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WO2015046365A1 - Préparation émulsifiable de substance liposoluble - Google Patents

Préparation émulsifiable de substance liposoluble Download PDF

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Publication number
WO2015046365A1
WO2015046365A1 PCT/JP2014/075499 JP2014075499W WO2015046365A1 WO 2015046365 A1 WO2015046365 A1 WO 2015046365A1 JP 2014075499 W JP2014075499 W JP 2014075499W WO 2015046365 A1 WO2015046365 A1 WO 2015046365A1
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WIPO (PCT)
Prior art keywords
fat
crocetin
ester
soluble
norbixin
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PCT/JP2014/075499
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English (en)
Japanese (ja)
Inventor
梓 西野
聡 脇坂
敬司 市原
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グリコ栄養食品株式会社
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Application filed by グリコ栄養食品株式会社 filed Critical グリコ栄養食品株式会社
Priority to JP2015516313A priority Critical patent/JP5934840B2/ja
Priority to CN201480048852.6A priority patent/CN105517575B/zh
Publication of WO2015046365A1 publication Critical patent/WO2015046365A1/fr

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    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7024—Esters of saccharides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
    • A23L2/52—Adding ingredients
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
    • A23L2/52—Adding ingredients
    • A23L2/58—Colouring agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A23L5/40—Colouring or decolouring of foods
    • A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
    • A23L5/43—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives
    • A23L5/44—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives using carotenoids or xanthophylls
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • A61K31/202—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having three or more double bonds, e.g. linolenic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/362—Polycarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/602—Glycosides, e.g. rutin
    • 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
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use

Definitions

  • the present invention relates to an emulsifiable preparation of a fat-soluble substance in which the emulsifiability of the fat-soluble substance is improved, or the emulsifiability and stability of the fat-soluble carotenoid are improved. Moreover, this invention relates to the food-drinks, cosmetics, a pharmaceutical, etc. using the emulsifiable preparation of the said fat-soluble substance.
  • Fat-soluble substances include various useful ingredients such as fat-soluble carotenoids, animal fats and oils, vegetable fats and oils, plant sterols, fat-soluble vitamins, and fragrances, and the range of use is in various fields such as foods, cosmetics, and pharmaceuticals.
  • fat-soluble carotenoids are naturally occurring terpenoid pigments that exhibit yellow to red color, and are used as coloring agents in various fields such as foods and drinks, cosmetics, and pharmaceuticals.
  • some fat-soluble carotenoids have not only been used as coloring agents but also have various physiological functions, and some are used as functional ingredients.
  • astaxanthin is known to have an excellent antioxidant effect and is effective in preventing skin aging, anti-inflammatory, eye strain recovery, and the like. Fucoxanthin is also known to be excellent in antioxidant action and effective for apoptosis-inducing activity, antitumor, anti-obesity and the like.
  • fat-soluble substances have low compatibility with water, and are conventionally used after being emulsified with a surfactant or the like to be dispersed in water.
  • some fat-soluble substances are difficult to emulsify or become unstable when emulsified.
  • fat-soluble carotenoids have an unstable structure and have a drawback that they are easily decomposed by oxygen, heat, moisture, etc. even when dispersed in an emulsified state.
  • the fat-soluble carotenoid is decomposed, not only the appearance of the product is impaired due to fading, but also the functional property of the carotenoid cannot be exhibited, so the stability of the fat-soluble carotenoid can be improved.
  • Planning is a major industrial issue. Therefore, establishment of a new technique for stably dispersing or emulsifying a fat-soluble substance in an aqueous system is required in the fields of foods and drinks, cosmetics, pharmaceuticals, and the like.
  • An object of the present invention is to provide an emulsifiable preparation of a fat-soluble substance with improved emulsifiability of the fat-soluble substance. Moreover, the objective of this invention is providing the emulsifiable preparation of the fat-soluble substance which improved stability with the emulsifiability of a fat-soluble substance. Furthermore, this invention is providing food / beverage products, cosmetics, a pharmaceutical, etc. with which the emulsifiability of a fat-soluble substance is improving, or both the emulsifiability and stability of a fat-soluble substance are improving.
  • the present inventors have found that at least one selected from the group consisting of crocetin, norbixin, and monoglycoside esters thereof is combined with a fat-soluble substance in the presence of water. It has been found that the emulsifiability of a fat-soluble substance can be remarkably improved by forming a body (micelle). It has also been found that the stability of a fat-soluble substance can be remarkably improved by coexisting with the complex (micelle) together with a diglycoside ester of crocetin and / or a diglycoside ester of norbixin. The present invention has been completed by further studies based on such knowledge.
  • Item 1 An emulsifiable preparation of a fat-soluble substance comprising (A) a fat-soluble substance and (B) at least one selected from the group consisting of crocetin, norbixin, and monoglycoside esters thereof as micelle constituents.
  • Item 2. Item 5. The emulsifiable preparation of a fat-soluble substance according to Item 1, further comprising (C) a diglycoside ester of crocetin and / or a diglycoside ester of norbixin.
  • Item 3. Item 3.
  • Item 4. Item 4. The emulsifiable preparation of a fat-soluble substance according to any one of Items 1 to 3, wherein the component (C) is crocin.
  • Item 7. The emulsifiable preparation of a fat-soluble substance according to any one of Items 1 to 6, wherein the component (A) is a fat-soluble carotenoid and is used as a pigment preparation.
  • Item 8. A hydrogel comprising a micelle comprising (A) a fat-soluble substance and (B) at least one selected from the group consisting of crocetin, norbixin, and monoglycoside esters thereof.
  • Item 9. Item 9.
  • Item 10 A food or drink containing a micelle comprising (A) a fat-soluble substance and (B) at least one selected from the group consisting of crocetin, norbixin, and monoglycoside esters thereof, or a dried product of the micelle.
  • Item 11 Item 11.
  • the food or drink according to Item 10 further comprising (C) a diglycoside ester of crocetin and / or a diglycoside ester of norbixin.
  • a cosmetic comprising (A) a fat-soluble substance and (B) at least one selected from the group consisting of crocetin, norbixin, and monoglycoside esters thereof, or a dried product of the micelle.
  • Item 13 Item 13.
  • a pharmaceutical comprising a micelle comprising (A) a fat-soluble substance and (B) at least one selected from the group consisting of crocetin, norbixin, and monoglycoside esters thereof, or a dried product of the micelle.
  • Item 15. Item 15.
  • Item 16 An emulsifying agent for fat-soluble substances, comprising as an active ingredient at least one selected from the group consisting of crocetin, norbixin, and monoglycoside esters thereof.
  • Item 17. The emulsifiability improver of a fat-soluble substance according to Item 16, which is a food or drink additive.
  • Item 19. Item 19.
  • Item 20. Use for manufacture of the emulsification improver of at least 1 sort (s) selected from the group which consists of crocetin, norbixin, and these monoglycoside ester.
  • Item 21. Use for the manufacture of an absorption enhancer of at least one fat-soluble substance selected from the group consisting of crocetin, norbixin, and monoglycoside esters thereof.
  • a method for emulsifying a fat-soluble substance comprising the step of emulsifying (A) a fat-soluble substance and (B) at least one selected from the group consisting of crocetin, norbixin, and monoglycoside esters thereof in the presence of water.
  • the surfactant is used by forming at least one selected from the group consisting of crocetin, norbixin, and monoglycoside esters thereof together with a fat-soluble substance to form these micelles.
  • the fat-soluble substance can be provided with excellent emulsifying properties.
  • hydrophilicity is imparted to the fat-soluble substance so that it can be easily absorbed, and the transdermal or enteral absorption of the fat-soluble substance can be improved. .
  • the storage stability means the property that the fat-soluble substance can be stably maintained by preventing discoloration of the fat-soluble substance and maintaining the functionality.
  • A shows the result of HPLC analysis of gardenia yellow pigments on a high molecular weight fraction obtained by gel filtration of a fat-soluble carotenoid emulsion (Example 1);
  • B shows a fat-soluble carotenoid aqueous dispersion ( As a result of HPLC analysis of gardenia yellow pigments for the low molecular weight fraction obtained by gel filtration in Example 1);
  • C shows the result of HPLC analysis of paprika oleoresin for the high molecular weight fraction. Show.
  • A shows the result of HPLC analysis of gardenia yellow pigments for the high molecular weight fraction obtained by gel filtration of the fat-soluble carotenoid emulsion (Example 2); B shows the high molecular weight fraction.
  • the result of having analyzed paprika oleoresin by HPLC is shown.
  • the high molecular weight fraction obtained by gel filtration of the fat-soluble carotenoid emulsion (Example 1) is subjected to a heat treatment at 50 ° C. for 20 hours and then subjected to HPLC for composition analysis.
  • a result of emulsifying a solution containing soybean oil and crocetin-monogenthiobioside ester or crocetin-digentiobide ester and observing the appearance thereof is shown.
  • the emulsifiable preparation of the fat-soluble substance of the present invention (hereinafter sometimes referred to as “the preparation of the present invention”) is the fat-soluble substance (hereinafter referred to as “component (A)”). And at least one selected from the group consisting of crocetin, crocetin-monoglycoside ester, and norbixin (hereinafter also referred to as “component (B)”) as a micelle component It is characterized by that.
  • the preparation of the present invention is a preparation used as a source of a fat-soluble substance by being blended with various products such as foods, cosmetics, and medicines.
  • the preparation of the present invention contains a fat-soluble carotenoid as a fat-soluble substance, a coloring agent or a pigment blended in various products such as foods, cosmetics, and pharmaceuticals as a functional source based on the fat-soluble carotenoid Used as a formulation.
  • a coloring agent or a pigment blended in various products such as foods, cosmetics, and pharmaceuticals as a functional source based on the fat-soluble carotenoid Used as a formulation.
  • Component (A) The preparation of the present invention contains a fat-soluble substance as component (A).
  • the fat-soluble substance used in the present invention is not particularly limited as long as it is fat-soluble and requires dispersibility in water.
  • fat-soluble carotenoids vegetable oils, animals Oils and fats, plant sterols, fat-soluble vitamins, higher fatty acids, essential oils and the like.
  • the fat-soluble carotenoid may be any of carotene, xanthophyll, or apocartoid.
  • carotene include ⁇ -carotene, ⁇ -carotene, ⁇ -carotene, lycopene, and the like.
  • xanthophylls include actinioerythritol, canthaxanthin, capsorubin, cucurbitaxanthin A, cryptocapsin, astaxanthin, fucoxanthin, lutein, zeaxanthin, capsanthin, ⁇ -cryptoxanthin, violaxanthin, and derivatives thereof (fatty acids Monoester or diester) and the like.
  • apocartoids examples include bixin, ⁇ -8′-apo-carotenal (apocarotenal), ⁇ -12′-apo-carotenal, derivatives thereof (such as esters with lower or higher alcohols), and the like. These fat-soluble carotenoids may be used individually by 1 type, and may be used in combination of 2 or more type.
  • the origin and production method of fat-soluble carotenoids are not particularly limited, and may be those derived from natural products such as plants, animals and microorganisms, and those obtained by fermentation or synthesis methods. Good.
  • natural pigments containing fat-soluble carotenoids can also be used as the component (A).
  • natural pigments include red pepper pigment (paprika pigment, paprika oleoresin), anato pigment, imo carotene, Dunaliella carotene, carrot carotene, shrimp pigment, krill pigment, orange pigment, crab pigment, corn pigment, Examples include tomato pigments, palm oil carotene, phafia pigments, Beninoki powder pigments, Haematococcus alga pigments, and marigold pigments.
  • vegetable oil examples include soybean oil, rice oil, salad oil, sesame oil, perilla oil, peanut oil, corn oil, rapeseed oil, coconut oil, palm oil, and hardened oils thereof. These vegetable fats and oils may be used alone or in combination of two or more.
  • animal fats include fish oil, beef tallow, pork tallow, chicken oil, and hardened oils thereof. These animal fats and oils may be used individually by 1 type, and may be used in combination of 2 or more type.
  • the plant sterol is a general term for sterols present in plants. Specifically, ⁇ -sitostanol, ⁇ -sitosterol, stigmasterol, campesterol, brassicasterol, brassicasterol, isofucosterol, 7- Examples thereof include stigmastenol, isofucostanol, stigmasteranol, 7-stigmasteranol, campestanol, cycloartenol, avenasterol, and glycosides thereof. These plant sterols may be used individually by 1 type, and may be used in combination of 2 or more type.
  • fat-soluble vitamin examples include vitamin A, vitamin D3, vitamin E, vitamin F, vitamin K, and the like. These fat-soluble vitamins may be used alone or in combination of two or more.
  • higher fatty acid examples include higher fatty acids having 12 to 30 carbon atoms such as docosahexaenoic acid (DHA), eicosapentaenoic acid (EPA), linoleic acid, and linolenic acid. These higher fatty acids may be used alone or in combination of two or more.
  • DHA docosahexaenoic acid
  • EPA eicosapentaenoic acid
  • linoleic acid examples include linolenic acid. These higher fatty acids may be used alone or in combination of two or more.
  • essential oil examples include peppermint oil, spearmint oil, bergamot oil, fennel oil, peppermint oil, lemon peel oil, and the like. These essential oils may be used individually by 1 type, and may be used in combination of 2 or more type.
  • the type of the fat-soluble substance may be appropriately selected according to the functionality to be provided in the preparation of the present invention.
  • the fat-soluble substance may be used alone or in combination of two or more.
  • fat-soluble carotenoids vegetable oils and fats, and fat-soluble vitamins are preferable from the viewpoint of more effectively improving dispersibility or emulsification.
  • the content of the component (A) is not particularly limited, and may be appropriately set according to the use of the preparation of the present invention, the type of fat-soluble substance, and the like.
  • 0.00001 to 99.9 % By weight preferably 0.00005 to 99% by weight, more preferably 0.0001 to 99% by weight.
  • Component (B) The preparation of the present invention contains at least one selected from the group consisting of crocetin, norbixin, and monoglycoside esters thereof as component (B) together with component (A). As shown in Test Example 1 to be described later, when the component (A) and the component (B) coexist in the presence of water, the component (B) and the component (A) are associated to form micelles. By forming such micelles, the emulsifiability of the fat-soluble substance can be remarkably improved.
  • Crocetin is a water-soluble carotenoid in which R 1 and R 2 are hydrogen atoms in the following general formula (1).
  • the crocetin used in the present invention may be a cis-trans isomer.
  • crocetin monoglycoside ester (that is, crocetin-monoglycoside ester) has a structure in which a sugar is bonded to one of the carboxyl groups of crocetin by an ester bond.
  • R 1 Is a water-soluble carotenoid in which R 2 is a sugar residue and R 2 is a hydrogen atom.
  • the saccharide bound to crocetin in the monoglycoside ester of crocetin may be a monosaccharide or an oligosaccharide such as a disaccharide, an acid saccharide, or a tetrasaccharide.
  • constituent sugars include monosaccharides such as glucose and (glucuronic acid); disaccharides such as gentiobiose, maltose, sucrose, and lactose (glucuronosylglucose and glucuronosylglucuronic acid); And trisaccharides such as maltotriose, raffinose, panose, glucuronosyl gentiobiose, glucosyl gentiobiose, and the like.
  • monosaccharides such as glucose and (glucuronic acid)
  • disaccharides such as gentiobiose, maltose, sucrose, and lactose (glucuronosylglucose and glucuronosylglucuronic acid)
  • trisaccharides such as maltotriose, raffinose, panose, glucuronosyl gentiobiose, glucosyl gentiobiose, and the like.
  • Examples of the saccharide having an ester bond to crocetin include monosaccharides and disaccharides, more preferably glucose and gentiobiose, and particularly preferably gentiobiose (that is, crocetin-monogenthiobioside ester; crocin-3).
  • the position of the sugar residue bonded to the carboxyl group of crocetin is not particularly limited, but the hydroxyl group at the 1-position of the sugar may be ester-bonded to the carboxyl group of crocetin. preferable.
  • the monoglycoside ester of crocetin used in the present invention may be a cis-trans isomer.
  • Norbixin is a water-soluble carotenoid in which R 3 and R 4 are hydrogen atoms in the following general formula (2).
  • the norbixin used in the present invention may be a cis-trans isomer.
  • Norubixin monoglycoside ester (ie, norbixin-monoglycoside ester) has a structure in which a sugar is bonded to one of the carboxyl groups of norbixin by an ester bond.
  • R 3 And R 4 is a water-soluble carotenoid in which one is a sugar residue and the other is a hydrogen atom.
  • the norbixin-monoglycoside ester the kind of sugar bonded to crocetin, the preferred one, the binding site and the like are the same as in the case of the monoglycoside ester of crocetin.
  • the monoglycoside ester of norbixin used in the present invention may be a cis-trans isomer.
  • components (B) are not particularly limited in their origin and production method, and may be those extracted from natural products such as plants, animals, and microorganisms, and obtained by fermentation methods or synthetic methods. It may be what was made.
  • crocetin, norbixin, crocetin-monoglycoside ester, more preferably crocetin, norbixin, crocetin-monogenthiobioside ester are preferable from the viewpoint of further improving the emulsifiability of the fat-soluble substance.
  • Crocin-3 crocetin-monoglycoside ester, more preferably crocetin-monogentiobioside ester can be mentioned.
  • natural pigments containing at least one of crocetin, norbixin, and monoglycoside esters thereof can also be used as component (B).
  • natural pigments containing at least one of crocetin, norbixin, and monoglycoside esters thereof can also be used as component (B).
  • gardenia yellow and saffron pigments are known to contain crocetin and crocetin-monogentiobioside ester, and gardenia yellow and / or saffron pigments are preferably used as component (B). be able to.
  • component (B) one type may be selected from crocetin, norbixin, and monoglycoside esters thereof, or two or more types may be used in combination.
  • the content of the component (B) is not particularly limited as long as it can form micelles with the fat-soluble substance.
  • the total amount of the component (B) 0.0005 to 1000 parts by weight, preferably 0.001 to 500 parts by weight, and more preferably 0.002 to 200 parts by weight.
  • the content of the component (B) is 0.5 ⁇ 10 ⁇ 5 to 10 g as the color value (E 10% 1 cm 2 ) of 5,000 per 1 g of the component (A), preferably 5,000 Examples include 0.1 ⁇ 10 ⁇ 4 to 5 g, and more preferably 0.2 ⁇ 10 ⁇ 4 to 2 g.
  • component (C) Component
  • the preparation of the present invention further includes diglycoside ester of crocetin and / or diglycoside ester of norbixin (hereinafter referred to as “component (C)”. May be included).
  • component (C) diglycoside ester of crocetin and / or diglycoside ester of norbixin
  • the stability of the fat-soluble substance can be remarkably improved.
  • the component (C) was solubilized in water without being associated with the micelles of the components (A) and (B) in the presence of water. It exists in a state and plays the role which improves stability of a fat-soluble substance.
  • the crocetin diglycoside ester (that is, crocetin-diglycoside ester) has a structure in which a sugar is bonded to each of two carboxyl groups of crocetin by an ester bond.
  • the types of sugars bonded to the crocetin diglycoside ester, preferred ones, binding sites and the like are the same as those for the monoglycoside ester of crocetin.
  • the two sugar residues bonded in the crocetin diglycoside ester may be the same or different from each other.
  • the diglycoside ester of crocetin is preferably one in which two disaccharides are ester-bonded to crocetin, one in which monosaccharide and disaccharide are each ester-bonded to crocetin, or two monosaccharides are ester-bonded to crocetin. More preferably, crocetin has two gentiobiose ester-linked (crocin; crocetin-digentiobioside ester), crocetin has gentiobiose and glucose ester-linked (crocetin-monogentiobio) Side-monoglucoside ester), crocetin in which two glucoses are ester-linked (crocetin-diglucoside ester); particularly preferably crocin.
  • the crocetin diglycoside ester used in the present invention may be a cis-trans isomer.
  • the diglycoside ester of norbixin (ie, norbixin-diglycoside ester) has a structure in which a sugar is bonded to each of two carboxyl groups of norbixin by an ester bond.
  • R 3 and A water-soluble carotenoid in which R 4 is a sugar residue are the same as those for the monoglycoside ester of crocetin.
  • the two sugar residues bonded in the diglycoside ester of norbixin may be the same or different.
  • the diglycoside ester of norbixin used in the present invention may be a cis-trans isomer.
  • crocetin diglycoside ester is preferable, and crocin is more preferable from the viewpoint of further improving the stability of the fat-soluble substance.
  • natural pigments containing crocetin diglycoside ester and / or norbixin diglycoside ester can also be used as component (C).
  • natural pigments containing crocetin diglycoside ester and / or norbixin diglycoside ester can also be used as component (C).
  • gardenia yellow pigment and saffron pigment contain crocin in addition to the component (B), and gardenia yellow pigment and / or saffron pigment are used as the source of the components (B) and (C). Therefore, since both the emulsifiability and stability of the fat-soluble substance excellent in the fat-soluble carotenoid can be provided, it can be suitably used in the fat-soluble carotenoid water-dispersible preparation of the present invention.
  • one kind may be selected from crocetin diglycoside ester and norbixin diglycoside ester, or two or more kinds may be used in combination. .
  • the content of the component (C) is not particularly limited.
  • the total amount of the component (C) is 0.0005 to 1000 parts by weight, preferably 0, per 100 parts by weight of the component (A). 0.001 to 500 parts by weight, more preferably 0.002 to 200 parts by weight.
  • the content of the component (C) is 0.5 ⁇ 10 ⁇ 5 to 10 g as the color value (E 10% 1 cm 2 ) of 5,000 per 1 g of the component (A), preferably 5,000 Examples include 0.1 ⁇ 10 ⁇ 4 to 5 g, and more preferably 0.2 ⁇ 10 ⁇ 4 to 2 g.
  • the content of the gardenia yellow and / or saffron pigment is the above (A).
  • the amount is 0.0005 to 1000 parts by weight, preferably 0.001 to 500 parts by weight, and more preferably 0.002 to 200 parts by weight per 100 parts by weight of the component.
  • the gardenia yellow and / or saffron dye has a color value (E) per 1 g of the component (A).
  • 10% 1 cm ) 5,000 is 0.5 ⁇ 10 ⁇ 5 to 10 g, preferably 0.1 ⁇ 10 ⁇ 4 to 5 g, and more preferably 0.2 ⁇ 10 ⁇ 4 to 2 g.
  • the preparation of the present invention may contain water as a dispersion medium for the components (A) and (B) in addition to the components described above.
  • an antioxidant, a thickener, a chelating agent, an emulsifying aid, a lower alcohol, a polyhydric alcohol, a pH adjuster, a buffer are added as necessary, as long as the effects of the present invention are not hindered.
  • An additive component such as an agent may be included.
  • the preparation of the present invention can stably emulsify a fat-soluble substance in water without containing a surfactant or an emulsifier, but may contain a surfactant or an emulsifier as necessary.
  • Form of the present invention preparation is a preparation in which the fat-soluble substance exhibits good emulsifiability when added to water or a composition containing water by including the component (A) and the component (B) as micelle constituents.
  • the preparation of the present invention may contain an emulsified preparation that contains water as a dispersion medium and is in an emulsified state, or is a self-emulsifying preparation that does not contain water and is in a non-emulsified state. May be.
  • the component (A) and the component (B) are present in the form of micelles.
  • the component (A) and the component (B) do not form micelles, but when added to and mixed with water or a composition containing water, the component (A) and the component (B) These micelles are formed, and the fat-soluble substance can be uniformly emulsified.
  • the preparation of the present invention is an emulsified preparation in an emulsified state
  • it may be not only liquid but also semi-solid such as paste.
  • this invention formulation is a formulation for self-emulsification in the non-emulsified state, solid forms, such as a powder form and a granular form, are mentioned as the form.
  • the preparation of the present invention is an emulsion preparation in which the (A) component and the (B) component are in the emulsified state by forming micelles, the water, the (A) component, the (B) component, and It can be prepared by adding and mixing component (C) and other additive components as necessary.
  • component (C) and other additive components in the presence of water, when the components (A) and (B) are added and coexisted in the presence of water, they are mixed and emulsified to form micelles of the components (A) and (B).
  • the preparation is uniformly emulsified.
  • the component (C) may be partly hydrolyzed and converted into the component (B) by receiving heat or physical stimulation in the emulsifying step, so that the component (B) can be used instead of the component (B).
  • the component (C) is added as a raw material and dispersed or emulsified so that a part of the component (C) is hydrolyzed in the presence of the component (A), the component (B) is added. At least, micelles of component (A) and component (B) can be formed.
  • component (A) is co-existing with component (B) while forming micelles with a surfactant, emulsifier, etc., micelles of component (A) and component (B) may not be formed, Since it may take time to form, from the viewpoint of promoting micelle formation of the component (A) and the component (B), at the time of producing the preparation of the present invention, the component (A) and ( When the component (B) is allowed to coexist, it is desirable that the component (A) is kept in a state in which micelles are not formed with a surfactant or an emulsifier.
  • the preparation of the present invention is a preparation for self-emulsification in which the component (A) and the component (B) do not form micelles
  • the preparation is a semi-solid or solid form
  • the emulsion preparation is prepared by the above method. After the production, it can be prepared by removing the water and subjecting it to a molding treatment such as powder or granule, if necessary.
  • a self-emulsifying preparation it should also be prepared by simply adding (A) component, (B) component, and (C) component, if necessary, other additive components and mixing. Can do.
  • the preparation of the present invention is used as an additive for supplying a fat-soluble substance to various products such as foods and drinks, cosmetics and pharmaceuticals.
  • a fat-soluble carotenoid is used as the fat-soluble substance
  • the preparation of the present invention is used as a pigment preparation (coloring agent) added to various products such as foods and drinks, cosmetics and pharmaceuticals.
  • this invention formulation can emulsify a fat-soluble substance stably, it can be used for the said various products as a supply source of the fat-soluble substance whose absorbency was improved.
  • the preparation of the present invention is used for the purpose of imparting the physiological function.
  • a functional additive it can also be used by adding to various foods, cosmetics, pharmaceuticals and the like.
  • the product to be added preferably contains water, but a product not containing water can also be added.
  • a product not containing water can also be added.
  • the preparation of the present invention can be preferably used.
  • the preparation of the present invention can also be used as a source of a fat-soluble substance with enhanced absorbability. Therefore, even if water is not contained in the product to be added, the fat to the product is added. It can be used for the purpose of imparting physiological functionality with a soluble substance.
  • hydrogel of the present invention is characterized by containing a micelle containing the components (A) and (B) and a gelling agent.
  • a micelle containing the components (A) and (B) and a gelling agent.
  • component (A) and component (B) used in the hydrogel of the present invention are the same as in the case of “1. Emulsifiable preparation of fat-soluble substance”.
  • the content of the component (A) for example, it may be 0.00001 to 50% by weight, preferably 0.00005 to 45% by weight, and more preferably 0.0001 to 40%. % By weight.
  • the hydrogel of the present invention may contain the component (C). By containing the component (C), it becomes possible to improve the stability of the fat-soluble carotenoid in the hydrogel.
  • the type of the component (C) used in the hydrogel of the present invention, the ratio of the component (C) to the component (A), and the like are the same as in the case of “1. Emulsifiable preparation of fat-soluble substance”.
  • the type of gelling agent contained in the hydrogel of the present invention is not particularly limited, and can be edible, cosmetically acceptable, or pharmaceutically acceptable depending on the use of the hydrogel. What is necessary is just to select suitably.
  • Specific examples of gelling agents include carrageenan, gellan gum, locust bean gum, pectin, sodium alginate, gelatin, tragacanth, agar, xanthan, gum arabic, guar gum, tamarind gum, starch, dextrin, cellulose, curdlan, pullulan, Guar gum derivative, cellulose derivative, ⁇ -glucan, psyllium seed gum, microgel, carbomer, PVP, PVA, silica, bentonite, dextrin fatty acid ester, inulin fatty acid ester, silicone-based thickening gelling agent, polyamide resin, amino acid-based gelation Agents, salt-resistant thickeners and the like.
  • These gelling agents may be used individually by 1 type, and may be used in combination of
  • the content of the gelling agent may be appropriately set according to the type of gelling agent to be used, the gel strength to be imparted, fluidity, and the like. For example, 0.0001 to 98 % By weight, preferably 0.0005 to 97% by weight, more preferably 0.001 to 95% by weight.
  • the hydrogel of the present invention includes sweeteners, fruit juices, fragrances, antioxidants, pH adjusters, pharmacological ingredients, moisturizing ingredients, whitening ingredients, etc., depending on the use of the hydrogel. It may be.
  • the method for producing the hydrogel of the present invention is not particularly limited as long as the component (A) and the component (B) coexist in the hydrogel and form micelles.
  • the method for producing the hydrogel of the present invention preferably includes a method of gelling after mixing water in which a gelling agent is dissolved, the preparation of the present invention, and other additive components as necessary. .
  • the preparation of the present invention after mixing the water in which the gelling agent is dissolved, the component (A), the component (B), and the component (C), if necessary, other additive components Even if it is the method of making it gelatinize, the hydrogel of this invention can be obtained.
  • the component (A) when the component (A) coexists with the component (B) in the state where the component is formed with a surfactant or an emulsifier, micelles of the component (A) and the component (B) are formed. Or when it takes time until the micelles are formed, when the hydrogel of the present invention is produced without using the preparation of the present invention, the component (A) When the component (B) is allowed to coexist, it is desirable that the component (A) is kept in a state in which micelles are not formed with a surfactant or an emulsifier.
  • the fat-soluble substance is uniformly emulsified, has an excellent appearance, and further has improved absorbability of the fat-soluble substance (particularly the fat-soluble carotenoid). It can be used in fields such as cosmetics and pharmaceuticals.
  • a product using the hydrogel of the present invention in the food and beverage field, jelly, a beverage blended with hydrogel, yogurt blended with hydrogel, and the like can be mentioned.
  • a beverage blended with hydrogel, yogurt blended with hydrogel, and the like can be mentioned.
  • gel-like cosmetics, sheet-like pack cosmetics, and the like can be given.
  • sheet-like patches and the like can be mentioned.
  • the food / beverage products, cosmetics, and pharmaceutical products of the present invention are characterized by containing micelles containing the component (A) and the component (B) or a dried product of the micelles.
  • the food / beverage products, cosmetics and pharmaceuticals of the present invention include the hydrogel or a form containing it, as well as a form not containing hydrogel.
  • fat-soluble substances are uniformly dispersed in the whole product or a predetermined part by including the micelle containing the component (A) and the component (B) or the dried product of the micelle. And can have excellent appearance properties.
  • the absorbability of fat-soluble substances is improved, so that the functionality of the fat-soluble substances can be effectively enjoyed. You can also.
  • component (A) and component (B) used in the food and drink, cosmetics and pharmaceuticals of the present invention, the ratio thereof, and the like are the same as in the case of “1. Emulsifiable preparation of fat-soluble substance”. It is.
  • the content of the micelle containing the component (A) and the component (B) or the dried product of the micelle, the type of the component (A) to be used, the hydrogel Although it may be set as appropriate according to the degree of coloring, the functionality to be provided to the hydrogel, etc., for example, it is 0.00001 to 50% by weight, preferably 0.00005 in terms of the content of the component (A). To 45% by weight, more preferably 0.0001 to 40% by weight.
  • the food / beverage products, cosmetics, and pharmaceuticals of the present invention may contain the component (C).
  • the stability of the fat-soluble substance can be improved.
  • the ratio of (C) component with respect to (A) component, etc. said "1. Emulsifiable preparation of fat-soluble substance”. Same as the case.
  • the micelle containing the component (A) and the component (B) or a dried product of the micelles is contained. It is not particularly limited as long as it can be made.
  • the method for producing the food / beverage products, cosmetics and pharmaceuticals of the present invention preferably includes a method of mixing the above-mentioned preparation of the present invention into the raw materials of the food / beverage products, cosmetics and pharmaceuticals and processing them into a desired form.
  • the (A) component and the (B) component form micelles by coexisting in the presence of water, and the emulsifiability is improved, so the ingredients (A) and (B) in the raw materials for food and drink, cosmetics, and pharmaceuticals
  • the micelles containing the components are once dispersed, even if water is removed by drying or the like, the fat-soluble substance becomes a dried product of micelles and maintains a uniformly dispersed state. Therefore, the food and drink, cosmetics, and pharmaceuticals of the present invention are not limited to forms containing water such as liquid, hydrogel, paste, etc., but dry micelles containing the components (A) and (B). It may be in a solid state.
  • supplements such as a tablet, a granule, a powder agent, a capsule, a soft capsule, etc .; , Yakitori sauce, salmon grilled sauce, dumpling sauce, dumpling sauce, sauces (tonkatsu sauce, curry sauce, white sauce, demiglace sauce, tomato sauce, shrimp sauce, etc.), soups (kimchi hot pot soup, ramen soup) , Consommé soup, potage soup, clam chowder, etc.) and processed foods using these liquid seasonings; dairy products such as yogurt and cheese; jams such as strawberry jam, apple jam, blueberry jam and marmalade ; Processed meat products such as ham, sausage, grilled pork; Fish sausage, fish meat Fish, fish paste, salmon, bamboo rings, hampen, fried satsuma, and other marine products; salted, miso pickled, pickled in salmon, pickled in pickles, shallow pickled, pickled in
  • the form of the cosmetic of the present invention is not particularly limited, and examples thereof include emulsions, creams, lotions, packs, cosmetic liquids, skin cleansing agents, makeup cosmetics, and the like.
  • the form of the pharmaceutical product of the present invention is not particularly limited, but for example, preparations for internal use such as tablets, granules, powders, capsules, soft capsules, syrups, etc .; external preparations, inhalants, suppositories, etc. Skin or transmucosal preparations; injections and the like.
  • Fat-soluble carotenoid emulsifier / absorptive improver As described above, the component (B) associates with a fat-soluble substance in the presence of water to form micelles, thereby improving the emulsifiability and absorbability of the fat-soluble substance. In order to improve, it can also be used as an emulsification improver of a fat-soluble substance or an absorbency improver of a fat-soluble substance.
  • the fat-soluble substance emulsification improver and the fat-soluble substance absorbability improver of the present invention are added to various products containing water and a fat-soluble substance to improve the emulsifiability or absorbability of the fat-soluble carotenoid. Used in.
  • the product to which the emulsifiability improver of the fat-soluble substance and the absorbency improver of the fat-soluble substance of the present invention are applied is not particularly limited as long as it contains water and the fat-soluble substance. Examples include pigment preparations containing fat-soluble carotenoids, raw materials for foods and drinks, raw materials for cosmetics, and raw materials for pharmaceuticals.
  • the fat-soluble substance emulsification improver and the fat-soluble substance absorbability improver of the present invention are food and drink additives for improving the emulsifiability of the fat-soluble substance. Or, it is used as a food or drink additive for improving the absorption of fat-soluble substances.
  • the type of the component (B) used, the type of the fat-soluble substance to be applied, the use mode, etc. are as described above. is there.
  • Test Example 1 Evaluation of aqueous dispersion of fat-soluble carotenoid (1) Emulsification of fat-soluble carotenoid with crocetin-monogenthiobioside ester, crocetin, and norbixin 0.1 g of paprika oleoresin containing fat-soluble carotenoid was added to 20 g of water and stirred. It was completely separated and did not mix.
  • Paprika oleoresin is a fat-soluble substance extracted from paprika or capsicum, and contains about 10% by weight of fat-soluble carotenoids such as capsanthin, ⁇ -cryptoxanthin, ⁇ -carotene, zeaxanthin, capsorbine.
  • this mixture of paprika oleoresin and water was mixed with gardenia yellow starch [crocin 40% by weight, crocetin-monogenthiobioside ester 18% by weight, other crocin analogs (crocetin-digentiobide ester, crocetin-monogenthiobioside] -Monoglucoside ester, crocetin-diglucoside ester, crocetin-monoglucoside ester, etc.) 42 wt%], crocetin, or norbixin 0.16g was added and stirring was continued. After about 10 minutes, paprika oleoresin was dissolved in water. In a uniform dispersion state (emulsified state). Thereafter, the liquid was kept still, but it was not separated, and a uniform dispersed state (emulsified state) was maintained.
  • gardenia yellow starch [crocin 40% by weight, crocetin-monogenthiobioside ester 18% by weight, other crocin analogs
  • Capsanthin the main carotenoid of paprika oleoresin, has a molecular weight of 584, crocetin-monogentiobioside ester has a molecular weight of 652, and crocetin has a molecular weight of 328.
  • capsanthin and crocetin-monogenthiobioside ester or crocetin are eluted simultaneously in the high molecular weight fraction.
  • the orange color derived from paprika oleoresin was also confirmed visually in the high molecular weight fraction.
  • the high molecular weight fraction and the low molecular weight fraction were analyzed by HPLC. Two types of HPLC analysis were performed: Method 1 below, which is suitable for analysis of gardenia yellow, and Method 2 below, which is suitable for analysis of paprika oleoresin.
  • ⁇ Method 2 Analysis of paprika oleoresin>
  • Low molecular fraction or high molecular weight fraction 100 ⁇ l, 50 wt% potassium hydroxide aqueous solution 10 ⁇ l and methanol 900 ⁇ l were mixed and allowed to stand at room temperature for 1 hour for saponification. Thereafter, the saponified solution was added to a 1: 1 mixed solvent of hexane and dimethyl ether and stirred to recover the ether layer.
  • the obtained ether layer was dried and solidified by centrifugal concentration, and then dissolved in 100 ⁇ l of the following eluent for HPLC analysis to prepare a sample for HPLC analysis.
  • the sample for HPLC analysis was subjected to HPLC analysis under the following conditions.
  • FIG. 2A shows the result of HPLC analysis of the high molecular weight fraction by method 1
  • FIG. 2B shows the result of HPLC analysis of the low molecular weight fraction by method 1
  • FIG. 2C shows the method of high molecular weight fraction.
  • 2 shows the result of HPLC analysis.
  • FIGS. 2A and 2C fat-soluble carotenoids derived from paprika oleoresin and crocetin-monogentiobioside ester were detected from the high molecular weight fraction. This result indicates that a fat-soluble carotenoid and a crocetin-monogenthiobioside ester complex are formed, and the complex is dispersed in water as micelles.
  • crocin was not detected in the high molecular weight fraction, but was detected alone in the low molecular weight fraction, and was not used for micelle formation, and was presumed to be in a single dispersed state.
  • the low molecular fraction was analyzed by HPLC in Method 2, no paprika oleoresin-derived fat-soluble carotenoid was detected. From the above results, it was revealed that crocetin-monogenthiobioside ester improves the emulsifiability of fat-soluble carotenoids by forming micelles with fat-soluble carotenoids in paprika oleoresin.
  • FIG. 3A shows the result of HPLC analysis of the high molecular weight fraction by Method 1
  • FIG. 3B shows the result of HPLC analysis of the high molecular weight fraction by Method 2.
  • This result also confirmed that crocetin formed micelles with fat-soluble carotenoids), and it became clear that the emulsifiability of fat-soluble carotenoids was improved by forming a complex (micelle) with crocetin. .
  • Norbixin monoglycoside ester was not tested, but norbixin itself improved the water-dispersibility of fat-soluble carotenoids (Example 3), both crocetin and crocetin-monogentiobioside ester
  • monoglycoside esters of norbixin can also form micelles with fat-soluble carotenoids and improve their emulsifiability. Is done. Therefore, the above results revealed that crocetin, norbixin, and their monoglycoside esters can improve the emulsifiability of fat-soluble carotenoids.
  • Test Example 2 Evaluation of stability of fat-soluble carotenoid (1) Evaluation of stability improvement effect by crocin-1 High molecular weight fraction obtained by gel filtration of fat-soluble carotenoid emulsion (Example 1) in PD-10 column in Test Example 1 (containing micelle of fat-soluble carotenoid and crocetin-monogenthiobioside ester) Then, crocin was added and heat treatment was performed at 50 ° C. for 20 hours. For comparison, heat treatment was performed under the same conditions without adding crocin. After the heat treatment, the HPLC analysis of the method 2 was performed, and the fat-soluble carotenoid was measured.
  • Examples 7 to 10 20 g of water was added to 20 g of water, [40% by weight of crocin, 18% by weight of crocetin-monogentiobioside ester, and other crocin analogs (crocetin-digentiobide ester, crocetin-monogentiobioside- Monoglycoside ester, crocetin-diglucoside ester, crocetin-monoglucoside ester, etc.) 42% by weight] were added in predetermined amounts shown in Table 2 and stirred to emulsify paprika oleoresin in water.
  • each paprika oleoresin-containing preparation prepared above is stored at 50 ° C for 45 hours, and the capsanthin remaining in each paprika oleoresin-containing preparation (one of the fat-soluble carotenoids contained in paprika oleoresin) is measured over time.
  • the residual ratio of capsanthin was calculated, and this was defined as the residual ratio of fat-soluble carotenoid.
  • Capsanthin was measured by the HPLC analysis of Method 2 above.
  • Table 2 shows the results obtained.
  • paprika oleoresin was dispersed in water using a surfactant (Comparative Examples 2 to 4)
  • the residual ratio of the fat-soluble carotenoid was significantly reduced in the accelerated test, and the stability of the fat-soluble carotenoid was insufficient.
  • the fat-soluble carotenoid derived from paprika oleoresin has already formed micelles with the surfactant. Even when added, it is considered that the fat-soluble carotenoid could not form a complex (micelle) with the crocetin-monogentiobioside ester contained in gardenia yellow.
  • Example 11 0.16 g of gardenia yellow pigment (40% by weight of crocin, 18% by weight of crocetin-monogentiobioside ester, 42% by weight of other crocin analogs) and 0.1 g of astaxanthin were added to 20 g of water. Astaxanthin was emulsified by stirring.
  • Table 3 shows the obtained results. From this result, even when astaxanthin is used as a fat-soluble terpenoid, stability cannot be improved with a normal surfactant, but crocetin-monogentiobioside ester and astaxanthin can be obtained using gardenia yellow. It was revealed that the stability of astaxanthin can be remarkably improved by forming a complex (micelle) and coexisting crocin contained in gardenia yellow.
  • Test Example 3 Evaluation of emulsifiability of vegetable oil (1) Emulsification of vegetable oil with crocetin-monogentiobioside ester A solution containing soybean oil and crocetin-monogentiobioside ester or crocetin-digentiobioside ester was prepared so as to have the composition shown in Table 4, and vortexed. The emulsification treatment was performed, and then the appearance was observed.
  • the obtained soybean oil emulsion was diluted 2 times with water, and 1 ml of the obtained diluted solution was subjected to gel filtration using a PD-10 column (GE Healthcare Life Sciences) and eluted with water to 1 ml. Each sample was collected and fractionated into fractions 1 to 10 in order of elution.
  • each obtained fraction is shown in FIG. As can be seen from FIG. 6, the fraction containing the emulsion was observed in fraction 2 (the second fraction collected). In addition, fractions 3 and 4 were yellow, and yellow was light in fraction 6, but yellow was again present in fractions 7 and above.
  • the solution before the emulsification treatment, the obtained fraction 2, the mixed fraction of fractions 3 to 5, and the mixed fraction after fraction 7 were analyzed by HPLC.
  • the HPLC analysis was performed under the same conditions as in Method 1 used for the analysis of gardenia yellow.
  • soybean oil was contained about the fraction 2, after removing soybean oil (breaking an emulsion), it used for the HPLC analysis. Soybean oil was removed by passing fraction 2 through a column (Sep-Pak C18 Cartridges manufactured by Waters), adsorbing oily components to the column, and then eluting components other than soybean oil with methanol.
  • Test Example 4 Evaluation of emulsifiability of vegetable oils and fats
  • the raw materials shown in Table 6 were mixed and emulsified for 5 minutes at 10,000 rpm using a homogenizer (TK homomixer MARKII, manufactured by Primix Co., Ltd.).
  • TK homomixer MARKII manufactured by Primix Co., Ltd.
  • a preparation in which rapeseed oil was uniformly emulsified was obtained.
  • the average particle size of micelles was measured with a laser diffraction particle size distribution analyzer (SALD2100, Shimadzu Corporation) using water as a diluent solvent and setting the refractive index to 1.60-0.10i.
  • SALD2100 laser diffraction particle size distribution analyzer
  • Test Example 5 Evaluation of emulsifiability of d- ⁇ -tocopherol
  • the raw materials shown in Table 7 were mixed and emulsified at 10,000 rpm for 5 minutes using a homogenizer (TK homomixer MARK II, manufactured by Primix Co., Ltd.).
  • TK homomixer MARK II manufactured by Primix Co., Ltd.
  • a preparation in which d- ⁇ -tocopherol was uniformly emulsified was obtained.
  • the average particle size of micelles was measured with a laser diffraction particle size distribution analyzer (SALD2100, Shimadzu Corporation) using water as a diluent solvent and setting the refractive index to 1.60-0.10i.
  • SALD2100 laser diffraction particle size distribution analyzer
  • Example 1 Beverage Using the paprika oleoresin-containing preparation obtained in Example 8, an orangeade was prepared according to the formulation shown in Table 8 below. Specifically, each raw material shown in Table 8 was mixed and heated in a container to obtain an orangeade. This orangeade contains 5 mg of paprika oleoresin derived from a paprika oleoresin water dispersible formulation.
  • Example 2 Jelly Beverage Using the paprika oleoresin-containing preparation obtained in Example 8, an orange-flavored jelly drink was prepared according to the formulation shown in Table 9 below. Specifically, saccharides and agar are added to water and dissolved by heating, and then other raw materials are dissolved. Next, after adjusting to a predetermined pH, after passing through a primary sterilization step and filling an aluminum pouch with a spout 80 g / pack at a time, secondary sterilization was further performed to obtain a jelly beverage. 80 g of orange-flavored jelly beverage contains 4 mg of paprika oleoresin derived from a water-dispersible preparation of paprika oleoresin.
  • Production Example 4 Cosmetic liquid Using the paprika oleoresin-containing preparation obtained in Example 8, a cosmetic liquid having the composition shown in Table 11 below was prepared according to a conventional method.
  • Example 5 Energy drink Using the paprika oleoresin-containing preparation obtained in Example 8, an energy drink having the composition shown in Table 12 below was prepared. Specifically, energy drinks were obtained by mixing the raw materials shown in Table 12 and heating and filling the containers. This energy drink contains 5 mg of paprika oleoresin derived from a paprika oleoresin-containing preparation.
  • Example 9 Sports drink Using the paprika oleoresin-containing preparation obtained in Example 8, a sports drink was prepared according to the formulation shown in Table 13 below. Specifically, sports drinks were obtained by mixing the raw materials shown in Table 13 and heating and filling the containers. This sports drink contains 5 mg of paprika oleoresin derived from a paprika oleoresin water-containing preparation.

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  • Toxicology (AREA)
  • Biophysics (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Cosmetics (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Medicines Containing Plant Substances (AREA)

Abstract

　La présente invention a pour but de fournir une préparation émulsifiable d'une substance liposoluble qui améliore l'émulsification de la substance liposoluble. L'aptitude à la dispersion de l'eau d'un caroténoïde liposoluble peut être améliorée considérablement en formant un complexe (micelle) d'au moins un choisi dans le groupe constitué par la crocétine, la norbixine et les esters de monoglycoside de ceux-ci, et d'un caroténoïde liposoluble en présence d'eau.
PCT/JP2014/075499 2013-09-25 2014-09-25 Préparation émulsifiable de substance liposoluble WO2015046365A1 (fr)

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JP2015516313A JP5934840B2 (ja) 2013-09-25 2014-09-25 脂溶性物質の乳化性製剤
CN201480048852.6A CN105517575B (zh) 2013-09-25 2014-09-25 脂溶性物质的乳化性制剂

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JP2013198613 2013-09-25
JP2013-198613 2013-09-25

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2016098562A1 (ja) * 2014-12-19 2017-09-28 グリコ栄養食品株式会社 π共役系の難溶性又は不溶性物質の可溶化又は分散化組成物
WO2017195504A1 (fr) * 2016-05-13 2017-11-16 グリコ栄養食品株式会社 Agent pour améliorer l'équilibre en caroténoïdes dans le sang

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0723736A (ja) * 1993-06-30 1995-01-27 Taishiyoo Technos:Kk カロチノイド色素の可溶化方法
JPH07501211A (ja) * 1991-09-06 1995-02-09 ベータティーン・リミテッド カロチノイド・コンポジション
JP2010285364A (ja) * 2009-06-10 2010-12-24 Riken Vitamin Co Ltd 一重項酸素消去剤
WO2012104576A2 (fr) * 2011-01-31 2012-08-09 Ip Science Limited Particules de caroténoïdes et leurs utilisations

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JPS578758A (en) * 1980-06-16 1982-01-18 Q P Corp Preparation of light green acidic food
JPS6036226B2 (ja) * 1981-11-28 1985-08-19 三栄化学工業株式会社 アナト−色素への耐酸性付与法
US6428816B1 (en) * 1994-04-08 2002-08-06 Cognis Australia Pty., Ltd. Carotenoid agent for inhibiting the conversion of epithelial cells to tumors
JPH11209642A (ja) * 1998-01-27 1999-08-03 Taito Kk アナトー色素製剤及びその製造方法

Patent Citations (4)

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Publication number Priority date Publication date Assignee Title
JPH07501211A (ja) * 1991-09-06 1995-02-09 ベータティーン・リミテッド カロチノイド・コンポジション
JPH0723736A (ja) * 1993-06-30 1995-01-27 Taishiyoo Technos:Kk カロチノイド色素の可溶化方法
JP2010285364A (ja) * 2009-06-10 2010-12-24 Riken Vitamin Co Ltd 一重項酸素消去剤
WO2012104576A2 (fr) * 2011-01-31 2012-08-09 Ip Science Limited Particules de caroténoïdes et leurs utilisations

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2016098562A1 (ja) * 2014-12-19 2017-09-28 グリコ栄養食品株式会社 π共役系の難溶性又は不溶性物質の可溶化又は分散化組成物
WO2017195504A1 (fr) * 2016-05-13 2017-11-16 グリコ栄養食品株式会社 Agent pour améliorer l'équilibre en caroténoïdes dans le sang
JPWO2017195504A1 (ja) * 2016-05-13 2019-03-22 グリコ栄養食品株式会社 血中カロテノイドバランス改善剤
JP7004644B2 (ja) 2016-05-13 2022-02-10 グリコ栄養食品株式会社 血中カロテノイドバランス改善剤

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JPWO2015046365A1 (ja) 2017-03-09
CN105517575A (zh) 2016-04-20
CN105517575B (zh) 2018-03-09
JP5934840B2 (ja) 2016-06-15

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