WO2016136285A1 - L-ascorbic acid fatty acid ester preparation - Google Patents

L-ascorbic acid fatty acid ester preparation Download PDF

Info

Publication number
WO2016136285A1
WO2016136285A1 PCT/JP2016/050285 JP2016050285W WO2016136285A1 WO 2016136285 A1 WO2016136285 A1 WO 2016136285A1 JP 2016050285 W JP2016050285 W JP 2016050285W WO 2016136285 A1 WO2016136285 A1 WO 2016136285A1
Authority
WO
WIPO (PCT)
Prior art keywords
fatty acid
acid ester
ascorbic acid
acid fatty
preparation
Prior art date
Application number
PCT/JP2016/050285
Other languages
French (fr)
Japanese (ja)
Inventor
敏和 鈴木
良子 立石
Original Assignee
理研ビタミン株式会社
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 理研ビタミン株式会社 filed Critical 理研ビタミン株式会社
Priority to JP2017501960A priority Critical patent/JP6796055B2/en
Publication of WO2016136285A1 publication Critical patent/WO2016136285A1/en

Links

Classifications

    • 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
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3544—Organic compounds containing hetero rings
    • 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
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • A61K31/375—Ascorbic acid, i.e. vitamin C; Salts thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen

Definitions

  • the present invention relates to an L-ascorbic acid fatty acid ester preparation.
  • L-ascorbic acid fatty acid ester is obtained by esterifying a fatty acid with L-ascorbic acid, has vitamin C action and antioxidant action, and is lipophilic, so it is nutritional for foods mainly containing edible fats and fats. It is used as a reinforcing agent and antioxidant.
  • L-ascorbic acid fatty acid ester has poor water dispersibility (water dispersibility), for example, even if it is used as it is in an aqueous food such as a soft drink, a crystalline product of L-ascorbic acid fatty acid ester in the food Will float without being dispersed. Accordingly, various preparation methods have been studied in order to make L-ascorbic acid fatty acid ester widely applicable to various foods and drinks.
  • a water-dispersible ascorbic acid fatty acid ester composition formed by blending an ascorbic acid fatty acid ester, a hydrophilic surfactant and an oligosaccharide, and L-ascorbic acid fatty acid ester are:
  • An antioxidant preparation characterized by being uniformly dispersed in an oily substance Patent Document 2
  • a hydrophilic inclusion complex comprising a higher fatty acid ester of L-ascorbic acid in a cyclodextrin Patent Document 3
  • Production of a powdered L-ascorbic acid fatty acid ester preparation in which L-ascorbic acid fatty acid ester, powdered base material and oil-soluble substance are added to water to emulsify, and the resulting oil-in-water emulsion composition is dried.
  • a method (Patent Document 4) and the like are known.
  • JP-A-7-115951 Japanese Patent Laid-Open No. 9-208986 JP-A-10-231244 JP 2014-155453 A
  • An object of the present invention is to provide an L-ascorbic acid fatty acid ester preparation that can provide a sufficient antioxidant effect when added to food dough mainly composed of flour and / or starch.
  • the present inventors have found that the above problems can be solved by the L-ascorbic acid fatty acid ester preparation obtained by formulating a specific method using a solid oil at room temperature.
  • the present invention has been found to be solved, and the present invention has been made based on this finding.
  • the present invention (1) a powdery L-ascorbic acid fatty acid ester preparation comprising particles containing (a) L-ascorbic acid fatty acid ester and (b) a solid oil at room temperature, (2) (a) L-ascorbic acid fatty acid ester preparation obtained by cooling and pulverizing a molten mixture containing (a) L-ascorbic acid fatty acid ester and (b) solid oil at room temperature, (3) The preparation according to claim 1 or 2 for suppressing an increase in peroxide value and / or flavor deterioration of food and drink, (4) A method for producing an L-ascorbic acid fatty acid ester preparation comprising a step of cooling and pulverizing a molten mixture containing (a) L-ascorbic acid fatty acid ester and (b) a solid fat at room temperature , Is included.
  • the L-ascorbic acid fatty acid ester preparation of the present invention In the food and drink to which the L-ascorbic acid fatty acid ester preparation of the present invention is added, an increase in peroxide value and / or flavor deterioration due to the progress of oxidation of fats and oils contained in the food and drink are sufficiently suppressed.
  • the L-ascorbic acid fatty acid ester preparation of the present invention is used by adding it to a dough of food mainly composed of flour and / or starch, the oxidation of the food can be sufficiently suppressed.
  • the constituent fatty acid of the L-ascorbic acid fatty acid ester used in the present invention is not particularly limited as long as it is a fatty acid derived from edible animal and vegetable oils and fats, for example, linear saturated or unsaturated having 6 to 24 carbon atoms. Examples thereof include fatty acids, and preferred are linear saturated or unsaturated fatty acids having 16 to 18 carbon atoms.
  • Examples of the L-ascorbic acid fatty acid ester used in the present invention include L-ascorbic acid stearic acid ester (food additive) and L-ascorbic acid palmitic acid ester (food additive).
  • L-ascorbyl palmitate is more preferred because of its relatively low melting point and high vitamin C activity due to its low molecular weight.
  • fats and oils that are solid at room temperature used in the present invention well-known edible fats and oils that are solid or semi-solid at room temperature (10 to 35 ° C.) can be used, such as milk fat, palm oil, palm oil, Animal fats such as beef tallow, lard, cocoa butter, vegetable fats, and even hardened fats obtained by hydrogenating liquid animal and vegetable oils (including extremely hardened fats with an iodine value of 2 or less) And is preferably an extremely hardened fat. These may be used alone or as a combination of two or more of them as oils and fats that are solid at room temperature used in the present invention.
  • the production method of the L-ascorbic acid fatty acid ester preparation of the present invention is not particularly limited.
  • a molten mixture containing (a) an L-ascorbic acid fatty acid ester and (b) a solid fat at normal temperature is used.
  • a powdered L-ascorbic acid fatty acid ester preparation comprising particles containing (a) L-ascorbic acid fatty acid ester and (b) solid oil at room temperature is obtained by a method including a step of cooling and pulverizing. It is done.
  • the specific production method is not particularly limited. For example, (1) one or more oils and fats that are solid at room temperature are heated to a melting point or higher (for example, 60 to 90 ° C.) to be melted and mixed.
  • the mixture was heated to 100-120 ° C., L-ascorbic acid fatty acid ester was added, and the mixture was melted and mixed.
  • the resulting mixture was spray-cooled under a temperature condition of ⁇ 196-30 ° C., and powdered L- A method of recovering as an ascorbic acid fatty acid ester preparation, (2) the mixture is allowed to stand, for example, at -196 ° C to room temperature, for example, for 1 to 72 hours, solidified by cooling, and then pulverized by a method known per se And the like, and the like.
  • the ratio of L-ascorbic acid fatty acid ester to fats and oils solid at normal temperature in the mixture is not particularly limited.
  • the mass ratio is preferably 1/99 to 60/40, more preferably 10/90 to 45/55.
  • spray cooling is performed by spraying the melt into, for example, a cooled gas-filled tower using, for example, a general spray cooling apparatus.
  • liquid nitrogen When liquid nitrogen is used to cool the gas in the tower, the liquid nitrogen may be injected from any of the upper, middle and lower stages in the tower, or may be injected from two or more locations.
  • a pressurized spray nozzle, a rotating disk spray nozzle, or the like is used for spraying.
  • the sprayed solution is cooled to become powder and falls to the bottom of the tower and is collected.
  • the average particle size of the obtained powder is not particularly limited, but is preferably 50 to 1000 ⁇ m, more preferably 100 to 500 ⁇ m.
  • the pulverization method may be physically finely pulverized.
  • a compression crusher, a shear crusher, an impact crusher, a roll mill, a high-speed rotary mill, a jet mill, etc. are used.
  • the degree of pulverization is not particularly limited, but for example, pulverization is preferably performed so that the average particle diameter is preferably in the range of 50 to 1000 ⁇ m, more preferably in the range of 100 to 500 ⁇ m.
  • the L-ascorbic acid fatty acid ester preparation of the present invention is in powder form.
  • the average particle diameter of the powder is not particularly limited, but is preferably 50 to 1000 ⁇ m, more preferably 100 to 500 ⁇ m.
  • the L-ascorbic acid fatty acid ester preparation of the present invention contains, for example, a food emulsifier, an antioxidant (except for L-ascorbic acid fatty acid ester) and the like within a range not inhibiting the purpose and effect of the present invention. be able to.
  • glycerin fatty acid ester examples include glycerin and fatty acid ester, sucrose fatty acid ester, sorbitan fatty acid ester, propylene glycol fatty acid ester, and lecithin.
  • glycerin fatty acid ester includes glycerin and fatty acid ester, glycerin acetate ester, glycerin acetic acid fatty acid ester, glycerin lactic acid fatty acid ester, glycerin citrate fatty acid ester, glycerin succinic acid fatty acid ester, glycerin diacetyl tartaric acid fatty acid ester, poly Examples include glycerin fatty acid ester and polyglycerin condensed ricinoleic acid ester.
  • Lecithin includes fractionated lecithin, enzyme-decomposed lecithin, enzyme-treated lecithin, and the like.
  • L-ascorbic acid fatty acid ester preparation of the present invention contains an emulsifier for food, water dispersibility and the like are enhanced, and it can be widely applied to various foods and drinks.
  • antioxidants examples include extracted tocopherol, rosemary extract, L-ascorbic acid and its salts, catechins, enzyme-treated rutin, sunflower seed extract, grape seed extract, enzyme-decomposed apple extract, BHA, BHT, Examples include TBHQ and EDTA.
  • foods mainly composed of flour and / or starch include bakery items such as bread, cookies, crackers, biscuits, cakes, pizzas and pies, spaghetti and pasta such as macaroni, noodles such as udon, buckwheat and ramen, Oyster, potato chips, snacks such as snacks, cake donuts, yeast donuts, fried bread, karinto, hemp blossoms, serta andagi, churros, fried buns, American dogs, piroshki, fritters, tempura, cutlets, fried pizza , Japanese confectionery such as buns, Japanese crocodiles, rice cakes and rice cakes.
  • flour examples include wheat flour, buckwheat flour, barley flour, and rice flour.
  • starch examples include potato starch, tapioca starch, waxy corn starch, corn starch, wheat starch, or etherified starch, esterified starch, cross-linked starch, oxidized starch and the like obtained using these as raw materials.
  • the food material to be contained (for example, dried potato powder, dried mashed potato, dried potato flakes, etc.) is also included in this.
  • the proportion of flour and / or starch in the raw material powder of the food is, for example, 50% by mass or more, preferably 70% by mass or more, more preferably 80% by mass of the whole raw material powder. % Or more.
  • the ratio of the flour and / or starch in the raw material of the food mainly composed of flour and / or starch is, for example, 20% by mass or more, preferably 40% by mass or more, more preferably 60% by mass or more of the whole raw material. May be.
  • confectionery materials such as chocolate and nuts, soy milk, soy foods such as koji and tofu, milk, cheese, butter, ice cream, cream
  • Milk foods and beverages such as pudding, yogurt, fermented milk drinks, milk ingredient-containing drinks, hamburger, sausage, fish sausage, tsumi, dried meat and other processed meat products, EPA (eicosapentaenoic acid), DHA (docosahexaenoic acid),
  • oils and processed oils such as fish oil, perilla oil, soybean oil, rapeseed oil, margarine, and shortening.
  • the method of using the L-ascorbic acid fatty acid ester preparation of the present invention is not particularly limited, and for example, in the production of food mainly composed of flour and / or starch, it can be used by adding to the dough of the food. More specifically, in the production of foods mainly composed of flour and / or starch, (1) L-ascorbic acid fatty acid ester preparation is added to and mixed with flour and / or starch, and the resulting mixture is used as raw material flour. And (2) a method of adding an L-ascorbic acid fatty acid ester preparation to a dough mainly comprising cereal flour and / or starch and kneading the dough. Since the method for producing food from the dough has been well established in the past, it can be followed in the present invention using the L-ascorbic acid fatty acid ester preparation.
  • the amount of the L-ascorbic acid fatty acid ester preparation of the present invention used for foods mainly composed of flour and / or starch is not particularly limited. For example, it is usually 0.01 to 1 per 100 parts by weight of flour and / or starch. Parts by mass, preferably 0.05 to 0.5 parts by mass.
  • the L-ascorbic acid fatty acid ester preparation of the present invention is used for applications such as suppression of oxidation of food and drink (including suppression of oxidation by light), suppression of increase in peroxide value, suppression of flavor deterioration, and the like.
  • L-ascorbic acid fatty acid ester preparation Table 1 shows the composition of the L-ascorbic acid fatty acid ester preparation prepared using the above raw materials.
  • L-ascorbic acid fatty acid ester preparations 1 to 6 are examples according to the present invention, and L-ascorbic acid fatty acid ester preparations 7 and 8 are comparative examples for them.
  • the preparation amount of preparations 1 to 6 and 8 was 100 g, and the preparation amount of preparation 7 was 420 g.
  • the obtained mixture was poured into a stainless steel tray, cooled at room temperature for 2 hours and solidified, and coarsely pulverized to obtain a flaky solid.
  • the solid was pulverized to an average particle size of about 100 ⁇ m using a pulverizer (model: SM-1C; set to “Speed 10”; manufactured by ASONE), and powdered L-ascorbic acid fatty acid ester preparations 1 to 5 Got.
  • the solid was pulverized to an average particle size of about 100 ⁇ m using a pulverizer (model: SM-1C; set to “Speed 10”; manufactured by ASONE) to obtain a powdered L-ascorbic acid fatty acid ester preparation 6 It was.
  • a pulverizer model: SM-1C; set to “Speed 10”; manufactured by ASONE
  • L-ascorbic acid fatty acid ester preparation 8 Since L-ascorbic acid fatty acid ester preparation 8 has only one raw material, the raw material itself was used as an L-ascorbic acid fatty acid ester preparation.
  • the snacks 1 to 12 obtained by adding the L-ascorbic acid fatty acid ester formulations 1 to 6 of the present invention have a peroxide value of 20 meq after storage at 60 ° C. for 10 days.
  • the sensory evaluation was an excellent result of “ ⁇ ” or more.
  • the snacks 13 to 16 obtained by adding the L-ascorbic acid fatty acid ester formulation 7 or 8 and the snack confections 17 manufactured without adding the L-ascorbic acid fatty acid ester formulation were heated at 60 ° C. for 10 days. After storage, the peroxide value increased to 20 meq / kg or more, and the sensory evaluation was a result of “ ⁇ ” or less, which was inferior to that of the present invention.

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Nutrition Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Microbiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
  • General Preparation And Processing Of Foods (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Non-Alcoholic Beverages (AREA)

Abstract

A powdery L-ascorbic acid fatty acid ester preparation comprising particles each containing (a) an L-ascorbic acid fatty acid ester and (b) an oil or fat that is in a solid state at ambient temperature is added to a food dough mainly composed of a cereal grain powder and/or a starch. In this manner, a sufficient anti-oxidative effect can be achieved.

Description

Ｌ－アスコルビン酸脂肪酸エステル製剤L-ascorbic acid fatty acid ester preparation
　本発明は、Ｌ－アスコルビン酸脂肪酸エステル製剤に関する。 The present invention relates to an L-ascorbic acid fatty acid ester preparation.
　Ｌ－アスコルビン酸脂肪酸エステルは、Ｌ－アスコルビン酸に脂肪酸をエステル結合させたものであり、ビタミンＣ作用、酸化防止作用を有し、且つ親油性なので主に食用油脂や脂肪を含む食品への栄養強化剤、酸化防止剤等として使用されている。しかし、Ｌ－アスコルビン酸脂肪酸エステルは水に対する分散性（水分散性）に乏しいため、例えば、清涼飲料水等の水性食品へそのまま使用しても該食品中でＬ－アスコルビン酸脂肪酸エステルの結晶物が分散せずに浮遊することとなる。そこで、Ｌ－アスコルビン酸脂肪酸エステルを各種の飲食品に広く適用可能にするため、様々な製剤化方法が検討されている。 L-ascorbic acid fatty acid ester is obtained by esterifying a fatty acid with L-ascorbic acid, has vitamin C action and antioxidant action, and is lipophilic, so it is nutritional for foods mainly containing edible fats and fats. It is used as a reinforcing agent and antioxidant. However, since L-ascorbic acid fatty acid ester has poor water dispersibility (water dispersibility), for example, even if it is used as it is in an aqueous food such as a soft drink, a crystalline product of L-ascorbic acid fatty acid ester in the food Will float without being dispersed. Accordingly, various preparation methods have been studied in order to make L-ascorbic acid fatty acid ester widely applicable to various foods and drinks.
　そのような方法としては、例えば、アスコルビン酸脂肪酸エステル、親水性界面活性剤及び少糖類を配合してなる水分散性アスコルビン酸脂肪酸エステル組成物（特許文献１）、Ｌ－アスコルビン酸脂肪酸エステルが、油性物質に均一に分散されていることを特徴とする酸化防止剤製剤（特許文献２）、Ｌ－アスコルビン酸の高級脂肪酸エステルをシクロデキストリンに包接させて成る親水性包接複合体（特許文献３）、Ｌ－アスコルビン酸脂肪酸エステル、粉末化基材及び油溶性物質を水に加えて乳化し、得られた水中油型乳化組成物を乾燥処理する粉末状Ｌ－アスコルビン酸脂肪酸エステル製剤の製造方法（特許文献４）等が知られている。 As such a method, for example, a water-dispersible ascorbic acid fatty acid ester composition (Patent Document 1) formed by blending an ascorbic acid fatty acid ester, a hydrophilic surfactant and an oligosaccharide, and L-ascorbic acid fatty acid ester are: An antioxidant preparation characterized by being uniformly dispersed in an oily substance (Patent Document 2), a hydrophilic inclusion complex comprising a higher fatty acid ester of L-ascorbic acid in a cyclodextrin (Patent Document) 3) Production of a powdered L-ascorbic acid fatty acid ester preparation in which L-ascorbic acid fatty acid ester, powdered base material and oil-soluble substance are added to water to emulsify, and the resulting oil-in-water emulsion composition is dried. A method (Patent Document 4) and the like are known.
　しかし、これら方法により得られる製剤を穀粉及び／又は澱粉を主体とする食品（例えば、スナック菓子等）の生地に添加して使用しても十分な酸化防止効果が得られないため、これらに替わり得る新規なＬ－アスコルビン酸脂肪酸エステル製剤が求められていた。 However, even if the preparation obtained by these methods is used by adding it to the dough of food (eg, snack confectionery) mainly composed of flour and / or starch, a sufficient antioxidant effect cannot be obtained. There has been a need for new L-ascorbic acid fatty acid ester formulations.
特開平７－１１５９５１号公報JP-A-7-115951 特開平９－２０８９８６号公報Japanese Patent Laid-Open No. 9-208986 特開平１０－２３１２４４号公報JP-A-10-231244 特開２０１４－１５５４５３号公報JP 2014-155453 A
　本発明は、穀粉及び／又は澱粉を主体とする食品の生地に添加することにより十分な酸化防止効果が得られるＬ－アスコルビン酸脂肪酸エステル製剤を提供することを目的とする。 An object of the present invention is to provide an L-ascorbic acid fatty acid ester preparation that can provide a sufficient antioxidant effect when added to food dough mainly composed of flour and / or starch.
　本発明者らは、上記課題に対して鋭意検討を行った結果、常温で固体状の油脂を用いて特定の方法で製剤化することにより得られるＬ－アスコルビン酸脂肪酸エステル製剤により、上記課題が解決されることを見出し、この知見に基づいて本発明を成すに至った。 As a result of earnest studies on the above problems, the present inventors have found that the above problems can be solved by the L-ascorbic acid fatty acid ester preparation obtained by formulating a specific method using a solid oil at room temperature. The present invention has been found to be solved, and the present invention has been made based on this finding.
　すなわち、本発明は、
（１）（ａ）Ｌ－アスコルビン酸脂肪酸エステルと（ｂ）常温で固体状の油脂とを含有する粒子を含む粉末状のＬ－アスコルビン酸脂肪酸エステル製剤、
（２）（ａ）Ｌ－アスコルビン酸脂肪酸エステルと（ｂ）常温で固体状の油脂とを含有する溶融状態の混合物を冷却し、粉末化することにより得られるＬ－アスコルビン酸脂肪酸エステル製剤、
（３）飲食品の過酸化物価の上昇及び／又は風味劣化を抑制するための請求項１又は２に記載の製剤、
（４）（ａ）Ｌ－アスコルビン酸脂肪酸エステルと（ｂ）常温で固体状の油脂とを含有する溶融状態の混合物を冷却し、粉末化する工程を含むＬ－アスコルビン酸脂肪酸エステル製剤の製造方法、
を包含する。 That is, the present invention
(1) a powdery L-ascorbic acid fatty acid ester preparation comprising particles containing (a) L-ascorbic acid fatty acid ester and (b) a solid oil at room temperature,
(2) (a) L-ascorbic acid fatty acid ester preparation obtained by cooling and pulverizing a molten mixture containing (a) L-ascorbic acid fatty acid ester and (b) solid oil at room temperature,
(3) The preparation according to claim 1 or 2 for suppressing an increase in peroxide value and / or flavor deterioration of food and drink,
(4) A method for producing an L-ascorbic acid fatty acid ester preparation comprising a step of cooling and pulverizing a molten mixture containing (a) L-ascorbic acid fatty acid ester and (b) a solid fat at room temperature ,
Is included.
　本発明のＬ－アスコルビン酸脂肪酸エステル製剤を添加した飲食品は、該飲食品に含まれる油脂の酸化の進行による過酸化物価の上昇及び／又は風味劣化が十分に抑制される。
　本発明のＬ－アスコルビン酸脂肪酸エステル製剤は、穀粉及び／又は澱粉を主体とする食品の生地に添加して使用することにより、該食品の酸化を十分に抑制できる。 In the food and drink to which the L-ascorbic acid fatty acid ester preparation of the present invention is added, an increase in peroxide value and / or flavor deterioration due to the progress of oxidation of fats and oils contained in the food and drink are sufficiently suppressed.
When the L-ascorbic acid fatty acid ester preparation of the present invention is used by adding it to a dough of food mainly composed of flour and / or starch, the oxidation of the food can be sufficiently suppressed.
　本発明で用いられるＬ－アスコルビン酸脂肪酸エステルの構成脂肪酸としては、食用可能な動植物油脂を起源とする脂肪酸であれば特に制限はなく、例えば炭素数６～２４の直鎖状の飽和又は不飽和脂肪酸が挙げられ、好ましくは炭素数１６～１８の直鎖状の飽和又は不飽和脂肪酸である。本発明で用いられるＬ－アスコルビン酸脂肪酸エステルとしては、例えばＬ－アスコルビン酸ステアリン酸エステル（食品添加物）及びＬ－アスコルビン酸パルミチン酸エステル（食品添加物）等が挙げられ、いずれも好ましく用いることができるが、相対的に融点が低いこと、また分子量が小さいためビタミンＣ活性が高いことから、Ｌ－アスコルビン酸パルミチン酸エステルがより好ましい。 The constituent fatty acid of the L-ascorbic acid fatty acid ester used in the present invention is not particularly limited as long as it is a fatty acid derived from edible animal and vegetable oils and fats, for example, linear saturated or unsaturated having 6 to 24 carbon atoms. Examples thereof include fatty acids, and preferred are linear saturated or unsaturated fatty acids having 16 to 18 carbon atoms. Examples of the L-ascorbic acid fatty acid ester used in the present invention include L-ascorbic acid stearic acid ester (food additive) and L-ascorbic acid palmitic acid ester (food additive). However, L-ascorbyl palmitate is more preferred because of its relatively low melting point and high vitamin C activity due to its low molecular weight.
　本発明で用いられる常温で固体状の油脂としては、常温（１０～３５℃）で固体又は半固体である周知の食用油脂を用いることができ、例えば、乳脂肪、やし油、パーム油、牛脂、豚脂（ラード）、カカオ脂等の動物性脂、植物性脂、更には液状の動物性、植物性油を水素添加して得られる硬化油脂（ヨウ素価２以下の極度硬化油脂を含む）が挙げられ、好ましくは極度硬化油脂である。本発明で用いられる常温で固体状の油脂として、これらを単独で使用してもよく、これらの２種以上を併用してもよい。 As fats and oils that are solid at room temperature used in the present invention, well-known edible fats and oils that are solid or semi-solid at room temperature (10 to 35 ° C.) can be used, such as milk fat, palm oil, palm oil, Animal fats such as beef tallow, lard, cocoa butter, vegetable fats, and even hardened fats obtained by hydrogenating liquid animal and vegetable oils (including extremely hardened fats with an iodine value of 2 or less) And is preferably an extremely hardened fat. These may be used alone or as a combination of two or more of them as oils and fats that are solid at room temperature used in the present invention.
　本発明のＬ－アスコルビン酸脂肪酸エステル製剤の製造方法に特に制限はないが、例えば、（ａ）Ｌ－アスコルビン酸脂肪酸エステルと（ｂ）常温で固体状の油脂とを含有する溶融状態の混合物を冷却し、粉末化する工程を含む方法により、（ａ）Ｌ－アスコルビン酸脂肪酸エステルと（ｂ）常温で固体状の油脂とを含有する粒子を含む粉末状のＬ－アスコルビン酸脂肪酸エステル製剤が得られる。その具体的な製造方法に特に制限はないが、例えば、（１）常温で固体状の１種又は２種以上の油脂を融点以上（例えば、６０～９０℃）に加熱して溶融及び混合し、これを１００～１２０℃に昇温してからＬ－アスコルビン酸脂肪酸エステルを加えて溶融及び混合し、得られた混合物を－１９６～３０℃の温度条件で噴霧冷却し、粉末状のＬ－アスコルビン酸脂肪酸エステル製剤として回収する方法、（２）該混合物を例えば－１９６℃～常温の温度条件で、例えば１～７２時間静置して冷却固化した後、自体公知の方法により粉砕し、粉末状のＬ－アスコルビン酸脂肪酸エステル製剤とする方法等を実施することができる。 The production method of the L-ascorbic acid fatty acid ester preparation of the present invention is not particularly limited. For example, a molten mixture containing (a) an L-ascorbic acid fatty acid ester and (b) a solid fat at normal temperature is used. A powdered L-ascorbic acid fatty acid ester preparation comprising particles containing (a) L-ascorbic acid fatty acid ester and (b) solid oil at room temperature is obtained by a method including a step of cooling and pulverizing. It is done. The specific production method is not particularly limited. For example, (1) one or more oils and fats that are solid at room temperature are heated to a melting point or higher (for example, 60 to 90 ° C.) to be melted and mixed. The mixture was heated to 100-120 ° C., L-ascorbic acid fatty acid ester was added, and the mixture was melted and mixed. The resulting mixture was spray-cooled under a temperature condition of −196-30 ° C., and powdered L- A method of recovering as an ascorbic acid fatty acid ester preparation, (2) the mixture is allowed to stand, for example, at -196 ° C to room temperature, for example, for 1 to 72 hours, solidified by cooling, and then pulverized by a method known per se And the like, and the like.
　上記（１）及び（２）の方法において、混合物中のＬ－アスコルビン酸脂肪酸エステルと常温で固体状の油脂の比率（Ｌ－アスコルビン酸脂肪酸エステル／常温で固体状の油脂）に特に制限はないが、例えば質量比で１／９９～６０／４０が好ましく、１０／９０～４５／５５がより好ましい。 In the above methods (1) and (2), the ratio of L-ascorbic acid fatty acid ester to fats and oils solid at normal temperature in the mixture (L-ascorbic acid fatty acid ester / fat solids at normal temperature) is not particularly limited. However, for example, the mass ratio is preferably 1/99 to 60/40, more preferably 10/90 to 45/55.
　また、上記（１）の方法において、噴霧冷却は、例えば、一般的な噴霧冷却装置を使用し、該溶融物を例えば冷却した気体の充填された塔内に噴霧することにより実施される。塔内の気体を冷却するために液体窒素を用いる場合、液体窒素は塔内の上段、中段及び下段のいずれから注入しても良く、また２箇所以上から注入しても良い。噴霧には加圧式噴霧ノズルや回転円盤式噴霧ノズル等が用いられる。噴霧された溶液は冷却されて粉末となって塔下部に落下し捕集される。得られる粉末の平均粒子径に特に制限はないが、好ましくは５０～１０００μｍ、より好ましくは１００～５００μｍである。 In the method (1), spray cooling is performed by spraying the melt into, for example, a cooled gas-filled tower using, for example, a general spray cooling apparatus. When liquid nitrogen is used to cool the gas in the tower, the liquid nitrogen may be injected from any of the upper, middle and lower stages in the tower, or may be injected from two or more locations. For spraying, a pressurized spray nozzle, a rotating disk spray nozzle, or the like is used. The sprayed solution is cooled to become powder and falls to the bottom of the tower and is collected. The average particle size of the obtained powder is not particularly limited, but is preferably 50 to 1000 μm, more preferably 100 to 500 μm.
　また、上記（２）の方法において、粉砕の方法としては、物理的に細かく粉砕すればよく、例えば、圧縮破砕機、剪断粗砕機、衝撃破砕機、ロールミル、高速回転ミル、ジェットミル等を使用した公知の粉砕方法が挙げられる。また、粉砕の程度に特に制限はないが、例えば平均粒子径が好ましくは５０～１０００μｍ、より好ましくは１００～５００μｍの範囲になるように粉砕することが好ましい。 In the method (2), the pulverization method may be physically finely pulverized. For example, a compression crusher, a shear crusher, an impact crusher, a roll mill, a high-speed rotary mill, a jet mill, etc. are used. Known pulverization methods. The degree of pulverization is not particularly limited, but for example, pulverization is preferably performed so that the average particle diameter is preferably in the range of 50 to 1000 μm, more preferably in the range of 100 to 500 μm.
　本発明のＬ－アスコルビン酸脂肪酸エステル製剤は粉末状である。粉末の平均粒子径は特に限定されないが、好ましくは５０～１０００μｍ、より好ましくは１００～５００μｍであることが好ましい。 The L-ascorbic acid fatty acid ester preparation of the present invention is in powder form. The average particle diameter of the powder is not particularly limited, but is preferably 50 to 1000 μm, more preferably 100 to 500 μm.
　尚、本発明のＬ－アスコルビン酸脂肪酸エステル製剤には、本発明の目的・効果を阻害しない範囲で、例えば食品用乳化剤、酸化防止剤（但し、Ｌ－アスコルビン酸脂肪酸エステルを除く）等を加えることができる。 The L-ascorbic acid fatty acid ester preparation of the present invention contains, for example, a food emulsifier, an antioxidant (except for L-ascorbic acid fatty acid ester) and the like within a range not inhibiting the purpose and effect of the present invention. be able to.
　食品用乳化剤としては、グリセリン脂肪酸エステル、ショ糖脂肪酸エステル、ソルビタン脂肪酸エステル、プロピレングリコール脂肪酸エステル又はレシチン等が挙げられる。ここで、グリセリン脂肪酸エステルには、グリセリンと脂肪酸のエステルの他、グリセリン酢酸エステル、グリセリン酢酸脂肪酸エステル、グリセリン乳酸脂肪酸エステル、グリセリンクエン酸脂肪酸エステル、グリセリンコハク酸脂肪酸エステル、グリセリンジアセチル酒石酸脂肪酸エステル、ポリグリセリン脂肪酸エステル及びポリグリセリン縮合リシノール酸エステル等が含まれる。またレシチンには、分別レシチン、酵素分解レシチン及び酵素処理レシチン等が含まれる。本発明のＬ－アスコルビン酸脂肪酸エステル製剤が食品用乳化剤を含有することにより水分散性等が高まり、各種の飲食品に広く適用可能になる。 Examples of the emulsifier for food include glycerin fatty acid ester, sucrose fatty acid ester, sorbitan fatty acid ester, propylene glycol fatty acid ester, and lecithin. Here, glycerin fatty acid ester includes glycerin and fatty acid ester, glycerin acetate ester, glycerin acetic acid fatty acid ester, glycerin lactic acid fatty acid ester, glycerin citrate fatty acid ester, glycerin succinic acid fatty acid ester, glycerin diacetyl tartaric acid fatty acid ester, poly Examples include glycerin fatty acid ester and polyglycerin condensed ricinoleic acid ester. Lecithin includes fractionated lecithin, enzyme-decomposed lecithin, enzyme-treated lecithin, and the like. When the L-ascorbic acid fatty acid ester preparation of the present invention contains an emulsifier for food, water dispersibility and the like are enhanced, and it can be widely applied to various foods and drinks.
　酸化防止剤としては、例えば抽出トコフェロール、ローズマリー抽出物、Ｌ－アスコルビン酸及びその塩類、カテキン類、酵素処理ルチン、ヒマワリ種子抽出物、ブドウ種子抽出物、酵素分解リンゴ抽出物、ＢＨＡ、ＢＨＴ、ＴＢＨＱ及びＥＤＴＡ等が挙げられる。 Examples of the antioxidant include extracted tocopherol, rosemary extract, L-ascorbic acid and its salts, catechins, enzyme-treated rutin, sunflower seed extract, grape seed extract, enzyme-decomposed apple extract, BHA, BHT, Examples include TBHQ and EDTA.
　本発明のＬ－アスコルビン酸脂肪酸エステル製剤の使用対象である飲食品の種類に特に制限はなく、穀粉及び／又は澱粉を主体とする食品を含む各種飲食品へ広く使用できる。穀粉及び／又は澱粉を主体とする食品としては、例えば、パン、クッキー、クラッカー、ビスケット、ケーキ、ピザ、パイ等のベーカリー類、スパゲティー、マカロニ等のパスタ類、うどん、そば、ラーメン等の麺類、おかき、ポテトチップス、スナック等のスナック菓子類、ケーキドーナツ、イーストドーナツ、揚げパン、かりんとう、麻花、サーターアンダギー、チュロス、揚げまんじゅう、アメリカンドッグ、ピロシキ、フリッター、天ぷら、カツレツ、揚げピザ等の油ちょう食品類、饅頭、ういろ、もち、おはぎ等の和菓子類等が挙げられる。 There are no particular restrictions on the type of food or drink for which the L-ascorbic acid fatty acid ester preparation of the present invention is used, and it can be widely used for various foods and drinks including foods mainly composed of flour and / or starch. Examples of foods mainly composed of flour and / or starch include bakery items such as bread, cookies, crackers, biscuits, cakes, pizzas and pies, spaghetti and pasta such as macaroni, noodles such as udon, buckwheat and ramen, Oyster, potato chips, snacks such as snacks, cake donuts, yeast donuts, fried bread, karinto, hemp blossoms, serta andagi, churros, fried buns, American dogs, piroshki, fritters, tempura, cutlets, fried pizza , Japanese confectionery such as buns, Japanese crocodiles, rice cakes and rice cakes.
　穀粉としては、例えば小麦粉、そば粉、大麦粉、米粉等が挙げられる。澱粉としては、例えば馬鈴薯澱粉、タピオカ澱粉、ワキシーコーンスターチ、コーンスターチ、小麦澱粉、又はこれらを原料として得られるエーテル化工澱粉、エステル化工澱粉、架橋化工澱粉、酸化工澱粉等が挙げられる他、澱粉を多く含有する食品素材（例えば、乾燥ポテト粉末、乾燥マッシュポテト、乾燥ポテトフレーク等）もこれに含まれる。 Examples of flour include wheat flour, buckwheat flour, barley flour, and rice flour. Examples of the starch include potato starch, tapioca starch, waxy corn starch, corn starch, wheat starch, or etherified starch, esterified starch, cross-linked starch, oxidized starch and the like obtained using these as raw materials. The food material to be contained (for example, dried potato powder, dried mashed potato, dried potato flakes, etc.) is also included in this.
　穀粉及び／又は澱粉を主体とする食品において、該食品の原料粉中の穀粉及び／又は澱粉の割合は、例えば原料粉全体の５０質量％以上、好ましくは７０質量％以上、更に好ましくは８０質量％以上であってもよい。また、穀粉及び／又は澱粉を主体とする食品の原材料中の穀粉及び／又は澱粉の割合は、例えば原材料全体の２０質量％以上、好ましくは４０質量％以上、更に好ましくは６０質量％以上であってもよい。 In a food mainly composed of flour and / or starch, the proportion of flour and / or starch in the raw material powder of the food is, for example, 50% by mass or more, preferably 70% by mass or more, more preferably 80% by mass of the whole raw material powder. % Or more. Moreover, the ratio of the flour and / or starch in the raw material of the food mainly composed of flour and / or starch is, for example, 20% by mass or more, preferably 40% by mass or more, more preferably 60% by mass or more of the whole raw material. May be.
　また、穀粉及び／又は澱粉を主体とする食品以外の飲食品としては、例えばチョコレート、ナッツ等の洋菓子素材類、豆乳、こうや豆腐等の大豆食品類、牛乳、チーズ、バター、アイスクリーム、クリーム、プリン、ヨーグルト、発酵乳飲料、乳成分含有飲料等の乳飲食品類、ハンバーグ、ソーセージ、魚肉ソーセージ、つみれ、煮干し等の畜肉・水産加工食品、ＥＰＡ（エイコサペンタエン酸）、ＤＨＡ（ドコサヘキサエン酸）、魚油、シソ油、大豆油、ナタネ油、マーガリン、ショートニング等の油脂及び加工油脂類等が挙げられる。 Moreover, as food and drink other than foods mainly composed of flour and / or starch, for example, confectionery materials such as chocolate and nuts, soy milk, soy foods such as koji and tofu, milk, cheese, butter, ice cream, cream, Milk foods and beverages such as pudding, yogurt, fermented milk drinks, milk ingredient-containing drinks, hamburger, sausage, fish sausage, tsumi, dried meat and other processed meat products, EPA (eicosapentaenoic acid), DHA (docosahexaenoic acid), Examples include oils and processed oils such as fish oil, perilla oil, soybean oil, rapeseed oil, margarine, and shortening.
　本発明のＬ－アスコルビン酸脂肪酸エステル製剤の使用方法に特に制限はないが、例えば、穀粉及び／又は澱粉を主体とする食品の製造において、該食品の生地に添加して使用できる。より具体的には、穀粉及び／又は澱粉を主体とする食品の製造においては、（１）穀粉及び／又は澱粉にＬ－アスコルビン酸脂肪酸エステル製剤を加えて混合し、得られた混合物を原料粉として生地を調製する方法、（２）穀粉及び／又は澱粉を主体とする生地にＬ－アスコルビン酸脂肪酸エステル製剤を加え、該生地を混練する方法等が挙げられる。生地から食品を製造する方法は、従来十分に確立されているので、Ｌ－アスコルビン酸脂肪酸エステル製剤を使用する本発明のおいてもそれらに従ってよい。 The method of using the L-ascorbic acid fatty acid ester preparation of the present invention is not particularly limited, and for example, in the production of food mainly composed of flour and / or starch, it can be used by adding to the dough of the food. More specifically, in the production of foods mainly composed of flour and / or starch, (1) L-ascorbic acid fatty acid ester preparation is added to and mixed with flour and / or starch, and the resulting mixture is used as raw material flour. And (2) a method of adding an L-ascorbic acid fatty acid ester preparation to a dough mainly comprising cereal flour and / or starch and kneading the dough. Since the method for producing food from the dough has been well established in the past, it can be followed in the present invention using the L-ascorbic acid fatty acid ester preparation.
　穀粉及び／又は澱粉を主体とする食品に対する本発明のＬ－アスコルビン酸脂肪酸エステル製剤の使用量に特に制限はないが、例えば、穀粉及び／又は澱粉１００質量部に対して通常０．０１～１質量部であり、好ましくは０．０５～０．５質量部である。 The amount of the L-ascorbic acid fatty acid ester preparation of the present invention used for foods mainly composed of flour and / or starch is not particularly limited. For example, it is usually 0.01 to 1 per 100 parts by weight of flour and / or starch. Parts by mass, preferably 0.05 to 0.5 parts by mass.
　本発明のＬ－アスコルビン酸脂肪酸エステル製剤は、飲食品の酸化抑制（光による酸化の抑制を含む）、過酸化物価の上昇の抑制、風味劣化の抑制等の用途に用いられる。 The L-ascorbic acid fatty acid ester preparation of the present invention is used for applications such as suppression of oxidation of food and drink (including suppression of oxidation by light), suppression of increase in peroxide value, suppression of flavor deterioration, and the like.
　以下、実施例をもって本発明を具体的に説明するが、本発明はこれらに限定されるものではない。 Hereinafter, the present invention will be specifically described with reference to examples, but the present invention is not limited thereto.
［Ｌ－アスコルビン酸脂肪酸エステル製剤の製造］
（１）原材料
　１）Ｌ－アスコルビン酸パルミチン酸エステル（渡辺ケミカル社製）
　２）Ｌ－アスコルビン酸ステアリン酸エステル（東京化成工業社製）
　３）パーム極度硬化油（融点５７℃；横関油脂社製）
　４）菜種極度硬化油（融点６７℃；横関油脂社製）
　５）大豆極度硬化油（融点６７℃；横関油脂社製）
　６）グリセリン脂肪酸エステル（製品名：ポエムＤＯ－１００Ｖ；理研ビタミン社製）
　７）中鎖脂肪酸トリグリセライド（製品名：アクターＭ－１；理研ビタミン社製）
　８）化工澱粉Ａ（製品名：エヌクリーマー４６；イングレディオンジャパン社製）
　９）化工澱粉Ｂ（製品名：ピュリティガムＢＥ；イングレディオンジャパン社製） [Production of L-ascorbic acid fatty acid ester preparation]
(1) Raw materials 1) L-ascorbic acid palmitate (manufactured by Watanabe Chemical Co.)
2) L-ascorbic acid stearate (manufactured by Tokyo Chemical Industry Co., Ltd.)
3) Palm extremely hardened oil (melting point 57 ° C; manufactured by Yokoseki Oil & Fats Co., Ltd.)
4) Rapeseed extremely hardened oil (melting point 67 ° C .; manufactured by Yokoseki Yushi Co., Ltd.)
5) Soybean extremely hardened oil (melting point 67 ° C; manufactured by Yokoseki Oil & Fats Co., Ltd.)
6) Glycerin fatty acid ester (Product name: Poem DO-100V; manufactured by Riken Vitamin Co., Ltd.)
7) Medium-chain fatty acid triglyceride (Product name: Actor M-1; manufactured by Riken Vitamin Co., Ltd.)
8) Modified starch A (Product name: N Creamer 46; manufactured by Ingledion Japan)
9) Modified starch B (Product name: Purity Gum BE; manufactured by Ingledion Japan)
（２）Ｌ－アスコルビン酸脂肪酸エステル製剤の配合
　上記原材料を用いて作製したＬ－アスコルビン酸脂肪酸エステル製剤の配合組成を表１に示した。この内、Ｌ－アスコルビン酸脂肪酸エステル製剤１～６は本発明に係る実施例であり、Ｌ－アスコルビン酸脂肪酸エステル製剤７及び８はそれらに対する比較例である。尚、製剤１～６及び８の作製量は１００ｇとし、製剤７の作製量は４２０ｇとした。 (2) Formulation of L-ascorbic acid fatty acid ester preparation Table 1 shows the composition of the L-ascorbic acid fatty acid ester preparation prepared using the above raw materials. Among these, L-ascorbic acid fatty acid ester preparations 1 to 6 are examples according to the present invention, and L-ascorbic acid fatty acid ester preparations 7 and 8 are comparative examples for them. The preparation amount of preparations 1 to 6 and 8 was 100 g, and the preparation amount of preparation 7 was 420 g.
Figure JPOXMLDOC01-appb-T000001
Figure JPOXMLDOC01-appb-T000001
（３）Ｌ－アスコルビン酸脂肪酸エステル製剤１～５の製造方法
　３００ｍＬ容ガラス製ビーカーに常温で固体状の油脂（即ち、パーム極度硬化油、菜種極度硬化油及び大豆極度硬化油のうちいずれか）を入れ、これをガラス棒で攪拌しながら８０℃付近まで加熱し、均一に溶解したことを確認した後、１１０℃まで昇温した。これをガラス棒で攪拌しながら同温度条件下でＬ－アスコルビン酸脂肪酸エステル（即ち、Ｌ－アスコルビン酸パルミチン酸エステル又はＬ－アスコルビン酸ステアリン酸エステル）を少量ずつ加え、完全に溶解した。得られた混合物をステンレス製のトレイに流し込み室温で２時間冷却して固化したものを粗く粉砕し、フレーク状の固形物を得た。該固形物を粉砕機（型式：ＳＭ－１Ｃ；「スピード１０」に設定；アズワン社製）を用いて平均粒子径が１００μｍ程度まで粉砕し、粉末状のＬ－アスコルビン酸脂肪酸エステル製剤１～５を得た。 (3) Method for producing L-ascorbic acid fatty acid ester preparations 1 to 5 Solid oil at room temperature in a 300 mL glass beaker (that is, any of palm extremely hardened oil, rapeseed extremely hardened oil and soybean extremely hardened oil) The mixture was heated to around 80 ° C. while stirring with a glass rod, and after confirming that it was uniformly dissolved, the temperature was raised to 110 ° C. While stirring this with a glass rod, L-ascorbic acid fatty acid ester (that is, L-ascorbic acid palmitic acid ester or L-ascorbic acid stearic acid ester) was added little by little under the same temperature condition and completely dissolved. The obtained mixture was poured into a stainless steel tray, cooled at room temperature for 2 hours and solidified, and coarsely pulverized to obtain a flaky solid. The solid was pulverized to an average particle size of about 100 μm using a pulverizer (model: SM-1C; set to “Speed 10”; manufactured by ASONE), and powdered L-ascorbic acid fatty acid ester preparations 1 to 5 Got.
（４）Ｌ－アスコルビン酸脂肪酸エステル製剤６の製造方法
　３００ｍＬ容ガラス製ビーカーにパーム極度硬化油及びグリセリン脂肪酸エステルを入れ、これをガラス棒で攪拌しながら８０℃付近まで加熱し、均一に溶解したことを確認した後、１１０℃まで昇温した。これをガラス棒で攪拌しながら同温度条件下でＬ－アスコルビン酸パルミチン酸エステルを少量ずつ加え、完全に溶解した。得られた混合物をステンレス製のトレイに流し込み室温で２時間冷却して固化したものを粗く粉砕し、フレーク状の固形物を得た。該固形物を粉砕機（型式：ＳＭ－１Ｃ；「スピード１０」に設定；アズワン社製）を用いて平均粒子径が１００μｍ程度まで粉砕し、粉末状のＬ－アスコルビン酸脂肪酸エステル製剤６を得た。 (4) Production method of L-ascorbic acid fatty acid ester preparation 6 Palm extremely hardened oil and glycerin fatty acid ester were placed in a 300 mL glass beaker and heated to around 80 ° C. while stirring with a glass rod, and dissolved uniformly. After confirming this, the temperature was raised to 110 ° C. While stirring this with a glass rod, L-ascorbyl palmitate was added in small portions under the same temperature condition, and completely dissolved. The obtained mixture was poured into a stainless steel tray, cooled at room temperature for 2 hours and solidified, and coarsely pulverized to obtain a flaky solid. The solid was pulverized to an average particle size of about 100 μm using a pulverizer (model: SM-1C; set to “Speed 10”; manufactured by ASONE) to obtain a powdered L-ascorbic acid fatty acid ester preparation 6 It was.
（５）Ｌ－アスコルビン酸脂肪酸エステル製剤７の製造方法
　１）３Ｌ容ステンレス製ジョッキに水道水２０００ｍＬを入れ８０℃に加温した。
　２）上記１）をクリアミキサー（型式：Ｓ９４２；エム・テクニック社製）で低速で攪拌しながら、これに粉末化基材として化工澱粉Ａ及び化工澱粉Ｂを加え、これを同ミクサーにて低速で１０分間撹拌及び溶解した。
　３）上記２）の水相を低速でさらに攪拌しながら、これにＬ－アスコルビン酸パルミチン酸エステルを加え、これを同ミクサーにて低速で１０分間撹拌及び分散し、Ｌ－アスコルビン酸パルミチン酸エステル及び粉末化基材を含有する水相とした。
　４）上記３）の水相を低速でさらに攪拌しながら、これに油溶性物質として予め６０℃に加温した中鎖脂肪酸トリグリセライドを徐々に加えた後、同ミクサーにて１００００ｒｐｍで１５分間攪拌及び乳化し、水中油型乳化組成物である均質化液を得た。
　５）上記４）の均質化液を、加圧ノズル式噴霧乾燥装置（型式：Ｌ－８ｉ；大川原化工機社）にて、熱風入口温度１７０℃、排気温度８０℃の条件下で噴霧乾燥し、乾燥物をサイクロンで捕集することにより粉末状のＬ－アスコルビン酸脂肪酸エステル製剤７を得た。 (5) Method for producing L-ascorbic acid fatty acid ester preparation 7 1) 2000 mL of tap water was placed in a 3 L stainless steel mug and heated to 80 ° C.
2) While stirring the above 1) with a clear mixer (model: S942; manufactured by M Technique Co., Ltd.) at low speed, chemical starch A and chemical starch B are added as powdered substrates to this, and this is mixed with the mixer at low speed. And stirred for 10 minutes.
3) While further stirring the aqueous phase of 2) above at low speed, add L-ascorbic acid palmitate to this, and stir and disperse it in the same mixer at low speed for 10 minutes to give L-ascorbyl palmitate And an aqueous phase containing a powdered substrate.
4) While further stirring the aqueous phase of 3) at a low speed, after gradually adding medium-chain fatty acid triglyceride previously heated to 60 ° C. as an oil-soluble substance, the mixture was stirred at 10,000 rpm for 15 minutes with the mixer. The mixture was emulsified to obtain a homogenized liquid that is an oil-in-water emulsion composition.
5) The homogenized liquid of 4) above is spray-dried under the conditions of a hot air inlet temperature of 170 ° C. and an exhaust temperature of 80 ° C. in a pressure nozzle type spray drying apparatus (model: L-8i; Okawara Chemical Co., Ltd.). The dried product was collected with a cyclone to obtain a powdered L-ascorbic acid fatty acid ester formulation 7.
（６）Ｌ－アスコルビン酸脂肪酸エステル製剤８について
　Ｌ－アスコルビン酸脂肪酸エステル製剤８は、原材料が１種類のみであるため、当該原材料そのものをＬ－アスコルビン酸脂肪酸エステル製剤とした。 (6) About L-ascorbic acid fatty acid ester preparation 8 Since L-ascorbic acid fatty acid ester preparation 8 has only one raw material, the raw material itself was used as an L-ascorbic acid fatty acid ester preparation.
［スナック菓子の作製と評価］
（１）スナック菓子の作製
　ポテトフレーク（製品名：マッシュポッテ；雪和食品社製）６００ｇ、馬鈴薯澱粉（製品名：片栗粉；メトロキャッシュアンドキャリージャパン社販売）４００ｇ及び表２に示す添加量となるようにＬ－アスコルビン酸脂肪酸エステル製剤を２Ｌ容のポリエチレン製の袋に入れ、その袋の口を縛ったものを手で持ち１分間撹拌して均一に混合した。得られた混合物を製麺機（型式：ＭＰＣ－２５００；不二精機社製）に投入して撹拌しながら、これに予め食塩１０ｇを溶解した水５００ｇを少量ずつ添加し、更に１０分間撹拌し、生地を調製した。その後、製麺機付属のマカロニ型より押し出したチューブ状の生地（直径約１ｃｍ）を１ｃｍ幅にカットし、これを１５０～１６０℃のフライ油〔パーム油（製品名：精製パーム油；ミヨシ油脂社製）とコメ油（製品名：コメサラダ油；ボーソー油脂社製）の混合物；パーム油／コメ油＝８／２（質量比）〕にて３分間フライし、スナック菓子１～１７を得た。 [Production and evaluation of snacks]
(1) Preparation of snacks Potato flakes (Product name: Mash Potte; manufactured by Yuwa Foods Co., Ltd.) 600 g, potato starch (Product name: Katakura powder; sold by Metro Cash and Carry Japan Co., Ltd.) 400 g and the addition amount shown in Table 2 The L-ascorbic acid fatty acid ester preparation was placed in a 2 L polyethylene bag, and the bag with its mouth tied was held by hand and stirred for 1 minute to mix uniformly. While stirring the resulting mixture in a noodle making machine (model: MPC-2500; manufactured by Fuji Seiki Co., Ltd.), 500 g of water in which 10 g of sodium chloride was dissolved in advance was added little by little, and the mixture was further stirred for 10 minutes. The dough was prepared. Then, the tube-shaped dough (about 1 cm in diameter) extruded from the macaroni mold attached to the noodle making machine was cut into a 1 cm width, and this was cut into 150 to 160 ° C. frying oil [palm oil (product name: refined palm oil; ) And rice oil (product name: rice salad oil; manufactured by Borso Oil & Oil Co., Ltd.); palm oil / rice oil = 8/2 (mass ratio)] for 3 minutes to obtain snacks 1-17.
Figure JPOXMLDOC01-appb-T000002
Figure JPOXMLDOC01-appb-T000002
（２）スナック菓子の保存
　スナック菓子１～１７を１００ｍＬ容のポリエチレン製の袋に各３０ｇ入れて密封し、これを６０℃の恒温槽にて５日間及び１０日間各々保存した。 (2) Storage of snack confectionery Snack confectionery 1 to 17 were placed in 100 mL polyethylene bags, sealed, and stored in a thermostat at 60 ° C. for 5 days and 10 days, respectively.
（３）過酸化物価の測定
　スナック菓子１～１７の各々を粉砕したものを試料とし、ジエチルエーテルを用いて該試料から油分を抽出し、得られた油分について、「基準油脂分析試験法（ＩＩ）」（公益社団法人　日本油化学会編）の「２．４－１９９６過酸化物価（クロロホルム法）」に基づき過酸化物価（ｍｅｑ／ｋｇ）を測定した。測定は、スナック菓子の製造直後並びに５日間及び１０日間の保存後に行った。結果を表４に示す。 (3) Measurement of peroxide value Samples obtained by pulverizing each of snack snacks 1 to 17 were extracted from the sample using diethyl ether, and the obtained oil was analyzed in accordance with “Standard Oil Analysis Test Method (II)”. The peroxide value (meq / kg) was measured based on “2.4-1996 peroxide value (chloroform method)” (edited by Japan Oil Chemists' Society). The measurement was performed immediately after the production of the snack and after storage for 5 days and 10 days. The results are shown in Table 4.
（４）官能評価試験
　１０日間保存したスナック菓子１～１７を喫食し、スナック菓子に含まれる油脂が酸化することによる劣化風味について評価した。試験では、下記表３に示す評価基準に従い１０名のパネラーで評価を行ない、評点の平均点を求め、以下の基準にしたがって記号化した。結果を表４に示す。
◎：極めて良好　　平均点３．５以上
○：良好　　　　　平均点３．０以上、３．５未満
△：やや悪い　　　平均点２．０以上、３．０未満
×：悪い　　　　　平均点２．０未満 (4) Sensory evaluation test The snacks 1 to 17 stored for 10 days were eaten, and the deterioration flavor caused by oxidation of fats and oils contained in the snack was evaluated. In the test, evaluation was performed by 10 panelists in accordance with the evaluation criteria shown in Table 3 below, the average score was obtained, and symbolized according to the following criteria. The results are shown in Table 4.
◎: Very good Average score of 3.5 or more ○: Good Average score of 3.0 or more and less than 3.5 Δ: Slightly bad Average score of 2.0 or more and less than 3.0 ×: Poor Average score of less than 2.0
Figure JPOXMLDOC01-appb-T000003
Figure JPOXMLDOC01-appb-T000003
Figure JPOXMLDOC01-appb-T000004
Figure JPOXMLDOC01-appb-T000004
　表４の結果から明らかなように、本発明のＬ－アスコルビン酸脂肪酸エステル製剤１～６を添加して得られたスナック菓子１～１２は、６０℃、１０日間の保存後において過酸化物価が２０ｍｅｑ／ｋｇ未満に抑制され、官能評価は「○」以上の優れた結果であった。これに対し、Ｌ－アスコルビン酸脂肪酸エステル製剤７又は８を添加して得られたスナック菓子１３～１６及びＬ－アスコルビン酸脂肪酸エステル製剤を添加せずに製造したスナック菓子１７では、６０℃、１０日間の保存後において過酸化物価が２０ｍｅｑ／ｋｇ以上に上昇し、官能評価は「△」以下の結果であり、本発明のものに比べて劣っていた。 As apparent from the results in Table 4, the snacks 1 to 12 obtained by adding the L-ascorbic acid fatty acid ester formulations 1 to 6 of the present invention have a peroxide value of 20 meq after storage at 60 ° C. for 10 days. The sensory evaluation was an excellent result of “◯” or more. On the other hand, the snacks 13 to 16 obtained by adding the L-ascorbic acid fatty acid ester formulation 7 or 8 and the snack confections 17 manufactured without adding the L-ascorbic acid fatty acid ester formulation were heated at 60 ° C. for 10 days. After storage, the peroxide value increased to 20 meq / kg or more, and the sensory evaluation was a result of “Δ” or less, which was inferior to that of the present invention.

Claims (4)

  1. 　（ａ）Ｌ－アスコルビン酸脂肪酸エステルと（ｂ）常温で固体状の油脂とを含有する粒子を含む粉末状のＬ－アスコルビン酸脂肪酸エステル製剤。 (A) L-ascorbic acid fatty acid ester preparation containing particles containing (a) L-ascorbic acid fatty acid ester and (b) solid fat at normal temperature.
  2. 　（ａ）Ｌ－アスコルビン酸脂肪酸エステルと（ｂ）常温で固体状の油脂とを含有する溶融状態の混合物を冷却し、粉末化することにより得られるＬ－アスコルビン酸脂肪酸エステル製剤。 An L-ascorbic acid fatty acid ester preparation obtained by cooling and pulverizing a molten mixture containing (a) L-ascorbic acid fatty acid ester and (b) solid oil and fat at room temperature.
  3. 　飲食品の過酸化物価の上昇及び／又は風味劣化を抑制するための請求項１又は２に記載の製剤。 3. The preparation according to claim 1 or 2 for suppressing an increase in peroxide value and / or flavor deterioration of food and drink.
  4. 　（ａ）Ｌ－アスコルビン酸脂肪酸エステルと（ｂ）常温で固体状の油脂とを含有する溶融状態の混合物を冷却し、粉末化する工程を含むＬ－アスコルビン酸脂肪酸エステル製剤の製造方法。 (A) A method for producing an L-ascorbic acid fatty acid ester preparation comprising a step of cooling and pulverizing a molten mixture containing (a) L-ascorbic acid fatty acid ester and (b) a solid oil and fat at room temperature.
PCT/JP2016/050285 2015-02-26 2016-01-07 L-ascorbic acid fatty acid ester preparation WO2016136285A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2017501960A JP6796055B2 (en) 2015-02-26 2016-01-07 L-ascorbic acid fatty acid ester preparation

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2015036351 2015-02-26
JP2015-036351 2015-02-26

Publications (1)

Publication Number Publication Date
WO2016136285A1 true WO2016136285A1 (en) 2016-09-01

Family

ID=56788357

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2016/050285 WO2016136285A1 (en) 2015-02-26 2016-01-07 L-ascorbic acid fatty acid ester preparation

Country Status (2)

Country Link
JP (1) JP6796055B2 (en)
WO (1) WO2016136285A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2019123816A (en) * 2018-01-17 2019-07-25 ミヨシ油脂株式会社 Powdered oil and fat, and production method of powdered oil and fat
CN112480046A (en) * 2020-12-14 2021-03-12 上虞新和成生物化工有限公司 Green synthesis method of vitamin C higher fatty acid ester

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5748050B2 (en) * 1978-02-17 1982-10-14
JPS5944327A (en) * 1982-09-06 1984-03-12 Taiyo Kagaku Kk Stabilization of l-ascorbic acid and its salt
JPS643118A (en) * 1987-06-25 1989-01-06 Kawasaki Kasei Chem Ltd L-ascorbic acid preparation
JPS643119A (en) * 1987-06-25 1989-01-06 Kawasaki Kasei Chem Ltd L-ascorbic acid preparation
JPH09208986A (en) * 1996-02-02 1997-08-12 Okatsune Shoji Kk Antioxidizing agent preparation
JP2014155453A (en) * 2013-02-15 2014-08-28 Riken Vitamin Co Ltd Method of producing powder l-ascorbic acid fatty acid ester formulation

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004123636A (en) * 2002-10-03 2004-04-22 Nof Corp Doubly coated granule and method for producing the same
KR20150064234A (en) * 2011-05-16 2015-06-10 옴니액티브 헬스 테크놀로지스 리미티드 A water soluble composition comprising curcumin having enhanced bioavailability and process thereof
US8551551B2 (en) * 2012-01-06 2013-10-08 Perlman Consulting, Llc Stabilization of omega-3 fatty acids in saturated fat microparticles having low linoleic acid content
KR102121082B1 (en) * 2012-04-20 2020-06-10 디에스엠 아이피 어셋츠 비.브이. Solid, color-stable l-ascorbic acid compositions
JP5937917B2 (en) * 2012-08-07 2016-06-22 株式会社ファンケル L-ascorbic acid preparation

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5748050B2 (en) * 1978-02-17 1982-10-14
JPS5944327A (en) * 1982-09-06 1984-03-12 Taiyo Kagaku Kk Stabilization of l-ascorbic acid and its salt
JPS643118A (en) * 1987-06-25 1989-01-06 Kawasaki Kasei Chem Ltd L-ascorbic acid preparation
JPS643119A (en) * 1987-06-25 1989-01-06 Kawasaki Kasei Chem Ltd L-ascorbic acid preparation
JPH09208986A (en) * 1996-02-02 1997-08-12 Okatsune Shoji Kk Antioxidizing agent preparation
JP2014155453A (en) * 2013-02-15 2014-08-28 Riken Vitamin Co Ltd Method of producing powder l-ascorbic acid fatty acid ester formulation

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2019123816A (en) * 2018-01-17 2019-07-25 ミヨシ油脂株式会社 Powdered oil and fat, and production method of powdered oil and fat
JP7018771B2 (en) 2018-01-17 2022-02-14 ミヨシ油脂株式会社 Powdered fats and oils and manufacturing method of powdered fats and oils
CN112480046A (en) * 2020-12-14 2021-03-12 上虞新和成生物化工有限公司 Green synthesis method of vitamin C higher fatty acid ester

Also Published As

Publication number Publication date
JP6796055B2 (en) 2020-12-02
JPWO2016136285A1 (en) 2018-02-01

Similar Documents

Publication Publication Date Title
AU2003208010B2 (en) Oil/fat powder
CN106413412B (en) Emulsified composition
JP5892295B2 (en) Powdered oil and fat composition and method for producing the same
JP7017043B2 (en) Powdered fats and oils, foods and drinks containing them
JP6393468B2 (en) Oil composition containing polyunsaturated fatty acid
JP2007525976A (en) Method for preserving foods and compositions comprising one or more phytosterols and / or phytostanols useful for this purpose
WO2015053252A1 (en) Oil/fat composition containing polyunsaturated fatty acid
JP6175199B2 (en) Method for producing powdered fats and oils containing polyunsaturated fatty acids and method for producing baked products
KR101757002B1 (en) Eating-assisting oil or fat composition for persons who have difficulty in swallowing/chewing, and food for persons who have difficulty in swallowing/chewing
JP2018064553A (en) Method for producing powder oil, method for producing oil-containing food, and powder oil
JPH099939A (en) Food or feed containing natural antioxidant extracted from palm oil
JP6796055B2 (en) L-ascorbic acid fatty acid ester preparation
JP2013209493A (en) Powdery oil and fat, method for producing the same, powdery oil and fat-containing food, powdery oil and fat-containing oral medicinal product, and method for producing the powdery oil and fat-containing food
JP2015057979A (en) Fat having improved oxidation stability and method for producing the same
CA2892673A1 (en) Oxidatively-stabilized fats containing very long-chain omega-3 polyunsaturated fatty acids and uses thereof
JP2009189335A (en) Carotenoid-containing emulsion composition and method for producing the same
JP2017018018A (en) Plastic oil and fat composition and milled pie dough using the plastic oil and fat composition
JP4587613B2 (en) Method for producing oil-in-fat composition for roll-in
US20240237670A1 (en) Synthetic mct oils having triglycerides with saturated fatty acids and solid and semi-solid oil-derivatives for food applications
JP6664970B2 (en) Powdered fat composition for noodles
JP2005110510A (en) Powdery or granular emulsifier composition and food containing the same
JP7279467B2 (en) Oil composition for powdered oil, powdered oil
JP2023074064A (en) Powder emulsion composition
JP2017209109A (en) Emulsion composition
JP2004097113A (en) Fat-soluble vitamins-containing food and drink product, and method for stabilizing fat-soluble vitamins

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 16755035

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2017501960

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 16755035

Country of ref document: EP

Kind code of ref document: A1