fat and oil Needs to be blended, and it becomes extremely poorly melted in the mouth. Furthermore, when using high melting point natural fats and oils such as lard, beef tallow and palm oil in order to obtain a preferable hardness, these high melting point natural fats and oils are prone to coarse crystallization, so The hardness changes over time or the smoothness decreases, resulting in a rough texture. In addition, as other methods, a method of using a fat composition comprising fractionated fat and extremely hardened oil as a substitute for partially hydrogenated fat by transesterifying with lipase (Patent Document 2), liquid to partially hydrogenated fat There is a method (Patent Document 3) in which an oil / fat mixture to which oil and palm oil-based fat / oil are added is transesterified and used as a fat / fat with reduced trans fatty acid. However, this method requires a reaction facility for transesterification, and requires an expensive catalyst such as lipase, and also requires reaction control, which is complicated and increases costs. There was a point.

JP 2004-121114 A JP 2006-160906 A JP-A-2005-120386

  Therefore, in the present invention, it can be easily produced at low cost without passing through a special process such as transesterification, there is no deterioration of coarse crystallization or melting in the mouth due to a high melting point oil and fat, and excellent stability over time, and It is an object of the present invention to provide margarine, shortening having a low trans fatty acid content, and a food having a good appearance and texture using the same.

  As a result of extensive research by the inventor, margarine and shortening contain 30% or more of fats and oils, reduce the amount of high melting point oils and fats, and contain polyglycerin fatty acid esters having a specific fatty acid composition. The inventors have found that the above problems can be achieved and have completed the present invention.

That is, the present invention contains 30% or more of oils and fats that are liquid at 20 ° C., and (A) a saturated fatty acid having 16 to 22 carbon atoms in which behenic acid is essential in the fatty acid constituting the polyglycerol fatty acid ester. And one or more selected from (B) a saturated fatty acid having 8 to 14 carbon atoms and one or two or more selected from unsaturated fatty acids having 16 to 22 carbon atoms. In the total molar amount of the fatty acids (A) and (B), the molar ratio of the constituent fatty acid (A) is 0.3 to 0.9, and the behenic acid 0.2 to 0.8, the molar ratio of the constituent fatty acid (B) The present invention relates to margarine and shortening, characterized in that the polyglycerin fatty acid ester is 0.1 to 0.7, the esterification rate is 40% or more, and the polyglycerin fatty acid ester is contained.

  The present invention is a food product using the margarine or shortening.

  According to the present invention, the content of trans fatty acid is low, there is no deterioration of coarse crystallization or melting in the mouth due to high melting point oil and fat, and high melting point oil or fat precipitates or liquid oil separates over time. It is possible to provide margarine, shortening, and a food product using the same, which are excellent in stability without causing odor.

The present invention will be described below based on embodiments. The polyglycerol fatty acid ester of the present embodiment has a predetermined fatty acid as a constituent fatty acid, and the molar ratio of the constituent fatty acid is limited. The fatty acid constituting the polyglycerin fatty acid ester is one or two or more selected from saturated fatty acids having 16 to 22 carbon atoms essential for behenic acid , saturated fatty acids having 8 to 14 carbon atoms, and 16 carbon atoms. 1 type or 2 types or more selected from -22 unsaturated fatty acids.

  If the saturated fatty acid having 16 to 22 carbon atoms, the saturated fatty acid having 8 to 14 carbon atoms, and the unsaturated fatty acid having 16 to 22 carbon atoms are applicable to the conditions of the carbon number and saturated or unsaturated, Although not particularly limited, linear fatty acids are mainly selected. Saturated fatty acids having 16 to 22 carbon atoms include palmitic acid, stearic acid, arachidic acid, and behenic acid, and saturated fatty acids having 8 to 14 carbon atoms include caprylic acid, capric acid, lauric acid, and myristic acid. Examples of the unsaturated fatty acid having 16 to 22 carbon atoms include palmitoleic acid, oleic acid, elaidic acid, linoleic acid, linolenic acid, arachidonic acid, erucic acid, eicosapentaenoic acid, and docosahexaenoic acid.

The molar ratio of each fatty acid in the constituent fatty acids of the polyglycerin fatty acid ester is
(A): one or two or more selected from saturated fatty acids having 16 to 22 carbon atoms and essentially containing behenic acid ,
(B): one or more selected from saturated fatty acids having 8 to 14 carbon atoms and unsaturated fatty acids having 16 to 22 carbon atoms,
In the total molar amount of (A) and (B), the molar ratio of (A) is 0.3 to 0.9 and behenic acid 0.2 to 0.8, and the molar ratio of (B) is 0. .1 to 0.7. In particular, the molar ratio of (A) is more preferably 0.6 to 0.9.

The average degree of polymerization of the polyglycerol constituting the polyglycerol fatty acid ester is not limited, but is preferably 2 to 20. Here, the average degree of polymerization is the average degree of polymerization (n) of polyglycerin calculated from the hydroxyl value by end group analysis. Specifically, the average degree of polymerization is calculated from the following formulas (Formula 1) and (Formula 2).
(Formula 1) Molecular weight = 74n + 18
(Formula 2) Hydroxyl value = 56110 (n + 2) / Molecular weight The hydroxyl value in the above (Formula 2) is a numerical value that serves as an index of the number of hydroxyl groups contained in polyglycerin, and is contained in 1 g of polyglycerin. The number of milligrams of potassium hydroxide required to neutralize the acetic acid required to acetylate the hydroxyl group. The number of milligrams of potassium hydroxide is calculated according to Japan Oil Chemists 'Society edited by “The Japan Oil Chemists' Society, Standard Oil Analysis Test Method (I), 2003 edition”.

  Since the polyglycerin fatty acid ester of this embodiment increases the esterification rate, the solid-liquid separation preventing effect of the oil / fat composition and the dispersibility in the oil / fat composition increase, so the esterification rate is 40% or more. There must be. Here, the esterification rate is the average degree of polymerization of polyglycerol (n) calculated from the hydroxyl value by end group analysis, the number of hydroxyl groups (n + 2) of this polyglycerol, and the fatty acid added to the polyglycerol. When the number of moles is (M), (M / (n + 2)) × 100 = value calculated by esterification rate (%). The hydroxyl value is a value calculated in the same manner as the hydroxyl value described above.

  The polyglycerol fatty acid ester of the present embodiment can be produced by a known esterification reaction. For example, a fatty acid and polyglycerin can be produced by an esterification reaction in the presence of an alkali catalyst such as sodium hydroxide. The esterification reaction is performed until almost all of the charged fatty acid is esterified. That is, the reaction is sufficiently performed until almost no free fatty acid is consumed.

  The oil / fat that is liquid at 20 ° C. used for margarine and shortening in the present embodiment needs to be contained in an amount of 30% or more, more preferably 50% or more. Examples of oils and fats that are liquid at 20 ° C. include, but are not limited to, soybean oil, rapeseed oil, corn oil, sesame oil, perilla oil, linseed oil, peanut oil, safflower oil, safflower oil with high oleic acid, cottonseed oil, grape Seed oil, macadamia nut oil, hazelnut oil, pumpkin seed oil, walnut oil, coconut oil, tea seed oil, egoma oil, olive oil, mustard oil, rice oil, rice bran oil, wheat germ oil, safflower oil, sunflower oil and fractionation thereof Oils and fats are exemplified. Furthermore, diglyceride and / or monoglyceride may be contained or formulated. Moreover, sterol, sterol ester, etc. may contain arbitrarily in fats and oils. As other fats and oils, palm oil, palm kernel oil, cocoa butter, coconut oil, lard, milk fat, chicken fat, beef tallow, and fractionated fats and oils thereof can be appropriately used.

  In the present embodiment, if necessary for margarine and shortening, margarine, other raw materials generally used for shortening, for example, propylene glycol fatty acid ester, sorbitan fatty acid ester, sucrose fatty acid ester, emulsifier such as phospholipid, Tocopherol, L-ascorbic acid palmitate, antioxidants such as tea extract, coloring agents such as carotene, milk components such as skim milk powder, cream, sucrose, liquid sugar, honey, glucose, fructose, brown sugar, maltose, lactose , Syrup, sorbitol, erythritol, isomerized liquid sugar, sucrose-bonded syrup, oligosaccharides, trehalose, hemicellulose and other saccharides, water, salt, acidulant, seasoning, flavor, polymerized phosphate and other emulsion stabilizers, locust Bean gum, carrageenan, alginic acids, pectin, xanthan gum, Heaven, glucomannan, gelatin, modified starch, a thickening stabilizer such as starch, etc., can be appropriately used.

  The margarine and shortening to which the polyglycerin fatty acid ester of the present embodiment is added can suppress physical crystallization and solid-liquid separation of oils and fats over time, so that physical properties such as plasticity, spreadability, shortening property, and creaming property are present. It is suitably applied and can be used for food.

  The polyglycerin fatty acid ester in the present embodiment can be blended with more liquid oils and fats with an increase in the amount of use thereof, and can suppress deterioration of mouth melting and solid-liquid separation due to high melting point oils and fats. The usage-amount of polyglyceryl fatty acid ester may be the quantity used as 0.01-10.0 weight% in an oil-fat composition, More preferably, it is 0.5 weight% or more.

  Since the margarine and shortening of this embodiment have a small amount of polyglycerin fatty acid ester, the deterioration of the flavor of food can be suppressed. The margarine and shortening food of the present invention is not particularly limited as long as it is a normal margarine or shortening food, but specifically, bread, confectionery bread, Danish pastry, pie, shoe, It can be used for bakery products such as donuts, cakes, cookies, waffles, muffins, hard biscuits and scones. Moreover, the usage-amount of the margarine and shortening of this invention in these uses changes with use uses, and is not specifically limited.

  EXAMPLES The present invention will be specifically described below based on examples, but the present invention is not limited to the examples. In Examples and Comparative Examples, “polyglycerin # 750” manufactured by Sakamoto Yakuhin Kogyo Co., Ltd. was used for polyglycerin having an average polymerization degree of 10, and “polyglycerin” manufactured by Sakamoto Yakuhin Kogyo Co., Ltd. was used for polyglycerin having an average polymerization degree of 6. “Polyglycerin # 310” manufactured by Sakamoto Yakuhin Kogyo Co., Ltd. was used as polyglycerin having an average degree of polymerization of “# 500”.

<Example 1>
Esterification rate: 100 g of polyglycerin having an average degree of polymerization of 10 and a mixed fatty acid consisting of 82.6 g of capric acid and 326.4 g of behenic acid are placed in a reaction vessel and reacted at 250 ° C. in an alkaline and nitrogen stream with sodium hydroxide. 90% polyglycerol fatty acid ester was obtained.

<Example 2>
Esterification rate: 100 g of polyglycerin having an average degree of polymerization of 4, mixed fatty acid consisting of 103.0 g of myristic acid and 307.3 g of behenic acid was placed in a reaction vessel and reacted at 250 ° C. in an alkaline and nitrogen stream with sodium hydroxide. 70% polyglycerol fatty acid ester was obtained.

<Example 3>
Esterification rate: 100 g of polyglycerin having an average degree of polymerization of 10 and a mixed fatty acid consisting of 81.2 g of oleic acid and 391.7 g of behenic acid are placed in a reaction vessel and reacted at 250 ° C. in an alkaline and nitrogen stream with sodium hydroxide. 90% polyglycerol fatty acid ester was obtained.

<Example 4>
A mixed fatty acid consisting of 100 g of polyglycerin having an average degree of polymerization of 10 and 86.3 g of stearic acid, 310.0 g of behenic acid, and 85.7 g of oleic acid is placed in a reaction vessel, and at 250 ° C. under alkaline and nitrogen flow with sodium hydroxide. The reaction was performed to obtain a polyglycerol fatty acid ester having an esterification rate of 95%.

<Example 5>
A mixed fatty acid consisting of 100 g of polyglycerin having an average degree of polymerization of 6 and 38.4 g of lauric acid, 54.5 g of stearic acid, and 195.8 g of behenic acid is placed in a reaction vessel, and at 250 ° C. under alkaline and nitrogen flow with sodium hydroxide. The reaction was performed to obtain a polyglycerol fatty acid ester having an esterification rate of 60%.

<Example 6>
A mixed fatty acid composed of 100 g of polyglycerin having an average degree of polymerization of 4 and 53.3 g of capric acid, 263.8 g of stearic acid, and 105.3 g of behenic acid was placed in a reaction vessel, and the mixture was alkalinized with sodium hydroxide and under a nitrogen stream at 250 ° C. Reaction was performed to obtain a polyglycerol fatty acid ester having an esterification rate of 80%.

<Comparative Example 1>
100 g of polyglycerin having an average degree of polymerization of 10 and 81.9 g of palmitic acid were placed in a reaction vessel and reacted at 250 ° C. in an alkaline and nitrogen stream with sodium hydroxide to obtain a polyglycerin fatty acid ester having an esterification rate of 20%. .

<Comparative example 2>
Esterification is performed by adding a mixed fatty acid consisting of 100 g of polyglycerin having an average polymerization degree of 6, 102.4 g of palmitic acid and 113.6 g of stearic acid to a reaction vessel at 250 ° C. in an alkaline and nitrogen stream with sodium hydroxide. A 50% polyglycerol fatty acid ester was obtained.

  The polyglycerol fatty acid esters of the above Examples and Comparative Examples are shown in Table 1. In Table 1, the molar ratio is the ratio of each constituent fatty acid to the total molar amount of fatty acid constituting the polyglycerol fatty acid ester. Based on the following Test Example 1, the polyglycerin fatty acid ester shown in Table 1 was confirmed to have an effect on the stability with margarine.

[Test Example 1]
Stability of margarine According to the formulation shown in Table 2, an oil / fat composition containing 1% by weight of the ester of Examples and Comparative Examples with respect to raw oil / fat composed of refined palm oil and soybean oil was heated to 80 ° C. and dissolved. This was used as the oil phase. On the other hand, salt, skim milk powder, soybean lecithin, and flavor were added to water, dissolved, and heated to 70 ° C. to obtain an aqueous phase. After gradually adding an aqueous phase to the oil phase and emulsifying it into a water-in-oil type, margarine was prepared by cooling and kneading in accordance with a normal margarine production process. Next, the container was filled with margarine and stored in a 20 ° C. incubator for 1 day, and the state was visually confirmed. Similarly, for margarine formulated with rapeseed extremely hardened oil and soybean oil as raw material fats and oils shown in Table 3, margarine was prepared by containing 1% by weight of the esters of each Example and Comparative Example, and an incubator at 20 ° C. After storage for 1 day, the state was visually confirmed.

Evaluation of Test Example 1 was performed as follows based on the state of margarine.
A: Solid-liquid separation is not seen at all, and it is in a uniform state.
○: Some liquid oil on the surface is spotted.
Δ: A considerable amount of liquid oil is observed on the surface.
X: Solid-liquid separation occurs and is completely separated.
The results of Test Example 1 are shown in Table 4.

  As shown in Table 4, solid-liquid separation occurred in the margarine to which the esters of Comparative Examples 1 and 2 were added. On the other hand, none of the margarine to which the ester of the example which is the polyglycerin fatty acid ester of the present invention was added had a solid-liquid separation, and was in a uniform and smooth state.

  Next, based on Test Example 2 below, using margarine prepared by adding the esters of Examples and Comparative Examples, the bread roll was baked, and the confirmation test for texture and texture of the inner phase of the roll bread thus obtained was conducted. Do.

[Test Example 2]
In accordance with the formulation shown in Table 5, after mixing strong powder, soft flour, sugar, yeast food, salt, and skim milk powder, yeast and whole eggs are added and mixed. Then, the margarine of an Example and a comparative example is added, and it raises to 28 degreeC, and makes 50 minutes pre-fermentation. Then, after punching, fermentation is performed at a floor time of 30 minutes, divided, and after a bench time of 30 minutes, it is molded to produce a roll bread at a proof of 38 ° C. for 50 minutes and a baking temperature of 200 ° C. for 10 minutes. A confirmation test is performed on the texture and texture of the inner phase of this bread roll. Table 6 shows the representative results of this test.

Evaluation of Test Example 2 is performed as follows based on the texture and texture of the inner phase of the roll.
○: Good △: Slightly inferior ×: Inferior

  As shown in Table 6, the roll using the margarine of Comparative Example 1 that had caused solid-liquid separation had a poor texture in the inner phase, and the texture was hard. On the other hand, roll bread using margarine to which the ester of the embodiment which is the polyglycerin fatty acid ester of the present invention is added has a good texture of the inner phase, and has a soft and soft texture.

  Subsequently, the effects of the esters of Examples and Comparative Examples shown in Table 1 on the stability in shortening were confirmed based on Test Example 3 below.

[Test Example 3]
Stability of shortening Refined palm oil heated to 80 ° C. and soybean oil were mixed at a ratio of 30:70, and 1% by weight and 3% by weight of the esters of Examples and Comparative Examples were added thereto, and heated to 80 ° C. After dissolution, cooling and kneading were performed according to a normal shortening manufacturing process to obtain a shortening. Subsequently, the shortening was filled in the container, and after tempering for one day in a 20 ° C. incubator, the state was visually confirmed. Also, shortening prepared by mixing rapeseed extremely hardened oil and soybean oil in a ratio of 3:97 and containing 1% by weight and 3% by weight of the esters of Examples and Comparative Examples was performed in an incubator at 20 ° C. After tempering for one day, the state was visually confirmed.

Evaluation of Test Example 3 was performed as follows based on the shortening state.
A: Solid-liquid separation is not seen at all, and it is in a uniform state.
○: Some liquid oil on the surface is spotted.
Δ: A considerable amount of liquid oil is observed on the surface.
X: Solid-liquid separation occurs and is completely separated.
The results of Test Example 3 are shown in Table 7.

  As shown in Table 7, Comparative Examples 1 and 2 caused solid-liquid separation. On the other hand, the shortening to which the ester of the example which is the polyglycerin fatty acid ester of the present invention was added had no solid-liquid separation, and was in a uniform and smooth state.

  Next, the butter cake was baked using the shortening prepared by adding 3 wt% of the esters of Examples and Comparative Examples based on Test Example 4 below, and the texture and food of the inner phase of the resulting butter cake were baked. A confirmation test was conducted for feeling.

[Test Example 4]
The cake dough was produced according to the formulation shown in Table 8 and according to the sugar batter method. Therefore, the shortening prepared by adding the polyglycerin fatty acid ester was stirred for several minutes, then added with sugar and stirred until the specific gravity reached 0.8. Next, the whole egg was added in four portions and stirred until evenly mixed. To this, weak flour, baking powder and water were added and stirred until uniform to obtain a cake dough. This cake dough was put in a pound mold and baked in an oven for about 50 minutes to prepare a butter cake. A confirmation test was conducted on the texture and texture of the inner phase of the obtained butter cake. The representative results of this test are shown in Table 9.

Evaluation of Test Example 4 was performed as follows based on the texture and texture of the inner phase of the butter cake.
○: Good △: Slightly inferior ×: Inferior

  As shown in Table 9, the butter cake using the shortening of the comparative example, which had caused solid-liquid separation, had a poor texture in the inner phase and a hard texture. On the other hand, the butter cake using the shortening to which the ester of the example which is the polyglycerin fatty acid ester of the present invention was added had a good texture of the inner phase and had a soft and soft texture.

Claims (2)

A margarine or shortening containing 30% or more of an oil that is liquid at 20 ° C. and containing a polyglycerin fatty acid ester that satisfies the following conditions.
The molar ratio of each fatty acid in the constituent fatty acid and the constituent fatty acid of the polyglycerol fatty acid ester is
(A): One or more selected from saturated fatty acids having 16 to 22 carbon atoms that essentially require behenic acid (B): Saturated fatty acids having 8 to 14 carbon atoms and imperfections having 16 to 22 carbon atoms One or more selected from saturated fatty acids, and in the total molar amount of (A) and (B), the molar ratio of (A) is 0.3 to 0.9, and behenic acid 0.2 to 0 .8 , the molar ratio of (B) is 0.1 to 0.7 ,
The esterification rate is 40% or more . A food comprising the margarine or shortening according to claim 1.