WO2013054694A1 - 蔗糖脂肪酸エステル濃縮物混合物の製造方法及びそれによって得られる蔗糖脂肪酸エステル濃縮混合物 - Google Patents

蔗糖脂肪酸エステル濃縮物混合物の製造方法及びそれによって得られる蔗糖脂肪酸エステル濃縮混合物 Download PDF

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WO2013054694A1
WO2013054694A1 PCT/JP2012/075489 JP2012075489W WO2013054694A1 WO 2013054694 A1 WO2013054694 A1 WO 2013054694A1 JP 2012075489 W JP2012075489 W JP 2012075489W WO 2013054694 A1 WO2013054694 A1 WO 2013054694A1
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fatty acid
sucrose fatty
acid ester
esterification
mass
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PCT/JP2012/075489
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English (en)
French (fr)
Japanese (ja)
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良枝 山内
知洋 粟飯原
生稲　淳一
聡 根岸
明 瀬戸
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日清オイリオグループ株式会社
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Priority to CN201280050533.XA priority Critical patent/CN103874765A/zh
Publication of WO2013054694A1 publication Critical patent/WO2013054694A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • C12P7/6436—Fatty acid esters
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/44—Preparation of O-glycosides, e.g. glucosides

Definitions

  • the present invention relates to a method for producing a modified sucrose fatty acid ester mixture and a sucrose fatty acid ester mixture obtained thereby.
  • the present invention is characterized in that the sucrose fatty acid ester mixture raw material is hydrolyzed in the presence of lipase to increase the content of sucrose fatty acid esters having a degree of esterification of 6 to 8 with respect to the total sucrose fatty acid esters.
  • the present invention relates to a method for producing a modified sucrose fatty acid ester mixture.
  • the sucrose fatty acid ester is obtained by esterifying an arbitrary hydroxyl group with a fatty acid among the eight hydroxyl groups contained in the sucrose molecule.
  • the degree of esterification of the sucrose fatty acid ester is determined by the number of esterified hydroxyl groups. For example, a sucrose fatty acid ester having a degree of esterification of 6 means that 6 hydroxyl groups are esterified. Since sucrose fatty acid esters have good safety and biodegradability, they have been conventionally used as surfactants, emulsifiers, food additives, cosmetic materials and the like.
  • Sucrose fatty acid esters are usually produced by transesterification with a fatty acid alkyl such as fatty acid methyl using dimethyl sulfoxide (DMSO), dimethylformamide (DMF) or the like as a solvent and an alkali such as K 2 CO 3 as a catalyst.
  • a fatty acid alkyl such as fatty acid methyl using dimethyl sulfoxide (DMSO), dimethylformamide (DMF) or the like as a solvent and an alkali such as K 2 CO 3 as a catalyst.
  • the degree of esterification of the sucrose fatty acid ester can be adjusted, it is possible to control the HLB (hydrophilic lipophilic balance) of the sucrose fatty acid ester, sometimes increasing the lipophilicity and using it as an emulsifier for w / o emulsion, It can be used as an emulsifier for o / w emulsions with increased hydrophilicity.
  • a method for reducing the degree of esterification of the sucrose fatty acid ester there is a method using a specific reaction solvent such as methyl ethyl ketone (Patent Document 3).
  • the present invention provides a modified sucrose characterized by hydrolyzing a sucrose fatty acid ester mixture raw material in the presence of lipase to increase the content of sucrose fatty acid ester having a degree of esterification of 6 to 8 with respect to the total sucrose fatty acid ester. It aims at providing the manufacturing method of a fatty-acid ester mixture. Another object of the present invention is to provide a sucrose fatty acid ester mixture containing 65% by mass or more of a sucrose fatty acid ester having an esterification degree of 6 to 8 with respect to the total sucrose fatty acid ester, which can be obtained by the above production method. And
  • the present inventors increased the content of sucrose fatty acid esters having a degree of esterification of 6 to 8 with respect to the total sucrose fatty acid esters by hydrolyzing the sucrose fatty acid ester mixture raw material in the presence of lipase.
  • the present invention has been found. That is, the present invention 1.
  • the present invention relates to a method for producing a modified sucrose fatty acid ester mixture characterized in that the sucrose fatty acid ester mixture raw material is hydrolyzed in the presence of lipase to increase the content of sucrose fatty acid ester having a degree of esterification of 6-8. 2.
  • the lipase is one or more of at least one selected from lipases derived from Candida rugosa, lipases derived from Rhizopus oryzae, and lipases derived from Thermomyces lanuginosus.
  • the modified sucrose fatty acid ester mixture contains 65% by mass or more of sucrose fatty acid ester having an esterification degree of 6 to 8 and 30% by mass or less of sucrose fatty acid ester having an esterification degree of 4 to 5 with respect to the total sucrose fatty acid ester. 5.
  • 6. The method according to any one of 1 to 5, wherein the sucrose fatty acid ester mixture raw material has an HLB value of 3 or less. 7).
  • a modified sucrose fatty acid ester mixture comprising 65% by mass or more of a sucrose fatty acid ester having an esterification degree of 6 to 8 with respect to the total sucrose fatty acid ester, which can be obtained by the method according to any one of 1 to 7 above. . 9. 9. The modified sucrose fatty acid ester mixture according to 8 above, comprising 15% by mass or more of a sucrose fatty acid ester having a degree of esterification of 6 with respect to all sucrose fatty acid esters and 15% by mass or less of a sucrose fatty acid ester having a degree of esterification of 5.
  • the content ratio of sucrose fatty acid ester having an esterification degree of 6 to 8 with respect to the total sucrose fatty acid ester can be increased.
  • the content ratio of the sucrose fatty acid ester having a degree of esterification of 6 to 8 is the mass ratio of the sucrose fatty acid ester having a degree of esterification of 6 to 8 to the total sucrose fatty acid ester contained in the modified sucrose fatty acid ester mixture before and after hydrolysis.
  • sucrose fatty acid ester having a degree of esterification of 6 to 8 to the total sucrose fatty acid ester contained in the sucrose fatty acid ester mixture raw material is increased by at least about 104/100, preferably at least about 105/100. Is possible. In addition, the content of sucrose fatty acid esters having a low esterification degree of 4-5 can be reduced.
  • the ratio of the mass ratio of sucrose fatty acid ester having a degree of esterification of 4 to 5 to the total sucrose fatty acid ester contained] can be 95/100 or less.
  • a sucrose fatty acid ester mixture containing 65% by mass or more of a sucrose fatty acid ester having an esterification degree of 6 to 8 with respect to the total sucrose fatty acid ester, preferably 15 masses of a sucrose fatty acid ester having an esterification degree of 6 %, And a sucrose fatty acid ester mixture containing 15% by mass or less of a sucrose fatty acid ester having an esterification degree of 5 can be obtained.
  • the sucrose fatty acid ester mixture thus obtained can be suitably used as a good surfactant, such as emulsifying use, oil absorption inhibiting use in foods, and oil crystallizing effect.
  • the sucrose fatty acid ester mixture raw material is a mixture containing a plurality of sucrose fatty acid esters having different degrees of esterification, which is used as a raw material in the method for producing the modified sucrose fatty acid ester mixture of the present invention.
  • the sucrose fatty acid ester is an ester in which 1 to 8 arbitrary fatty acids are bonded to 8 hydroxyl groups of sucrose. Depending on the number of bound fatty acids (ie constituent fatty acids), sucrose fatty acid esters exist from 1-substituted (monoester) to 8-substituted (octaester).
  • the esterification degree of the sucrose fatty acid ester indicates the number of the constituent fatty acids, and the 1-substituted product is expressed as 1 degree of esterification and the 8-substituted product is expressed as 8 degree of esterification.
  • aliphatic carboxylic acid is mentioned as said constituent fatty acid.
  • a straight chain saturated aliphatic carboxylic acid a straight chain unsaturated aliphatic carboxylic acid, a branched chain of an aliphatic carboxylic acid having 2 to 22, preferably 8 to 22, and more preferably 14 to 22 carbon atoms. Chain saturated aliphatic carboxylic acids and mixtures thereof can be used.
  • Examples include caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, lignoceric acid, serotic acid, palmitooleic acid, oleic acid, elaidic acid, linoleic acid Linolenic acid, eicosapentaenoic acid, docosahexaenoic acid, arachidonic acid, erucic acid, acetic acid, isobutyric acid and the like, but are not limited thereto.
  • the constituent fatty acid of the total sucrose fatty acid ester is particularly preferably a linear saturated aliphatic carboxylic acid having 14 to 22 carbon atoms. Most preferred are linear saturated aliphatic carboxylic acids such as stearic acid, palmitic acid, and behenic acid.
  • constituent fatty acids other than the linear saturated aliphatic carboxylic acid having 14 to 22 carbon atoms may be included, but constituent fatty acids other than the linear saturated aliphatic carboxylic acid having 14 to 22 carbon atoms are 50
  • the amount is preferably less than mass%, more preferably 0 to 40 mass%, further preferably 0 to 10 mass%, and most preferably 0 to 5 mass%.
  • the sucrose fatty acid ester mixture raw material of the present invention is a ratio of 70% by mass or less of sucrose fatty acid ester having a degree of esterification of 6 to 8 to the total sucrose fatty acid ester of the sucrose fatty acid ester mixture, preferably less than 68% by mass, more preferably
  • the content is preferably 50 to 67% by mass, more preferably 60 to 67% by mass, and most preferably 60 to 65% by mass.
  • the sucrose fatty acid ester mixture raw material of the present invention is a ratio of 15% by mass or more of sucrose fatty acid ester having a degree of esterification of 4 to 5 to the total sucrose fatty acid ester of the sucrose fatty acid ester mixture, preferably 20 to 50% by mass, More preferably, it is contained in a proportion of 25 to 40% by mass, most preferably 25 to 35% by mass.
  • the preferred ester composition of the sucrose fatty acid ester mixture raw material of the present invention is 0 to 20% by mass, preferably 0 to 5% by mass of sucrose fatty acid ester having a degree of esterification of 1 with respect to the total sucrose fatty acid ester of the sucrose fatty acid ester mixture.
  • HLB Hydrophile Lipophile Balance and serves as an index for knowing whether an emulsifier is hydrophilic or lipophilic, and takes a value of 0 to 20. It shows that lipophilicity is so strong that an HLB value is small.
  • the Griffin calculation method is used.
  • the hydrophilic part means a part obtained by removing the hydrocarbon chain of the constituent fatty acid from the whole sucrose fatty acid ester molecule.
  • the HLB value of the sucrose fatty acid ester mixture raw material is, for example, 3 or less, preferably 0 to 2, more preferably 0 to 1.
  • lipases examples include lipoprotein lipase, monoacyl glycero lipase, diacyl glycero lipase, triacyl glycero lipase, galacto lipase, and phospho lipase. Of these, triacylglycerolipase is preferred.
  • the microorganisms that produce these lipases are not particularly limited to bacteria, yeasts, filamentous fungi, actinomycetes, and the like, but include the genus Alcaligenes sp., Pseudomonas sp., And Arthrobacter.
  • Alcaligenes sp. Lipase derived from Candida rugosa, lipase derived from Aspergillus niger, Aspergillus genus Rhizomucor muesi musi musi musimoe grassae
  • a lipase derived from Thermomyces lanuginosus, a lipase derived from Rhizopus delemar, and a lipase derived from Rhizopus oryzae are more preferred.
  • Particularly preferred are lipases derived from Candida rugosa, lipases derived from Rhizopus oryzae, and lipases derived from Thermomyces lanuginosus.
  • the lipase used in the present invention may or may not have positional specificity. If it has positional specificity, it is preferably 1,3-specificity.
  • the lipase used in the present invention may be obtained by culturing and drying a lipase-containing aqueous liquid containing a lipase medium component or the like, but it does not contain these, that is, the lipase itself substantially. What is comprised from this is preferable.
  • a lipase-containing aqueous liquid or a powder containing lipase can be used.
  • a lipase-containing aqueous liquid produced by removing cells after culturing lipase, immobilized, or further powdered is more preferable.
  • the lipase-containing aqueous liquid As the lipase-containing aqueous liquid, the lipase culture solution from which the bacterial cells have been removed, the purified culture solution, the lipase powder obtained from these dissolved and dispersed again in water, and the commercially available lipase powder dissolved and dispersed again in water And commercially available liquid lipases. Further, those obtained by removing low molecular components such as salts in order to further increase the lipase activity are more preferable, and those obtained by removing low molecular components such as sugars in order to further improve the powder properties.
  • Immobilized lipase should be lipase immobilized on a carrier such as silica, celite, diatomaceous earth, pearlite, polyvinyl alcohol, anion exchange resin, phenol adsorption resin, hydrophobic carrier, cation exchange resin, chelate resin, etc. Can do.
  • a carrier such as silica, celite, diatomaceous earth, pearlite, polyvinyl alcohol, anion exchange resin, phenol adsorption resin, hydrophobic carrier, cation exchange resin, chelate resin, etc. Can do.
  • Such an immobilized lipase is not particularly limited, and examples thereof include a product Lipozyme TLIM of Novozymes Japan Co., Ltd. derived from Thermomyces lanuginosus.
  • the immobilized lipase can be used as it is, or one obtained by pulverizing the immobilized lipase can be used.
  • the powder lipase is obtained by drying and pulverizing a lipase-containing aqueous liquid by a method such as spray drying, freeze drying, or drying after solvent precipitation, and is not particularly limited.
  • a method such as spray drying, freeze drying, or drying after solvent precipitation.
  • Candida rugosa Products derived from Amano Enzyme Co., Ltd .: Lipase AY “Amano” 50G, Lipase DF “Amano” 15 derived from Rhizopus oryzae, etc. can be used.
  • a hydrolysis reaction of the sucrose fatty acid ester mixture raw material of the present invention using lipase a commonly used hydrolysis reaction can be used. Specifically, for example, water and optionally a solvent are added to a sucrose fatty acid ester mixture as a raw material, and a predetermined amount of lipase is added to perform a hydrolysis reaction.
  • a predetermined amount of lipase is added to perform a hydrolysis reaction.
  • 1 to 50 g preferably 5 to 25 g, more preferably 10 to 20 g is added to 1 g of sucrose fatty acid ester mixture raw material.
  • DMSO dimethyl sulfoxide
  • DMF dimethylformamide
  • methyl ethyl ketone isooctane
  • acetone xylene
  • toluene hexane
  • chloroform chlorobenzene and the like
  • the solvent only needs to have an amount capable of dissolving the sucrose fatty acid ester mixed raw material to some extent, and DMSO, DMF, ketone-based, and alcohol-based solvents are preferable because they dissolve both sucrose fatty acid ester and water.
  • 0.5 to 30 g, preferably 1 to 20 g, more preferably 3 to 10 g is added to 1 g of sucrose fatty acid ester mixture raw material.
  • the lipase described above and optionally an auxiliary agent can be used.
  • 1 to 30 mL, preferably 2 to 20 mL, more preferably 3 to 15 mL of lipase having an enzyme concentration of 10,000 U / mL is added.
  • the hydrolysis reaction is carried out, for example, under normal pressure at room temperature (20 ° C.) to 80 ° C., preferably 30 to 70 ° C., more preferably 40 to 60 ° C., for example 1 to 48 hours, preferably 6 to 36 hours. More preferably, it is carried out with optional stirring for 12 to 24 hours.
  • the hydrolysis reaction may include a preliminary stirring step of stirring without adding lipase, and a reaction step of adding the lipase and performing the hydrolysis reaction thereafter. The preliminary stirring step is continued, for example, for 5 to 60 minutes, preferably 10 to 50 minutes, and more preferably 20 to 40 minutes.
  • the predetermined amount of lipase may be added at a time, but the predetermined amount of lipase is added in 2 to 30 times, preferably 3 to 20 times, more preferably 5 to 15 times. May be.
  • the lipase may be added every 1 to 2 hours after the first lipase is added.
  • the content of the sucrose fatty acid ester having a degree of esterification of 6 to 8 is increased, preferably 1 to 20% by mass, more preferably compared to before the hydrolysis.
  • a modified sucrose fatty acid ester mixture is obtained which is increased by 2 to 15% by weight.
  • the modified sucrose fatty acid ester mixture of the present invention is a ratio of 65% by mass or more of sucrose fatty acid ester having a degree of esterification of 6 to 8 to the total sucrose fatty acid ester of the modified sucrose fatty acid ester mixture, preferably more than 65% by mass.
  • the content is preferably less than mass%, more preferably 68 to 90 mass%, still more preferably 68 to 80 mass%.
  • the modified sucrose fatty acid ester mixture of the present invention has a ratio of sucrose fatty acid ester having an esterification degree of 4 to 5 to 30% by mass or less, preferably 1 to 25% based on the total sucrose fatty acid ester of the modified sucrose fatty acid ester mixture.
  • the content is preferably 5% by mass, more preferably 5 to 25% by mass, and still more preferably 5 to 15% by mass.
  • a preferred ester composition of the modified sucrose fatty acid ester mixture of the present invention is 0 to 5% by mass, preferably 0, of sucrose fatty acid ester having a degree of esterification of 1 with respect to the total sucrose fatty acid ester of the modified sucrose fatty acid ester mixture.
  • the modified sucrose fatty acid ester mixture can be used as an emulsifier, a crystal modifier, an antifo
  • sucrose fatty acid ester before and after hydrolysis By the hydrolysis reaction using the lipase of the present invention, a modified sucrose fatty acid ester mixture having an increased content of sucrose fatty acid esters having a degree of esterification of 6 to 8 is obtained.
  • the content ratio of the sucrose fatty acid ester having an esterification degree of 6 to 8 can be confirmed by the mass ratio of the sucrose fatty acid ester having a specific esterification degree contained in the sucrose fatty acid ester before and after hydrolysis.
  • [mass of sucrose fatty acid ester having an esterification degree of 6 to 8 contained in the modified sucrose fatty acid ester mixture] / [mass of sucrose fatty acid ester having an esterification degree of 6 to 8 contained in the raw material of the sucrose fatty acid ester mixture] Is, for example, 104/100 or more, preferably 104/100 to 200/100, more preferably 105/100 to 200/100 or 106/100 to 200/100, still more preferably 108/100 to 150. / 100 is appropriate.
  • a modified sucrose fatty acid ester mixture in which the content of sucrose fatty acid esters having a degree of esterification of 4 to 5 is reduced is obtained.
  • the content ratio of the sucrose fatty acid ester having a degree of esterification of 4 to 5 can be confirmed by the mass ratio of the sucrose fatty acid ester having a specific degree of esterification contained in the sucrose fatty acid ester before and after hydrolysis.
  • [mass of sucrose fatty acid ester having an esterification degree of 4 to 5 contained in the modified sucrose fatty acid ester mixture] / [mass of sucrose fatty acid ester having an esterification degree of 4 to 5 contained in the raw material of the sucrose fatty acid ester mixture] Is, for example, 95/100 or less, preferably 10/100 to 85/100, more preferably 30/100 to 75/100, still more preferably 40/100 to 70/100 or 40/100 to 65. / 100 is appropriate.
  • sucrose fatty acid esters having an esterification degree of 1, 2, 3 and an esterification degree of 4 or more was measured using a GPC column.
  • the composition ratio of sucrose fatty acid esters having esterification degrees of 4, 5, 6, 7 and 8 was measured.
  • Each composition having an esterification degree of 1 to 8 was calculated from the measurement result of the previous GPC column and the composition ratio result of the ODS column.
  • lipase AY “Amano” 50G manufactured by Amano Enzyme Co., Ltd., hereinafter referred to as lipase AY: derived from Candidalosa
  • This lipase AY was dissolved in water to prepare a lipase solution having an enzyme concentration of 10,000 U / mL.
  • Example 2 Example 1 except that lipase DF “Amano” 15 (manufactured by Amano Enzyme Co., Ltd., hereinafter referred to as lipase DF: derived from Rhizopus oryzae), which is a powder lipase having 1,3-specificity, was used as the lipase.
  • lipase DF derived from Rhizopus oryzae
  • a modified sucrose fatty acid ester mixture was obtained in the same manner.
  • Example 3 The same method as in Example 1 except that Lipozyme TLIM (manufactured by Novozymes Japan Ltd., hereinafter referred to as TLIM: derived from Thermomyces lanogeneus), which is an immobilized lipase having 1,3-specificity, was used as the lipase.
  • TLIM manufactured by Novozymes Japan Ltd.
  • the modified sucrose fatty acid ester mixture was obtained.
  • Lipozyme TLIM used was pulverized using a pulverizer.
  • FIG. 1 A first figure.
  • the vertical axis represents the acid value, and indicates the degree of generation of fatty acid by hydrolysis reaction (when the acid value increases, ester hydrolysis proceeds and fatty acid is generated), and the horizontal axis represents time.
  • Show. AY is the lipase AY used in Example 1
  • DF is the lipase DF used in Example 2. From the results shown in FIG. 1, it can be seen that the hydrolysis reaction of both lipases AY and DF is completed at least 20 hours after the start of the reaction (when lipase is first charged).
  • the reaction product containing the modified sucrose fatty acid ester mixture obtained in Examples 1, 2, and 3 was placed in a 50 mL centrifuge tube and centrifuged at 3000 rpm for 5 minutes.
  • a centrifuge GS-6KR manufactured by Beckman was used. After centrifugation, the resulting supernatant (isooctane layer) was collected, the solvent was removed by an evaporator, the solvent was further removed by vacuum decompression (0.5 to 1 Pa), and the modified sucrose fatty acid ester mixture was isolated.
  • Ryoto sugar ester S-070 manufactured by Mitsubishi Chemical Foods Co., Ltd.
  • FIG. 1 A first figure.
  • the mass ratio of sucrose fatty acid ester having an esterification degree of 6 to 8 to the total sucrose fatty acid ester contained] is 123/100 (Example 1), 114/100 (Example 2), and 106/100 (Example 3), respectively.
  • sucrose fatty acid ester having a degree of esterification of 4 to 5 to the total sucrose fatty acid ester contained in the modified sucrose fatty acid ester mixture [included in the sucrose fatty acid ester mixture raw material of Examples 1, 2, and 3]
  • the mass ratio of the sucrose fatty acid ester having a degree of esterification of 4 to 5 to the total sucrose fatty acid ester is 42/100 (Example 1), 68/100 (Example 2), and 71/100 (Example 3), respectively. there were.
  • sucrose fatty acid ester mixture raw material was hydrolyzed in the presence of lipase to increase the content of sucrose fatty acid esters having a degree of esterification of 6 to 8 with respect to the total sucrose fatty acid esters. And the content of sucrose fatty acid esters having a degree of esterification of 4-5 with respect to the total sucrose fatty acid esters could be reduced.
  • Example 4 A modified sucrose fatty acid ester mixture produced in the same manner as in Example 1 (types of sucrose fatty acid esters contained are shown in Table 2) was purified at 50 ° C. with refined soybean oil (“Nisshin Soy Salad Oil” manufactured by Nisshin Oillio Group, Inc.) ) was added at a ratio of 1% by mass with respect to the total mass of the refined soybean oil and mixed to obtain a modified sucrose fatty acid ester-containing oil and fat. 30 g of the obtained modified sucrose fatty acid ester-containing fats and oils was put into a domestic frying pan, and eggplants (thickness: about 4 mm, diameter of cut surface: about 4 cm) were fried.
  • refined soybean oil (“Nisshin Soy Salad Oil” manufactured by Nisshin Oillio Group, Inc.)
  • the modified sucrose fatty acid ester-containing oil / fat had a lower oil absorption rate than the refined soybean oil. That is, the fats and oils containing the modified sucrose fatty acid ester mixture according to the present invention were good with less fat and oil permeating into the cooking object.

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PCT/JP2012/075489 2011-10-14 2012-10-02 蔗糖脂肪酸エステル濃縮物混合物の製造方法及びそれによって得られる蔗糖脂肪酸エステル濃縮混合物 WO2013054694A1 (ja)

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JP2016037466A (ja) * 2014-08-07 2016-03-22 日清オイリオグループ株式会社 蔗糖脂肪酸エステルの分別製造方法

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JP6459115B2 (ja) * 2014-08-29 2019-01-30 日清オイリオグループ株式会社 改質蔗糖脂肪酸エステル混合物とその製造方法
CN106562079A (zh) * 2016-09-20 2017-04-19 湖北华扬科技发展有限公司 酶联乳化剂及其应用

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