JP3514922B2 - Food additive consisting of polyglycerin fatty acid ester - Google Patents

Description

Detailed Description of the Invention

[0001]

The present invention relates to relates Poriguriseri down fat <br/> fatty acid ester le or Ranaru food additive. More particularly, to a food additive comprising a Poriguriseri emissions fatty acid esters containing a high purity than the mono-fatty acid ester to conventional products.

[0002]

2. Description of the Related Art In recent years, polyglycerin fatty acid ester has been approved as a food additive, and its usage amount is gradually increasing. In general, this ester can be obtained as an ester having a wide range of HLB values by combining polyglycerin having a different degree of polymerization as a raw material with a fatty acid having a different chain length, and exhibits high stability in an acidic region. It is widely used as an emulsifier and a viscosity modifier in the food field. The method for producing this polyglycerin fatty acid ester includes (1) esterification reaction of polyglycerin and fatty acid,
(2) Transesterification reaction of polyglycerin and fatty acid ester, (3) Transesterification reaction of polyglycerin and oil and fat, (4) Addition polymerization reaction of glycidol and fatty acid monoglyceride, (5) Addition polymerization of glycidol and fatty acid There is a reaction. Among these, the methods (2) to (3) are methods that have many restrictions in terms of reactivity, quality and purity of the produced polyglycerin fatty acid ester.

The method (1) is based on JAOCS (Journal of A).
merican 0il Chemists' Society) Volume 58, 878
Page (1981), a method for obtaining a polyglycerin fatty acid ester by carrying out an esterification reaction of polyglycerin and a fatty acid in the presence of an alkali catalyst is disclosed. A similar method is disclosed in Japanese Patent Laid-Open No. 6-41007. For the method (4), refer to USP4.
515,775. Regarding the method (5), a monofatty acid ester of glycerin has been described so far in JP-A-51-65705. However, according to the technique disclosed in this publication, in the presence of an inert solvent, a high percentage of carboxylic acid-1-monoglyceride (in formula [1] below, n
The value of is 1 on average. ), The degree of polymerization of glycerin is 1 on average, and no mention is made of a monofatty acid ester of polyglycerin, and no actual study has been made.

As a technique using the addition polymerization reaction of glycidol, the addition polymerization reaction of glycerin and glycidol in producing polyglycerin used in the methods (1) to (3) (Japanese Patent Publication No. 1-55254). Japanese Patent Publication No. 4-11532, Japanese Patent Publication No. 5-1291) or a polyglycerin produced through a hydrolysis reaction after addition polymerization of fatty acid and glycidol (Japanese Patent Publication No. 4-6962).
No. 1), production of polyglycerin monoalkyl ether, polyglycerin monoalkyl thioether (USP
3,821,372, USP 3,966,398, US
P4,087,466) and the like are disclosed.

However, in the production of polyglycerin through a hydrolysis reaction after the addition polymerization reaction of a fatty acid and glycidol described in JP-B-4-69621, the fatty acid used is a lower fatty acid (having 2 to 6 carbon atoms). And the aim is the production of polyglycerin, no mention is made of polyglycerin fatty acid esters.

[0006]

[Problems to be Solved by the Invention]
When manufacturing the emission fatty acid esters are prepared by the method of (1). In this method, in general, the raw material polyglycerin has an average of 4 to 10 reactive hydroxyl groups.
Mono are used ones, attempting to produce a fatty acid ester of mono-substituted, based on the equivalents of the fatty acid used, the ratio of the reactive hydroxyl groups is large, the Poriguriseri emissions during fatty acid ester generated, for the purpose It has been pointed out that not only fatty acid esters but also polyreacted ester compounds such as unreacted polyglycerin, diesters, triesters and tetraesters remain (N. Garti, et al, J. of
Am. Oil Chem. Soc., 59, 317-319 (1982)).

Further, even when the glycidol is added to the fatty acid monoglyceride of (4) to carry out the addition polymerization reaction, the purity of the reaction product is greatly affected by the degree of purification of the raw material fatty acid monoglyceride. In particular, when a fatty acid monoglyceride obtained by the reaction of glycerin and a fatty acid is used as a raw material, the glycerin component remains in the raw material as in the above (1), and is obtained by an addition polymerization reaction of glycidol. the resulting Poriguriseri emissions mono fatty acid ester content in the fatty acid ester is about 40%, the remainder of about 60% has been observed that the glycerol and 2-substituted or more unreacted ester (Shigeru Tsuda , Monoglyceride, P67 (1985), Maki Shoten).

[0008] Thus, the Poriguri <br/> serine fatty acid esters which are conventionally used, polyglycerol and disubstituted or more esters of unsubstituted many remain, they surfactant, emulsifying When applied to food additives such as stabilizers, it is feared that the surface tension, the dispersive power, the foaming power, and the emulsion stability will be reduced.

On the other hand, as a method for removing unsubstituted polyglycerin, at least one selected from water-soluble organic solvents and water is used in combination with at least one selected from non-water-soluble organic solvents. To remove unreacted polyglycerin with the mixed solvent described above (JP-A-63-23837), and to remove unreacted polyglycerin by contacting and adsorbing a solution of an esterification reaction product with alkylsilylated silica gel. (JP-A-3-81252), a method of extracting and removing unreacted polyglycerin using a water-soluble organic solvent and an aqueous solution containing water or a salting-out agent (JP-A-6-41).
No. 007) has been proposed.

However, in the method described in JP-A-63-23837, aromatic hydrocarbons such as benzene and toluene, which are described as non-water-soluble organic solvents, have doubts about their safety, so There are problems with the use. Further, in this method, the reaction molar ratio of the fatty acid to the polyglycerin is limited to 1 or less, and the effectiveness in the case of the molar ratio exceeding 1 is not described. Even when the reaction molar ratio is 1 or less, toluene /
In methanol systems, etc., a considerable amount of high HLB polyglycerin fatty acid ester was found to migrate to the water-containing methanol phase, and in toluene / methanol systems, etc., unreacted polyglycerin was extremely insufficiently separated. There are several problems in industrial implementation.
Further, the method of partitioning with an alkylsilylated silica gel described in JP-A-3-81252 has the drawbacks that the operating cost is high and the operation is complicated. further,
These prior arts can remove unreacted polyglycerin, including the method described in JP-A-6-41007, but have a drawback in that it is impossible to remove an ester compound having two or more substitutions.

Therefore, when it is applied to a food additive such as a surfactant or an emulsion stabilizer, it is expected to improve the surface tension, the dispersion power, the foaming power, and the emulsion stability. high Poriguriseri emissions fatty acid ester and a method of manufacturing the same fatty acid ester content has been demanded.

[0012]

SUMMARY OF THE INVENTION The present invention is based on the finding that been made to solve the above problems, high Poriguriseri emissions fatty acid esters of mono-fatty acid ester content is obtained by a specific method, there is provided a food additive comprising the polypeptide <br/> glycerin fatty acid ester obtained in that way. That is, according to the present onset bright, the general formula following general formula a fatty acid and glycidol represented obtained by reacting in the presence of a phosphoric acid-based acidic catalyst in [2] [1] mono fatty acid ester derivatives represented Alcohol solvent and
Octadecylsilyl group bond with / or distilled water as eluent
High performance liquid chromatography using a silica gel column
Peak planes separated by UV and detected using an ultraviolet absorption detector
Food additive comprising a content of 70% or more on including Poriguriseri down fatty <br/> ester expressed by the product ratio.

[Chemical 2] Will be provided.

[0013] In the poly <br/> glycerin fatty acid ester peak area ratio is less than 70%, surfactant, when applied to food additives such as emulsion stabilizers, surface tension reduction,
A decrease in dispersibility, a decrease in foaming power, and a decrease in emulsion stability are observed.

[0014]

When manufacturing the Poriguriseri down fat <br/> fatty acid ester used in the Detailed Description of the Invention The present invention, as the fatty acid of the formula used in the addition polymerization reaction of a glycidol with a fatty acid [2], A fatty acid having 7 to 22 carbon atoms is used, preferably one having 8 or more carbon atoms, which may be a saturated fatty acid or an unsaturated fatty acid, a linear fatty acid or a fatty acid having a side chain, and further, a carbon chain having a hydroxyl group. It may be a substituted fatty acid substituted with a group. Examples of these fatty acids include caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid,
Examples include isostearic acid, oleic acid, linoleic acid, behenic acid, erucic acid, ricinoleic acid and hydroxystearic acid. These can be used alone, or two or more kinds may be arbitrarily mixed and used in the reaction. Among the above fatty acids, lauric acid, myristic acid, palmitic acid, stearic acid and oleic acid are preferred.

The reaction between the fatty acid and glycidol must be carried out in the presence of a phosphoric acid-based acidic catalyst. The phosphoric acid-based acidic catalyst referred to here is phosphoric acid or an ester of phosphoric acid, and specifically, phosphoric acid, phosphoric anhydride, polyphosphoric acid, orthophosphoric acid, metaphosphoric acid, pyrophosphoric acid, triphosphoric acid, Phosphoric acids such as tetraphosphoric acid or acidic phosphoric acid esters such as methyl acid phosphate, ethyl acid phosphate, isopropyl acid phosphate, butyl acid phosphate and 2-ethylhexyl acid phosphate can be used. In addition, as these acidic phosphoric acid esters, any of a monoester body, a diester body, and a mixture thereof can be used. Of the above, phosphoric acid and acidic phosphoric acid ester are preferably used.

The above catalysts may be used alone or in combination of two or more. The amount of the catalyst added is 0.01 to 10% by weight, preferably 0.1 to 5% by weight, based on the fatty acid. If the amount is less than 0.01% by weight, the reaction rate is low, and if it exceeds 10% by weight, the effect cannot be expected to be improved, and depending on the catalyst used, a large amount of glycidol addition polymer in which the catalyst serves as an initiator is produced, which is preferable. Absent.

The reaction method is to take fatty acid in a reaction vessel,
The above catalyst is added to this, and the reaction is carried out while adding glycidol little by little. The reaction temperature is 50 to 180 ° C., preferably 70 to 160 ° C., more preferably 120.
~ 140 ° C. If the temperature is less than 50 ° C, the reaction rate is low,
Further, if it exceeds 180 ° C, coloring becomes severe, and if it exceeds 230 ° C, glycidol is decomposed to cause a side reaction, which is not preferable. In this case, a low boiling point compound that does not react with glycidol may be added to prevent the reaction temperature from rising. The reaction is preferably carried out in a nitrogen gas atmosphere, and may be pressurized if necessary.

[0018] A glycidol fatty the above reaction Poriguriseri emissions fatty acid ester of higher degree of polymerization and addition polymerization to produce. N of the generated Poriguriseri down fatty acids formula contained in high concentrations in ester [1] mono fatty acid ester derivatives represented is the average amount number of repeating glycerol, substantially the same as the molar ratio of the fatty acid and glycidol are reacted Yes, and can be easily changed. The product, a high mono-fatty acid esters content, is Poriguriseri emissions fatty acid ester. That is, Poriguriseri emissions fatty acid esters for use in the present invention obtained by the method, and eluted by column chromatography analysis method, mono-fatty acid ester represented by the general formula which is detected using an ultraviolet absorption detector [1] The content rate represented by the peak area ratio is 70% or more. Here, the column chromatographic analysis method is a reversed-phase partition column analysis method using silica gel having an octadecylsilyl group, an octylsilyl group, a butylsilyl group, a trimethylsilyl group, and a phenylsilyl group as a carrier as a functional group, and a cyanopropyl group as a functional group. The normal phase partitioning column analysis method using silica gel having an aminopropyl group as a carrier, the ion exchange column analysis method having a quaternary ammonium group or a phenylsulfonic acid group as a functional group, and the adsorption column analysis method of porous silica gel can be mentioned. In these analytical methods, a reversed phase partition column analytical method is preferably used in which silica gel having octadecylsilyl (ODS) groups bonded thereto is used as a carrier. Further, in order to improve the separation performance, the column size is preferably 4.6 mmφ × 250 mm or more, and it is more preferable to connect the columns in series because the separation ability can be improved. The peak area ratio of the mono-fatty acid ester of 70% or more means that the peak area ratio attributed to the mono-fatty acid ester is 70% of the total peak area under the following HPLC (high performance liquid chromatography) analysis conditions. It means that it is more than%.

The case of analysis by the reversed phase partition column analysis method will be described below. Developing solvent is different by the addition molar number of types and glycidol fatty Poriguriseri emissions fatty acid esters, it is preferable to determine the eluent from solubility and separation of the analyte. Specifically, as the superior specific developing solvent solubility and the separation of the analyte, solvent and / or distilled water is preferred for alcohol, specifically, the Poriguriseri Nra Gaulin ester Methanol , the Poriguriseri Nsu stearate ester it is preferable to use ethanol.

The flow rate of the developing solvent is selected according to the pressure resistance of the column used and the degree of separation of the obtained chromatogram.
It is usually in the range of 0.05 to 1.0 ml / min, more preferably in the range of 0.1 to 0.8 ml / min. The column temperature is preferably in the range of 30-60 ° C. The wavelength of the ultraviolet absorption detector is 210 nm.

The sample to be subjected to HPLC preferably uses the developing solution used as a solvent, and the concentration and injection amount are selected such that the solubility and the separability of the analyte are excellent. Specifically, the concentration of the sample is preferably 1 to 50%, and the injection amount is preferably 0.1 to 20 μl.

The content is measured as follows. In HPLC analysis with an ODS column, elution is generally in polar order. Therefore, in the case of polyglycerin, the highly polar unsubstituted polyglycerin is eluted first, and then the polyglycerin monofatty acid ester and the polyglycerin difatty acid ester are detected. On the other hand, if among glycerol mono-fatty acid esters, highly polar Poriguriseri N'e ester is eluted first, last glycerin monoester is eluted. Thus the standard of polyglycerol and glycerin fatty acid ester and analyzed by HPLC under the same conditions, to compare the retention times of the standard and the analyte, multi eluted as those of the above diester after elution of glycerol monoesters It was replaced <br/> ester le component. The content rate (%) of the mono-fatty acid ester form is represented by the peak area ratio according to the following.
From the analysis chart, the peak area of polyglycerin, monofatty acid ester of polyglycerin (“polyglycerin”
However, in the present invention, the glycerin moiety includes polyglycerin to monoglycerin. ), And the peak area of the polysubstituted ester component of diester or more were obtained. Then, it was calculated according to the following calculation formula.
The solvent was selected such that the peak position did not overlap with any peak of polyglycerin, monofatty acid ester, and polysubstituted ester of diester or more. Further, the following calculation formula is based on the assumption that the retention time of the solvent is after the elution of the diester. Typical HPLC analytical conditions other than those used in the examples are as follows.

Formula: Polyglycerin monofatty acid ester content (%) = {Polyglycerin monofatty acid ester peak area / (Polyglycerin peak area + Polyglycerin monofatty acid ester peak area + Diester The peak area of the above polysubstituted ester)} ×
100 (%)

<HPLC analysis condition (1)> Column: Wakosil 5C18 × 2 (manufactured by Wako Pure Chemical Industries, Ltd .: column having octadecylsilyl group as a functional group, which is a reverse phase distribution column, size: 4.6 mmφ × Two
50 mm), developing solvent: methanol, flow rate: 0.75 m
l / min. , Column oven temperature: 40 ° C., detection method: ultraviolet absorption method (λ = 210 nm), sample concentration: 10
% (Solvent: methanol), injection volume: 5 μl. Retention time of each component, for example, in the case of Poriguriseri Nra Ulin acid esters, polyglycerol: 8 minutes before monolaurate ester: 8 minutes to 12 minutes, dilaurate ester or: is 12 minutes later.

<HPLC analysis condition (2)> Column: Wakosil II 5C18HG (manufactured by Wako Pure Chemical Industries, Ltd .: a column having octadecylsilyl group as a functional group, which is a reverse phase distribution column, size: 4.6 mm)
φ × 250 mm), developing solvent: methanol, flow rate: 0.
2 ml / min. , Column oven temperature: 40 ° C., detection method: ultraviolet absorption method (λ = 210 nm), sample concentration: 5
% (Solvent: methanol), injection amount: 10 μl, retention time of each component is polyglycerin: before 14 minutes,
Monoester form: 14 minutes to 16.5 minutes, diester form or more: 16.5 minutes or later, methanol component: 18 minutes.

<HPLC analysis conditions (3)> Column: Wakosil 5C18 and Wakosil
II 5C18HG (both manufactured by Wako Pure Chemical Industries, Ltd .:
A column having octadecylsilyl group as a functional group, which is a reverse phase distribution column, size: 4.6 mmφ × 250 mm)
Are connected in series. Developing solvent: ethanol, flow rate: 0.
2 ml / min. , Column oven temperature: 40 ° C., detection method: ultraviolet absorption method (λ = 210 nm), sample concentration: 5
% (Solvent: EtOH), injection volume: 10 μl. The retention time of each component is polyglycerin: 28.5 minutes or less, monoester form: 28.5 to 34 minutes, diester form or more: 34 minutes or more, ethanol component: 39 minutes.

Further, Poriguriseri down fatty <br/> ester obtained in above, it is also possible to use the food additive of the present invention After further purified through various purification steps if necessary, It is also preferable. As a specific purification method,
(A) A deodorizing method in which saturated heated steam is blown under reduced pressure to deodorize steam, and (b) a decolorizing method such as bleaching with sodium hypophosphite or hydrogen peroxide. As another method (C), there is a method of adding water, heating and then dehydrating. The heating temperature is 60 to 200 ° C., and the heating time is 0.5 to 15 hours, particularly preferably 1 to 7 hours, depending on the temperature. Dehydration can be performed by distillation, azeotropic distillation, vacuum distillation, etc., and the heating temperature for distillation is 100
Is in the range of up to 200 ° C. The amount of water to be added is 0.1 to 20% by weight relative to Porigurise <br/> Li down fatty acid esters, preferably 1 to 10 wt%. For example, the case of implementing the method of (c) an oxirane oxygen concentration in Poriguriseri emissions fatty acid ester is reduced from the degree 500 ppm (0.05%) to less than 100 ppm. The oxirane oxygen concentration is the Cd. Of J. of Am. Oil Chem. Soc. 9-57
The methylene derived from the oxirane group relative to the peak area value of the chemical shift between 3.4 ppm and 4.4 ppm attributed to the methylene and methine protons derived from polyglycerin using the titration method defined in 1. 2.7 attributed by proton
It can be measured by measuring the peak area value of the chemical shift between ppm and 2.8 ppm.

[0028] As described above, containing in the present invention, high Poriguriseri emissions fatty acid esters of mono-fatty acid esters content, particularly where the addition polymerization reaction of a glycidol with a fatty acid, represented by the peak area of the mono-fatty acid ester because it uses the rate is 70% or more Poriguriseri emissions fatty acid esters as food additives such as a surfactant and an emulsion stabilizer, improved surface tension, improved dispersion forces, improvement of foaming power, emulsifying stability There is an effect such as improvement of.

[0029] Therefore, high Poriguriseri emissions of mono-fatty acid ester content represented by the general formula [1] used in the present invention
Fatty acid ester (hereinafter, referred to as highly pure Poriguriseri emissions fatty acid ester.) Is used for various applications as a food additive Poriguriseri down fatty acid esters have been conventionally used, and an object The function can be fully exerted. These are exemplified below.

[0030] (1) high purity Poriguriseri emissions used in the present invention
Fatty acid esters can be used as emulsifiers fat composition used bread, cakes, during the manufacture of confectionery. For example, as described in JP-A-6-22690, when baking bread dough made of wheat flour or the like, each component in the wheat flour undergoes physical, chemical and biochemical reaction changes, but In order to obtain good bread, it is necessary to strictly control the baking process, and in order to obtain stable quality, it consists of soybean oil, cottonseed oil, rapeseed oil and other oils and fats, and if necessary, an aqueous phase containing a seasoning. A fat composition is used.
Its the fat composition emulsifier is used, but can be as emulsifiers such bakery fat composition for use the high-purity Porigu <br/> Riseri emissions fatty acid ester. Similarly, JP-A-6-53 discloses a method of using a water-in-oil type oil / fat composition when producing butter cakes by an all-in-mix method. At that time, as an emulsifier for the entire oil and fat composition to emulsifiers in the range of 0.2 to 10 wt% is used, the high-purity Poriguriseri emissions fatty acid esters confectionery fat composition, such as the butter cakes Is also useful. Further, in JP-A-6-269244, in the production of cakes such as sponge cakes, snack cakes, chiffon cakes, and half-baked sweets, the dough is stable, it is difficult to drop the kettle, and a cake with a large volume is prepared. A foamable emulsified oil / fat composition obtained by adding an emulsifier, whey protein and the like to an aqueous phase such as sorbitol and liquid sugar is used. Even such emulsifiers can be used the high purity Poriguri <br/> serine fatty acid ester. Furthermore, JP-A-6-78672 discloses that when applied to bread, the dough gives less stickiness and gives a good flavor and texture, and an oil-in-water emulsion containing water, oils and fats, sugars and emulsifiers. In the composition, the content of fats and oils is 35 to 75% by weight, the sugar is at least 10 to 50% by weight including sorbitol, and the content of the emulsifier is 5 to 2 with respect to the aqueous phase.
A high oil content oil-in-water emulsion composition of 5% by weight is described. And as the emulsifier, Poriguriseri emissions fatty acid ester having an HLB value of 7-16 is used. Such the high-purity Poriguriseri emissions fatty acid esters for applications can be used as well.

(2) Japanese Patent Laid-Open No. 6-125711 discloses that
To prevent the floating of oils and fats and the precipitation of cocoa powder that occur when storing cocoa beverages, sucrose oleic acid ester 1 to 25% by weight, glycerin fatty acid ester 3 to 36% by weight, sorbitan fatty acid ester 1 to 11% by weight, crystalline cellulose 26-90 wt%, and κ- carrageenan 2-5 consisting wt% cocoa beverage emulsion stabilizer is disclosed, wherein the high-purity Poriguriseri emissions fatty acid esters instead of the glycerol fatty acid ester, or it Together, it can be used as an emulsion stabilizer compounding agent for cocoa drinks. Further, in Japanese Patent Laid-Open No. 6-38682, a lipophilic polyglycerin fatty acid ester is added to a mixture containing a cocoa component, a milk component, a sweetener and water in an amount of 0.2 to 0.2% of lipophilic polyglycerin fatty acid ester with respect to the fat content in the mixture. A cocoa beverage added at a ratio of 5.0% by weight is disclosed. The high purity Porigu <br/> Riseri emissions fatty acid esters can be used in place of the lipophilic polyglycerol fatty acid ester.

[0032] (3) the high-purity Poriguriseri emissions fatty acid esters can be used as an additive of starch food as follows. Japanese Patent Laid-Open No. 6-276972 discloses that
To make noodles that boil quickly, add 0.5 to 40 eggs.
A noodle quality improving agent containing 0.01 to 0.5 part by weight of a lysolin oil quality is disclosed. It also describes that 0.1 to 10 parts by weight of a food-grade surfactant may be added, if necessary. Can be used the high purity Poriguriseri emissions fatty acid esters as such noodles improving agent compounded surfactant. In addition, JP-A-6-1977
No. 17 discloses that when the steamed noodles are boiled and used, mung bean-treated starch or a combination thereof with an emulsifier makes the noodles extremely loose, and that polyglycerin fatty acid ester or the like is used as the emulsifier. Has been done. 0.1-20% by weight of emulsifier based on noodle raw materials
Are used, it is possible to use the high-purity Poriguriseri emissions fatty acid esters as such emulsifiers. Further, JP-A-6-225684 discloses edible oils and fats 0 to 20.
% By weight, glycerin organic acid fatty acid ester and stearyl lactate 0.05 to 20% by weight, polyglycerin fatty acid ester having HLB of 12 or more and / or sucrose fatty acid ester 0.01 to 5% by weight, water content 50 to 90% by weight A composition for improving the quality of a starch food product which is fluid at 10 ° C. is disclosed. When this composition is used for foods such as bread, donuts, steamed buns, dumplings, noodles and spaghetti, it prevents adhesion of the dough to each other or a machine at the time of production, an increase in volume and an improvement in texture, and the time-lapse of starch after production. It is said that it exerts the effect of preventing the deterioration of the texture due to a change in taste. The high purity Poriguriseri emissions fatty acid esters, in place of the polyglycerol fatty acid ester can be used as a blend of quality improvement composition of such starch foods.

[0033] (4) the high-purity Poriguriseri emissions fatty acid esters can be used as an additive Fisheries kneading product as follows. JP-A-6-22730 discloses
A method for producing a frozen surimi, which comprises adding a quality improver containing a polyglycerin fatty acid ester to a fish paste product, is disclosed. That is, it has been clarified that the frozen surimi has an effect of retaining the foot-forming ability and an effect of improving whiteness. The amount added is 1% by weight or less, preferably 0.1 to 0.5% by weight, based on the surimi. In addition, JP-A-6-9071
No. 3, gazette of scallop ovary and / or fishmeat surimi containing testis was prepared by adding 0.1 to 2% by weight of polyglycerol fatty acid ester emulsifier with HLB of 13 or more together with water, oil and fat and reduced starch saccharified product. Kneading with salt,
A method for producing a kneaded product which is subjected to heat treatment after molding is described. The high purity Poriguriseri emissions fatty acid ester, instead polyglycerol fatty acid ester can be used as an additive marine paste products such as these. Further, JP-A-6-113727 describes a technique for improving the binding property between fish meat and fats and oils by injecting an oil-in-water emulsion containing egg white and carrageenan into fish meat. . It is described that this makes it possible to obtain a fish meat ham which has an appropriate texture without sacrificing the texture and flavor of the fish and has an excellent texture without being dry. Further, glycerin fatty acid ester is mentioned as one of the emulsifiers added to this emulsion. Even such a fish meat ham producing oil-in-water emulsion emulsifiers, can be used the high purity Poriguri <br/> serine fatty acid ester.

(5) Japanese Patent Laid-Open No. 6-209704 discloses that
Oil-in-water type emulsion oil composition which does not have feathering or oil-off when added to coffee or tea, or can be used for cooking, etc. and contains polyglycerin saturated fatty acid ester having an esterification degree of 3 or less as an emulsifier Is disclosed. It is disclosed that 0.1 to 1.5% by weight of an emulsifying agent is added to the dissolved oil and fat. The high purity Poriguriseri emissions fatty acid esters can also be used for the same purpose.

(6) Japanese Patent Laid-Open No. 6-253718 discloses that
Bread made by adding at least 0.1% by weight of calcium carbonate, 0.5% by weight or less of glycerin fatty acid ester, and 0.5% by weight or less of egg white to wheat flour at room temperature for a long period of time in the medium seed method. Wheat flour formulations are described. It is said that this makes it possible to produce high-quality bread even if the fermentation time of the medium variety is extended. The high purity poly <br/> glycerin fatty acid ester, as an alternative of the glycerin fatty acid ester, can be used.

(7) Japanese Patent Laid-Open No. 6-113799 discloses that
Lactic acid bacteria are inoculated into a cheese homogeneous liquid obtained by homogenizing natural cheese, water, and skim milk powder, and lactic acid fermentation is performed.
H3.6-4.5 Lactic acid cheese fermented liquor was obtained, and about 5
Sour cheese beverages with ~ 50% sugar added are described. In addition to skimmed milk powder, it is described that a surfactant such as glycerin fatty acid ester may be used as a fat dispersion emulsification accelerator. The high purity Poriguri <br/> serine fatty acid esters may also be used as such for sour cheese beverage fatty dispersive emulsification enhancer.

(8) Japanese Patent Laid-Open No. 6-153884 discloses that
Disclosed is a food freshness-retaining agent characterized by comprising persimmon leaf extract (flavonoids) and tocopherol, or persimmon leaf extract, tocopherol and gallic acid as active ingredients. It is convenient for use that this freshness-retaining agent is prepared as a lipophilic emulsion, and in that case, polyglycerin fatty acid ester is exemplified as an emulsifier (surfactant). High purity poly <br/> glycerin fatty acid esters provided by the present invention can also be used as the surfactant.

(9) Japanese Unexamined Patent Publication No. 6-62734 discloses a fatty acid-containing sour milk drink containing chitosan and polyglycerin fatty acid ester, which is a sour milk drink containing fat. Thus, although there is a stability of fat globules under acidic conditions is preferred sourness is improved, the high-purity Poriguriseri emissions fatty acid ester in place of the polyglycerol fatty acid ester, such fats It can be used as an additive for a contained lactic acid beverage.

(10) Japanese Patent Laid-Open No. 6-189682 discloses that
A chocolate dough that has been rolled and conched, an aqueous component, a high-HLB polyglycerin fatty acid ester and a low-HLB polyglycerin fatty acid ester are mixed to emulsify into a water-in-oil type water content of 2% by weight or more and 50% by weight or less. Of water-containing chocolates are described. The low-HLB polyglycerin fatty acid ester is preferably HLB 2 to 4, and the high-HLB polyglycerin fatty acid ester is preferably HLB 11 to 13. Can be used the high purity Poriguriseri emissions fatty acid ester as the one of the polyglycerol fatty acid ester.

(11) JP-A-6-90663 discloses that the fat content is 10 to 40% by weight, the enzyme-treated lecithin containing lysolecithin as an emulsifier, and the monoglycerin fatty acid ester content is 50% by weight. To 70% by weight of medium purity monoglycerin fatty acid ester, succinic acid monoglyceride and lecithin are disclosed. It is described that, as a result, a coffee cream having a stable emulsion at room temperature and freezing resistance that does not cause emulsion destruction even if it is thawed after being stored at 0 ° C. or lower is described. Further, in the examples, 0.2 part of the intermediate-purity monoglyceride is used together with another emulsifier with respect to 25.5 parts by weight of palm kernel oil that constitutes the oil phase part. The high purity Poriguriseri emissions fatty acid esters can be used as coffee cream emulsifier as described above.

[0041]

EXAMPLES The following high purity Porigurise <br/> high purity Porigu <br/> Riseri emissions fatty acid ester surfactants or emulsifiers that are re down fatty acid esters prepared and obtained to be used in the present invention The results of evaluation of the effects of the use of the above as food additives will be specifically described with reference to Examples and the like. The HPLC analysis conditions are as follows throughout the examples and comparative examples.

(Analysis conditions of HPLC) Column: Wakosil 5C18 × 2 (manufactured by Wako Pure Chemical Industries, Ltd .: column having octadecylsilyl group as a functional group which is a reverse phase distribution column, size: 4.6 mmφ × 2)
50 mm), developing solvent: methanol, flow rate: 0.75 m
l / min. , Column oven temperature: 40 ° C., detection method: ultraviolet absorption method (λ = 210 nm), sample concentration: 10
% (Solvent: methanol), injection volume: 5 μl. Retention time of each component, for example, in the case of Poriguriseri Nra Ulin acid esters, polyglycerol: 8 minutes before monolaurate ester: 8 minutes to 12 minutes, dilaurate ester or: is 12 minutes later.

Example 1 0.5 mol (100.16 g) of lauric acid and phosphoric acid (85%) were placed in a 1-liter four-necked flask equipped with a nitrogen introducing tube, a stirrer, a cooling tube, a temperature controller and a dropping cylinder. % Product)
0.0622 g was added and heated to 140 ° C. Then
Glycidol 3.0m while keeping the reaction temperature at 140 ℃
ol (222.24 g) was added dropwise over 5 hours, and the reaction was continued until the oxirane concentration in the system became less than 0.1%. After cooling the reaction product was taken out Poriguriseri Nra Gaulin ester (Hekisaguriseri Nra Ureto) about 300
g was obtained. The resulting Poriguriseri Nra Gaulin esters were evaluated by analytical conditions HPLC described above. Further, as a common and basic evaluation method for evaluating the effect of use in various food applications as additives such as emulsifiers and surfactants, a 10% aqueous solution of the resulting Poriguriseri Nra Gaulin acid ester to 30 seconds It was vibrated (manually) and the foamability and state were visually observed. The chart obtained by HPLC is shown in FIG. In addition, Table 1 shows the results of component analysis and the results of evaluation of foamability and state by analysis from HPLC.

Example 2 0.5 mol (100.16 g) of lauric acid and phosphoric acid (85%) were placed in a 1-liter four-necked flask equipped with a nitrogen introduction tube, a stirrer, a cooling tube, a temperature controller, and a dropping cylinder. % Product)
0.0810 g was added and heated to 140 ° C. Then
Glycidol 3.0m while keeping the reaction temperature at 140 ℃
ol (222.24 g) was added dropwise over 5 hours, and the reaction was continued until the oxirane concentration in the system became less than 0.1%. After cooling the reaction product was taken out Poriguriseri Nra Gaulin ester (Hekisaguriseri Nra Ureto) about 300
g was obtained. The resulting Poriguriseri Nra Gaulin ester was evaluated by HPLC. The obtained to prepare a Poriguriseri Nra <br/> 10% aqueous solution of Ulin ester, then 30 seconds of shaking (manually), it was visually observed foaming property and state. The chart obtained by HPLC is shown in FIG.
In addition, Table 1 shows the results of component analysis and the results of evaluation of foamability and state by analysis from HPLC.

(Example 3) 0.5 mol (100.16 g) of lauric acid and phosphoric acid (85%) were placed in a 1-liter 4-necked flask equipped with a nitrogen introduction tube, a stirrer, a cooling tube, a temperature controller, and a dropping cylinder. % Product)
0.0810 g was added and heated to 140 ° C. Then
Glycidol 4.0m while keeping the reaction temperature at 140 ℃
ol (296.32 g) was added dropwise over 5 hours, and the reaction was continued until the oxirane concentration in the system became less than 0.1%. After cooling the reaction product was taken out Poriguriseri Nra Gaulin ester (Okutaguriseri Nra Ureto) about 400
g was obtained. The resulting Poriguriseri Nra Gaulin ester was evaluated by HPLC. The obtained to prepare a Poriguriseri Nra <br/> 10% aqueous solution of Ulin ester, then 30 seconds of shaking (manually), it was visually observed foaming property and state. The chart obtained by HPLC is shown in FIG.
In addition, Table 1 shows the results of component analysis and the results of evaluation of foamability and state by analysis from HPLC.

Example 4 0.5 mol (100.16 g) of lauric acid and phosphoric acid (85%) were placed in a 1-liter four-necked flask equipped with a nitrogen introducing tube, a stirrer, a cooling tube, a temperature controller, and a dropping cylinder. % Product)
0.118g was added and it heated at 140 degreeC. Next, while maintaining the reaction temperature at 140 ° C, 5.0 g of glycidol
1 (370.40 g) was added dropwise over 5 hours, and the reaction was continued until the oxirane concentration in the system became less than 0.1%.
After cooling the reaction was removed to obtain about 470g of Poriguriseri Nra Gaulin ester (Dekaguriseri Nra Ureto). The resulting Poriguriseri Nra Ulin acid ester HP
It was evaluated by LC. The obtained to prepare a Poriguriseri Nra Uri <br/> 10% aqueous solution of phosphate esters, it is 30 seconds of shaking (manually), was visually observed foaming property and state.
The chart obtained by HPLC is shown in FIG. In addition, Table 1 shows the results of component analysis and the results of evaluation of foamability and state by analysis from HPLC.

(Example 5) 0.5 mol (100.16 g) of lauric acid and EAP (monoethyl) were placed in a 1-liter four-necked flask equipped with a nitrogen introduction tube, a stirrer, a cooling tube, a temperature controller, and a dropping cylinder. A mixture of acid phosphate and diethyl acid phosphate (manufactured by Nippon Kagaku Kogyo Co., Ltd.) (0.105 g) was added, and the mixture was heated to 140 ° C. Then, the reaction temperature is 140 ℃
Glycidol 5.0 mol (370.40)
g) was added dropwise over 5 hours, and the reaction was continued until the oxirane concentration in the system became less than 0.1%. After cooling the reaction was removed to obtain about 470g of Poriguriseri Nra Gaulin ester (Dekagu <br/> Riseri Nra Ureto). Obtained poly <br/> glycerin Nra Gaulin ester was evaluated by HPLC.
Further, the resulting Poriguriseri Nra Gaulin ester 1
A 0% aqueous solution was prepared, shaken (manual) for 30 seconds, and the foamability and state were visually observed. The chart obtained by HPLC is shown in FIG. In addition, Table 1 shows the results of component analysis and the results of evaluation of foamability and state by analysis from HPLC.

(Comparative Example 1: When no catalyst was used) 0.5 mol of lauric acid (100.16 g) was placed in a 1-liter 4-necked flask equipped with a nitrogen introduction tube, a stirrer, a cooling tube, a temperature controller, and a dropping cylinder. ) Was added and heated to 140 ° C. Then, 3.0 mol (222.24 g) of glycidol was added dropwise over 5 hours while maintaining the reaction temperature at 140 ° C., and the reaction was continued until the oxirane concentration in the system became less than 0.1%. After cooling the reaction was removed to obtain about 300g of Poriguri <br/> Seri Nra Gaulin ester. The resulting Poriguriseri Nra Gaulin ester was evaluated by HPLC. The obtained Poriguriseri Nra to prepare a 10% aqueous solution of Ulin ester, then 30 seconds of shaking (manually),
The foamability and state were visually observed. The chart obtained by HPLC analysis is shown in FIG. In addition, Table 1 shows the results of the component analysis and the evaluation results of the foamability and the state by the analysis from the HPLC analysis.

Comparative Example 2: Using paratoluene sulfonic acid (PTS) as a catalyst Laurine was placed in a 1-liter 4-necked flask equipped with a nitrogen introducing tube, a stirrer, a cooling tube, a temperature controller and a dropping cylinder. Acid 0.5 mol (100.16 g) and PTS 0.371 g
Was added and heated to 140 ° C. Then, the reaction temperature is set to 14
Glycidol 3.0 mol (222.
24 g) was added dropwise over 5 hours, and the reaction was continued until the oxirane concentration in the system became less than 0.1%. After cooling the reaction was removed, about 3 Poriguriseri Nra Gaulin ester
00g was obtained. The resulting Poriguriseri Nra Gaulin ester was evaluated by HPLC. Also, the obtained polyglyceride
To prepare a 10% aqueous solution of Nra Ulin ester, then 30 seconds of shaking (manually), it was visually observed foaming property and state. The chart obtained by HPLC is shown in FIG. 7. In addition, Table 1 shows the results of component analysis and the results of evaluation of foamability and state by analysis from HPLC.

(Comparative Example 3: Reaction of fatty acid monoglyceride with glycidol) 0.5 mol of lauric acid monoglyceride was placed in a 1-liter four-necked flask equipped with a nitrogen introducing tube, a stirrer, a cooling tube, a temperature controller, and a dropping cylinder. (137 g) was added, and 0.45 g of sodium methylate (NaOCH ₃ : 28% methanol solution) was added as a catalyst and heated to 90 ° C. Then, 2.5 mol (185.2 g) of glycidol was added dropwise over 5 hours while maintaining the reaction temperature at 90 ° C., and the reaction was continued until the oxirane concentration in the system became less than 0.1%. After cooling the reaction product was taken out Poriguriseri down
La Ulin acid ester to obtain about 300g. The resulting Porigu <br/> Riseri Nra Gaulin ester was evaluated by HPLC. Further, the resulting Poriguriseri Nra Gaulin ester 10
% Aqueous solution was prepared, shaken (manual) for 30 seconds, and the foamability and state were visually observed. The chart obtained by HPLC analysis is shown in FIG. In addition, Table 1 shows the results of component analysis and the results of evaluation of foamability and state by analysis from HPLC.

Comparative Example 4: In the case of reaction of fatty acid with polyglycerin Polyglycerin (Daicel chemistry) was placed in a 1-liter 4-necked flask equipped with a nitrogen introduction tube, a stirrer, a cooling tube, a temperature controller, and a dropping cylinder. PGL06 manufactured by Kogyo Co., Ltd .: hexaglycerin, hydroxyl value 960, 175.3 g (0.5 mo)
1) was taken and heated to 80 ° C., and 0.5 mol (100.16 g) of lauric acid was added and dissolved while keeping the reaction temperature at 80 ° C. Next, 0.75 g of sodium carbonate and 0.25 g of sodium hydrogen sulfite were added, and an esterification reaction was carried out at 210 ° C. Acid value is 0.89 in 2 hours reaction
After cooling to 100 ° C., the reaction product was taken out. The resulting Poriguriseri Nra Gaulin ester was evaluated by HPLC. Furthermore, 10% aqueous solution of the resulting Poriguriseri Nra Gaulin ester was prepared, 30 seconds of shaking (manually)
The foamability and condition were visually observed. HPLC
The chart obtained by the analysis is shown in FIG. In addition, HPL
Table 1 shows the result of the component analysis by the analysis from C and the evaluation result of the foamability and the state.

[0052]

[Table 1]

Comparative Examples 5 to 14: Evaluation Results of Commercially Available Polyglycerin Fatty Acid Ester As commercially available polyglycerin fatty acid ester produced by reaction of polyglycerin and fatty acid, SY Glister (manufactured by Sakamoto Yakuhin Kogyo) No. 5 ( MO-310, MO-7
50, ML-310, ML-500, ML-750),
2 Poems (made by RIKEN Vitamin) (J-6021, J
-0021), 2 product numbers (GO)
-106, GL-106) and Sunsoft Q12S
(Manufactured by Taiyo Kagaku) was selected to prepare a 10% aqueous solution of each polyglycerin fatty acid ester, which was vibrated (manually) for 30 seconds, and the foamability and state were visually observed. The charts obtained by HPLC analysis are shown in FIGS. 10 to 19. In addition, the results of the component analysis by the analysis from HPLC and the evaluation results of the foamability and the state are shown.
Shown in 2.

[0054]

[Table 2]

[0055] (Production Example 1: Hekisaguriseri Preparation of Nsu Teareto) nitrogen inlet tube, stirrer, condenser, temperature controller, 1 liter four-necked flask stearate 0.5 mol (142g) equipped with a dropping cylinder And phosphoric acid (85% product)
3 g was added and heated to 140 ° C. Then set the reaction temperature to 1
While maintaining the temperature at 40 ° C, 3.0 mol of glycidol (222
g) was added dropwise over 5 hours so that the oxirane concentration in the system was 0.1.
The reaction was continued until it was less than 1%. Was obtained Hekisaguriseri Nsu Teareto removed after cooling the reaction product. The resulting Hekisaguriseri Nsu Teareto was measured monoester content by HPLC described above was 75%.

[0056] (Production Example 2: Dekaguriseri Preparation of lymph Rumiteto) nitrogen inlet tube, stirrer, condenser, temperature controller, four-necked 1 liter flask equipped with a dropping cylinder, palmitic acid 0.5 mol (128 g) And phosphoric acid (85% product)
0.2 g was added and heated to 140 ° C. Then, while maintaining the reaction temperature at 140 ° C, 5.0 mol (3 mol of glycidol)
70 g) was added dropwise over 7 hours and the reaction was continued until the oxirane concentration in the system became less than 0.1%. After cooling, the reaction product was obtained was taken out Dekaguriseri damper Rumiteto. The resulting Dekaguriseri damper Rumiteto was measured monoester content by HPLC described above, was 72%.

[0057] (Production Example 3: Dekaguriseri Preparation of oleate) nitrogen introducing tube, a stirrer, condenser, temperature controller, four-necked 1 liter flask equipped with a dropping cylinder, oleic acid 0.5 mol (141 g) And phosphoric acid (85% product)
3 g was added and heated to 140 ° C. Then set the reaction temperature to 1
Glycidol 5.0mol (370
g) was added dropwise over 7 hours so that the oxirane concentration in the system was 0.1.
The reaction was continued until it was less than 1%. After cooling, the reaction product was obtained was taken out Dekaguriseri oleate. The resulting Dekaguri <br/> glyceryl oleate was measured monoester content by HPLC described above was 75%.

[0058] (Production Example 4: Hekisaguriseri Preparation of Nsu Teareto) nitrogen introducing tube, a stirrer, was placed a condenser, a four-necked 5-liter flask equipped with a temperature controller of sodium hydroxide and glycerine 3000 g 30 g, nitrogen 150 mmHg under air flow
Heat to 240 ° C while removing the generated water under the reduced pressure of 2
After holding for 4 hours, a reaction product of hexaglycerin was obtained. The obtained hexaglycerin is de-Na-ized using an ion exchange resin.
OH was done. The hydroxyl value of the obtained product was 970. Stearic acid 0.5mo in a 1-liter four-necked flask equipped with a nitrogen introduction tube, a stirrer, a cooling tube, and a temperature controller.
1 (142 g) and 0.4 g of sodium hydroxide were added, and the hexaglycerin obtained above 0.5 mol (231
g) was charged and while removing the produced water under a nitrogen stream, 25
It was obtained Hekisaguriseri Nsu Teareto to react at 0 ℃.
HP The resulting Hekisaguriseri Nsu Teareto was said
When the monoester content was measured using LC,
It was 56%.

[0059]: nitrogen inlet (Production Example 5 Dekaguriseri damper Rumiteto Preparation of), stirrer, was placed a condenser, a four-necked 5-liter flask equipped with a temperature controller of sodium hydroxide and glycerine 3000 g 30 g, a nitrogen stream Lower 150 mmHg
Heat to 240 ° C while removing the generated water under the reduced pressure of 3
It was kept for 5 hours to obtain a reaction product of decaglycerin. The resulting decaglycerin is treated with an ion exchange resin to remove NaOH.
I went. The hydroxyl value of the obtained product was 890.
In a 1-liter four-necked flask, palmitic acid 0.6mo
1 (153.6g) was added and sodium hydroxide 0.4g
0.6 mol (45 mol of decaglycerin obtained above
While removing the generated water under a nitrogen stream were charged 4.8 g), was obtained Dekaguriseri damper Rumiteto react at 250 ° C.. The resulting Dekaguriseri damper Rumiteto using HPLC described above was measured for a monoester content was 63%.

[0060]: the (preparation 6 Dekaguriseri Preparation of oleate) 1. liter four-necked flask, 0.6 mol of oleic acid
(153.6 g) was added, and sodium hydroxide 0.5 g was added, and decaglycerin obtained in Production Example 5 was 0.6 mol.
While removing the generated water under a stream of nitrogen charged (454.8g), was obtained Dekaguriseri oleate was reacted at 250 ° C.. HP The resulting Dekaguriseri oleate was the
When the monoester content was measured using LC,
It was 59%.

[0061]: fish hardened oil 60 parts by weight of the melting point of 35 ° C. and purified soybean oil 15 parts by weight (Example 6 preparation of butter cakes fat composition for), stearic Thang Riseraido (monoester content 90%) 5 weight Part was heated and dissolved to obtain an oil phase part. Then the Hekisaguriseri Nsu <br/> stearate ester 6 parts by weight of the obtained from the Production Example 1 of water 14 parts by weight was added dispersed, was heated aqueous phase. While stirring the oil phase part, the water phase part was gradually added, emulsified and mixed, and then passed through a quenching plasticizer (combinator) to obtain an oil and fat composition.

[0062] (Comparative Example 15) mp 35 ° C. fish oil hardened oil 60 parts by weight and the purified soybean oil 15 parts by weight of stearic Thang Riseraido (monoester content 90%) and 5 parts by weight were heated and dissolved, and the oil phase did. Next, 6 parts by weight of a commercially available polyglycerin lauric acid ester was added and dispersed in 14 parts by weight of water and heated to obtain an aqueous phase part. While stirring the oil phase part, the water phase part was gradually added, emulsified and mixed, and then passed through a quenching plasticizer (combinator) to obtain an oil and fat composition.

Test Example 1 Using the oil and fat compositions obtained in Example 6 and Comparative Example 15, butter cake dough was blended as shown in Table 3 by an all-in-mix method and the dough specific gravity was 0.8. After whipped until 400 g, 400 g of the obtained dough was baked in an oven at 180 ° C. The obtained butter cake was sensory-evaluated for the dough state and texture. The results are shown in Table-4.

[0064]

[Table 3]

[0065]

[Table 4]

As shown in Table 4, the butter cake obtained in Example 6 had better dough condition and texture than those obtained in Comparative Example 15.

[0067] (Example 7: cocoa beverages) cocoa powder (cocoa butter 10% by weight content) 1 part by weight, 15 parts by weight of milk, sucrose, 5 parts by weight Dekaguriseri damper Rumiteto 1 part by weight obtained from Production Example 2 and Hot water 7
8 parts by weight were mixed, heated to 70 ° C., stirred for 5 minutes with a high speed mixer, homogenized with a homogenizer, and then filled in a can.

[0068] (Comparative Example 16) cocoa powder (cocoa butter 10% by weight content) 1 part by weight, 15 parts by weight of milk, sucrose 5 parts by weight, obtained from Preparation Example 5 Dekaguriseri damper palmitic acid ester 1 part by weight and hot water 78 parts by weight were mixed, heated to 70 ° C., stirred with a high speed mixer for 5 minutes, homogenized with a homogenizer, and then filled.

(Test Example 2) The cans prepared in Example 7 and Comparative Example 16 were allowed to stand at room temperature, and 10 cans were opened with time, and the presence or absence of floating substances was observed. The results are shown in Table-5.

[0070]

[Table 5]

The cocoa drink obtained in Example 7 did not show any floating matter on the 5th day, and the cocoa drink obtained in Comparative Example 16 showed floating matter on the 5th day.

[0072] (Example 8) with respect to the quasi-hard flour 1000 g, deca <br/> glycerin oleate 3g powder Brine 7g obtained from Production Example 3, brine 10
g, 300g of water, and mix for 15 minutes with a mixer,
Rolling and cutting (final noodle band 1.5 mm, cutting teeth # 20 square) were carried out by a conventional method, and the resulting noodles were steamed in a steamer for 7 minutes and washed with running water for 30 seconds. After draining, 170 g of steamed noodle was filled in a polyethylene bag and sealed.

[0073] (Comparative Example 17) with respect to the quasi-hard flour 1000 g, powder Kansui 7g to deca <br/> glycerin oleate 3g obtained from Preparation Example 6, sodium chloride 10
g, 300g of water, and mix for 15 minutes with a mixer,
Rolling and cutting (final noodle band 1.5 mm, cutting teeth # 20 square) were carried out by a conventional method, and the resulting noodles were steamed in a steamer for 7 minutes and washed with running water for 30 seconds. After draining, 170 g of steamed noodle was filled in a polyethylene bag and sealed.

(Test Example 3) The steamed noodles prepared in Example 8 and Comparative Example 17 were stored in a refrigerator at 5 ° C for 5 days, then oiled in a frying pan, the steamed noodles were fried, and the noodles were prepared by 20 panelists. Line looseness,
The taste and texture were evaluated. For the evaluation of the unraveling of the noodle line, when tasting with chopsticks,
A 10-point evaluation was conducted with 10 points being extremely good and 1 point being extremely bad, and the average value of 20 panelists was shown.
The evaluation of taste and texture is performed by a panel of 20 panelists, with 10 points for extremely good and 1 point for extremely bad.
The average of the names is shown. The results are shown in Table-6.

[0075]

[Table 6]

The steamed noodles obtained in Example 8 were the same as Comparative Example 1
As compared with the steamed noodles obtained in No. 7, the looseness, texture and taste were good.

Example 9 750 g of sorbit powder was heated to 105 ° C. and melted,
Added thereto, heated it to the Dekaguriseri oleate 100g obtained in Production Example 3 in 80 ° C., and vigorously stirred for 5 minutes with a homomixer while keeping above 90 ° C.. 80
Transfer the dispersion to a jacketed kneader kept at around ℃,
130 g of sorbit fine powder having a particle size of 80 mesh or less was added and mixed for 10 minutes. The mixture was cooled and then ground, 16
After passing through a mesh sieve, a powdered quality improver for addition of frozen surimi was obtained.

(Comparative Example 18) 750 g of sorbit powder was heated to 105 ° C. and melted,
Added thereto, heated it to the Dekaguriseri oleate 100g obtained in Production Example 6 to 80 ° C., and vigorously stirred for 5 minutes with a homomixer while keeping above 90 ° C.. 80
Transfer the dispersion to a jacketed kneader kept at around ℃,
130 g of sorbit fine powder having a particle size of 80 mesh or less was added and mixed for 10 minutes. The mixture was cooled and then ground, 16
After passing through a mesh sieve, a powdered quality improver for addition of frozen surimi was obtained.

(Test Example 4) To 5 kg of dehydrated meat obtained from Alaska pollack by a conventional method,
125 g of the improver of Example 9 or Comparative Example 18 and sucrose 20
0 g, 5 g each of pyrophosphate and sodium polyphosphate were added, and mixed by a small silent cutter for 5 minutes to make the mixture uniform. The surimi was filled in a polyethylene bag in an amount of 2.5 kg each, frozen at −30 ° C., and allowed to stand in a refrigerator (5 ° C.) overnight for 3 weeks to allow it to thaw naturally. Put 2 kg of this surimi into a silent cutter, add 3% salt and 5% potato starch to the surimi, knead for 13 minutes, fill in a film made of vinylidene chloride with a folding diameter of 48 mm, and bind it in hot water at 90 ° C. And heated for 30 minutes to produce a kamaboko. The whiteness of the hunter and the elasticity of the kamaboko were measured. The results are shown in Table-7.

[0080]

[Table 7]

Example 9 was superior to Comparative Example 18 in terms of whiteness and elasticity.

Example 10 Salad oil 40 parts by weight, acetic acid 15 parts by weight, salt 2.0 parts by weight, xanthan gum 0.2 parts by weight, water 41.8 parts by weight,
It was added Hekisaguriseri Nsu Teareto 1 part by weight obtained in Production Example 1, by using a homomixer, 10000R
pm, emulsification was carried out for 2 minutes to prepare a dressing. The pH of the resulting dressing was 4.0.

(Comparative Example 19) Salad oil 40 parts by weight, acetic acid 15 parts by weight, salt 2.0 parts by weight, xanthan gum 0.2 parts by weight, water 41.8 parts by weight,
It was added Hekisaguriseri Nsu Teareto 1 part by weight obtained in Production Example 4, using a homomixer, 10000R
pm, emulsification was carried out for 2 minutes to prepare a dressing. The pH of the resulting dressing was 4.0.

Test Example 5 The emulsified dressings obtained from Example 10 and Comparative Example 19 were stored at 40 ° C. for 10 days. As a result, in Example 10, no oil layer separation was observed, whereas in the emulsified dressing obtained in Comparative Example 19, 10% by weight of the salad oil caused separation.

Example 11 88.8 parts by weight of soy sauce, 10 parts by weight of salad oil, and 0.2 parts by weight of xanthan gum were added to the hexaglyceride obtained in Production Example 1.
It was added Nsu Teareto 1 part by weight, to prepare a sauce perform emulsification of 10000 rpm, 2 minutes using a homomixer.

[0086] (Comparative Example 20) soy sauce 88.8 parts by weight, 10 parts by weight of salad oil, xanthan gum 0.2 part by weight, the addition of Hekisagurise <br/> Li Nsu Teareto 1 part by weight obtained in Production Example 4, Using a homomixer, an emulsion was prepared by emulsifying at 10,000 rpm for 2 minutes.

Test Example 6 The sag obtained in Example 11 or Comparative Example 20 was 40%.
Stored at 4 ° C for 4 days. As a result, the sauce of Example 11 did not cause oil layer separation, whereas the sauce of Comparative Example 20 caused separation of 20% by weight of the salad oil.

[0088] (Example 12) coconut hardened oil 20.0 parts by weight, skimmed milk powder 2.5 parts by weight of sodium caseinate 2.5 part by weight, Hekisaguriseri Nsu Tereto 1 obtained in Production Example 1 in water 74 parts by weight Add parts by weight, and use a homomixer at 10,000 rpm, 2
An emulsification treatment was carried out for a minute to prepare a coffee cream.

[0089] (Comparative Example 21) coconut hardened oil 20.0 parts by weight, skimmed milk powder 2.5 parts by weight, sodium caseinate 2.5 part by weight, Hekisaguriseri Nsu stearate obtained in Preparation Example 4 in water 74 parts by weight Ester 1
Add 10,000 parts by weight using a homomixer
The coffee cream was prepared by emulsifying at rpm for 2 minutes.

Test Example 7 The coffee creams obtained in Example 12 and Comparative Example 21 were stored at 40 ° C. for 4 days. Table 8 shows the changes in the state visually.

[0091]

[Table 8]

The coffee cream obtained in Example 12 was more stable in emulsification than the coffee cream obtained in Comparative Example 21.

[0093]

As is apparent from the specific description of the examples, comparative examples, test examples, etc., the present invention
The high mono fatty acid ester content Poriguriseri down fatty <br/> ester surfactant, when applied to food additives such as emulsion stabilizers, improving the surface tension, improved dispersing power, foaming power And a significant improvement in emulsion stability are achieved.

[Brief description of drawings]

1 is a chart by HPLC for Poriguriseri Nra Gaulin ester obtained in Example 1.

2 is a chart by HPLC for Poriguriseri Nra Gaulin ester obtained in Example 2.

3 is a chart by HPLC for Poriguriseri Nra Gaulin ester obtained in Example 3.

4 is a chart by HPLC for Poriguriseri Nra Gaulin ester obtained in Example 4.

5 is a chart by HPLC for Poriguriseri Nra Gaulin ester obtained in Example 5.

6 is a chart by HPLC for Poriguriseri Nra Gaulin ester obtained in Comparative Example 1.

7 is a chart by HPLC for Poriguriseri Nra Gaulin ester obtained in Comparative Example 2.

8 is a chart by HPLC for Poriguriseri Nra Gaulin ester obtained in Comparative Example 3.

9 is a chart by HPLC for Poriguriseri Nra Gaulin ester obtained in Comparative Example 4.

FIG. 10 is an HPLC chart of a commercially available polyglycerin fatty acid ester used in Comparative Example 5.

FIG. 11 is an HPLC chart of a commercially available polyglycerin fatty acid ester used in Comparative Example 6.

FIG. 12 is an HPLC chart of a commercially available polyglycerin fatty acid ester used in Comparative Example 7.

FIG. 13 is an HPLC chart of a commercially available polyglycerin fatty acid ester used in Comparative Example 8.

FIG. 14 is an HPLC chart of a commercially available polyglycerin fatty acid ester used in Comparative Example 9.

FIG. 15 is an HPLC chart of a commercially available polyglycerin fatty acid ester used in Comparative Example 10.

16 is a HPLC chart for a commercially available polyglycerin fatty acid ester used in Comparative Example 11. FIG.

FIG. 17 is an HPLC chart of a commercially available polyglycerin fatty acid ester used in Comparative Example 12.

18 is an HPLC chart of a commercially available polyglycerin fatty acid ester used in Comparative Example 13. FIG.

FIG. 19 is an HPLC chart of a commercially available polyglycerin fatty acid ester used in Comparative Example 14.

─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁷ Identification code FI A23L 1/325 101 A23L 1/325 101D 2/38 2/38 C 3/3517 3/3517 B01F 17/38 B01F 17/38 ( 56) References JP 62-153256 (JP, A) JP 58-185537 (JP, A) JP 6-41007 (JP, A) JP 3-81252 (JP, A) JP Sho 63-23837 (JP, A) (58) Fields investigated (Int.Cl. ⁷ , DB name) A23L 1/03-1/035 C07C 69/33-69/675

Claims (11)

(57) [Claims] 1. A mono-fatty acid ester represented by the following general formula [1] obtained by reacting a fatty acid represented by the general formula [2] with glycidol in the presence of a phosphoric acid-based acid catalyst.
Octet using alcohol solvent and / or distilled water as eluent
High-performance liquid using a silica gel column bonded with tadecylsilyl group
Separation by body chromatography and using UV absorption detector
Food additive comprising a content of 70% or more on containing <br/> No Poriguriseri emissions fatty acid ester represented by the peak area ratio detected Te. [Chemical 1] 2. A food additive comprising a Poriguriseri emissions fatty acid ester to claim 1 serial <br/> placing carbon number of 7 or more R. 3. The food additive according to claim 1 or 2 , wherein the food additive is an emulsifier for an oil and fat composition for bread making and confectionery. 4. The food additive according to claim 1 or 2 , wherein the food additive is an emulsion stabilizer for cocoa beverages. 5. The food additive according to claim 1 or 2 , wherein the food additive is a starch food additive. 6. The food additive, food additive according to claim 1 or 2 which is additive marine paste products. 7. A food additive, a food additive according to claim 1 or 2 which is an emulsifier for oil-in-water emulsified oil composition. 8. The food additive according to claim 1 or 2 , wherein the food additive is a wheat flour mixture for bread making at room temperature for a long time. 9. The food additive according to claim 1 or 2 , wherein the food additive is a fat dispersion emulsification accelerator for sour cheese beverages. 10. A food additive, a food additive according to claim 1 or 2 which is an emulsifier for food freshness retaining agent. 11. The food additive according to claim 1 or 2 , wherein the food additive is an emulsifier for coffee cream.