WO2006088188A1 - Composition d’acides gras d’huile - Google Patents

Composition d’acides gras d’huile Download PDF

Info

Publication number
WO2006088188A1
WO2006088188A1 PCT/JP2006/302976 JP2006302976W WO2006088188A1 WO 2006088188 A1 WO2006088188 A1 WO 2006088188A1 JP 2006302976 W JP2006302976 W JP 2006302976W WO 2006088188 A1 WO2006088188 A1 WO 2006088188A1
Authority
WO
WIPO (PCT)
Prior art keywords
oil
fatty acid
fat
content
acid
Prior art date
Application number
PCT/JP2006/302976
Other languages
English (en)
Japanese (ja)
Inventor
Naoki Hosoya
Shin Koike
Takatoshi Murase
Original Assignee
Kao Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Kao Corporation filed Critical Kao Corporation
Publication of WO2006088188A1 publication Critical patent/WO2006088188A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/158—Fatty acids; Fats; Products containing oils or fats
    • 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
    • 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
    • A23D9/013—Other fatty acid esters, e.g. phosphatides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A23L33/12—Fatty acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/20—Reducing nutritive value; Dietetic products with reduced nutritive value
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
    • C11B5/0035—Phenols; Their halogenated and aminated derivates, their salts, their esters with carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/02—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with glycerol
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • the present invention relates to an oil and fat composition having a high diacylglycerol content containing conjugated linoleic acid.
  • Patent Documents 7 to 8 fats and oils containing diacylglycerol having a high content of specific fatty acids such as ⁇ 3 fatty acids and linoleic acid are known (Patent Documents 9 to 11).
  • Patent Document 12 an oil and fat composition combining diacylglycerol and plant sterol has been found to have an effect of improving blood cholesterol level.
  • Conjugated linoleic acid is a free fatty acid, so it was not suitable for ingestion or use in foods due to the unique taste of fatty acids. Therefore, attempts have been made to expand the application range of conjugated linoleic acid by making conjugated linoleic acid into an ester form (Patent Documents 13 to 18 and Non-Patent Document 2).
  • Patent Document 1 International Publication No. 96 ⁇ 06605 Pamphlet
  • Patent Document 2 Pamphlet of International Publication No. 97 ⁇ 46230
  • Patent Document 3 Japanese Patent Laid-Open No. 2003-171272
  • Patent Document 4 Pamphlet of International Publication No. 02Z009691
  • Patent Document 5 Pamphlet of International Publication No. 02 ⁇ 009693
  • Patent Document 6 International Publication No.OOZ21379 Pamphlet
  • Patent Document 7 Japanese Patent Laid-Open No. 4-300826
  • Patent Document 8 JP-A-10-176181
  • Patent Document 9 Pamphlet of International Publication No. 01Z109899
  • Patent Document 10 International Publication No. 02Z11552 Pamphlet
  • Patent Document 11 European Publication No. 0679712
  • Patent Document 12 Pamphlet of International Publication No. 99Z48378
  • Patent Document 13 International Publication No. 00Z64854 Pamphlet
  • Patent Document 14 International Publication No.04Z96748 Pamphlet
  • Patent Document 15 Japanese Patent Application Laid-Open No. 2003-113396
  • Patent Document 16 US Patent No. 6432453
  • Patent Document 17 US Patent No. 6608222
  • Patent Document 18 European Patent Publication No. 1097708
  • Non-Patent Document 1 "Lipids”, 1997, 32 ⁇ , p. 853-858
  • Non-Patent Document 2 “Biotechnology Letters”, 1998, 20 ⁇ , 6, p. 617-621 Disclosure of the Invention
  • the present invention provides the following components (A) and (B):
  • the oil-and-fat composition containing this is provided.
  • an object of the present invention is to provide an oil composition with a high diacylglycerol content containing conjugated linoleic acid having a remarkable anti-obesity effect and excellent stability, and further, the storage stability of the oil composition. Is to remarkably improve.
  • the present inventors have determined that the diacylglycerol content of the oil and fat composition, It has been found that the above problems can be solved by adjusting the conjugated linoleic acid content, tocopherol content, etc. in the lyserol to specific ranges. Furthermore, they have found that the obtained oil and fat composition has an anti-feeding effect, leading to the present invention.
  • the oil and fat composition of the present invention contains the oil and fat of component (A) as an essential component.
  • the fat (A) contains 15% by weight (hereinafter simply referred to as “%”) of diacylglycerol (DAG), but preferably 15 to 95%, more preferably 20 to 95%. Further, 35 to 95%, particularly 60 to 90%, especially 70 to 85%, is preferable in terms of physiological effects, industrial productivity of fats and oils, appearance, and food applications.
  • diacylglycerol contained in the oil and fat (A) is a force in which 80 to LOO% of the constituent fatty acid is an unsaturated fatty acid, preferably 85 to LOO%. Further, 90 to 98%, particularly 93 to 98% is preferable from the viewpoint of appearance, physiological effect, and industrial productivity of fats and oils.
  • the carbon number of the unsaturated fatty acid is preferably 14 to 24, and more preferably 16 to 22.
  • the content of conjugated linoleic acid (CLA) is preferably 2 to 85%. 5-80%, 15-75%, especially 35-70%, especially 40-55% S body fat loss, suppression of feeding, storage, appearance, fatty acid intake balance Is preferable.
  • Examples of the conjugated linoleic acid include 9,11-octadecadienoic acid, 10,12-octadecadienoic acid, their positions and geometric isomers, and mixtures thereof. Specific examples include cis-9, trans-11-octadecadienoic acid, trans-9, cis-11-octadecadienoic acid, trans-10, cis-12-octadecadienoic acid, and the like.
  • Conjugated linoleic acid is produced by, for example, using linoleic acid or oils with high linoleic acid content as raw materials, biochemical conjugation using ruminant or microbial enzymes, and chemical treatment by heating under alkaline conditions. Conjugation and the like.
  • the content of oleic acid is 1 to 65% among the fatty acids constituting diacylglycerol contained in the fat (A). Power of -50%, especially 3-30%, especially 4-15% It is preferable in terms of storage stability, appearance, and fatty acid intake balance. Furthermore, in terms of appearance and physiological effects, dioleyl glycerin in diacylglycerol The roll content is preferably less than 45%, especially 0-40%! /.
  • the content of the ⁇ 3-unsaturated fatty acid is less than 15%. % Is preferable in terms of stability, appearance, and fatty acid intake balance.
  • the ⁇ 3 unsaturated fatty acid include a linolenic acid, icosapentaenoic acid, docosahexaenoic acid, and the like.
  • the content of saturated fatty acids is less than 20%, preferably 0 to 10%, more preferably 0 to 7%, especially 2 to 7%, particularly 2 to 6%, is preferable in view of appearance, physiological effect, and oil and fat industrial productivity.
  • Saturated fatty acids are more preferably palmitic acid and stearic acid, preferably those having 14 to 24 carbon atoms, particularly 16 to 22 carbon atoms.
  • the content of trans-unsaturated fatty acids other than conjugated linoleic acid among the fatty acids constituting diacylglycerol contained in the fat (A) is 0 to 3.5%.
  • 0.1 to 3% is preferred in terms of flavor, physiological effect, appearance, preservability, and industrial productivity of fats and oils.
  • the content of fatty acids having 12 or less carbon atoms is 5% or less in terms of flavor. It is preferably 0 to 2%, more preferably 0 to 1%, particularly preferably substantially free.
  • the remaining constituent fatty acids preferably have 14 to 24 carbon atoms, especially 16 to 22 carbon atoms.
  • the ratio of 1,3 diacylglycerol in diacylglycerol contained in the fat (A) is preferably 50% or more, further 52 to 100%, and further 5 It is preferably 4 to 90%, particularly 56 to 80% from the viewpoints of physiological effects, storage stability, industrial productivity of fats and oils, and flavor.
  • the fat (A) is triacylglycerol (TAG) 4.9-84.
  • Power to contain 9% S preferably 4.9 to 64.9%, further 6.9 to 39.9%, especially 6.9 to 29.9%, especially 9.8 to 19.8%
  • S preferably 4.9 to 64.9%
  • further 6.9 to 39.9% especially 6.9 to 29.9%, especially 9.8 to 19.8%
  • the constituent fatty acid of triacylglycerol contained in the fat (A) Among them, the content of conjugated linoleic acid is preferably 50% or less, more preferably 1 to 35%, especially 2 to 20%, and especially 5 to 15%. It is preferable in terms of productivity.
  • the content of conjugated linoleic acid in the fatty acid constituting diacylglycerol contained in the fat (A) and the synergistic linole in the fatty acid constituting triacylglycerol is preferably 1 to 10, more preferably 2 to 9, especially 3 to 8, and especially 4 to 7 to improve storage stability and physiological effects. This is preferable.
  • the content of oleic acid in the constituent fatty acid of triacylglycerol contained in the fat (A) is 15 to 70%, more preferably 20 to 65%, particularly 30 to 60%, especially 45 to 55%, is preferable from the viewpoint of storage stability, physiological effect, and industrial productivity of fats and oils.
  • the constituent fatty acid of triacylglycerol contained in the fat (A) is preferably 80 to 100% of unsaturated fatty acid, more preferably 80 to 100%, and further 90 to 100%.
  • 93 to 98%, especially 94 to 98% is preferable from the viewpoints of physiological effects and industrial productivity of fats and oils.
  • the number of carbon atoms of the unsaturated fatty acid is preferably 10 to 24 and more preferably 16 to 22 in view of physiological effects and industrial productivity of fats and oils.
  • the oil and fat (A) contains 5% or less of monoacylglycerol (MAG), preferably 0.1 to 5%, and more preferably 0.1 to 2%, 0.1 to 1.5%, especially 0.1 to 1.3%, especially 0.2 to 1% for flavor, appearance, fuming, oil and fat industrial productivity, foods, etc. Preferred in terms of application.
  • MAG monoacylglycerol
  • the constituent fatty acid of monoacylglycerol contained in the fat and oil (A) is the same constituent fatty acid as diacylglycerol. From the viewpoint of sex.
  • the content of free fatty acid and Z or salt (FFA) contained in the oil and fat (A) is 5% or less, but preferably 0 to 3.5%. Further, 0 to 2%, particularly 0.01 to 1%, especially 0.05 to 0.5% is preferred in terms of flavor, smoke generation, work comfort during cooking, and industrial productivity of fats and oils. ,.
  • the content of unsaturated fatty acid is preferably 80 to 100% of all fatty acids constituting the fat (A), and further 85 to 100%, particularly 90 to 100%. %, Especially 93 to 98%, is preferable from the viewpoint of physiological effects and industrial productivity of fats and oils.
  • the content of fatty acids having 4 or more carbon-carbon double bonds is the oxidation stability, work comfort during cooking, physiological In terms of effect, coloring, flavor, etc., it is preferably 0 to 40%, arabic 0 to 20%, arabic 0 to 10%, in particular 0 to 1%, and substantially free! Is the most preferred.
  • the content of trans-unsaturated fatty acid is 0 to 4% of the total fatty acids constituting the fat (A). Further 0.1 to 3.5% From the viewpoint of flavor, physiological effect, appearance, and industrial productivity of fats and oils.
  • the content of trans-unsaturated fatty acid is a value measured by the AOCS method (American Oi 1 Chem. Soc. Official Method: Celf-96, 2002).
  • the content of conjugated linoleic acid is preferably 2 to 85% of the total fatty acids constituting the fat (A).
  • S is preferable, and further 5 to 75%, particularly 15 to 50%.
  • % is preferred in terms of physiological effects, storage stability, application to foods, etc., and industrial productivity of fats and oils.
  • the content of oleic acid is preferably 20 to 65% of the total fatty acids constituting the fat (A).
  • S is preferable, and further 25 to 60%, particularly 30 to 55%, In particular, it is preferably 35 to 50% from the viewpoints of storage stability, application to foods and the like, and industrial productivity of fats and oils.
  • the content of linolenic acid is 15% or less of the total fatty acids constituting the fat (A). Further 0.1 to 12%, particularly 1 to 10% Particularly, 3 to 8% is preferable in terms of storage stability, application to foods, industrial productivity of fats and oils, and physiological effects.
  • the raw material for the fat (A) may be either vegetable or animal fat.
  • specific examples of the raw material include rapeseed oil, sunflower oil, corn oil, soybean oil, rice oil, safflower oil, cottonseed oil, and beef tallow.
  • the fatty acid composition is adjusted by separating and mixing these fats and oils, hydrogenation, transesterification, etc.
  • the power that can be used as a raw material is preferably not hydrogenated, because it reduces the trans acid content in the total fatty acids that make up the fat composition.
  • fats and oils used as the raw material for the fats and oils (A) deodorized oils and undeodorized fats and oils that have not been deodorized in advance can be used.
  • the use of undeodorized fat or oil as part or all of the raw material reduces trans-unsaturated fatty acids other than conjugated linoleic acid, and the raw material fat or oil-derived plant sterol, plant sterol fatty acid ester, tocopherol , Because it can survive.
  • the fat (A) includes the conjugated linoleic acid, the esterification reaction between the fatty acid derived from fat and glycerin and the ester exchange reaction between the fat and oil containing conjugated linoleic acid and glycerin, and the like.
  • Excess monoacyl derrol produced by the reaction can be removed by molecular distillation or chromatography.
  • These reactions can also be carried out by chemical reactions using an alkali catalyst or the like. However, it is desirable to carry out the reaction under mild conditions enzymatically using a 1,3-position selective lipase or the like in terms of flavor and the like. Excellent and preferred.
  • the oil and fat composition of the present invention needs to contain the component Tocopherol.
  • the content of tocopherol (B) is 0.001 to 2 parts per 100 parts by weight of fat (A) (hereinafter simply referred to as “parts”) in terms of flavor, oxidation stability, coloring, etc.
  • a force of 0.005-1. 5 parts of force S is preferred, more preferably 0.01 to 1 ⁇ ⁇ , especially 0.01 to 0.5 ⁇ ⁇ , especially 0.02 to 0.2 ⁇ . .
  • ⁇ , ⁇ , ⁇ , ⁇ tocopherol or a mixture thereof can be used as the tocopherol (B).
  • ⁇ -tocopherol from the viewpoint of acid / acid stability.
  • the use of ⁇ -tocopherol is a flavor. It is preferable to prevent deterioration and off-flavor generation.
  • tocopherols include, for example, imix D, imix 80 (Eisai ( Co., Ltd.), MDE-6000 (Yatsushiro Co., Ltd.), E Oil-400 (RIKEN Vitamin Co., Ltd.) and the like.
  • the oil and fat composition may be supplemented with an antioxidant in addition to the tocopherol (B).
  • Any antioxidant can be used as long as it is usually used in foods. Examples include butylhydroxytoluene (BHT), butylhydroxyl-sol (BHA), tertiary butylhydroquinone (TBHQ), catechin, vitamin C or its derivatives, phospholipids, rosemary extract, etc. Of these, it is preferable to use vitamin C or a derivative thereof, catechin, or rosemary extract, and it is particularly preferable to use a mixture of one or more of these.
  • vitamin C or a derivative thereof a higher fatty acid ester of vitamin C that is soluble in fats and oils (A), for example, a fatty acid ester having an acyl group having 12 to 22 carbon atoms is more preferable.
  • Ascorbic acid palmitate, L-ascorbic acid stearate is particularly preferred, and L-ascorbyl palmitate is most preferred!
  • the content of vitamin C or a derivative thereof is 0.0004 to 0.1 part ascorbic acid with respect to 100 parts of fat (A). 08 ⁇ ⁇ Especially from 0.008 to 0.06 ⁇
  • the oil and fat composition when the oil and fat composition is mixed with water or used in foods containing water, and when stored for a long time or in a light place, as an antioxidant. It is also preferred that the L-ascorbic acid fatty acid ester is not substantially contained to prevent deterioration of flavor and occurrence of off-flavors.
  • the oil and fat composition preferably contains the component (C) plant sterols.
  • the plant sterols in the present specification also include those containing derivatives such as ester forms in which the hydroxyl group is not in a ester bond with a fatty acid but in a free state (free form).
  • the content of the plant sterols (C) is preferably a force S of 0.05 to 30%, more preferably 0.1 to 15%, particularly 0 to 100 parts of the fat (A). 3-8 parts, especially 0.5-4. 7 parts are preferred from the viewpoint of cholesterol lowering effect, flavor, appearance, and industrial productivity of fats and oils.
  • the plant sterols (C) also include plant stanols.
  • Plant sterols include, for example, brassicasterol, isofucosterol, stigmasterol, 7-stigmastenol, -sitosterol, ⁇ -sitosterol, campesterol, brassicastanol, isofcostanol, stigmasteranol, 7-stigma
  • Examples include free forms such as stanol, ⁇ -sitostanol, 13-sitostanol, campestanol, cycloartenol, cholesterol, and avenasterol, and ester forms such as fatty acid esters, ferulic acid esters, and cinnamic acid esters.
  • brass castellonoles, campesteronoles, stigmastellonoles, ⁇ -sitosterol strength are preferred in terms of industrial productivity and flavor.
  • the total content of brassicasterol, campesterol, stigmasterol, and / 3-sitosterol in the plant sterols (C) is preferably 90% or more.
  • LOO%, particularly 94-99% is preferable in terms of flavor, appearance, industrial production of fats and oils, crystal precipitation, storage at low temperature, and physiological effects.
  • the content of brassicasterol in the plant sterols (C) is preferably 0.5 to 8%, more preferably 1 to 7.5%, particularly 3 to 7%. In view of appearance, industrial productivity of fats and oils, crystal precipitation, storage at low temperature, and physiological effects.
  • the content of campesterol in the plant sterols (C) is preferably 10 to 40%, and more preferably 15 to 35%, especially 22 to 30%. It is preferable in terms of productivity, crystal precipitation, storage at low temperature, and physiological effects.
  • the content of stigmasterol in the plant sterols (C) is preferably 3 to 30%, and more preferably 5 to 25%, especially 7 to 15%. From the viewpoints of productivity, crystal precipitation, storage at low temperature, and physiological effects.
  • the content of 13-sitosterol in the plant sterols (C) is preferably 30 to 60%, and more preferably 35 to 58%, particularly 40 to 56%. From the viewpoints of productivity, crystal precipitation, storage at low temperature, and physiological effects.
  • the content of cholesterol in the plant sterols (C) is preferably 1% or less, more preferably 0.01 to 0.8%, particularly 0.1 to 0.7%, and particularly 0. Power of 2 to 0.6% is preferred in terms of blood cholesterol lowering, industrial productivity of fats and oils.
  • the content of unsaturated fatty acids among the constituent fatty acids is 80% or more.
  • S preferably 85 to: LOO%, especially 86 to 98%, especially 88 to 93% S, flavor, appearance, storage at low temperature, crystal precipitation, industrial production of fats and oils, oxidation stability From the viewpoint of the physiological effect.
  • the oil and fat composition preferably further contains a crystallization inhibitor (D).
  • the crystallization inhibitor include polyol fatty acid esters such as polyglycerin condensed ricinoleic acid ester, polyglycerin fatty acid ester, sucrose fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, and propylene glycol fatty acid ester.
  • Polyglycerin fatty acid ester, sucrose fatty acid ester and sorbitan fatty acid ester are preferred, and polyglycerin fatty acid ester is particularly preferred.
  • the HLB value of the polyol fatty acid ester is 4 or less, particularly 0.1 to 3.5 calculated by Griffin's formula (J. Soc. Cosmet. Chem., 1, 311 (1949)). It is preferable.
  • the content of unsaturated fatty acid among the fatty acids constituting the polyglycerin fatty acid ester is 50 to 95. Further, it is preferably 51 to 80%, and more preferably 52 to 60%, from the viewpoints of crystallization suppression, solubility in fats and oils, and acid / acid stability. Further, from the viewpoint of facilitating dissolution of the polyglycerin fatty acid ester in fats and oils, the content of unsaturated fatty acid is preferably 50% or more.
  • the content of unsaturated fatty acid is preferably 95% or less from the viewpoint of suppressing crystallization of fats and oils.
  • the unsaturated fatty acid constituting the polyglycerin fatty acid ester preferably has 10 to 24 carbon atoms, more preferably 16 to 22 carbon atoms. Specific examples include palmitoleic acid, oleic acid, petrothelic acid, elaidic acid, linoleic acid, linolenic acid, gatrenic acid, erucic acid, and the like, with oleic acid, linoleic acid and gatrenic acid being preferred.
  • the content of oleic acid is preferably 80% or more, more preferably 90-99.8%, crystal suppression, oil solubility, cost, It is preferable in terms of oxidation stability and flavor.
  • the content of linoleic acid in the unsaturated fatty acids constituting the polyglycerol fatty acid ester is 10 It is preferably 0.1 to 5%, and more preferably 0.1 to 5% in terms of crystallization suppression, solubility in fats and oils, cost, oxidation stability, and flavor.
  • the content of gatrenic acid is preferably 10% or less, and particularly 0.1 to 5% is crystal suppression, solubility in fats and oils, cost, It is preferable in terms of oxidation stability and flavor.
  • the content of the saturated fatty acid among the fatty acids constituting the polyglycerol fatty acid ester is 5 to 50. Further, it is preferably 20% to 49%, and particularly preferably 40% to 48%, from the viewpoints of crystal suppression, solubility in fats and oils, and acidity stability.
  • the saturated fatty acid preferably has 10 to 24 carbon atoms, more preferably 12 to 22 carbon atoms.
  • the saturated fatty acids constituting the polyglycerin fatty acid ester include lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, and behenic acid, and myristic acid, palmitic acid, and stearic acid are preferable.
  • the content of palmitic acid is preferably 80% or more, particularly 90 to 99.8%, which suppresses crystallization, solubility in fats and oils, cost, It is preferable in terms of oxidation stability and flavor.
  • the content of myristic acid in the constituent saturated fatty acid of polyglycerin fatty acid ester is preferably 10% or less, especially 0.1-5%, crystal suppression, solubility in fats and oils, cost, oxidation stability It is preferable in terms of properties and flavor.
  • the content of stearic acid in the saturated fatty acid of the polyglycerin fatty acid ester is preferably 10% or less, and particularly 0.1 to 5% is crystal suppression, solubility in fats and oils, cost, oxidation stability It is preferable in terms of sex and flavor.
  • the content of the crystallization inhibitor (D) is from 0.01 to 2 parts, more preferably from 0.02 to 0.5 parts, particularly from 0.05 to 100 parts of the fat (A). It is preferable that it is -0.2 part from the point of the solubility to fats and oils, cost, flavor, and crystal
  • the oil and fat composition preferably further contains an organic carboxylic acid having 2 to 8 carbon atoms and Z or a salt thereof.
  • organic carboxylic acid having 2 to 8 carbon atoms is
  • the oil and fat composition is prepared by selecting the raw oil and fat and the production method so that the component (A) of the composition has a predetermined ratio, and adding the component (B) thereto, If necessary, component (C), component (D), antioxidant, organic carboxylic acid and Z or a salt thereof can be added, heated appropriately and carried in a frame.
  • the oil and fat composition of the present invention is excellent in terms of storage stability, flavor, texture, appearance, work comfort during cooking, physiological effects, and the like, and can be applied to various foods.
  • oils and fats that contain the oil and fat composition as part of the food.
  • powerful processed oils and fats include health foods, functional foods, foods for specified health use, etc. that promote specific health by promoting specific functions.
  • Specific products include bakery foods such as bread, cakes, biscuits, pies, pizza crusts, bakery mixes, oil-in-water emulsions such as soups, sauces, dressings, mayonnaise, coffee whiteners, ice creams, whipped creams, Water-in-oil emulsions such as margarine, spreads and butter cream, snacks such as potato chips, confectionery such as chocolate, caramel, candy and dessert, processed foods such as ham, sausage and hamburger, milk, cheese and yogurt And dairy products such as dough, enrober fats and oils, filling fats and oils, koji, frozen foods, retort foods, beverages and roux.
  • bakery foods such as bread, cakes, biscuits, pies, pizza crusts
  • bakery mixes oil-in-water emulsions such as soups, sauces, dressings, mayonnaise, coffee whiteners, ice creams, whipped creams, Water-in-oil emulsions such as margarine, spreads and butter cream
  • snacks such as
  • oil and fat composition of the present invention In addition to the oil and fat composition of the present invention, food materials generally used can be added and produced according to the type of processed oil and fat food.
  • the blending amount of the oil and fat composition of the present invention in food varies depending on the type of food, but is generally 0.1 to 100%, particularly preferably 1 to 80%.
  • the oil and fat composition of the present invention can be used as a food ingredient such as cooking oil used for fried foods or fried foods.
  • cooking oil used for fried foods or fried foods In particular, croquettes, tempura, tonkatsu, fried fish, fried fish, spring rolls, etc. Suitable for cooking instant rice cakes.
  • the weight ratio of the oil and fat derived from the food material and the oil and fat composition of the present invention is as follows. Fats and oils derived from food materials Z
  • the oil and fat composition of the present invention is preferably 95Z5 to 1Z99, more preferably 95/5 to 5/95, particularly 85/15 to 5/95, especially 40/60 to 5/95. Power to be S preferable.
  • the oil and fat composition of the present invention can be used for an oil-in-water emulsion.
  • the weight ratio between the oil phase and the aqueous phase is preferably 1Z99 to 90Z10 for the oil phase Z and the water phase, more preferably 10 to 90 to 20, more preferably 30 to 70 to 75.
  • emulsifiers include egg protein, soybean protein, milk protein, proteins separated from these proteins, various proteins such as (partial) degradation products of these proteins, sucrose fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid.
  • examples include esters, daridine fatty acid monoesters, polyglycerin fatty acid esters, polyglycerin condensed ricinoleic acid esters, glycerin organic acid fatty acid esters, propylene glycol fatty acid esters, lecithin, and enzymatic degradation products thereof.
  • the oil or fat composition of the present invention is used in an oil-in-water emulsion, it is preferable to contain 0 to 5%, particularly 0.01 to 2% of a stabilizer.
  • Stabilizers include thickening polysaccharides such as xanthan gum, dielan gum, guar gum, carrageenan, pectin, tragacanth gum, konjac mannan, starch, and the like.
  • flavoring agents such as salt, sugar, vinegar, fruit juice, seasoning, flavoring agents such as snow and flavor, coloring agents, preservatives, antioxidants, etc. can be used as appropriate. .
  • oil-in-water type oil-containing foods such as mayonnaise, dressing, coffee whitener, ice cream, whipped cream, beverages, etc. can be produced by conventional methods.
  • the oil and fat composition of the present invention can be used in a water-in-oil emulsion.
  • the weight ratio of the water phase to the oil phase is preferably 85 to 15 to 1 to 99 for the water phase to the oil phase, more preferably 80 to 20: LOZ 90, and particularly preferably 70 to 30 to 35 to 65.
  • emulsifiers include egg protein, soybean protein, milk protein, proteins separated from these proteins, various proteins such as (partial) degradation products of these proteins, sucrose fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid. Ester, Daricelin fatty acid monoester, Polyglycerin fatty acid ester, Polyglycerin condensed ricinoleic acid ester, Glycerin organic acid fatty acid ester, Propylene glycol fatty acid ester Tellurium, lecithin or enzymatic degradation products thereof.
  • flavors such as salt, sugar, vinegar, fruit juice, seasonings, flavorings such as spices and flavors, stabilizers such as thickening polysaccharides and starches, coloring agents, preservatives, etc.
  • stabilizers such as thickening polysaccharides and starches, coloring agents, preservatives, etc.
  • Antioxidants and the like can be used.
  • water-in-oil type oil-containing foods such as margarine, spreads, butter cream and the like can be prepared by a conventional method.
  • the oil and fat composition of the present invention has a body fat accumulation inhibitory action, a visceral fat accumulation inhibitory action, a body weight gain inhibitory action, a serum triglyceride increase inhibitory action, an insulin resistance improving action, a blood sugar level rise inhibitory action, a HOMA index Has excellent physiological activities such as an improving action and an antifeedant action. Since it has excellent properties, the oil and fat composition of the present invention can be used for pharmaceuticals in the form of capsules, tablets, condyles, powders, liquids, gels and the like.
  • excipients in addition to the oil and fat composition described above, excipients, disintegrants, binders, lubricants, surfactants, alcohols, water, water-soluble polymers, sweeteners commonly used depending on the form. It can be produced by adding a flavoring agent, an acidulant and the like.
  • the amount of the oil / fat composition of the present invention to be added to a pharmaceutical product varies depending on the use and form of the pharmaceutical product. preferable.
  • the dosage is preferably 0.2 to 50 g per day as an oil or fat composition, divided into 1 to several times.
  • the administration period is preferably 1 month or more, 2 months or more, and 3 to 12 months.
  • the oil and fat composition of the present invention can be used for feed.
  • feed examples include livestock feed used for cattle, pigs, chickens, sheep, horses, goats, etc., small animal feed used for rabbits, rats, mice, etc., and fishery products used for eels, Thailand, hamachi, shrimp, etc.
  • the blending amount of the oil and fat composition of the present invention into the feed is generally 1 to 30%, particularly preferably 1 to 20%, which varies depending on the use of the feed. The combination is performed by replacing all or part of the fat and oil in the feed with the fat and oil composition of the present invention.
  • feed is mixed with feed ingredients generally used such as meat, protein, cereals, bran, potatoes, sugars, vegetables, vitamins, minerals, etc., as necessary. Manufactured.
  • meat examples include livestock such as beef, pig, sheep (mutton or lamb), rabbit, kangaroo, Animal meat and its by-products, processed products (rendered products of the above ingredients such as meatballs, meatbone meal, chicken meal), fishery products such as tuna, bonito, horse mackerel, sardines, scallops, sazae, fish meal (fish meal) Can be mentioned.
  • the protein examples include milk proteins such as casein and whey, animal proteins such as egg protein, and plant proteins such as soybean protein.
  • cereals examples include wheat, barley, rye, my mouth, and corn.
  • Examples of the strength include rice bran and bran.
  • potatoes include soybean meal. The total amount of meat, protein, cereals, bran and potatoes in the feed is preferably 5-93.9%.
  • saccharide examples include glucose, oligosaccharide, sugar, molasses, starch, liquid sugar and the like, and preferably 5 to 80% in feed.
  • examples of vegetables include vegetable extracts and the like, and it is preferable to contain 1 to 30% in the feed.
  • vitamins include A, B, B, D, E, niacin, pantothenic acid, carotene and the like.
  • % Content is preferable.
  • minerals include calcium, phosphorus and sodium
  • Potassium, iron, magnesium, zinc and the like, and 0.05 to 10% in feed is preferable.
  • gelling agents, shape-preserving agents, pH adjusters, seasonings, preservatives, nutritional supplements and the like that are generally used in feeds can be contained as necessary.
  • hexane, hexyl acetate (97: 3, VZV), hexane acetate acetyl (9: 1, VZV), hexane acetate (4: 1, VZV), hexane acetate (3: (1, VZV) and hexane-ethyl acetate (2.5: 1, VZV) were eluted in this order to obtain a DG fraction.
  • Oil 100 was obtained by distilling off the solvent with an evaporator, and oil A was obtained by adding 0.02 part of tocopherol (mixed tocopherol MDE-6000, manufactured by Yatsushiro) to 100 parts of the oil obtained.
  • Table 1 shows the glyceride yarn composition and fatty acid composition.
  • fat E was obtained by adding 0.02 parts of Tocopherol (Mixed Tocopherol MDE-6000, manufactured by Yatsushiro) to 100 parts of fat obtained by mixing each fraction.
  • Table 1 shows the glyceride yarn composition and fatty acid composition.
  • Tocopherol (Mixtocopherol MDE-6000, manufactured by Yatsushiro) 0.02 parts, plant sterol fatty acid ester (CardioAid- S, ADM) for 100 parts of fat and oil E mixed with rapeseed oil in a weight ratio of 1: 2 4 parts) was added to obtain fat F.
  • Table 1 shows the glyceride composition and fatty acid composition of fat F.
  • Methyl esterified fatty acid was subjected to analysis by GLC.
  • a storage test was conducted by using the fats and oils A and B by the following method.
  • a glass sample bottle 50 mL was charged with 20 g of oil and fat, sealed with nitrogen, and sealed. This was stored in a freezer at 20 ° C. Five years later, the sample was allowed to stand at room temperature, thawed, opened, and subjected to sensory evaluation of odor and appearance according to the following criteria. The results are shown in Table 2.
  • the gel-like portion occupies the majority and is defective.
  • feed was produced according to a conventional method. Six to seven week old Zucker rats were divided into 4 groups of 6 animals per group. First, the animals were preliminarily raised with feed 1 for 4 days (constant food intake). Each feed was then bred for 9 days. The amount of food intake at this time was measured every day. On the last day of the administration of the feed, dissection was performed, and the liver, perirenal adipose tissue, and adipose testicle adipose tissue were removed and their weights were measured. In addition, the amount of triglyceride in the liver was measured. The results are shown in Table 4.
  • Feed composition (parts by weight) Feed 1 Feed 2 Feed 3 Feed 4 Corn oil 10 10 10 10 Casein 20 20 20 20 Cellulose 4 4 4 4 Mineral mixture 3.5 5 3. 5 3. 5 3. 5 Vitamin mixture 1 1 1 1 Potato starch 61. 5 57. 5 57. 5 57. 5 Oil A 0 4 0 0 Oil C 0 0 4 0 Oil D 0 0 0 4 [Table 4]
  • the amount of triglycerides in the liver, the amount of perirenal adipose tissue, and the amount of adipose tissue around the epididymis may be lower than those of the comparative product (Feed 1, 3, 4). It became clear. In addition, the total amount of food intake was significantly reduced, indicating that it has an anti-feeding effect.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Wood Science & Technology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nutrition Science (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Mycology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Child & Adolescent Psychology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Animal Husbandry (AREA)
  • Zoology (AREA)
  • Emergency Medicine (AREA)
  • Obesity (AREA)
  • Edible Oils And Fats (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Fats And Perfumes (AREA)
  • Fodder In General (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L’invention concerne une composition d’acides gras d’huile comprenant : (A) 100 parties en poids d’acides gras d’huile qui contient 15 % en poids ou plus de diacylglycérol présentant une teneur d’acide gras non saturé, en poids, de 80 % ou plus, une teneur d’acide linoléique conjugué, en poids, comprise entre 2 et 85 % et une teneur d’acide gras non saturé, en poids, ω3 inférieure à 15 % du composant d’acides gras, et qui présente une teneur de monoacylglycérol, en poids, de 5 % ou moins et une teneur d’acide gras libre, en poids, de 5 % ou moins ; et (B) 0,001 à 2 parts, en poids, de tocophérol. La composition assure une fonction contre l’obésité et une stabilité de stockage excellentes.
PCT/JP2006/302976 2005-02-21 2006-02-20 Composition d’acides gras d’huile WO2006088188A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2005-043941 2005-02-21
JP2005043941A JP2008069184A (ja) 2005-02-21 2005-02-21 油脂組成物

Publications (1)

Publication Number Publication Date
WO2006088188A1 true WO2006088188A1 (fr) 2006-08-24

Family

ID=36916584

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2006/302976 WO2006088188A1 (fr) 2005-02-21 2006-02-20 Composition d’acides gras d’huile

Country Status (2)

Country Link
JP (1) JP2008069184A (fr)
WO (1) WO2006088188A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008061577A (ja) * 2006-09-07 2008-03-21 Kao Corp 油脂組成物
WO2008128765A1 (fr) * 2007-04-24 2008-10-30 Lipid Nutrition B.V. Composition de boisson comprenant de l'acide linoléique conjugué
ES2335959A1 (es) * 2008-08-27 2010-04-06 Laboratorios Casen-Fleet, S.L. Composicion alimenticia y uso.
JP2010180195A (ja) * 2008-02-13 2010-08-19 Kao Corp 食後高血糖改善剤
CN101177399B (zh) * 2007-11-23 2011-04-27 东营广元生物工程有限公司 无催化共轭亚油酸甘油酯的制备方法
JP2012501175A (ja) * 2008-08-28 2012-01-19 ネステク ソシエテ アノニム 痩せの表現型に関連する遺伝子発現プロファイルおよびその使用

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5550282B2 (ja) * 2008-08-04 2014-07-16 花王株式会社 ジアシルグリセロール高含有油脂の製造方法
WO2010109737A1 (fr) * 2009-03-27 2010-09-30 日清オイリオグループ株式会社 Huile et matière grasse de cuisson comestibles et leur procédé de préparation
ES2618069T3 (es) * 2010-03-09 2017-06-20 Stepan Specialty Products, Llc Método para tratar un aceite comestible y el aceite obtenido de esta manera
JP5717356B2 (ja) * 2010-05-18 2015-05-13 花王株式会社 ビタミンｂ１含有油脂組成物
JP6166984B2 (ja) * 2012-09-04 2017-07-19 花王株式会社 油脂組成物

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999048378A1 (fr) * 1998-03-24 1999-09-30 Kao Corporation Composition grasse contenant du phytosterol
WO2002017903A1 (fr) * 2000-08-26 2002-03-07 Metagenics, Inc. Composition a base d'acide linoleique conjugue, dotee d'une meilleure stabilite et utile dans les complements dietetiques et l'alimentation

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999048378A1 (fr) * 1998-03-24 1999-09-30 Kao Corporation Composition grasse contenant du phytosterol
WO2002017903A1 (fr) * 2000-08-26 2002-03-07 Metagenics, Inc. Composition a base d'acide linoleique conjugue, dotee d'une meilleure stabilite et utile dans les complements dietetiques et l'alimentation

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
ZHENG ET AL.: "Solvent-Free Enzymatic Synthesis of 1,3-Diconjugated Linoleoyl Glycerol Optimized by Response Surface Methodology", BIOTECHNOL. PROG., vol. 20, no. 2, 2004, pages 619 - 622, XP003001954 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008061577A (ja) * 2006-09-07 2008-03-21 Kao Corp 油脂組成物
WO2008128765A1 (fr) * 2007-04-24 2008-10-30 Lipid Nutrition B.V. Composition de boisson comprenant de l'acide linoléique conjugué
CN101177399B (zh) * 2007-11-23 2011-04-27 东营广元生物工程有限公司 无催化共轭亚油酸甘油酯的制备方法
JP2010180195A (ja) * 2008-02-13 2010-08-19 Kao Corp 食後高血糖改善剤
ES2335959A1 (es) * 2008-08-27 2010-04-06 Laboratorios Casen-Fleet, S.L. Composicion alimenticia y uso.
JP2012501175A (ja) * 2008-08-28 2012-01-19 ネステク ソシエテ アノニム 痩せの表現型に関連する遺伝子発現プロファイルおよびその使用

Also Published As

Publication number Publication date
JP2008069184A (ja) 2008-03-27

Similar Documents

Publication Publication Date Title
JP5155863B2 (ja) 油脂組成物
JP4381037B2 (ja) 油脂組成物
JP5636398B2 (ja) 油脂組成物
WO2006088188A1 (fr) Composition d’acides gras d’huile
KR100951756B1 (ko) 유지 조성물
JP5100974B2 (ja) 油脂組成物
EP1544281B1 (fr) Composition de corps gras
US20070141220A1 (en) Composition enriched in diglyceride with conjugated linoleic acid
AU2002328058A1 (en) Oil composition
JP5039291B2 (ja) 油脂組成物
JP4268473B2 (ja) 油脂組成物

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application
NENP Non-entry into the national phase

Ref country code: DE

NENP Non-entry into the national phase

Ref country code: JP

122 Ep: pct application non-entry in european phase

Ref document number: 06714116

Country of ref document: EP

Kind code of ref document: A1