WO2024095311A1 - アスコルビン酸誘導体含有組成物 - Google Patents

アスコルビン酸誘導体含有組成物 Download PDF

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Publication number
WO2024095311A1
WO2024095311A1 PCT/JP2022/040630 JP2022040630W WO2024095311A1 WO 2024095311 A1 WO2024095311 A1 WO 2024095311A1 JP 2022040630 W JP2022040630 W JP 2022040630W WO 2024095311 A1 WO2024095311 A1 WO 2024095311A1
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Prior art keywords
ascorbic acid
glucoside
salt
composition
basic amino
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PCT/JP2022/040630
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English (en)
French (fr)
Japanese (ja)
Inventor
明男 山本
克 中村
昌彦 中野
隆 宮原
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Dr's Choice Co Ltd
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Dr's Choice Co Ltd
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Priority to PCT/JP2022/040630 priority Critical patent/WO2024095311A1/ja
Priority to JP2024553937A priority patent/JPWO2024095311A1/ja
Publication of WO2024095311A1 publication Critical patent/WO2024095311A1/ja
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    • 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
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/15—Vitamins
    • 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
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
    • 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
    • A61K8/67—Vitamins
    • 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
    • A61P3/02—Nutrients, e.g. vitamins, minerals
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms

Definitions

  • the present invention relates to a stable composition containing ascorbic acid 2-glucosides.
  • Ascorbic acid acts as a reducing agent, a collagen synthesis promoter, and an antioxidant.
  • the excellent antioxidant effect of ascorbic acid suppresses melanin production in the skin and is known as an ingredient that prevents pigmentation such as age spots and freckles, and is widely used in medicines, foods, cosmetics, etc.
  • ascorbic acid is unstable in its raw powder form when it is hygroscopic or under alkaline conditions, and an aqueous solution of ascorbic acid is not only strongly acidic and irritating, but also easily oxidizes, and browning occurs due to the Maillard reaction caused by typical amines involved in decomposition, and the browning reaction progresses.
  • Non-Patent Document 1 a technique of blending a flavonoid glycoside with ascorbic acid to suppress browning of ascorbic acid has been reported (Patent Documents 1 and 2). It has also been reported that ascorbic acid 2-glucoside is used instead of ascorbic acid. However, the aqueous solution of ascorbic acid 2-glucoside has a low pH and, although its stability is somewhat improved, the drawback of browning remains. Therefore, techniques for blending a strong base, lecithin, an ether compound, an ester compound, citric acid, etc. with ascorbic acid 2-glucoside have been reported (Patent Documents 3 to 6).
  • an object of the present invention is to provide a composition which contains ascorbic acid 2-glucosides and which is stable and has a good feel when used.
  • the inventors therefore mixed various ingredients with ascorbic acid 2-glucoside basic amino acid salts and investigated their stability and the feel when applied to the skin. They discovered that the combined use of ascorbic acid 2-glucoside basic amino acid salts and ascorbic acid 2-glucoside alkali metal salts improves stability and the feel when applied to the skin, thus completing the present invention.
  • the present invention provides the following inventions [1] to [6].
  • [1] A food composition, cosmetic composition or pharmaceutical composition containing a basic amino acid salt of ascorbic acid 2-glucoside and an alkali metal salt of ascorbic acid 2-glucoside.
  • [2] The composition according to [1], wherein the ascorbic acid 2-glucoside basic amino acid salt is one or more selected from the group consisting of ascorbic acid 2-glucoside lysine salt, ascorbic acid 2-glucoside arginine salt, ascorbic acid 2-glucoside histidine salt, and ascorbic acid 2-glucoside tryptophan salt.
  • composition according to [1] or [2], wherein the alkali metal salt of ascorbic acid 2-glucoside is one or two selected from sodium ascorbic acid 2-glucoside and potassium ascorbic acid 2-glucoside.
  • the ascorbic acid 2-glucoside basic amino acid salt is ascorbic acid 2-glucoside arginine salt.
  • alkali metal salt of ascorbic acid 2-glucoside is sodium salt of ascorbic acid 2-glucoside.
  • Aqueous solutions containing ascorbic acid 2-glucoside basic amino acid salts and ascorbic acid 2-glucoside alkali metal salts are significantly less likely to discolor and have a pH that ranges from weakly acidic to neutral, so they have the various functions of ascorbic acid, including a whitening effect by inhibiting melanin production and an anti-wrinkle effect by activating collagen production, and are useful as safe, non-irritating ingredients in foods, medicines, or cosmetics.
  • FIG. 1 shows the FT/IR spectrum of ascorbic acid 2-glucoside arginine salt powder.
  • One aspect of the present invention is a composition containing ascorbic acid 2-glucoside basic amino acid salt and ascorbic acid 2-glucoside alkali metal salt.
  • This composition is particularly useful as a food composition, cosmetic composition, or pharmaceutical composition.
  • Ascorbic acid in this invention is a compound whose IUPAC name is (R)-3,4-dihydroxy-5-((S)-1,2-dihydroxyethyl)furan-2(5H)-one, and is also known as vitamin C and L-ascorbic acid.
  • ascorbic acid acts as a reducing agent, collagen synthesis promoter, and antioxidant.
  • the excellent antioxidant effect of ascorbic acid inhibits melanin production in the skin, and it is known as an ingredient that prevents pigmentation such as age spots and freckles, and is widely used in medicines, foods, and cosmetics.
  • Ascorbic acid 2-glucoside is a substance in which glucose is bound to the carbon atom at position 2 of ascorbic acid, and since it is metabolized in the body to become ascorbic acid, it is considered to be a provitamin of ascorbic acid.
  • the ascorbic acid 2-glucoside basic amino acid salt used in the present invention is a basic amino acid salt of ascorbic acid 2-glucoside.
  • the ascorbic acid 2-glucoside basic amino acid may be one or more selected from ascorbic acid 2-glucoside lysine salt, ascorbic acid 2-glucoside arginine salt, ascorbic acid 2-glucoside histidine salt, and ascorbic acid 2-glucoside tryptophan salt.
  • ascorbic acid 2-glucoside lysine salt and ascorbic acid 2-glucoside arginine salt are more preferred, and ascorbic acid 2-glucoside arginine salt is even more preferred.
  • the molar ratio of ascorbic acid 2-glucoside to a basic amino acid in the basic amino acid salt of ascorbic acid 2-glucoside is preferably 1:1.5 to 1.5:1, and more preferably 1:1.2 to 1.2:1.
  • Ascorbic acid 2-glucoside basic amino acid salt can be produced by reacting ascorbic acid 2-glucoside with a basic amino acid. Specifically, ascorbic acid 2-glucoside and a basic amino acid are added to ion-exchanged water in which the dissolved oxygen concentration has been reduced by ultrasonic treatment or the like at 40 to 60° C., and the pH is adjusted to 5.22 to 5.55, thereby adjusting the amount of basic amino acid added and allowing the reaction to proceed. After completion of the reaction, ascorbic acid 2-glucoside basic amino acid salt can be isolated as a powder by freeze-drying, spray-drying, or the like.
  • the obtained powder of ascorbic acid 2-glucoside basic amino acid salt is stable for a long period of time and does not brown, so it is useful as a raw material for blending at high concentrations in cosmetics and pharmaceutical compositions.
  • there is a limit to the upper limit of the concentration because it is mixed with other bases.
  • a preservative sterilize it by passing it through a filter, fill it into a sterile container, or store it at a low temperature, but by powdering it, it becomes possible to store it stably and compactly at room temperature without adding other ingredients.
  • the content of the ascorbic acid 2-glucoside basic amino acid salt in the composition of the present invention is preferably 1 to 40% by mass, more preferably 2 to 35% by mass, and even more preferably 5 to 30% by mass, from the viewpoints of stability, usability, and the ability of the ascorbic acid 2-glucoside basic amino acid salt to exhibit its function as ascorbic acid.
  • alkali metal salt of ascorbic acid 2-glucoside examples include sodium ascorbic acid 2-glucoside, potassium ascorbic acid 2-glucoside, and lithium ascorbic acid 2-glucoside. Of these, sodium ascorbic acid 2-glucoside and potassium ascorbic acid 2-glucoside are preferred, and sodium ascorbic acid 2-glucoside is more preferred.
  • the molar ratio of ascorbic acid 2-glucoside to the alkali metal in the ascorbic acid 2-glucoside alkali metal salt is preferably 1:1.5 to 1.5:1, and more preferably 1:1.2 to 1.2:1.
  • the alkali metal salt of ascorbic acid 2-glucoside can be produced by the method described in JP-A-2002-88095, Japanese Patent No. 6895436, etc.
  • ascorbic acid 2-glucoside may be reacted with an alkali metal salt such as sodium hydroxide, sodium carbonate, or sodium hydrogencarbonate.
  • an alkali metal salt such as sodium hydroxide, sodium carbonate, or sodium hydrogencarbonate.
  • ascorbic acid 2-glucoside and an alkali metal salt are added at 40 to 60° C., and the pH is adjusted to 6.0 to 6.5, and the reaction is carried out while adjusting the amount of the alkali metal salt added.
  • alkali metal salt of ascorbic acid 2-glucoside can be isolated as a powder by freeze-drying, spray-drying, or the like.
  • alkali metal ascorbic acid 2-glucoside salts are known to have physiological activities similar to those of ascorbic acid, it is not known that their stability and usability are improved by their combined use with basic amino acid salts of ascorbic acid 2-glucoside.
  • the content of the alkali metal salt of ascorbic acid 2-glucoside in the composition of the present invention is preferably 1 to 50% by mass, more preferably 2 to 45% by mass, and even more preferably 5 to 40% by mass, from the viewpoints of stability, usability, and the ability of the alkali metal salt of ascorbic acid 2-glucoside to exhibit its function as ascorbic acid.
  • the molar ratio (a/b) of the ascorbic acid 2-glucoside basic amino acid salt (a) to the ascorbic acid 2-glucoside alkali metal salt (b) in the composition of the present invention is preferably 0.2 to 5.0, more preferably 0.3 to 3.0, and even more preferably 0.5 to 2.0, from the viewpoints of the effect of preventing discoloration of the composition, the effect of exerting the functions of ascorbic acid, and the feeling of use such as stickiness.
  • the pH of the composition of the present invention is preferably 5.0 to 7.5, more preferably 5.0 to 6.5, and even more preferably 5.0 to 6.0, from the viewpoint of preventing discoloration and reducing irritation when applied to the skin.
  • compositions containing ascorbic acid 2-glucoside basic amino acid salts and ascorbic acid 2-glucoside alkali metal salts include food compositions, pharmaceutical compositions, and cosmetic compositions. These compositions may be in the form of a liquid composition, an emulsion composition, a powder composition, or a solid composition.
  • food compositions include functional foods, foods for specified health uses, etc.
  • pharmaceutical compositions include oral preparations such as tablets, granules, and syrups, transdermal preparations such as creams, ointments, and liquids, eye drops, and injections.
  • the cosmetic composition may be a liquid cosmetic, an emulsion cosmetic, a powder cosmetic, a solid cosmetic, etc.
  • these cosmetics preferably contain ascorbic acid or a salt thereof, water, an oil, a surfactant, a moisturizing component, alcohols, polyols, an ultraviolet absorbing agent, an ultraviolet protection agent, various powders, various cosmetic components, an antioxidant, an antibacterial agent, a fragrance, etc.
  • the cosmetic of the present invention is more preferably a skin cosmetic, and is preferably in the form of an aqueous liquid cosmetic, an oil-in-water emulsion cosmetic, or a water-in-oil emulsion cosmetic.
  • the pH is preferably 5.22 to 5.55, more preferably 5.35.
  • the molar concentration of arginine added was finely adjusted by pH. This solution was freeze-dried to obtain a powder of ascorbic acid 2-glucoside arginine salt (7.55 g, 90.03%).
  • the FT/IR spectrum of the obtained powder of ascorbic acid 2-glucoside arginine salt is shown in FIG. 1. As a result of the spectrum, a band at 1720 cm -1 (non-ionic COOH, antisymmetric stretching vibration) and a characteristic band at 1400 cm -1 were observed, confirming the introduction of ionic bonds of arginine.
  • Example 1 Matture of ascorbic acid 2-glucoside arginine salt (ASA2-G Arg) and ascorbic acid 2-glucoside sodium salt (ASA2-G Na)
  • the solubility of ASA2-G is 879 g/L (25° C.), i.e., 46.8% by weight.
  • ASA2-G ⁇ Arg and ASA2-G ⁇ Na have improved solubility in water and can be dissolved in water at a high concentration of 70% by weight or more.
  • ASA2-G ⁇ Arg and ASA2-G ⁇ Na can be dissolved in water simultaneously, and it was also possible to increase the combined concentration of the ascorbic acid 2-glucoside derivatives.
  • Test products 2-5 had roughly the same feel when used, and none of the subjects felt sticky. It was found that the feel when used was significantly improved when ASA2-G Na was mixed in a ratio of 1/4 or more to ASA2-G Arg. Furthermore, test products 2-5 showed similar levels of browning when stored at 40°C for two weeks, with no difference.
  • Example 2 A formulation example and manufacturing method for producing a beauty essence by blending 5% by mass of ascorbic acid 2-glucoside arginine salt (ASA2-G ⁇ Arg) and 5% by mass of ascorbic acid 2-glucoside sodium salt (ASA2-G ⁇ Na) are shown below.
  • Composition (unit: mass%) 1. Water 67.98% 2. Propanediol 17.0% 3. ASA2-G Arg 5.0% 4. ASA2-G Na 5.0% 5. Glycerin 3.9% 6. Sodium citrate 0.5% 7. 1,3-BG 0.30% 8. Glycosphingolipids 0.15% 9.
  • Xanthan gum 0.12% 10.
  • Acetylhydroxyproline 0.01% 13 A formulation example and manufacturing method for producing a beauty essence by blending 5% by mass of ascorbic acid 2-glucoside arginine salt (ASA2-G ⁇ Arg) and 5% by mass of ascorbic acid 2-glucoside sodium salt (ASA2-G ⁇ Na) are shown below.
  • Composition (unit:

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PCT/JP2022/040630 2022-10-31 2022-10-31 アスコルビン酸誘導体含有組成物 Ceased WO2024095311A1 (ja)

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PCT/JP2022/040630 WO2024095311A1 (ja) 2022-10-31 2022-10-31 アスコルビン酸誘導体含有組成物
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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005336095A (ja) * 2004-05-26 2005-12-08 Clariant Finance (Bvi) Ltd 外用組成物
JP2006188461A (ja) * 2005-01-06 2006-07-20 Kose Corp 化粧料
JP2010189351A (ja) * 2009-02-20 2010-09-02 Shiseido Co Ltd 経皮吸収促進剤及びこれを含有する皮膚外用剤
WO2014104171A1 (ja) * 2012-12-27 2014-07-03 株式会社林原 アンチエイジング用皮膚外用組成物及びその製造方法
WO2016056648A1 (ja) * 2014-10-10 2016-04-14 株式会社林原 酸性水系媒体中での２－Ｏ－α－Ｄ－グルコシル－Ｌ－アスコルビン酸の安定化方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005336095A (ja) * 2004-05-26 2005-12-08 Clariant Finance (Bvi) Ltd 外用組成物
JP2006188461A (ja) * 2005-01-06 2006-07-20 Kose Corp 化粧料
JP2010189351A (ja) * 2009-02-20 2010-09-02 Shiseido Co Ltd 経皮吸収促進剤及びこれを含有する皮膚外用剤
WO2014104171A1 (ja) * 2012-12-27 2014-07-03 株式会社林原 アンチエイジング用皮膚外用組成物及びその製造方法
WO2016056648A1 (ja) * 2014-10-10 2016-04-14 株式会社林原 酸性水系媒体中での２－Ｏ－α－Ｄ－グルコシル－Ｌ－アスコルビン酸の安定化方法

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