WO2002060270A1 - Composition grasse comestible contenant du phytosterol, presentant une excellente stabilite au stockage, et son procede de production - Google Patents

Composition grasse comestible contenant du phytosterol, presentant une excellente stabilite au stockage, et son procede de production Download PDF

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Publication number
WO2002060270A1
WO2002060270A1 PCT/JP2002/000334 JP0200334W WO02060270A1 WO 2002060270 A1 WO2002060270 A1 WO 2002060270A1 JP 0200334 W JP0200334 W JP 0200334W WO 02060270 A1 WO02060270 A1 WO 02060270A1
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WO
WIPO (PCT)
Prior art keywords
fatty acid
mass
acid ester
emulsifier
oil
Prior art date
Application number
PCT/JP2002/000334
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English (en)
Japanese (ja)
Inventor
Shinji Seki
Ichirou Hidaka
Shin Arimoto
Hisako Yoshino
Junichi Ikuina
Original Assignee
The Nisshin Oillio, Ltd.
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 The Nisshin Oillio, Ltd. filed Critical The Nisshin Oillio, Ltd.
Publication of WO2002060270A1 publication Critical patent/WO2002060270A1/fr

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Classifications

    • 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
    • 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
    • C11B5/0028—Carboxylic acids; Their derivates

Definitions

  • the present invention relates to an edible oil-and-fat composition containing plant sterol having excellent storage stability and a method for producing the same.
  • cholesterol control in the body is used in diet therapy.
  • dietary treatments include the simultaneous ingestion of a component having an inhibitory effect on cholesterol absorption.
  • Cholesterol is abundant in meat, fish, eggs, etc., and is known to have a cholesterol absorption inhibitory effect in edible oils used for cooking these foods. It is effective to contain plant sterols (phytosterols).
  • Plant sterols can exert some cholesterol absorption inhibitory effect under appropriate dietary restrictions, but at least 2 cholesterol absorption inhibitory effects can be observed. It is said that about 3% by mass is required. However, plant sterols contain only about 0.1 to 1.5% by mass of edible oil derived from plants in free form and fatty acid ester form. Plant sterols must be added.
  • a main object of the present invention is to suppress the precipitation of plant sterol in edible fats and oils, and to improve the storage stability (refrigeration resistance) of edible fats and oils containing phytosterols at low temperatures. .
  • the present inventors have conducted intensive studies to achieve the above object, and as a result, by adding a predetermined amount of a specific emulsifier, the precipitation of plant sterols in edible oils and fats has been suppressed, and the plant
  • the present inventors have found that refrigeration resistance of sterol-containing edible oils and fats can be improved, and completed the present invention.
  • the precipitation inhibitory effect of the plant sterol of the present invention can last for several months to several years at room temperature, and the refrigeration resistance (1-5 ° C) effect can last for several months or more. This effect of suppressing the precipitation of plant sterol is effective even when the amount of water in the edible oil / fat is the amount of water (about 100 ppm) at which plant sterol is likely to precipitate. .
  • the present invention relates to sucrose fatty acid ester, glycerin fatty acid ester, sorbitan fatty acid ester, and propylene glycol having an HLB value of 6 or less for edible fats and oils, respectively.
  • the present invention provides a method for suppressing the precipitation of plant sterols in edible oils and fats, wherein the at least one emulsifier and the plant sterol are added simultaneously or separately.
  • the present invention relates to sucrose fatty acid esters, glycerin fatty acid esters, sorbitan fatty acid esters, and propylene glycol fatty acid esters, each having an HLB value of 6 or less for edible oils and fats.
  • the at least one emulsifier selected from the group consisting of the sterols in a free form is used in an amount of 0.001 to 5 parts by mass per 1 part by mass of the plant sterol in free form.
  • a method for improving the refrigeration resistance of edible fats and oils characterized by adding at least one emulsifier and a plant sterol simultaneously or separately.
  • the present invention relates to a sucrose fatty acid ester and a glycerol having an HLB value of 6 or less, each containing up to 0.1% by mass of sterol containing edible oil and fat in a free form up to 0.1% by mass and 10% by mass.
  • At least one emulsifier selected from the group consisting of phosphoric acid esters, sorbitan fatty acid esters, and propylene glycol fatty acid esters, in an amount of 1 part by mass of plant sterol in the free form.
  • the present invention provides a vegetable sterol-containing edible oil / fat composition in which the precipitation of plant sterols is suppressed, wherein the edible oil / fat composition is contained in an amount of 0.0001 to 5 parts by mass.
  • the present invention relates to a sucrose fatty acid ester having a HLB value of 6 or less, with respect to edible oil or fat, in a ratio of plant sterols in a free form of 0.1% to 10% by mass.
  • Glycerin fatty acid ester, sorbitan fatty acid ester ⁇ At least one emulsifier selected from the group consisting of propylene glycol fatty acid esters is used in an amount of at least one emulsifier per part by mass of plant free cellulose in free form.
  • a plant in which the precipitation of plant sterols is characterized in that the plant sterol and at least one emulsifier are added simultaneously or separately so as to be contained in a proportion of 1 part by mass to 5 parts by mass.
  • Provided is a method for producing a sterol-containing edible oil / fat composition.
  • the present invention relates to a sucrose fatty acid ester containing 0.1% to 10% by weight of plant sterols containing edible fats and oils, each having an HLB value of 6 or less.
  • At least one emulsifier selected from the group consisting of phosphoric acid esters, sorbitan fatty acid esters and propylene glycol fatty acid esters in the free form of the plant sterol in the free form.
  • an edible oil / fat composition containing a plant sterol with improved refrigeration resistance, wherein the edible oil / fat composition has an improved refrigeration resistance, wherein the edible oil / fat composition is contained in a proportion of 0.0001 to 5 parts by mass per 1 part by mass of the paste.
  • the present invention relates to an edible oil / fat with a plant sterol in a free form in a ratio of 0.1% to 10% by mass, each having an HLB value of 6 or less.
  • the at least one emulsifier may be used simultaneously or separately.
  • the edible oil / fat composition of the present invention has a small amount selected from the group consisting of sucrose fatty acid ester and dalyserine fatty acid ester each having an HLB value of 7 or less in order to suppress foaming during cooking.
  • one second emulsifier can be further included in a proportion of from 0.001 to 5 parts by weight per part by weight of the plant sterols in free form.
  • the emulsifiers used for suppressing plant sterol precipitation and improving refrigeration resistance are sucrose fatty acid esters, glycerin fatty acid esters having an HLB (hydrophilic lipophilic balance) value of 1 or more and 6 or less, respectively. It comprises at least one emulsifier selected from the group consisting of sorbitan fatty acid esters and propylene glycol fatty acid esters.
  • Glycerin fatty acid esters include polyglycerin fatty acid esters, especially polyglycerin condensed ricinoleate.
  • Sorbitan fatty acid esters include sonorebitan monooleate.
  • the propylene glycol fatty acid ester preferably contains propylene glycol monooleate.
  • polyglycerin condensed ricinoleate and propylene glycol fatty acid ester are particularly preferred.
  • the emulsifier of the present invention is used in a free form.
  • the plant sterol in free form is added to the edible fat or oil simultaneously or separately so that the ratio is 0.0001 to 5 parts by mass with respect to 1 part by mass of the product sterol.
  • the emulsifier of the present invention is preferably used in a ratio of 0.1 to 4 parts by mass with respect to 1 part by mass of the plant sterol in a free form, and it is preferably 0.1 to 2 parts by mass. It is more preferable to use them together.
  • the emulsifier is used in an amount of 0.001 to 5 mass with respect to the edible oil / fat composition of the present invention. It is preferred that the content be contained at a ratio of / 0 .
  • the emulsifier of the present invention is preferably used in an amount of 1 to 5 parts by mass per 1 part by mass of the plant sterol in a free form. It is added to the edible fat at the same time or separately as the plant sterol in free form, so that the proportion is in parts.
  • the emulsifier of the present invention is preferably used in a ratio of 0.1 to 2 parts by mass with respect to 1 part by mass of the plant sterol in a free form.
  • the refrigeration resistance means that when edible fats and oils are stored in a low-temperature (1 to 5 ° C) environment such as a refrigerator, not only does plant sterol not precipitate, but also And no high-melting-point triglycerides cause cloudy precipitation.
  • the emulsifier is preferably contained in the edible fat / oil composition of the present invention at a rate of 0.001 to 5% by mass.
  • the edible fats and oils used in the present invention include vegetable fats and oils, animal fats and oils, diglycerides and edible refined processed fats and oils. These fats and oils are those of the decolorized oil before the deodorization step. In addition, process oils such as extracted oil, crude oil, deoxidized oil, degummed oil, de-oiled oil, and refined oil Can be used.
  • Vegetable oils include soybean oil, soybean germ oil, rapeseed oil, corn oil, sesame oil, sesame oil, perilla oil, linseed oil, peanut oil, safflower oil, safflower oil, and castor oil Dwarf oil, high oleic sunflower oil, cottonseed oil, bud seed oil, macadamia nut oil, hazelnut oil, kapotiya seed oil, walnut oil, camellia oil, teaseed oil, sesame oil, borage oil, olive oil Bu oil. Includes, but is not limited to, rice bran oil, wheat germ oil, palm oil, palm kernel oil, coconut oil, potato oil, algal oil and their fractionated oils.
  • Animal fats include, but are not limited to, beef tallow, lard, chicken oil, milk fat, fish oil, seal oil, and their fractionated oils.
  • Diglyceride is a ester of glycerin and fatty acids derived from animal and vegetable oils, purified after hydrolysis of fats or oils, or purified by esterifying glycerin and fatty acids. But can be, but not limited to.
  • the edible refined oils and fats include the above-mentioned vegetable oils and fats, hydrogenated oils of animal oils and fats, synthetic fats and oils such as medium chain fatty acid triglyceride (MCT) and triacetin, and ester exchange oil (MLCT ) Etc., but are not limited to these. Needless to say, in the present invention, each component other than the edible oil and fat is contained and blended in the edible oil and fat.
  • the plant sterols used in the present invention include soybean oil, soybean germ oil, rapeseed oil, corn oil, sesame oil, sesame salad oil perilla oil, linseed oil, peanut oil, safflower oil, and safflower oil.
  • the components of these plant stenoles include brassicasterols, campesterols, stegumaster steles, sitosterones, isofcosterones, and deltas. 5-Abenasterols, 7-Ergosterols, etc., but also include components with similar structures such as cytostanols, campestanols, and stigmasterols.
  • the plant sterol used in the present invention does not limit the components, and the plant sterol in a free form has a fatty acid or the like esterified to a hydroxyl group bonded to the sterol skeleton.
  • the edible oil / fat composition of the present invention includes a plant sterol in which a fatty acid is esterified to a hydroxyl group bonded to a sterol skeleton.
  • the plant sterol used in the present invention may be referred to as a vegetable sterol.
  • the plant sterol used in the present invention is obtained by concentrating and purifying the above deodorized distillate by a combination of solvent separation, hydrolysis, distillation and adsorption treatment, but is not limited thereto. Alternatively, plant sterols having a low degree of purification may be used. Hexane, acetate, methanol, ethanol, isopropynole alcohol (IPP)
  • acetic acid and the like can be preferably exemplified, but are not limited thereto. Not something.
  • the emulsifier of the present invention can be added to an edible fat or oil simultaneously with or separately from the plant sterol. That is, the emulsifier of the present invention may be added to an edible oil or fat to which a plant sterol has been previously added, or may be added to an edible oil or fat together with a plant sterol.
  • the plant sterol has a melting point of 120 ° C or more, and when subjected to ordinary fat and oil degreasing treatment as it is, the droplets adhere to the vacuum line of the degreasing and deodorizing device, solidify, and solidify. Problems can occur, such as clogging and inability to deodorize.
  • the present inventors have found that this problem can be solved by deodorizing a raw material mixture containing a plant sterol in an edible oil and fat. In this case, the amount of phytosterol role in the raw material mixture is less ho it is laid preferred, 0 1-1 0% by weight good or properly, the rather to preferred Ri good 0;..! ⁇ 5 mass 0 / It is 0 .
  • the present inventors have studied the deodorizing treatment of a raw material mixture containing such plant sterols and edible oils and fats, and have found that the organic solvents used in the step of extracting edible oils and fats and the step of purifying the deodorized distillate, for example, acetate, Methynorethinoleketone (MEK), methanol, ethanol, IPA, ptinoreal alcohol, isobutinorea alcohol, acetic acid, butyric acid, isobutyric acid, dimethylformamide (DMF), dimethylformamide Volatility of molecular weight of 110 or less, such as tyl sulfoxide (DMSO), ether, tetrahydrofuran (THF), pentane, hexane, heptane, benzene, toluene and xylene It has been found that volatile organic compounds adversely affect the flavor, and that the flavor can be further improved by sufficiently removing these volatile organic compounds.
  • the deodorizing treatment of the mixture containing the plant sterol and the edible oil / fat has a molecular weight of 110 or less.
  • High enough to remove volatile organic compounds, but low enough not to remove significant plant sterols 100 ° C to 270 ° C Perform at a temperature of.
  • the deodorization temperature is preferably in the range of 150 ° C. to 260 ° C., and is preferably in the range of 180 ° C. to 260 ° C. Preferred.
  • the deodorizing treatment of the present invention is preferably performed by reduced-pressure water vapor distillation used for ordinary edible fats and oils. Vacuum steam distillation requires a certain level of temperature and decompression conditions to remove volatile organic compounds that have an adverse effect on flavor, but too severe conditions will also remove plant sterols themselves.
  • the deodorization treatment by reduced pressure steam distillation is carried out at 100 ° C. to 270 ° C., preferably at 150 ° C. to 260 ° C. (and more preferably It is preferable to perform the reaction at a temperature of 180 ° C to 260 ° C under a reduced pressure of l to 30 Torr.
  • the deodorization time is within a range of 30 minutes to 600 minutes.
  • the deodorization time is preferably longer at low temperatures, shorter at higher temperatures, and the amount of steam used is particularly important. There is no limit, and the amount used for deodorizing ordinary edible fats and oils (usually, Le containing edible oil composition An object weight of 0.01 to 30 ⁇ / ⁇ ) is sufficient.
  • the raw material mixture containing plant sterols and edible fats and oils contains less than 5 / 100,000 (5 mass!) Pm of a volatile organic compound having a molecular weight of 110 or less based on the mass of plant sterol. It is particularly preferable to deodorize so that the edible oil-and-fat composition containing a plant sterol having a more excellent flavor can be obtained.
  • an improved flavor can be provided.
  • the improved flavor includes both the improvement of the flavor of the fat or oil composition itself and the improvement of the flavor of a cooked product prepared using the fat or oil composition, for example, a fried cooked product.
  • phytosterols are also removed in this deodorization step, they are recovered and used again as all or part of the phytosterols in the mixture of edible oil and vegetable sterol to be deodorized. If added to the plant and deodorized, plant sterols can be effectively used without waste, and it is cost effective.
  • the emulsifier of the present invention can be added to the mixture of plant sterol and edible fat / oil thus deodorized as described above.
  • the emulsifier of the present invention can be added to the plant sterol before the deodorization treatment. It may be added to a mixture of edible fats and oils, and the mixture may be subjected to the above deodorization treatment.
  • the plant sterol in a free form is preferably contained in a ratio of 0.1 to 10% by mass, more preferably in a ratio of 0.1 to 7% by mass. Is more preferable. Suppression of plant sterol precipitation by the emulsifier of the present invention The antibacterial effect is remarkable when the content of the plant sterol in the free form in the edible oil / fat composition is 1 mass or more. Therefore, the free form of the plant sterol in the edible oil / fat composition of the present invention is contained. More preferably, the ratio is from 1 to 7% by mass.
  • the edible fat / oil composition of the present invention containing an emulsifier and a plant sterol can be used as it is as a cooking fat / oil, as a frying oil, a frying oil, a release oil or the like.
  • the edible oil-and-fat yarn composition of the present invention may be used for dressing, coffee whitener, whipped cream, mayonnaise, emulsified dressing, margarine, and fat spoon. It can be used as edible emulsified fats and oils for red, short toning, ice cream, fermented dairy foods, etc., and for breads and pastries.
  • an edible oil / fat composition containing a plant sterol tends to foam when used for cooking.
  • the present inventors have found that this foaming is at least selected from the group consisting of polyglycerol sugar fatty acid esters having a HLB value of 7 or less and sucrose sugar fatty acid ester.
  • the amount of the one emulsifier (second emulsifier) is adjusted so as to be 0.0001 to 5 parts by mass, preferably 0.1 to 2 parts by mass, per 1 part by mass of the free form of plant sterol. It has been found that the addition can be sufficiently suppressed by further adding to the oil composition for use of the present invention.
  • foaming suppressing emulsifiers are preferably contained in the edible oil / fat composition of the present invention in a proportion of 0.001 to 5% by mass.
  • This foaming suppressing emulsifier is the same as the above-mentioned emulsifier for suppressing phytosterol precipitation and improving refrigeration resistance, having a HLB value of 6 or less. It is an overlapping emulsifier in Dali serine fatty acid ester and sucrose fatty acid ester. If glycerin sugar fatty acid ester and / or sucrose fatty acid ester are used, the amount should be adjusted to the above amount to prevent phytosterol precipitation or increase the amount to improve refrigeration resistance. What is necessary is just to add the amount for suppression.
  • Edible oil and fat compositions having the compositions shown in Tables 1 to 3 below were prepared, and examined for their refrigeration resistance and phytosterol precipitation. The results are shown in the same table.
  • Soybean oil Seiyo Oil Co., Ltd. Soybean white squeezed oil (vegetable sterols in soybean oil are included in the oil from the beginning).
  • Vegetable sterols Uses plant sterols (food additives) manufactured by ADM.
  • Emulsifier Polyglycerin ester (hexaglycerin condensed ricinoleate), HLB-1.7 used.
  • Emulsifier ratio vegetable sterol ⁇ parts by mass of emulsifier per part by mass.
  • ⁇ Adjust the water content to about 1000ppm, seal tightly, store in a refrigerator for 5 months at refrigeration for 1 month, and if no clouding occurs
  • c X Adjust the water content to about 1000ppm, seal tightly, and bring to 5 ° C. Refrigerated for 1 month, if cloudy 'crystal precipitation occurs.
  • Vegetable sterols Use ADM vegetable sterols (food additives).
  • Emulsifier ratio parts by mass of emulsifier with respect to 1 part by mass of vegetable sterol.
  • the emulsifier of the present invention As described above, by adding the emulsifier of the present invention, the precipitation of plant sterols in edible oils and fats is suppressed, and the refrigeration resistance of the edible oil and fat composition containing plant sterols is improved. In addition, by adding a specific emulsifier, foaming during cooking of edible fats and oils is suppressed.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Emergency Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Edible Oils And Fats (AREA)
  • Fats And Perfumes (AREA)

Abstract

Au moins un agent émulsifiant sélectionné dans le groupe comprenant les esters d'acides gras de saccharose, les esters d'acides gras du glycérol, les esters d'acides gras du sorbitane et les esters d'acides gras du propylène glycol, présentant chacun un HLB inférieur ou égal à 6, est ajouté à une graisse comestible contenant du phytostérol dans un rapport de 0,0001 à 5 parties en poids par partie en poids de phytostérol à l'état libre. Ceci permet d'empêcher la précipitation du phytostérol dans la graisse.
PCT/JP2002/000334 2001-01-19 2002-01-18 Composition grasse comestible contenant du phytosterol, presentant une excellente stabilite au stockage, et son procede de production WO2002060270A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2001-012329 2001-01-19
JP2001012329A JP5005129B2 (ja) 2001-01-19 2001-01-19 保存安定性に優れた植物ステロール含有食用油脂組成物

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WO2002060270A1 true WO2002060270A1 (fr) 2002-08-08

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TW (1) TWI330521B (fr)
WO (1) WO2002060270A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2798049A1 (es) * 2019-06-04 2020-12-04 Univ Alicante Procedimiento y sistema para la eliminacion de olores en plasticos reciclados

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4571925B2 (ja) * 2006-05-17 2010-10-27 辻製油株式会社 機能性離型油組成物、その製造方法と利用
JP6399789B2 (ja) * 2014-04-16 2018-10-03 日清オイリオグループ株式会社 乳化油脂組成物

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3865939A (en) * 1973-02-23 1975-02-11 Procter & Gamble Edible oils having hypocholesterolemic properties
JPS62148424A (ja) * 1985-12-23 1987-07-02 Riken Vitamin Co Ltd ステリン含有組成物
WO1999059423A1 (fr) * 1998-04-30 1999-11-25 Kao Corporation Composition d'huile-corps gras contenant du phytosterol
JP2001220595A (ja) * 2000-02-08 2001-08-14 Kao Corp 油脂組成物

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Publication number Priority date Publication date Assignee Title
US6123978A (en) * 1998-08-31 2000-09-26 Mcneil-Ppc, Inc. Stable salad dressings

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3865939A (en) * 1973-02-23 1975-02-11 Procter & Gamble Edible oils having hypocholesterolemic properties
JPS62148424A (ja) * 1985-12-23 1987-07-02 Riken Vitamin Co Ltd ステリン含有組成物
WO1999059423A1 (fr) * 1998-04-30 1999-11-25 Kao Corporation Composition d'huile-corps gras contenant du phytosterol
JP2001220595A (ja) * 2000-02-08 2001-08-14 Kao Corp 油脂組成物

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2798049A1 (es) * 2019-06-04 2020-12-04 Univ Alicante Procedimiento y sistema para la eliminacion de olores en plasticos reciclados
WO2020245476A1 (fr) * 2019-06-04 2020-12-10 Universidad De Alicante Procédé et système pour élimination d'odeurs dans des plastiques recyclés

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JP2002209517A (ja) 2002-07-30
TWI330521B (fr) 2010-09-21
JP5005129B2 (ja) 2012-08-22

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