WO2015115584A1 - Composition de graisse ou d'huile - Google Patents

Composition de graisse ou d'huile Download PDF

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Publication number
WO2015115584A1
WO2015115584A1 PCT/JP2015/052619 JP2015052619W WO2015115584A1 WO 2015115584 A1 WO2015115584 A1 WO 2015115584A1 JP 2015052619 W JP2015052619 W JP 2015052619W WO 2015115584 A1 WO2015115584 A1 WO 2015115584A1
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Prior art keywords
oil
mass
fat
fat composition
fatty acid
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English (en)
Japanese (ja)
Inventor
和也 東方
里佳 本間
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Kao Corp
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Kao Corp
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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings or cooking oils characterised by ingredients other than fatty acid triglycerides
    • A23D9/013—Other fatty acid esters, e.g. phosphatides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings or cooking oils characterised by ingredients other than fatty acid triglycerides

Definitions

  • the present invention relates to an oil and fat composition useful for cooking.
  • Fats, monoacylglycerols, odorous components and the like are included in addition to triacylglycerols in oils and fats that have been compressed from plant seeds, germs, and pulp.
  • a so-called deodorization treatment is generally performed in which it is brought into contact with water vapor under high temperature and reduced pressure (Patent Document 1).
  • by-products such as chloropropanols may increase by the conventional deodorizing operation performed for improving the flavor.
  • 3-monochloropropanediol fatty acid ester which is a kind of chloropropanols, is produced from lipids and chloride ions in the course of high-temperature treatment in the deodorizing process of edible oil.
  • 3-MCPDE is an ester in which one or two fatty acids are ester-bonded to 3-monochloropropanediol, and is contained in a trace amount in fats and oils.
  • Patent Document 2 A method for purifying palm oil after passing through the decolorization and deodorization processes with an alkaline aqueous solution (Patent Document 2), palm oil and fat A method of adsorbent treatment and / or alkali treatment (Patent Document 3) and a method of adding sodium carbonate or sodium hydrogencarbonate during high-temperature heating of fats and oils (Non-Patent Document 1) have been reported.
  • Patent Literature A method for purifying palm oil after passing through the decolorization and deodorization processes with an alkaline aqueous solution
  • Patent Document 3 A method of adsorbent treatment and / or alkali treatment
  • Patent Document 1 a method of adding sodium carbonate or sodium hydrogencarbonate during high-temperature heating of fats and oils
  • Patent Document 1 JP-A-59-68398 (Patent Document 2) International Publication No. 2011/055732 (Patent Document 3) International Publication No. 2010/126136 (Non-patent Document)
  • Non-Patent Document 1 Eur. J. et al. Lipid Sci. Tech. 2013, vol. 115, p. 286-294
  • the present invention includes the following components (A) and (B): (A) Diacylglycerol 20% by mass or more, (B) One or more components selected from alkali metals and alkaline earth metals provide an oil and fat composition containing 0.1 ppm or more. Further, the present invention provides an oil and fat composition containing 20 ppm by mass or more of diacylglycerol and containing 0.1 ppm or more of (B) one or more components selected from alkali metals and alkaline earth metals. The present invention provides a method for suppressing the formation of 3-monochloropropanediol fatty acid ester.
  • the present invention relates to providing an oil and fat composition in which the formation of 3-MCPDE is suppressed when heated to a high temperature in the presence of water and salt.
  • the present inventor has found that if the diacylglycerol concentration and the alkali concentration in the oil and fat composition are adjusted, even if the oil and fat composition is heated to a high temperature in the presence of water and salt, 3-MCPDE is produced. It was found that can be suppressed.
  • the oil and fat composition of the present invention contains oil and fat.
  • the content of the oil and fat in the oil and fat composition is preferably 85% by mass (hereinafter simply referred to as “%”) or more, more preferably 90% or more, more preferably 95% or more, and more preferably 98% or more. Also, it is preferably 99.99% or less, more preferably 99.95% or less, and further 99.9% or less from the viewpoint of cooking ability.
  • the “oil / fat” includes one or more of triacylglycerol, diacylglycerol, and monoacylglycerol.
  • the oil and fat composition of the present invention contains 20% or more of the component (A) diacylglycerol, but is 25% or more, further 30% or more, and further 50% or more from the viewpoint of physiological effect and 3-MCPDE production suppression. Further, it is preferably 60% or more, more preferably 80% or more, and from the viewpoint of industrial productivity, it is 99.5% or less, further 98% or less, further 95% or less, and further 90% or less. preferable.
  • the content of diacylglycerol in the oil / fat composition is preferably 20 to 99.5%, more preferably 25 to 98%, further 30 to 95%, further 60 to 90%, and more preferably 80 to 90%.
  • the fatty acid constituting the diacylglycerol is not particularly limited and may be either a saturated fatty acid or an unsaturated fatty acid.
  • the content of the unsaturated fatty acid in the constituent fatty acid is 80% or more. Further, it is preferably 85% or more, more preferably 90% or more, and from the viewpoint of industrial productivity of fats and oils, it is preferably 100% or less, more preferably 99% or less, and further preferably 98% or less.
  • the content of unsaturated fatty acid in the fatty acid constituting diacylglycerol is preferably 80 to 100%, more preferably 85 to 99%, and further preferably 90 to 98%.
  • the unsaturated fatty acid preferably has 14 to 24 carbon atoms, more preferably 16 to 22 carbon atoms from the viewpoint of physiological effects.
  • the content of saturated fatty acid in the fatty acid constituting diacylglycerol is preferably 1% or more, more preferably 2% or more from the viewpoint of appearance, and 20% or less, further 15% or less from the viewpoint of physiological effects. Further, it is preferably 10% or less. Further, the content of saturated fatty acid in the fatty acid constituting diacylglycerol is preferably 0 to 15%, more preferably 2 to 10%. Saturated fatty acids having 14 to 24 carbon atoms, more preferably 16 to 22 carbon atoms are preferred.
  • the content of the trans unsaturated fatty acid is preferably 0 to 5%, more preferably 0.01 to 3.5%, and further preferably 0.01 to 3%. It is preferable from the viewpoint of physiological effects and appearance.
  • the oil and fat composition of the present invention contains triacylglycerol in an amount of 1 to 80%, further 5 to 80%, further 10 to 80%, further 10 to 40%, and further 10 to 20%. From the viewpoint of productivity and appearance.
  • the monoacylglycerol content in the oil / fat composition is preferably 5% or less, more preferably 0.01 to 3%, further 0.01 to 2%, and still more preferably 0.01 to 1.5%.
  • the content of the free fatty acid or salt thereof in the oil / fat composition is preferably 3.5% or less, and more preferably 0.01 to 1.5% in view of flavor and the like.
  • the constituent fatty acids of triacylglycerol and monoacylglycerol are preferably the same constituent fatty acids as diacylglycerol in view of physiological effects and industrial productivity of fats and oils.
  • the origin of the fats and oils in the fat and oil composition may be vegetable oils or animal fats as long as they can be used as edible fats and oils.
  • Specific raw materials include rapeseed oil (canola oil), sunflower oil, corn oil, soybean oil, sesame oil, rice oil, safflower oil, cottonseed oil, palm oil, palm oil, olive oil, grape oil, avocado oil, sesame oil Peanut oil, macadamia nut oil, hazelnut oil, walnut oil, lard, beef tallow, chicken oil, butter oil, fish oil and the like.
  • rapeseed oil sunflower oil
  • corn oil soybean oil
  • sesame oil rice oil
  • safflower oil cottonseed oil
  • palm oil palm oil
  • olive oil grape oil
  • avocado oil, sesame oil Peanut oil, macadamia nut oil, hazelnut oil, walnut oil, lard, beef tallow, chicken oil, butter oil, fish oil and the like.
  • the liquid oil means an oil that is liquid at 20 ° C. when a cooling test is conducted according to the standard oil analysis test method 2.3.8-27.
  • the fats and oils in an oil-fat composition are the refined fats and oils which passed through the refinement
  • refined fats and oils are oils from which impurities contained in oil (crude oil) in a state of being compressed or extracted from oil raw materials are removed, preferably degumming step, top cut distillation step, acid treatment step, It is oil which performed any one process or more chosen from a decoloring process, a water washing process, and a deodorizing process.
  • the degumming step includes a method using hydration, a method using acid, and the like, and is a step of removing gums such as phospholipids and proteins.
  • a top cut distillation process is a process of removing light by-products, such as a fatty acid, from fats and oils by distilling fats and oils.
  • the acid treatment step is a step of removing impurities by adding and mixing a chelating agent such as citric acid to fats and oils and further dehydrating under reduced pressure.
  • a decoloring process is a process of making an oil etc. contact an adsorbent etc. and making a hue and flavor still more favorable.
  • a water-washing process is a process of performing operation which makes water contact oil and fat and performs oil-water separation.
  • the deodorization step is a step of steam distillation of oil and fat under reduced pressure.
  • Oils and fats containing diacylglycerol can be obtained by esterification reaction between fatty acids derived from fats and oils and glycerin reaction between fats and oils and glycerin. These reactions are carried out by a chemical method using a chemical catalyst such as an alkali metal or an alloy thereof, an alkali metal or alkaline earth metal oxide, a hydroxide or an alkoxide having 1 to 3 carbon atoms, and an enzymatic method using an enzyme such as lipase. It is divided roughly into. Among these, it is preferable in terms of flavor and the like that the reaction is performed enzymatically using lipase or the like as a catalyst under mild conditions.
  • a chemical catalyst such as an alkali metal or an alloy thereof, an alkali metal or alkaline earth metal oxide, a hydroxide or an alkoxide having 1 to 3 carbon atoms
  • an enzyme such as lipase. It is divided roughly into. Among these, it is preferable in terms of
  • One or more components selected from the component (B) alkali metal and alkaline earth metal used in the present invention are one or more components selected from sodium, potassium, calcium and magnesium, and 1 selected from sodium and potassium. It is preferable from the viewpoint of suppression of 3-MCPDE production that it is a component of more than seeds.
  • the alkali metal and alkaline earth metal supply source is preferably an alkali salt that can be added to food, for example, alkali metal or alkaline earth metal hydroxides (calcium hydroxide, magnesium hydroxide, etc.), carbonates.
  • Sodium bicarbonate, sodium carbonate, potassium carbonate, potassium bicarbonate, etc.), sulfates (magnesium sulfate, magnesium calcium sulfate, etc.), fatty acid salts having 12 to 22 carbon atoms can be used.
  • alkali metal or alkaline earth metal hydroxides, carbonates, and fatty acid salts having 12 to 22 carbon atoms are preferred from the viewpoints of suppressing the production of 3-MCPDE and blending with fats and oils.
  • Sodium bicarbonate, sodium carbonate, potassium carbonate, and potassium bicarbonate are preferred.
  • the content of one or more components selected from (B) alkali metal and alkaline earth metal is 0.1 ppm or more, but from the viewpoint of suppressing 3-MCPDE production, 0.2 ppm.
  • the content of one or more components selected from (B) alkali metals and alkaline earth metals in the oil and fat composition can be measured by atomic absorption spectrophotometry.
  • the oil and fat composition of the present invention preferably contains 0.01 to 2% of an antioxidant in the oil and fat composition from the viewpoint of oxidation stability during storage and cooking, and more preferably 0.01 to 1 %, Preferably 0.01 to 0.5%.
  • the antioxidant is preferably one or more selected from natural antioxidants, tocopherols, ascorbyl palmitate, ascorbyl stearate, dibutylhydroxytoluene (BHT), butylhydroxyanisole (BHA), and the like.
  • BHT dibutylhydroxytoluene
  • BHA butylhydroxyanisole
  • One or more antioxidants selected from an agent, tocopherol and ascorbyl palmitate are more preferred. Among these, the combined use of ascorbyl palmitate and tocopherol is preferable.
  • the content of 3-MCPDE is preferably 1 ppm or less, more preferably 0.5 ppm or less, from the viewpoint of suppressing the amount of 3-MCPDE after cooking.
  • 3-MCPDE in the oil and fat composition is a standard method C-VI 18 (10) (DGF Standard Methods 2010 (16. Supplement), C-VI 18 (10). , “Fatty-acid-bound 3-chloropropane-1,2-diol (3-MCPD) and 2,3-epoxy-propane-1-ol (glycidol)”).
  • the value obtained by the standard method assay B is used as the 3-MCPDE content. Details of the measurement method are described in the examples.
  • the oil / fat composition of the present invention is not particularly limited.
  • an oil / fat containing a high amount of diacylglycerol, or a normal edible oil / fat as necessary is added to the oil / fat and the component (B), and further if necessary. It can be obtained by mixing other components and appropriately heating, stirring and the like.
  • the oil and fat composition of the present invention produces little 3-MCPDE even when heated to a high temperature in the presence of water and salt.
  • the content of 3-MCPDE measured after the high temperature cooking model test described in the examples is 1 ppm or less, further 0.8 ppm or less, further 0.5 ppm or less, and further 0.3 ppm or less. It is preferable.
  • the oil and fat composition of the present invention can be used in the same manner as general edible oils and fats, and can be widely applied to various foods and drinks using oils and fats. Especially, it is suitable as fats and oils for cooking by heating, especially fried foods such as fried food and tempura, fried foods and fats for cooking by heating, and further by oils and fats for cooking at high temperatures of 160 ° C. or higher and further 170 ° C. or higher.
  • the present invention further discloses the following oil composition or method with respect to the above-described embodiment.
  • ⁇ 1> The following components (A) and (B): (A) Diacylglycerol 20% by mass or more, (B) One or more components selected from alkali metals and alkaline earth metals. An oil and fat composition containing 0.1 ppm or more.
  • the content of diacylglycerol is preferably 25% by mass or more, more preferably 30% by mass or more, still more preferably 50% by mass or more, still more preferably 60% by mass or more, and further preferably 80% by mass or more. In addition, it is preferably 99.5% by mass or less, more preferably 98% by mass or less, further preferably 95% by mass or less, still more preferably 90% by mass or less, and preferably 20 to 99.5% by mass,
  • the oil and fat composition according to ⁇ 1> more preferably 25 to 98% by mass, still more preferably 30 to 95% by mass, still more preferably 60 to 90% by mass, and still more preferably 80 to 90% by mass.
  • the content of unsaturated fatty acid in the fatty acid constituting diacylglycerol is preferably 80% by mass or more, more preferably 85% by mass or more, still more preferably 90% by mass or more, and preferably 100% by mass. % Or less, more preferably 99% by mass or less, still more preferably 98% by mass or less, preferably 80 to 100% by mass, more preferably 85 to 99% by mass, and still more preferably 90 to 98% by mass.
  • ⁇ 4> The fat composition according to ⁇ 3>, wherein the unsaturated fatty acid preferably has 14 to 24 carbon atoms, more preferably 16 to 22 carbon atoms.
  • the content of saturated fatty acid in the fatty acid constituting diacylglycerol is preferably 1% by mass or more, more preferably 2% by mass or more, and preferably 20% by mass or less, more preferably 15% by mass.
  • the fat composition according to ⁇ 5>, wherein the saturated fatty acid preferably has 14 to 24 carbon atoms, more preferably 16 to 22 carbon atoms.
  • the content of the trans unsaturated fatty acid in the fatty acid constituting the diacylglycerol is preferably 0 to 5% by mass, more preferably 0.01 to 3.5% by mass, and still more preferably 0.01 to 3%.
  • the oil / fat composition according to any one of ⁇ 1> to ⁇ 6>, wherein the oil / fat composition is mass%.
  • the content of ⁇ 8> fat is preferably 85% by mass or more, more preferably 90% by mass or more, still more preferably 95% by mass or more, still more preferably 98% by mass or more, and preferably 99.99% by mass.
  • the oil and fat in the oil and fat composition preferably has undergone a purification step, more preferably any one or more steps selected from a degumming step, a top cut distillation step, an acid treatment step, a decolorization step, a water washing step and a deodorization step.
  • Component (B) is preferably one or more components selected from sodium, potassium, calcium and magnesium, more preferably one or more components selected from sodium and potassium ⁇ 1> to ⁇ 9>
  • the supply source of ⁇ 11> component (B) is preferably an alkali metal or alkaline earth metal hydroxide, carbonate, sulfate or a fatty acid salt having 12 to 22 carbon atoms, more preferably an alkali metal or alkali An earth metal hydroxide, carbonate or a fatty acid salt having 12 to 22 carbon atoms, more preferably an alkali metal carbonate, more preferably sodium bicarbonate, sodium carbonate, potassium carbonate or potassium bicarbonate.
  • ⁇ 12> The content of one or more components selected from alkali metals and alkaline earth metals is 0.1 ppm or more, preferably 0.2 ppm or more, more preferably 0.5 ppm or more, and even more preferably. Is 1 ppm or more, more preferably 1.4 ppm or more, preferably 50 ppm or less, more preferably 20 ppm or less, still more preferably 10 ppm or less, still more preferably 5 ppm or less, and further preferably 3 ppm or less.
  • an antioxidant is preferably contained in an amount of 0.01 to 2% by mass, more preferably 0.01 to 1% by mass, and still more preferably 0.01 to 0.5% by mass.
  • the oil-and-fat composition of any one of. ⁇ 14> The oil and fat composition according to any one of ⁇ 1> to ⁇ 13>, wherein the content of 3-MCPDE is preferably 1 ppm or less, more preferably 0.5 ppm or less.
  • the content of 3-MCPDE measured after the high temperature cooking model test is preferably 1 ppm or less, more preferably 0.8 ppm or less, still more preferably 0.5 ppm or less, and further preferably 0.3 ppm or less. 1.
  • the oil / fat composition according to any one of ⁇ 1> to ⁇ 15> which is preferably a cooking oil / fat, more preferably 160 ° C or higher, and still more preferably 170 ° C or higher.
  • An oil or fat composition containing 20% by mass or more of diacylglycerol contains 3 ppm of one or more components selected from (B) alkali metal and alkaline earth metal in the oil and fat composition. -A method for inhibiting the formation of monochloropropanediol fatty acid esters.
  • a refined fat a containing a high amount of diacylglycerol (DAG) was produced by the following steps. 455 parts by mass of soy fatty acid wintered to reduce saturated fatty acid, 195 parts by mass of rapeseed fatty acid and 107 parts by mass of glycerin were prepared as a commercially available lipase formulation (Lipozyme RM IM, Novozymes Japan) was used as a catalyst, and the esterification reaction was carried out for 5 hours under the conditions of 0.07 hPa and 40 ° C. Subsequently, the lipase preparation was filtered and subjected to molecular distillation at 235 ° C.
  • DAG diacylglycerol
  • Examples 1 to 12 and Comparative Examples 1 to 6 Preparation of oil and fat composition
  • the raw material fats and oils were blended with an alkali salt as an aqueous solution so as to have the ratio shown in Table 2, and dehydrated by heating at 120 ° C. for 0.5 hours to prepare fats and oils compositions.
  • the content of diacylglycerol and the content of alkali metal or alkaline earth metal in each oil and fat composition (100% by mass in total) are as shown in Table 2.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Edible Oils And Fats (AREA)

Abstract

L'invention porte sur une composition de graisse ou d'huile qui est supprimée dans la formation de 3-MCPDE lorsqu'elle est chauffée à des températures élevées en présence d'eau et de sel ordinaire. Cette composition de graisse ou d'huile contient les composants suivants (A) et (B). (A) 20 % en masse ou plus d'un diacylglycérol (B) 0,1 ppm ou plus d'un ou plusieurs composants qui sont choisis parmi les métaux alcalins et les métaux alcalino-terreux
PCT/JP2015/052619 2014-01-31 2015-01-30 Composition de graisse ou d'huile Ceased WO2015115584A1 (fr)

Applications Claiming Priority (2)

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JP2014-017290 2014-01-31
JP2014017290A JP2015142529A (ja) 2014-01-31 2014-01-31 油脂組成物

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WO2015115584A1 true WO2015115584A1 (fr) 2015-08-06

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Publication number Priority date Publication date Assignee Title
JP6518165B2 (ja) * 2015-08-03 2019-05-22 日清オイリオグループ株式会社 加熱調理用油脂組成物およびその製造方法、ならびに加熱調理用油脂の加熱による劣化を抑制する方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011055732A1 (fr) * 2009-11-06 2011-05-12 不二製油株式会社 Procédé de réduction de chloropropanols et de substances formant du chloropropanol dans une huile ou matière grasse glycéridique
WO2011074575A1 (fr) * 2009-12-15 2011-06-23 花王株式会社 Composition à base d'huile ou de graisse
WO2011122184A1 (fr) * 2010-03-31 2011-10-06 花王株式会社 Composition à base d'huile et de graisse
WO2012169718A1 (fr) * 2011-06-09 2012-12-13 Cj Cheiljedang Corp. Procédé de traitement pour une huile comestible à teneur réduite en substances formant du 3-chloro-1,2-propanediol et produit préparé par ce procédé
WO2012173281A1 (fr) * 2011-06-15 2012-12-20 Kao Corporation Procédé de fabrication de graisses et huiles raffinées

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011055732A1 (fr) * 2009-11-06 2011-05-12 不二製油株式会社 Procédé de réduction de chloropropanols et de substances formant du chloropropanol dans une huile ou matière grasse glycéridique
WO2011074575A1 (fr) * 2009-12-15 2011-06-23 花王株式会社 Composition à base d'huile ou de graisse
WO2011122184A1 (fr) * 2010-03-31 2011-10-06 花王株式会社 Composition à base d'huile et de graisse
WO2012169718A1 (fr) * 2011-06-09 2012-12-13 Cj Cheiljedang Corp. Procédé de traitement pour une huile comestible à teneur réduite en substances formant du 3-chloro-1,2-propanediol et produit préparé par ce procédé
WO2012173281A1 (fr) * 2011-06-15 2012-12-20 Kao Corporation Procédé de fabrication de graisses et huiles raffinées

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
FREUDENSTEIN A. ET AL.: "Influence of precursors on the formation of 3-MCPD and glycidyl esters in a model oil under simulated deodorization conditions", EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY, vol. 115, no. 3, March 2013 (2013-03-01), pages 286 - 294, XP055162454 *

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