WO2022034874A1 - Préparation ou composition contenant un composé d'acide ascorbique et procédé de stabilisation d'un composé d'acide ascorbique - Google Patents

Préparation ou composition contenant un composé d'acide ascorbique et procédé de stabilisation d'un composé d'acide ascorbique Download PDF

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WO2022034874A1
WO2022034874A1 PCT/JP2021/029474 JP2021029474W WO2022034874A1 WO 2022034874 A1 WO2022034874 A1 WO 2022034874A1 JP 2021029474 W JP2021029474 W JP 2021029474W WO 2022034874 A1 WO2022034874 A1 WO 2022034874A1
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group
carbon atoms
ascorbic acid
alkyl moiety
base end
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PCT/JP2021/029474
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English (en)
Japanese (ja)
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亜紀良 矢下
恒太郎 金子
功治 河合
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ミヨシ油脂株式会社
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Priority to JP2022542848A priority Critical patent/JPWO2022034874A1/ja
Publication of WO2022034874A1 publication Critical patent/WO2022034874A1/fr

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    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin

Definitions

  • the present invention relates to a compounding agent or composition containing an ascorbic acid-based compound and a method for stabilizing the ascorbic acid-based compound.
  • L-ascorbic acid has a melanin production inhibitory effect, an anti-inflammatory effect, an acne improving effect, an antiaging effect, an antioxidant effect, a cell activation effect by promoting the synthesis of biological components such as collagen, and cell damage caused by ultraviolet rays of epidermal keratinocytes.
  • the effect of suppressing DNA damage the effect of promoting absorption of minerals (iron, copper, etc.), the therapeutic effect of vitamin C deficiency (necrotic disease), antioxidation, and various other effects (immunity enhancing effect by leukocyte increase, suppression of cholesterol production) It is known to exert various effects such as anti-arteriosclerosis and anti-allergic action due to anti-histamine action), and is widely used as cosmetics and external skin preparations in anticipation of these effects.
  • L-ascorbic acid and its derivatives have low stability in an aqueous solution, it is difficult to maintain their appearance for a long period of time, and their effects are reduced. Therefore, even if they are used as cosmetics, their original functions are sufficient. I wouldn't show it. Therefore, for the purpose of stabilization, L-ascorbic acid 2-phosphate ester trisodium (Patent Document 1), 3-O-ethyl-L-ascorbic acid (Patent Document 2), 2-O- ( ⁇ -D-).
  • Patent Document 3 Derivatives such as glucopyranosyl) -L-ascorbic acid (Patent Document 3), derivatives and salts such as ascorbic acid monoethanol salt (Patent Document 4) have been proposed, and it is said that the above effects are exhibited, but their effects are reduced. There was a problem.
  • Japanese Unexamined Patent Publication No. 52-018191 Japanese Unexamined Patent Publication No. 03-15369 Japanese Unexamined Patent Publication No. 2002-114635 U.S. Pat. No. 2,187,467
  • the present invention has been made in view of the above circumstances, and it is possible to stabilize an ascorbic acid-based compound for a long period of time regardless of the presence or absence of water, and the effect of the ascorbic acid-based compound is also obtained. It is an object of the present invention to provide a compounding agent or composition which is excellent and can maintain its effect for a long period of time, and a stabilizing method.
  • the compounding agent or composition of the present invention is characterized by containing the following components (A) and (B).
  • R 1 is a hydroxyl group, —O — X (X represents an alkali metal cation, an alkaline earth metal cation, or an ammonium cation), and an organic oxy group having 1 to 22 carbon atoms having an ether bond at the base end.
  • X represents an alkali metal cation, an alkaline earth metal cation, or an ammonium cation
  • an organic oxy group having 1 to 22 carbon atoms having an ether bond at the base end A linear or branched hydroxyl group-containing organic oxy group having 1 to 22 carbon atoms having an ether bond at the base end, an organic ester group having 2 to 40 carbon atoms having an ester bond at the base end, and a phosphorus atom at the base end.
  • the alkyl moiety is a linear or branched chain having 1 to 10 carbon atoms, the alkyl moiety has at least one hydroxyalkyl group which may contain an oxygen atom, and an amine or ammonium.
  • the compound has two or more hydroxyl groups in total (however, in the case of an ammonium compound, the cation moiety), or (ii) the alkyl moiety is in the form of a branched chain having 3 to 10 carbon atoms, and the alkyl moiety contains an oxygen atom.
  • an amine or ammonium compound (however, in the case of an ammonium compound, the cation moiety) has a total of two or more oxygen atoms, or the alkyl moiety is linear with 2 to 10 carbon atoms and the hydroxyalkyl group. Is an amine or ammonium compound having a hydroxyl group at the 2-position or higher.
  • the method for stabilizing the ascorbic acid-based compound of the present invention is the following method for stabilizing the ascorbic acid-based compound (A), in which the following amine or ammonium compound (B) is coexisted to form a composition or a component. It is characterized by forming a salt of (A) and (B).
  • A Ascorbic acid represented by the following formula (I) or a derivative thereof or a salt thereof.
  • R 1 is a hydroxyl group, —O — X (X represents an alkali metal cation, an alkaline earth metal cation, or an ammonium cation), and an organic oxy group having 1 to 22 carbon atoms having an ether bond at the base end.
  • X represents an alkali metal cation, an alkaline earth metal cation, or an ammonium cation
  • an organic oxy group having 1 to 22 carbon atoms having an ether bond at the base end A linear or branched hydroxyl group-containing organic oxy group having 1 to 22 carbon atoms having an ether bond at the base end, an organic ester group having 2 to 40 carbon atoms having an ester bond at the base end, and a phosphorus atom at the base end.
  • the alkyl moiety is a linear or branched chain having 1 to 10 carbon atoms, the alkyl moiety has at least one hydroxyalkyl group which may contain an oxygen atom, and an amine or ammonium.
  • the compound has two or more hydroxyl groups in total (however, in the case of an ammonium compound, the cation moiety), or (ii) the alkyl moiety is in the form of a branched chain having 3 to 10 carbon atoms, and the alkyl moiety contains an oxygen atom.
  • an amine or ammonium compound (however, in the case of an ammonium compound, the cation moiety) has a total of two or more oxygen atoms, or the alkyl moiety is linear with 2 to 10 carbon atoms and the hydroxyalkyl group. Is an amine or ammonium compound having a hydroxyl group at the 2-position or higher.
  • the ascorbic acid-based compound can be stabilized for a long period of time regardless of the presence or absence of water, and the effect of the ascorbic acid-based compound is also excellent. The effect can be maintained for a long time without volatilization.
  • the mixture of the components (A) and (B) or the anhydride or hydrate of the salt of (A) and (B) is liquid at 25 ° C., it is uniform on the object such as skin and hair. Can be coated on the surface to efficiently exert the effect of the ascorbic acid-based compound.
  • the compounding agent of the present invention is mainly targeted at an agent compounded in an arbitrary step when producing a target product.
  • the compounding agent of the present invention contains the components (A) and (B).
  • the term "containing” includes the addition of the components (A) and (B) before the final preparation of the compounding agent, and the components (A) and (B) are used as starting materials. This includes the case where the salt formed by A) and (B) is synthesized and the salt is used as a compounding agent, and the case where the salt is dissolved in a solvent such as water as necessary to form a compounding agent.
  • the compounding agent of the present invention may be a mixture consisting of only the components (A) and (B) (including the case of salts thereof), and may be other than the components (A) and (B) or salts thereof. It may be a composition containing an ingredient, for example, water.
  • the composition of the present invention is mainly intended for the target product.
  • the composition of the present invention includes a product produced by blending the compounding agent of the present invention in any step thereof, and includes not only the compounding agent but also the components (A) and (B).
  • the term "contains” in the present invention includes the addition of components (A) and (B) before the final composition is prepared. When a salt is once formed before the composition of the present invention is finally prepared, it is also referred to as "containing the salt of the components (A) and (B)".
  • the compounding agent or composition of the present invention stabilizes the ascorbic acid-based compound of the component (A), and the effects of the ascorbic acid-based compound, such as, but not limited to, the melanin production inhibitory effect of L-ascorbic acid and anti-inflammatory.
  • the component (A) is ascorbic acid represented by the above formula (I) or a derivative thereof or a salt thereof, and these are collectively referred to as an ascorbic acid-based compound.
  • R 1 is a hydroxyl group, —O — X (X represents an alkali metal cation, an alkaline earth metal cation, or an ammonium cation), and has an ether bond at the base end and has 1 to 22 carbon atoms.
  • Organic oxy group, linear or branched hydroxyl group-containing organic oxy group having 1 to 22 carbon atoms having an ether bond at the base end, organic ester group having 2 to 40 carbon atoms having an ester bond at the base end, base end Indicates a phosphorus-containing group having a phosphorus atomic group having a carbon number of 0 to 35, or a sulfur-containing group having a sulfur atomic group at the base end and having a sulfur number of 0 to 35.
  • the above-O - X indicates a salt structure
  • X (cation) constituting the salt is an alkali metal cation, an alkaline earth metal cation, or an ammonium cation.
  • the alkali metal include lithium, sodium, potassium, rubidium, cesium and the like
  • examples of the alkaline earth metal include beryllium, magnesium, calcium, strontium, barium and the like, and the ammonium cation is not particularly limited.
  • ammonium cations such as NR 4+ ( R is at least one organic group and the other is a hydrogen atom) and NH 4+ substituted organic ammonium cations
  • the ascorbic acid-based compound having these groups are not particularly limited, but for example, sodium ascorbic acid, potassium ascorbic acid, magnesium ascorbic acid, calcium ascorbic acid, ammonium ascorbic acid, calcium ascorbic acid, and phosphoric acid.
  • X is a cation having a valence of 2 or more
  • the anion ascorbic acid ion may be equimolar to the valence of the cation, although it is not particularly limited.
  • the organic oxy group has an ether bond with a carbon atom of the 5-membered ring of the component (A) at the base end, and has 1 to 22 carbon atoms (preferably 1 to 22 carbon atoms) in which the carbon atom and the oxygen atom of the organic group are bonded. It is the basis of 18).
  • the organic group is preferably a hydrocarbon group (preferably an alkyl group) which may have a substituent, and more preferably a hydrocarbon group.
  • the substituent is not particularly limited, and examples thereof include those described in the column of [Substituent] described later, and the hydrocarbon group is not particularly limited, but for example, the column of [Hydrocarbon group] described later. The ones described in are mentioned.
  • the organic oxy group does not contain a hydroxyl group.
  • the organic oxy group is not particularly limited, but for example, a methyloxy group, an ethyloxy group, a propyloxy group, a butyloxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a nonyloxy group, and the like.
  • ethyloxy group, butyloxyl group, hexyloxyl group, dodecyloxy group, hexadecyloxy group, octyloxy group (capryloxy group) and tetradecyloxy group (myristyloxy group) are preferable.
  • Specific examples of the ascorbic acid-based compound having these groups are not particularly limited, but for example, 2-O-ethyl-L-ascorbic acid, myristyl 3-glyceryl ascorbic acid, and caprylyl 3-glyceryl ascorbic acid.
  • the linear or branched hydroxyl group-containing organic oxy group has an ether bond with the carbon atom of the 5-membered ring of the component (A) at the base end, and has the number of carbon atoms in which the carbon atom and the oxygen atom of the organic group are bonded. It is a group of 1 to 22 (preferably 1 to 18 carbon atoms).
  • the organic group is a group having one or more hydroxyl groups and having 1 to 22 carbon atoms (preferably 1 to 18, more preferably 1 to 12).
  • the organic group is preferably a hydrocarbon group having one or more hydroxyl groups and may have other substituents, and more preferably a hydrocarbon group having one or more hydroxyl groups.
  • the substituent other than the hydroxyl group is not particularly limited, and examples thereof include those described in the column of [Substituent] described later.
  • the hydrocarbon group contained in the organic group is not particularly limited, and examples thereof include linear or branched aliphatic hydrocarbons among those described in the column of [hydrocarbon group] described later.
  • Specific examples of the hydroxyl group-containing organic oxy group include, but are not limited to, a glyceryloxy group, a hydroxyethyloxy group, a hydroxypropyloxy group, a glyceryl etheroxy group and the like.
  • ascorbic acid-based compound having these groups are not particularly limited, but for example, ethylhexyl glyceryl ascorbic acid, caprylyl 2-glyceryl ascorbic acid, cetyl 2-glyceryl ascorbic acid, bisglyceryl ascorbic acid, butyl 2 -Glyceryl ascorbic acid, hexyl 2-glyceryl ascorbic acid, myristyl 2-glyceryl ascorbic acid, lauryl 2-glyceryl ascorbic acid and salts thereof (salt cations include alkali metal cations, alkaline earth metal cations, ammonium cations, etc. ) And so on.
  • the organic group is preferably a hydrocarbon group which may have a substituent, and more preferably a hydrocarbon group.
  • the substituent is not particularly limited, and examples thereof include those described in the column of [Substituent] described later, and the hydrocarbon group is not particularly limited, but for example, the column of [Hydrocarbon group] described later. The ones described in are mentioned.
  • the organic group is preferably a group containing a heterocycle.
  • the heterocycle is preferably a heterocycle containing an oxygen atom, more preferably a 6-membered ring containing an oxygen atom, and even more preferably a dihydropyran ring.
  • the heterocycle preferably contains a linear or branched alkyl group having 1 to 22 carbon atoms.
  • the ascorbic acid-based compound having an organic ester group include ascorbyl tetrahexyldecanoate, ascorbyltocopheryl maleate, tetrahexyldecyl ascorbate and salts thereof (the salt cations are alkali metal cations and alkaline earth metal cations). , Or ammonium cations and the like.) And the like.
  • the phosphorus-containing group has a phosphorus atomic group at the base end having 0 to 35 carbon atoms.
  • Examples of the phosphorus atomic group include a phosphoric acid group, a phosphite group, a phosphonic acid group, a phosphinic acid group, a phosphonic acid group, a phosphinic acid group, a pyrophosphate group, and residues thereof.
  • Examples of the phosphorus-containing group include a phosphoric acid group, a phosphite group, a phosphonic acid group, a phosphinic acid group, a phosphonic acid group, a phosphinic acid group, a pyrophosphate group, and an ester thereof, and the number of carbon atoms thereof. Is preferably 0 to 30.
  • the acid type phosphorus-containing group may be a salt type (the above-mentioned alkali metal cation, alkaline earth cation, ammonium cation). Among these, phosphoric acid, a salt thereof, and a phosphoric acid ester are preferable.
  • the organic group is preferably a hydrocarbon group which may have a substituent. More preferably, it is a hydrocarbon group having a hydrocarbon group and a nitrogen-containing group.
  • the substituent is not particularly limited, and examples thereof include those described in the column of [Substituent] described later, and the hydrocarbon group is not particularly limited, but for example, the column of [Hydrocarbon group] described later. The ones described in are mentioned.
  • the organic group is preferably a group containing a heterocycle.
  • the group containing a heterocycle further contains at least one selected from a hydrocarbon group and a benzene ring.
  • a heterocycle containing oxygen is preferable, a 6-membered ring containing an oxygen atom is more preferable, and a dihydropyran ring is further preferable.
  • the heterocycle preferably contains a linear or branched alkyl group having 1 to 22 carbon atoms. Further, it is preferable to contain a benzene ring or the like between the phosphoric acid ester group and the heterocycle.
  • the ascorbic acid-based compound having a phosphorus-containing group are not particularly limited, but for example, L-ascorbyl phosphate, (ascorbyl / tocopheryl) phosphoric acid, isostearyl ascorbyl phosphoric acid, ascorvirlin isopalmitate.
  • examples thereof include acids, ascorbyl phosphoric acid palmitate, ascorbyl aminopropyl phosphate and salts thereof (examples of the salt cation include alkali metal cations, alkaline earth metal cations, ammonium cations and the like).
  • the sulfur-containing group has a sulfur atomic group at the base end having 0 to 35 carbon atoms.
  • the sulfur atomic group is not particularly limited, but for example, a sulfate group, a sulfonyl group, a sulfonic acid group, a mercapto group, a thioether group, a thiocarbonyl group, a thiourea group, a thiocarboxy group, a thiocarboxylate group, a dithiocarboxy group, and the like.
  • Examples thereof include a dithiocarboxylate group, a thiophene group, a thiazole group, a thiol group, a sulfo group, a sulfide group, a disulfide group, a thioester group, a thioamide group, a thiocarbamate group, a dithiocarbamate group, and residues thereof.
  • the sulfur-containing group is not particularly limited, but for example, a sulfate group, a sulfonyl group, a sulfonic acid group, a mercapto group, a thioether group, a thiocarbonyl group, a thiourea group, a thiocarboxy group, a thiocarboxylate group, and a dithiocarboxy group.
  • the acid type sulfur-containing group may be a salt type (the above-mentioned alkali metal cation, alkaline earth cation, ammonium cation). Of these, a sulfate ester group is preferable.
  • the ascorbic acid-based compound having a sulfur-containing group are not particularly limited, but for example, L-ascorbic acid sulfate ester and salts thereof (the cation of the salt is an alkali metal cation or an alkaline earth metal cation). , Or ammonium cation, etc.). Specific examples are not particularly limited, but L-ascorbic acid sulfate disodium is preferable.
  • R 2 is a hydroxyl group, —O — X (X represents an alkali metal cation, an alkaline earth metal cation, or an ammonium cation), and an organic having 1 to 22 carbon atoms having an ether bond at the base end.
  • X represents an alkali metal cation, an alkaline earth metal cation, or an ammonium cation
  • An oxy group, a hydroxyl group-containing organic oxy group having 1 to 22 carbon atoms having an ether bond at the base end, or an organic ester group having 2 to 40 carbon atoms having an ester bond at the base end is shown.
  • the content described as R 1 is referred to.
  • Specific examples of the ascorbic acid-based compound having —O — X in R 2 are not particularly limited, but for example, L-ascorbyl phosphate, (ascorbyl / tocopheryl) phosphate, ethylhexylglyceryl ascorbic acid, isostearyl ascorbyl. Examples thereof include phosphoric acid, ascorbyl phosphate isopalmitate, ascorbyl phosphate palmitate and salts thereof (examples of the salt cation include an alkali metal cation, an alkaline earth metal cation, an ammonium cation and the like).
  • the content described as R 1 is referred to.
  • Specific examples of the ascorbic acid-based compound having an organic oxy group in R 2 are not particularly limited, but for example, 3-O-ethyl-L-ascorbic acid, 3-O-cetyl-L-ascorbic acid, and caprylyl.
  • 2-Glyceryl ascorbic acid diethyl ascorbic acid, cetyl 2-glyceryl ascorbic acid, butyl 2-glyceryl ascorbic acid, hexyl 2-glyceryl ascorbic acid, myristyl 2-glyceryl ascorbic acid, lauryl 2-glyceryl ascorbic acid and their salts (salts)
  • the cation include alkali metal cations, alkaline earth metal cations, ammonium cations and the like).
  • the hydroxyl group-containing organic oxy group has an ether bond with a carbon atom of a 5-membered ring of the component (A) at the base end, and has 1 to 22 carbon atoms (preferably carbon atoms) in which a carbon atom and an oxygen atom of the organic group are bonded. It is the basis of 1-18).
  • the organic group is a group having one or more hydroxyl groups and having 1 to 22 carbon atoms (preferably 1 to 18, more preferably 1 to 12).
  • the organic group is preferably a hydrocarbon group having one or more hydroxyl groups and may have other substituents, and more preferably a hydrocarbon group having one or more hydroxyl groups.
  • the substituent other than the hydroxyl group is not particularly limited, and examples thereof include those described in the column of [Substituent] described later.
  • the hydrocarbon group contained in the organic group is not particularly limited, and examples thereof include those described in the column of [hydrocarbon group] described later.
  • Specific examples of the hydroxyl group-containing organic oxy group include, but are not limited to, glyceryloxy group, hydroxyethyloxy group, hydroxypropyloxy group, glyceryl etheroxy group, glucoside group, galactoside group and the like. ..
  • the ascorbic acid-based compound having these groups are not particularly limited, but for example, myristyl 3-glyceryl ascorbic acid, 3-ethylhexyl glyceryl ascorbic acid, 3-glyceryl ascorbic acid, 3-butyl glyceryl ascorbic acid. , 3-lauryl glyceryl ascorbic acid, capryl 3-glyceryl ascorbic acid, cetyl 3-glyceryl ascorbic acid, bisglyceryl ascorbic acid, butyl 3-glyceryl ascorbic acid, hexyl 3-glyceryl ascorbic acid, lauryl 3-glyceryl ascorbic acid and theirs.
  • the salt cation include an alkali metal cation, an alkaline earth metal cation, an ammonium cation and the like.
  • the content described as R 1 is referred to.
  • Specific examples of the ascorbyl acid-based compound having an organic ester group in R 2 are not particularly limited, but for example, ascorbyl tetrahexyldecanoate, ascorbyl dipalmitate, tetrahexyldecyl ascorbylate, and salts thereof (salt cations). Examples thereof include alkali metal cations, alkaline earth metal cations, ammonium cations and the like.
  • X represents an alkali metal cation, an alkaline earth metal cation, or an ammonium cation
  • the organic ester group having 2 to 22 carbon atoms is shown.
  • the organic group is preferably a hydrocarbon group which may have a substituent, and more preferably a hydrocarbon group.
  • the substituent is not particularly limited, and examples thereof include those described in the column of [Substituent] described later, and the hydrocarbon group is not particularly limited, but for example, the column of [Hydrocarbon group] described later. The ones described in are mentioned.
  • Examples of the ascorbic acid-based compound having an organic ester group include dipalmitic acid ascorbyl, L-ascorbic acid palmitate, tetrahexyldecanoate ascorbyl, ascorbic acid tetrahexyldecyl, L-ascorbic acid stearate, and isopalmitic acid.
  • Examples thereof include ascorvir phosphate, palmitate ascorvir phosphate and salts thereof (examples of the salt cation include an alkali metal cation, an alkaline earth metal cation, an ammonium cation and the like) and the like.
  • R 1 is a hydroxyl group, -OX , and an organic oxy group in terms of stabilization of the ascorbic acid-based compound, expression of the effect of the ascorbic acid-based compound, and long-term maintenance.
  • R 2 is a hydroxyl group, ⁇ OX , an organic oxy group, a hydroxyl group-containing organic oxy group.
  • Or a combination of organic ester groups is preferred.
  • R 1 is a hydroxyl group and R 2 is a hydroxyl group
  • R 1 is a hydroxyl group and R 2 is an organic oxy group
  • R 1 is a hydroxyl group and R 2 is an organic ester group
  • R 1 is an organic oxy group and R 2 is a hydroxyl group-containing organic oxy group
  • R 1 is an organic oxy group and R 2 is a hydroxyl group
  • R 1 is an organic oxy group and R 2 is a hydroxyl group
  • R 1 is an organic oxy group and R 2 is a hydroxyl group
  • R 1 is an organic oxy group and R 2 is a hydroxyl group
  • R 1 is an organic oxy group and R 2 is.
  • R 1 is a linear or branched hydroxyl group-containing organic oxy group
  • R 2 is -OX
  • R 1 is a linear or branched hydroxyl group-containing organic oxy group
  • R 2 is organic.
  • Oxy group R 1 is a linear or branched hydroxyl group-containing organic oxy group
  • R 2 is a hydroxyl group-containing organic oxy group
  • R 1 is an organic ester group
  • R 2 is an organic ester group
  • R 1 is an organic ester group.
  • R 2 is a hydroxyl group
  • R 1 is a phosphorus-containing group and R 2 is a hydroxyl group
  • R 1 is a phosphorus-containing group and R 2 is ⁇ OX
  • R 1 is a sulfur-containing group and R 2 is a hydroxyl group.
  • R 1 is not particularly limited, but for example, R 1 listed in the designated additive list (food additive) based on the pharmaceutical non-medicinal product raw material standard or Article 10 of the Food Sanitation Law is a hydroxyl group.
  • 2 is a hydroxyl group
  • R 1 is a hydroxyl group
  • R 2 is an organic oxy group
  • R 1 is a hydroxyl group
  • R 2 is an organic ester group
  • R 1 is an organic ester group
  • R 2 is an organic ester group
  • R 1 is a phosphorus-containing group
  • 2 is —O — X or R 1 is a sulfur-containing group and R 2 is a hydroxyl group.
  • R 1 is a hydroxyl group and R 2 is a hydroxyl group
  • R 1 is a hydroxyl group and R 2 is an organic oxy group
  • R 1 is a phosphorus-containing group and R 2 is —O — X
  • R 1 is a hydroxyl group and R 2 is a hydroxyl group.
  • R 1 and R 2 are the above combination is not particularly limited, but for example, L-ascorbic acid, calcium L-ascorbic acid, sodium L-ascorbic acid, magnesium L-ascorbic acid, L- Zinc ascorbic acid, L-ascorbic phosphate, L-ascorbic sodium phosphate, L-ascorbic magnesium phosphate, 3-O-ethyl-L-ascorbic acid, potassium (ascorbic / tocopheryl) phosphate, L-ascorbic acid sulfate ester Disodium, ascorbic tetrahexyldecanoate, ascorbic dipalmitate, L-ascorbic acid palmitate, ascorbic copheryl maleate, 2-O-ethyl-L-ascorbic acid, 3-O-cetyl-L-ascorbic acid, 3 -Ethylhexyl glyceryl ascorbic acid, 3-glyceryl ascorbic acid,
  • the component (A) is not particularly limited from the viewpoint of safety, but for example, L-ascorbic acid listed in the designated additive list (food additive) based on the pharmaceutical non-medicinal product raw material standard or Article 10 of the Food Sanitation Law.
  • L-ascorbic acid L-ascorbic sodium phosphate, L-ascorbic magnesium phosphate, L-phosphate.
  • Ascorbic acid and 3-O-ethyl-L-ascorbic acid are preferable, L-ascorbic acid and 3-O-ethyl-L-ascorbic acid are more preferable, and L-ascorbic acid is further preferable.
  • R 1 and / or R 2 can have a salt structure, and at least one of R 1 and R 2 is a hydroxyl group, ⁇ OX , or a hydroxyl group.
  • a combination of an organic oxy group, a phosphorus-containing group, or a sulfur-containing group is preferable.
  • R 1 and R 2 R 1 is a hydroxyl group and R 2 is a hydroxyl group, R 1 is a hydroxyl group and R 2 is an organic oxy group, R 1 is a hydroxyl group and R 2 is an organic ester group, and R 1 is.
  • R 2 is a hydroxyl group-containing organic oxy group
  • R 1 is an organic oxy group
  • R 2 is a hydroxyl group-containing organic oxy group
  • R 1 is an organic oxy group
  • R 2 is a hydroxyl group
  • R 1 is a linear or branched chain.
  • R 2 is a hydroxyl group-containing organic oxy group
  • R 1 is an organic ester group and R 2 is a hydroxyl group
  • R 1 is a phosphorus-containing group and R 2 is -OX
  • R 1 is a sulfur-containing group and R. 2 is preferably a hydroxyl group, and among them, at least one of R 1 and R 2 is preferably a hydroxyl group or —O - X
  • R 1 is a hydroxyl group
  • R 2 is a hydroxyl group
  • R 1 is a hydroxyl group.
  • R 2 is an organic oxy group
  • R 1 is a hydroxyl group and R 2 is an organic ester group
  • R 1 is a hydroxyl group and R 2 is a hydroxyl group-containing organic oxy group
  • R 1 is an organic oxy group and R 2 is a hydroxyl group
  • R 1 is a direct Chain-shaped or branched hydroxyl-containing organic oxy groups
  • R 2 is -O - X
  • R 1 is an organic ester group
  • R 2 is a hydroxyl group
  • R 1 is a phosphorus-containing group
  • R 2 is -O - X, or R. It is more preferable that 1 is a sulfur-containing group and R 2 is a hydroxyl group.
  • R 1 and R 2 are the above combination is not particularly limited, but for example, L-ascorbic acid, L-calcium L-ascorbic acid, sodium L-ascorbic acid, magnesium L-ascorbic acid, L- Zinc ascorbic acid, L-ascorbic sodium phosphate, L-ascorbic magnesium phosphate, 3-O-ethyl-L-ascorbic acid, potassium (ascorbic / tocopheryl) phosphate, L-ascorbic acid sulfate disodium, dipalmitic acid Ascorbic, L-ascorbic acid palmitate, maleate ascorbic acid, 2-O-ethylascorbic acid, 3-O-cetyl ascorbic acid, 3-ethylhexyl glyceryl ascorbic acid, 3-glyceryl ascorbic acid, 3-butyl glyceryl ascorbic acid Acid, 3-lauryl glyceryl ascorbic acid, ethylhex
  • Specific compounds are not particularly limited, but for example, L-ascorbic acid, calcium L-ascorbic acid, sodium L-ascorbic acid, magnesium L-ascorbic acid, zinc L-ascorbic acid, sodium L-ascorbic acid phosphate, and the like.
  • L-ascorbic magnesium phosphate 3-O-ethyl-L-ascorbic acid, potassium (ascorbic / tocopheryl) phosphate, L-ascorbic acid sulfate disodium, dipalmitate ascorbic acid, L-ascorbic acid palmitate, malein Ascorbic acid ascorbic acid, 2-O-ethylascorbic acid, 3-O-cetyl ascorbic acid, 3-ethylhexyl glyceryl ascorbic acid, 3-glyceryl ascorbic acid, 3-butyl glyceryl ascorbic acid, 3-lauryl glyceryl ascorbic acid, ethylhexyl glyceryl More preferred are sodium ascorbic acid, L-ascorbic acid stearate, isostearyl ascorbic acid disodium, ascorbic acid trisodium isopalmitate, ascorbic acid trisodium palmitate, and ascorbic acid aminopropyl phosphate
  • the organic group constituting a part of the components (A) and (B) requires a carbon atom, and is also selected from a hydrogen atom, an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom, and a halogen atom. It may contain at least one of these.
  • the atomic group contained in the organic group is not particularly limited, and examples thereof include hydrocarbons, heterocycles, and substituents described in the [Substituent] column below.
  • substituents and the like described in the column of [Substituents] described later replace with the hydrogen atom of the hydrocarbon group, interrupt the hydrocarbon group, and / or include at the base end of the hydrocarbon group, or aromatic hydrocarbon.
  • a group forming a fused ring with a water group is also included.
  • the hydrocarbon group constituting a part of the components (A) and (B) is not particularly limited, but for example, an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group and the like. Can be mentioned.
  • the monovalent aliphatic hydrocarbon group may be monovalent or polyvalent depending on the context, and the monovalent aliphatic hydrocarbon group is not particularly limited, and examples thereof include a linear or branched alkyl group, an alkenyl group, and an alkynyl group. ..
  • the alkyl group includes a linear group or a branched chain, and is not particularly limited, and is, for example, a methyl group, an ethane-1-yl group, a propane-1-yl group, a 1-methylethane-1-yl group, and a butane-1-yl group.
  • butane-2-yl group 2-methylpropane-1-yl group, 2-methylpropane-2-yl group, pentan-1-yl group, pentan-2-yl group, hexane-1-yl group , Heptane-1-yl group, octane-1-yl group, 2-ethylhexane-1-yl group, 1,1,3,3-tetramethylbutane-1-yl group, nonan-1-yl group, decane -1-yl group, undecane-1-yl group, dodecane-1-yl group, tridecane-1-yl group, tetradecane-1-yl group, pentadecane-1-yl group, hexadecane-1-yl group, 2- Hexyldecane-1-yl group, heptadecane-1-yl group, octadecane-1-yl group, nonadecan-1-yl group,
  • the alkenyl group includes a linear group or a branched chain, and is not particularly limited, and is, for example, a vinyl group, a propa-1-en-1-yl group, an allyl group, an isopropenyl group, and a pig-1-en-1-yl.
  • the alkynyl group includes a linear or branched chain, and is not particularly limited, and is, for example, ethynyl, propa-1-in-1-yl group, propa-2-in-1-yl group, pig-1-in-.
  • the alicyclic hydrocarbon group is not particularly limited, and examples of the monovalent group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group and the like.
  • the aromatic hydrocarbon group is not particularly limited, and examples thereof include a phenyl group, a naphthalene group, an anthracene group, and a group containing aromatic ring residues such as those residues.
  • a fused ring may be formed together with the substituents and the like described in the following [Substituents].
  • the monovalent aromatic hydrocarbon group is not particularly limited, and is, for example, a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 2,4-dimethylphenyl group, 2,5.
  • -Dimethylphenyl group 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,4,5-trimethylphenyl group, 2,4,6-trimethylphenyl group, 4-ethylphenyl group, 4-propyl Phenyl group, 4-isopropylphenyl group, 4-butylphenyl group, 4-tert-butylphenyl group, 4-pentylphenyl group, 4-tert-pentylphenyl group, 2,4-bis (4-tert-pentyl) phenyl Group, 1,1,3,3-tetramethylbutylphenyl group, 2-methyl-5-tert-butylphenyl group, 4-pentylphenyl group, 4-hexylphenyl group, 4-heptylphenyl group, 4-octylphenyl Group, 4-nonylphenyl group, 4-decanylphenyl group, 4-undecylphenyl group, 4-dode
  • the substituent is not particularly limited, and examples thereof include a hydrocarbon group, an oxygen-containing group, a nitrogen-containing group, a sulfur-containing group, a phosphorus-containing group, and a halogen. Substituents also include groups to which these substituents are attached. Examples of the hydrocarbon group include those listed in the above [hydrocarbon group].
  • the oxygen-containing group is not particularly limited, but for example, a hydroxyl group, an alkoxy group, an acetoxy group, an acetyl group, an aldehyde group, a carboxy group, a urea group, a urethane group, an amide group, an imide group, an ether group, a carbonyl group and an ester group.
  • the nitrogen-containing group is not particularly limited, but for example, a cyano group, a cyanato group, an isocyanate group, a nitro group, a nitroalkyl group, an amide group, a urea group, a urethane group, an imide group, a carbodiimide group, an azo group, a pyridine group, and the like.
  • a cyano group a cyanato group, an isocyanate group, a nitro group, a nitroalkyl group, an amide group, a urea group, a urethane group, an imide group, a carbodiimide group, an azo group, a pyridine group, and the like.
  • Examples thereof include an imidazole group, a primary amino group, a secondary amino group, a tertiary amino group, a quaternary ammonium group and an aminoalkyl group.
  • the sulfur-containing group is not particularly limited, but for example, a sulfate group, a sulfonyl group, a sulfonic acid group, a mercapto group, a thioether group, a thiocarbonyl group, a thiourea group, a thiocarboxy group, a thiocarboxylate group, a dithiocarboxy group, and the like.
  • Examples thereof include dithiocarboxylate group, sulfate ester, thiophene group, thiazole group, thiol group, sulfo group, sulfide group, disulfide group, thioester group, thioamide group, thiocarbamate group, dithiocarbamate group and their esters, and the number of carbon atoms thereof. Is preferably 0 to 30.
  • the acid-type sulfur-containing group may be a salt-type (alkali metal cation, alkaline earth cation, ammonium cation described in R 1 above).
  • the phosphorus-containing group is not particularly limited, and is, for example, a phosphate group, a phosphite group, a phosphonic acid group, a phosphinic acid group, a phosphonic acid group, a phosphinic acid group, a pyrophosphate group, a phosphoric acid ester group, and a sub.
  • the acid type phosphorus-containing group may be a salt type (alkali metal cation, alkaline earth cation, ammonium cation described in R 1 above).
  • halogens include fluorine, chlorine, bromine and iodine.
  • the component (B) stabilizes the component (A).
  • the effect of the ascorbic acid-based compound can be further enhanced, and the effect can be maintained for a long period of time without volatilization.
  • the component (B) has (i) a linear or branched (preferably linear) alkyl moiety having 1 to 10 carbon atoms, and the alkyl moiety is an oxygen atom. It has at least one hydroxyalkyl group which may contain, and has two or more hydroxyl groups in total in the amine or ammonium compound (however, in the case of the ammonium compound, the cation site).
  • the alkyl moiety is in the form of a branched chain having 3 to 10 carbon atoms, and the alkyl moiety has at least one hydroxyalkyl group which may contain an oxygen atom, or (iii) The alkyl moiety has at least one hydroxyalkyl group which may contain an oxygen atom, and the alkyl moiety is linear with 1 to 10 carbon atoms and is contained in an amine or ammonium compound (provided that the ammonium compound is used. In the case of a cation site), there are a total of two or more oxygen atoms, or the alkyl site is linear with 2 to 10 carbon atoms, and the hydroxyalkyl group has a hydroxyl group at the 2-position or higher position. It is a compound.
  • the skeleton of the amine compound is not particularly limited, and for example, primary amine, secondary amine, tertiary amine, imidazole, pyridine, pyrrolidine, piperidine, pyrrol, pyrazine, triazole, isoquinoline, oxazoline, thiazole, morpholine, guanidine, pyrimidine, etc.
  • Examples thereof include piperazine, triazine, quinoline, indolin, quinoxazoline, isooxazoline and amino acids.
  • the ammonium compound include salts of the above amine compounds or quaternized amine compounds.
  • the oxygen atom when the alkyl moiety contains an oxygen atom, the oxygen atom contains the oxygen-containing group mentioned above, for example, an ether bond, a carbonyl group, a hydroxyl group, a carboxylate group, an ester bond, an amide bond, etc. at the alkyl moiety.
  • hydroxyalkyl group examples include a monohydroxyalkyl group and a polyhydroxyalkyl group, and each alkyl group may contain an oxygen atom. Specific examples of these include, but are not limited to, hydroxyalkoxyalkyl groups, alkoxyhydroxyalkyl groups, hydroxypolyalkyleneoxyalkyl groups and the like.
  • the monohydroxyalkyl group is not particularly limited, and for example, a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropane-1-yl group, a 2-hydroxypropane-1-yl group, and the like.
  • the polyhydroxyalkyl group is not particularly limited, and examples thereof include di, tri, tetra, penta, hexa, hepta, and octahydroxyalkyl groups.
  • the present invention is not particularly limited, but for example, a dihydroxyethyl group such as a 1,2-dihydroxyethyl group; a 1,2-dihydroxypropane-1-yl group, a 2,3-dihydroxypropane-1-yl group and the like.
  • the linear hydroxyalkyl group preferably has 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, further preferably 1 to 3 carbon atoms, particularly preferably 2 to 3 carbon atoms, and most preferably 3.
  • the number of hydroxyl groups per linear hydroxyalkyl group is preferably 1 to 8, more preferably 1 to 4, and even more preferably 1 to 3.
  • the number of linear hydroxyalkyl groups is preferably 2 to 3.
  • the branched hydroxyalkyl group preferably has 3 to 6 carbon atoms, and more preferably 3 to 4 carbon atoms.
  • the number of hydroxyl groups per branched hydroxyalkyl group is preferably 1 to 8, more preferably 1 to 4, and even more preferably 1 to 3.
  • the branched-chain hydroxyalkyl group preferably has 3 to 6 carbon atoms, and more preferably 3 to 4 carbon atoms.
  • the number of hydroxyl groups per branched hydroxyalkyl group is preferably 1 to 8, more preferably 1 to 4, further preferably 2 to 4, and particularly preferably 2 to 3.
  • the number of branched hydroxyalkyl groups is preferably 1 to 2, more preferably 1.
  • the linear hydroxyalkyl group preferably has 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, and further preferably 1 to 3 carbon atoms when the amine or ammonium compound has two or more oxygen atoms.
  • the number of hydroxyl groups per linear hydroxyalkyl group is preferably 1 to 8, more preferably 1 to 4, and even more preferably 1 to 3.
  • the number of carbon atoms of the alkyl group is preferably 2 to 6, more preferably 2 to 4, further preferably 2 to 3, and particularly preferably 3.
  • the number of hydroxyl groups per linear hydroxyalkyl group is preferably 1 to 8, more preferably 1 to 4, and even more preferably 1 to 3.
  • the portion of the component (B) other than the hydroxyalkyl group bonded to the nitrogen moiety is not particularly limited, but a hydrogen atom or an organic group is preferable.
  • the organic group is more preferably a hydrocarbon group (hereinafter, also referred to as hydrocarbon group H) which may have a substituent and may contain an oxygen atom at the hydrocarbon moiety.
  • hydrocarbon group H a hydrocarbon group which may have a substituent and may contain an oxygen atom at the hydrocarbon moiety.
  • a hydrogen atom is preferable in terms of stabilization of the ascorbic acid-based compound, expression of the effect of the ascorbic acid-based compound, and long-term maintenance.
  • the hydrocarbon group H the content described in the above [hydrocarbon group] column is referred to.
  • the hydrocarbon group is preferably an aliphatic hydrocarbon group, more preferably an alkyl group.
  • the alkyl group is preferably linear or branched with 1 to 18 carbon atoms, more preferably linear or branched with 1 to 12 carbon atoms, and more preferably linear or branched with 1 to 8 carbon atoms. Is more preferable, and a linear or branched chain having 1 to 4 carbon atoms is particularly preferable.
  • the alkyl group is not particularly limited, but for example, a methyl group, an ethyl group, a propane-1-yl group, a propane-2-yl group, a butane-1-yl group, a 2-methylpropane-1-yl group, and a butane group.
  • the above-mentioned hydrocarbon group H may have a substituent, and the substituent is not particularly limited, and examples thereof include those described in the above-mentioned [Substituent] column.
  • substituents those having an oxygen-containing group are preferable, among them, an alkoxy group, an acetoxy group, an acetyl group, an aldehyde group, a carboxy group, an ether group, a carbonyl group and an ester group are more preferable, and a carbonyl group is further preferable.
  • the carbonyl group examples include, but are not limited to, formyl group (methanoyl group), ethanoyl group (acetyl group), propanoyl group (propionyl group), benzoyl group, propenoyl group (acrylyl group) and the like.
  • formyl group methanoyl group
  • ethanoyl group acetyl group
  • propanoyl group propionyl group
  • benzoyl group propenoyl group
  • acrylyl group acrylyl group
  • an etanoyl group is preferable.
  • the hydrocarbon moiety may contain an oxygen atom, in which case the hydrocarbon moiety contains the oxygen-containing group, eg, ether bond, carbonyl group, hydroxyl group, carboxylate group, ester bond, amide bond, urea. Form or contain a bond or urethane bond. Therefore, in the present invention, "the hydrocarbon moiety contains an oxygen atom” includes the case where the alkyl moiety is interrupted or the hydrogen atom is replaced by a group containing a hetero atom such as a nitrogen atom as an atomic group containing an oxygen atom. ..
  • the amine or ammonium compound of the component (B) has the composition of (i), (ii) or (iii) above.
  • the amine or ammonium compound of the component (B) has the constitution of the above (i)
  • the constitution having two or three linear hydroxyalkyl groups is that it has two or more of the above hydroxyalkyl groups.
  • those having one or more hydroxyalkyl groups having two or more hydroxyl groups can be mentioned.
  • the diethanolamine, triethanolamine, diisopropanolamine, triisopropanolamine, 2 -Amino-2-hydroxymethyl-1,3-propanediol, 2-amino-2-methyl-1,3-propanediol are preferable, diisopropanolamine, triisopropanolamine, 2-amino-2-hydroxymethyl-1 , 3-Propanediol, 2-amino-2-methyl-1,3-propanediol are more preferred, 2-amino-2-hydroxymethyl-1,3-propanediol, 2-amino-2-methyl-1, 3-Propanediol is particularly preferred.
  • the configuration having a branched hydroxyalkyl group is not particularly limited, but for example, 2- (dimethyl).
  • 2-amino-2-hydroxymethyl-1,3-propanediol is not particularly limited from the viewpoint of the effect of suppressing melanin production by the combination of the components (A) and (B) and the stability of the ascorbic acid-based compound. , 2-Amino-2-methyl-1,3-propanediol is preferred.
  • the amine or ammonium compound of the component (B) has the composition of (iii) above, it has a linear hydroxyalkyl group and oxygen is contained in the amine or ammonium compound (however, in the case of the ammonium compound, the cation moiety).
  • oxygen is contained in the amine or ammonium compound (however, in the case of the ammonium compound, the cation moiety).
  • it may have only a hydroxyalkyl group, or may have two or more oxygen atoms in total of a hydroxyalkyl group and the above-mentioned hydrocarbon group having an oxygen-containing group.
  • examples thereof include diethanolamine, triethanolamine, diisopropanolamine, triisopropanolamine, N-lauryldihydroxyethanolamine, N- (2-hydroxyethyl) iminodiacetic acid, 2-acetamidoethanol and the like, and their safety.
  • diethanolamine, triethanolamine, diisopropanolamine, triisopropanolamine, N-lauryldihydroxyethanolamine, and 2-acetamidoethanol listed in the specifications for raw materials for non-pharmaceutical products are preferable.
  • diethanolamine and triethanolamine are preferable, although not particularly limited.
  • the configuration in which the linear hydroxyalkyl group has a hydroxyl group at the 2-position or higher is not particularly limited, but is, for example, monoisopropanolamine, diisopropanolamine, triisopropanolamine, N-ethyl.
  • -D-Glucamine 1-Amino-1-deoxy-D-Glucitol, 1-Deoxy-1- (Methylamino) -D-Glucitol, 1-Deoxy-1- (n-octylamino) -D-Glucitol, 2 , 3,4,5,6-pentahydroxyhexylamine, 6-amino-1,2,3,4,5-hexanepentaol, 6-methylamino-1,2,3,4,5-hexanepentaol , 3-Amino-1,2-propanediol, 3-methylamino-1,2-propanediol, 3- (dimethylamino) -1,2-propanediol, 3- (diethylamino) -1,2-propanediol From the viewpoint of safety, for example, monoisopropanolamine, diisopropanolamine, and triisopropanolamine listed in the specifications for raw materials for non-pharmaceutical products are
  • the amine or ammonium compound of the component (B) is an amine compound
  • the amine compound represented by the following formula (II) is preferable as the component (B).
  • R 4 are independent and (i) R 4 is a hydroxyalkyl group in which the alkyl moiety may contain an oxygen atom, and at least one of them has a linear alkyl moiety having 1 to 10 carbon atoms and the alkyl moiety is an oxygen atom. Is a hydroxyalkyl group that may contain, and n is 2 or 3 or (ii) R 4 is a hydroxyalkyl group in which the alkyl moiety may contain an oxygen atom, and at least one of them has an alkyl moiety in the form of a branched chain having 3 to 10 carbon atoms, and the alkyl moiety is an oxygen atom.
  • R 4 is a hydroxyalkyl group in which the alkyl moiety may contain an oxygen atom, and at least one of the hydroxyalkyl groups has the alkyl moiety in a linear form having 1 to 10 carbon atoms and is an amine or. It has a total of two or more oxygen atoms in the ammonium compound (however, in the case of an ammonium compound, the cation moiety), or at least one of the hydroxyalkyl groups has a linear alkyl moiety having 2 to 10 carbon atoms.
  • the hydroxyalkyl group has a hydroxyl group at a position of 2 or more, and n is an integer of 1 to 3.
  • R 5 may independently have a hydrogen atom or a substituent, and the hydrocarbon moiety may contain an oxygen atom directly having 1 to 18 carbon atoms. It is a chain or branched hydrocarbon group.
  • R 4 is independent of each other.
  • R 4 is a hydroxyalkyl group in which the alkyl moiety is linear with 1 to 10 carbon atoms and the alkyl moiety may contain an oxygen atom, and n is 2 or 3 or not.
  • the alkyl moiety is a branched chain having 3 to 10 carbon atoms, the alkyl moiety is a hydroxyalkyl group which may contain an oxygen atom, and n is an integer of 1 to 3.
  • R 4 is a hydroxyalkyl group in which the alkyl moiety may contain an oxygen atom, and the alkyl moiety is linear with 1 to 10 carbon atoms and is contained in an amine or an ammonium compound (provided that the ammonium compound is used).
  • the cation moiety has two or more oxygen atoms in total, or the alkyl moiety is linear with 2 to 10 carbon atoms, the hydroxyalkyl group has a hydroxyl group at the 2-position or higher, and n is It is an integer of 1 to 3 and
  • R 5 is independently a hydrogen atom or an organic group having 1 to 18 carbon atoms.
  • the linear hydroxyalkyl group of R 4 preferably has 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, further preferably 1 to 3 carbon atoms, and particularly preferably 2 to 3 carbon atoms. 3 is the most preferable.
  • the number of hydroxyl groups is preferably 1 to 8, more preferably 1 to 4, and even more preferably 1 to 3.
  • the branched-chain hydroxyalkyl group of R 4 preferably has 3 to 6 carbon atoms, and more preferably 3 to 4 carbon atoms.
  • the number of hydroxyl groups is preferably 1 to 8, more preferably 1 to 4, further preferably 2 to 4, and particularly preferably 2 to 3.
  • n is preferably 1 to 2, more preferably 1.
  • the linear hydroxyalkyl group of R 4 has 1 to 6 carbon atoms when the amine compound has two or more oxygen atoms in total of all R 4 and R 5 .
  • the number of hydroxyl groups is preferably 1 to 8, more preferably 1 to 4, and even more preferably 1 to 3.
  • the number of carbon atoms is preferably 2 to 6, more preferably 2 to 4, and even more preferably 2 to 3.
  • the number of hydroxyl groups is preferably 1 to 8, more preferably 1 to 4, and even more preferably 1 to 3.
  • the cation is an ammonium cation represented by the following formula (II').
  • R 4 are independent and (i) R 4 is a hydroxyalkyl group in which the alkyl moiety may contain an oxygen atom, and at least one of them has a linear alkyl moiety having 1 to 10 carbon atoms and the alkyl moiety is an oxygen atom. Is a hydroxyalkyl group that may contain, and n is an integer of 2-4, (ii) R 4 is a hydroxyalkyl group in which the alkyl moiety may contain an oxygen atom, and at least one of them has an alkyl moiety in the form of a branched chain having 3 to 10 carbon atoms, and the alkyl moiety is an oxygen atom.
  • R 4 is a hydroxyalkyl group in which the alkyl moiety may contain an oxygen atom, and at least one of the hydroxyalkyl groups has the alkyl moiety in a linear form having 1 to 10 carbon atoms and is an amine or. It has a total of two or more oxygen atoms in the ammonium compound (however, in the case of an ammonium compound, the cation moiety), or at least one of the hydroxyalkyl groups has a linear alkyl moiety having 2 to 10 carbon atoms.
  • the hydroxyalkyl group has a hydroxyl group at a position of 2 or more, and n is an integer of 1 to 4.
  • each of R 5 is a straight chain having 1 to 18 carbon atoms which may have a hydrogen atom or a substituent and the hydrocarbon moiety may contain an oxygen atom. It is a state or branched hydrocarbon group.
  • R 4 is independent of each other.
  • R 4 is a hydroxyalkyl group in which the alkyl moiety is linear with 1 to 10 carbon atoms and the alkyl moiety may contain an oxygen atom, and n is an integer of 2 to 4 or not.
  • the alkyl moiety is a branched chain having 3 to 10 carbon atoms, the alkyl moiety is a hydroxyalkyl group which may contain an oxygen atom, and n is an integer of 1 to 4.
  • R 4 is a hydroxyalkyl group in which the alkyl moiety may contain an oxygen atom, and the alkyl moiety is linear with 1 to 10 carbon atoms and is contained in an amine or an ammonium compound (provided that the ammonium compound is used).
  • the cation moiety) has two or more oxygen atoms in total, or the alkyl moiety is linear with 2 to 10 carbon atoms, the hydroxyalkyl group has a hydroxyl group at the 2-position or higher, and n is It is an integer of 1 to 4,
  • R 5 is independently a hydrogen atom or an organic group having 1 to 18 carbon atoms.
  • the anion is not particularly limited, but for example, hydroxide anion, halogen-based anion, sulfur-based anion, phosphorus-based anion, cyanide-based anion, boron-based anion, fluorine-based anion, nitrogen oxide-based anion, and the like.
  • hydroxide anion examples include carboxylic acid anions, and among these, hydroxide anions are preferable.
  • Examples of the hydroxyalkyl group of R 4 in the formulas (II) and (II') of the component (B) include the above.
  • the organic group of R 5 in the formulas (II) and (II') is preferably a hydrocarbon group having 1 to 18 carbon atoms which may have a substituent and the hydrocarbon moiety may contain an oxygen atom.
  • the contents described as the above-mentioned hydrocarbon group H are referred to.
  • the hydrocarbon group is preferably an aliphatic hydrocarbon group, more preferably an alkyl group. Further, a linear or branched chain is preferable.
  • a hydrogen atom is preferable for R 5 from the viewpoint of stabilizing the ascorbic acid-based compound, exhibiting the effect of the ascorbic acid-based compound, and maintaining the ascorbic acid-based compound for a long period of time.
  • Examples of the hydroxyalkyl group of R 4 in the formulas (II) and (II') of the component (B) include the above-mentioned hydroxyalkyl and polyhydroxyalkyl groups depending on the context, and among them, the linear chain of (i).
  • the hydroxyalkyl group in the form is not particularly limited, but for example, a hydroxyethyl group, a 2-hydroxypropane-1-yl group, a 1,2-dihydroxypropane-3-yl group is preferable, and a hydroxyethyl group and a 2-hydroxypropane group are preferable.
  • the -1-yl group is more preferable, and the hydroxyethyl group is even more preferable.
  • the branched hydroxyalkyl group of (ii) is not particularly limited, but is, for example, a 1-hydroxy-2-methylpropan-2-yl group and a 1,3-dihydroxy-2-hydroxymethylpropane-2-yl group. , 1,3-Dihydroxy-2-methylpropane-2-yl group, 1,3-dihydroxy2-ethylpropane-2-yl group, 1-hydroxy-3-methylbutane-2-yl group, 2-hydroxy-2 -Methylpropane-2-yl group, 2-hydroxy-2-methylbutane-2-yl group, 2-ethyl-2-hydroxybutane-2-yl group, 2-hydroxy-3-methylpentane-2-yl group, 3-Ethyl-2-hydroxypentane-2-yl group, 2-ethyl-1-hydroxy-3-methylbutane-2-yl group, 1-hydroxy-3-methyl-2- (1-methylethyl) butane-2 -Il group, 2-ethyl-1-hydroxypentan
  • the linear hydroxyalkyl group of (iii) is not particularly limited, but for example, a hydroxyethyl group and a 2-hydroxypropane-1-yl group are preferable, and a hydroxyethyl group and a 2-hydroxypropane-1-yl group are preferable. More preferably, a hydroxyethyl group is more preferable, and those having a hydroxyl group at the 2-position or higher position are not particularly limited, but for example, 2-hydroxypropane-1-yl group and 1,2-dihydroxypropane-3-yl group. Is preferable, and 2-hydroxypropane-1-yl group is more preferable.
  • the specific amine compound is not particularly limited, but for example, the linear amine compounds listed in (i) of the component (B) used in combination with the above component (A), (ii), (. Examples thereof include the amine compounds listed in iii).
  • the compounding agent or composition of the present invention preferably contains at least one of the hydroxyalkyl groups of the component (B).
  • R 6 represents a hydrogen atom, a linear alkyl group having 1 to 4 carbon atoms, or a linear hydroxyalkyl group having 1 to 4 carbon atoms.
  • R 7 has 1 to 4 carbon atoms.
  • R 6 and R 7 in the component (B) is a hydroxyalkyl group having 1 to 4 carbon atoms, and R 6 and R 7 in the component (B) have 1 to 4 carbon atoms. It is more preferably the hydroxyalkyl group of. In this case, it is excellent in stabilizing the ascorbic acid-based compound of the component (A), expressing the effect of the ascorbic acid-based compound, and maintaining it for a long period of time.
  • the branched-chain hydroxyalkyl group preferably has 3 to 6 carbon atoms, and more preferably 3 to 4 carbon atoms.
  • the number of hydroxyl groups per branched hydroxyalkyl group is preferably 1 to 8, more preferably 1 to 4, further preferably 2 to 4, and particularly preferably 2 to 3.
  • the number of n is preferably 1 to 2, more preferably 1.
  • the hydroxyalkyl group represented by the formula (III) is not particularly limited, and is, for example, 1-hydroxy-2-methylpropan-2-yl group and 1,3-dihydroxy-2-hydroxymethylpropane-2-yl.
  • the 1,3-dihydroxy-2-hydroxymethylpropane-2-yl group and 1,3-dihydroxy-2-methylpropane-2-yl group listed in the specifications for external raw materials are preferable, while the components (A) and ( From the viewpoint of stability and effect of ascorbic acid-based compound by the combination of B), 1,3-dihydroxy-2-hydroxymethylpropane-2-yl group and 1,3-dihydroxy-2-methylpropane-2-yl group Is preferable.
  • the specific amine compound is not particularly limited, and examples thereof include the amine compounds listed in (ii) of the component (B) used in combination with the above component (A).
  • the alkyl moiety is a polyhydroxyalkyl group having two or more and having a linear or branched alkyl moiety having 1 to 10 carbon atoms and which may contain an oxygen atom. In this case, it is excellent in stabilizing the ascorbic acid-based compound of the component (A), expressing the effect of the ascorbic acid-based compound, and maintaining it for a long period of time.
  • any of the following is preferable.
  • -In the component (A) either R 1 or R 2 is a hydroxyl group.
  • R 1 is a hydroxyl group and R 2 is a hydroxyl group, or R 1 is a hydroxyl group and R 2 is an organic oxy group.
  • a hydroxyalkyl group in which R 1 is a hydroxyl group and R 2 is a hydroxyl group (A) and at least one (preferably all) of R 4 is a branched chain hydroxyalkyl group having an alkyl moiety having 3 to 10 carbon atoms (preferably all).
  • the number of hydroxyl groups is preferably 1 to 8, more preferably 1 to 4, still more preferably 2 to 4, particularly preferably 2 to 3.
  • the number of carbon atoms in the alkyl moiety is preferably 3 to 6, more preferably. 3 to 4)
  • R 5 is a combination of all hydrogen atom components (B). From the viewpoint of expressing the effect of the ascorbic acid compound and maintaining it for a long period of time, any of the following is preferable.
  • R 1 and R 2 are preferably a functional group (preferably a hydroxyl group) that can have a salt structure, R 1 is a hydroxyl group, R 2 is a hydroxyl group, and R 1 contains phosphorus. It is more preferable that R 2 is a hydroxyl group, R 1 is a hydroxyl group and R 2 is an organic oxy group, R 1 is a hydroxyl group, R 2 is a hydroxyl group, R 1 is a phosphorus-containing group and R 2 is a hydroxyl group. It is more preferable that R 1 is a hydroxyl group and R 2 is a hydroxyl group.
  • R 1 is a hydroxyl group
  • R 2 is a hydroxyl group component (A)
  • at least one (preferably all) of R 4 is a branched chain hydroxyalkyl group having an alkyl moiety having 3 to 10 carbon atoms (preferably all).
  • the number of hydroxyl groups is preferably 1 to 8, more preferably 1 to 4, still more preferably 2 to 4, particularly preferably 2 to 3.
  • the number of carbon atoms in the alkyl moiety is preferably 3 to 6, more preferably. 3-4), where R 5 is a combination of hydrogen atom components (B).
  • the compounding agent or composition of the present invention may contain the components (A) and (B), and may contain a salt formed from the components (A) and (B) as described above. ..
  • the molar ratio of the component (A) to (B) contained in the compounding agent or composition of the present invention is particularly considered to be the molar ratio of the functional group having a salt structure in the component (A) and the component (B).
  • it can be, for example, 1:99 to 99: 1, preferably 1: 9 to 9: 1, more preferably 1: 4 to 4: 1, and even more preferably 1: 4.
  • It is ⁇ 1: 2, particularly preferably 1: 2 to 1: 1, and particularly preferably 1: 1 mol.
  • the mixture of the components (A) and (B) used in the present invention or the anhydride or hydrate of the salt composed of the components (A) and (B) may be either liquid or solid at 25 ° C. ..
  • the hydrate means a salt composed of the components (A) and (B) that absorbs water when left in the air at 25 ° C. and the water content is saturated. Those that do not absorb water when left in the air at 25 ° C. are hydrate-free and anhydrous.
  • a mixture of components (A) and (B) or components (A) and (B) not only immediately after application to the skin or hair but also after water evaporation.
  • the molar ratio is not limited as long as the salt composed of the components (A) and (B) is obtained in a liquid state, but the molar ratio of the components (A) and (B) is preferably 1: 6 to 6: 1. , 1: 4 to 4: 1, more preferably 1: 4 to 1: 1, particularly preferably 1: 3 to 1: 1, and even more preferably 1: 2 to 1: 1.
  • the compounding agent or composition of the present invention can be used for various uses in which the effect of the component (A) is required, and is not particularly limited, but for example, a melanin production inhibitor, an anti-inflammatory agent, an acne improving agent, and aging.
  • Inhibitors antioxidants, cell activators by promoting the synthesis of biological components such as collagen, suppressors of cell damage and DNA damage caused by ultraviolet rays of epidermal keratinocytes, absorption promoters of minerals (iron, copper, etc.), vitamin C Maintaining, promoting, and oxidizing the health of the living body using various other actions (immunity enhancing action by increasing leukocyte, anti-arteriosclerosis by suppressing cholesterol production, anti-allergic action by anti-histamine action, etc.) It can be applied to preparations related to prevention.
  • the above-mentioned uses can be the composition of the present invention as a target product.
  • the agent itself having that use can be the blending agent of the present invention.
  • the above-mentioned melanin production-suppressing combination agent effectively suppresses and improves skin pigmentation such as darkening of the skin caused by spots, freckles, dullness, or exposure to ultraviolet rays by the effect of inhibiting the activity of tyrosinase in pigment cells. It is a compounding agent that can also obtain a whitening effect, and since the compounding agent or composition of the present invention has these effects, it can be suitably used for suppressing melanin production.
  • the compounding agent or composition of the present invention can be suitably used as a compounding agent or cosmetic composition for cosmetics.
  • the cosmetics are not particularly limited, and for example, the skin care compositions are not particularly limited, for example, soap compositions, body soaps, hand soaps, facial cleansers, cleansing oils, cleansing liquids, cleansing lotions, cleansing creams, etc.
  • the external skin preparation is not particularly limited, and examples thereof include ointments, patches, lotions, liniments, and liquid coating agents.
  • composition and manufacturing method in the compounding agent or composition of the present invention The contents of the components (A) and (B) in the compounding agent or composition of the present invention can be appropriately selected depending on the type and the type, amount, form and the like of other components to be blended, but usually they are blended. 0.00001 to 100% by mass based on the total amount of the agent or composition.
  • the content of the components (A) and (B) is, for example, within the above range, and in the case of the composition of the present invention, the purpose according to the application is taken into consideration.
  • the solvent is not particularly limited, but for example, water, alcohols, polyhydric alcohols, higher alcohols, ethers, ketones, cellosolves, hydrocarbons, fats and oils, esters, fatty acids, silicone oils, etc. Examples include waxes and steroids. These may be used alone or in combination of two or more. Of these, water is preferred.
  • the compounding agent or composition of the present invention comprises components (A), (B), and water.
  • the compounding agent of the present invention contains a salt of the components (A) and (B), and water.
  • the compounding agent or composition of the present invention may contain water, whereby the viscosity is lowered and the handling is improved.
  • other components can be blended according to the purpose as long as the effect of the component (A) is not impaired.
  • Such other components are not particularly limited and may be appropriately selected depending on the intended purpose.
  • an anionic surfactant for example, an anionic surfactant, a nonionic surfactant, a cationic surfactant, and an amphoteric surfactant.
  • Surfactants cationic polymers, water-soluble polymers, viscosity regulators, brighteners, higher alcohols, polyhydric alcohols, polysaccharides, higher fatty acids, amidoamines, hydrocarbons, waxes, esters, silicone derivatives, physiological activity
  • Ingredients extracts, antioxidants, metal ion blockers, preservatives, UV absorbers (including organic and inorganic), fragrances, moisturizers, carbons, metal oxides, minerals, salts, neutralization Agents, pH regulators, pigments, resin particles, colorants, natural plant extract components, seaweed extract components, biopharmaceutical components, refreshing agents, insect repellents, enzymes and the like.
  • the compounding agent or composition of the present invention may be produced by mixing, for example, the components (A) and (B) and, if necessary, the other components, water or solvent, or the component (A) in advance. ) And (B) may be obtained, and this salt may be added to and mixed with other components, water or a solvent, if necessary.
  • the order of addition and mixing is not particularly limited.
  • the properties of the compounding agent or composition of the present invention are not particularly limited and may be uniform or non-uniform.
  • it may be in the form of a liquid to a solid, and may be a dispersion, a gel or an emulsion.
  • the emulsion is not particularly limited, but is, for example, a water-in-oil (W / O type) emulsion, an oil-in-water (O / W type) emulsion, and a composite emulsion (W / O / W type, O). / W / O type) and the like.
  • the compounding agent or composition of the present invention preferably has a pH of 9 to 2, more preferably 8 to 3, and particularly preferably 7 to 4 from the viewpoint of stability and effect of the ascorbic acid-based compound.
  • the compounding agent or composition of the present invention is excellent in the stability of the component (A) and the effect thereof, and is due to the non-volatile nature of the mixture or salt of the components (A) and (B) used in the present invention.
  • Specially sustained component (A) especially excellent in melanin production inhibitory effect.
  • the compounding agent liquid at 25 ° C. is used, for example, on the skin or hair, it is excellent in the feeling of use such as elongation, stickiness, moisturizing feeling, and familiarity with the skin, and is particularly excellent in non-stickiness.
  • the skin or hair is uniformly coated in a liquid state and retained for a long period of time, and the effect of the component (A) can be sufficiently and efficiently obtained.
  • the ascorbic acid-based compound (A) can be stabilized by coexisting the component (B) to form a composition or by forming a salt of the components (A) and (B).
  • the description in the above-mentioned "Combining agent or composition of the present invention” column is referred to.
  • Combinations 1-14 The compounding agents 1 to 14 were prepared at the molar ratios shown in Tables 1A and 1B. Details of formulation, synthesis, and acquisition of each formulation are as follows. Combinations 1 to 4, 6, 8, 12 to 14: L-ascorbic acid (ascorbic acid), 3-O-ethyl-L-ascorbic acid (3-O-ethylascorbic acid), 2-O-ethylascorbic acid manufactured by Tokyo Kasei Co., Ltd.
  • O- ⁇ -D-glucopyranosyl-L-ascorbic acid (ascorbic glucoside) was used and blended and synthesized by the method described in JP-A-2019-23185.
  • water was distilled off from each of the obtained compounding agents, and when confirmed by NMR using heavy DMSO as the salt structure of the components (A) and (B), the components (R 1 and / or R 2 ) were found. It was confirmed that B) formed a salt structure.
  • Blending agent 5 L-ascorbic acid 2-phosphate ester trisodium (0.5 g, 1.55 mmol: manufactured by Tokyo Kasei Co., Ltd.) and 35% hydrochloric acid (0.49 g, 4.65 mmol) are neutralized in ion-exchanged water. After desalting, the obtained L-ascorbyl phosphate (ascorbyl phosphoric acid) (1.18 g, 4.65 mmol) was added to 2-amino-2-hydroxymethyl-1,3-propanediol (0.54 g, A compounding agent was obtained by blending 4.65 mmol) in ion-exchanged water.
  • Combination agent 7 A reagent of L-ascorbic acid (ascorbic acid) manufactured by Tokyo Kasei Co., Ltd. was used.
  • Combination Agent 9 A reagent of L-ascorbic acid 2-phosphate ester trisodium (Na ascorbyl phosphate) manufactured by Fuji Film Wako Chemical Co., Ltd. was used.
  • Combination Agent 10 A reagent of 3-O-ethyl-L-ascorbic acid (3-O-ethylascorbic acid) manufactured by Tokyo Kasei Co., Ltd. was used.
  • Combination Agent 11 A reagent of 2-O- ⁇ -D-glucopyranosyl-L-ascorbic acid (ascorbic glucoside) manufactured by Tokyo Kasei Co., Ltd. was used.
  • it When compared with Example 4), it generally showed the same stability as the comparative example compounding agent of the ascorbic acid derivative product in which ascorbic acid was stabilized. That is, it was shown that the component (A) was stabilized by the combination of the component (A) and the component (B), and the component (B) of the formula (III) was particularly effective.
  • tyrosinase activity inhibitory rate (melanin production inhibitory effect)
  • a 0.2 mg / mL aqueous solution of compounding agents 1 to 14 was prepared, the tyrosinase activity inhibitory rate was measured, and the melanin production inhibitory effect was evaluated.
  • Tyrosinase (SIGMA-ALDRICH) was dissolved in 67 mM phosphate buffer (pH 6.8) to a concentration of 2500 unit / mL to prepare an enzyme solution, and the substrate solution was DL-DOPA (Tokyo Kasei Kogyo) 3 mg 67 mM. Prepared by dissolving in 10 mL of phosphate buffer.
  • tyrosinase activity inhibition rate (melanin production inhibitory effect) was evaluated as follows. Regarding the tyrosinase activity inhibition rate, it is judged that the evaluation of ⁇ or ⁇ is desirable in solving the problem of the present invention.
  • ⁇ Tyrosinase activity inhibition rate 50% or more
  • ⁇ Tyrosinase activity inhibition rate 5% or more and less than 50%
  • ⁇ Tyrosinase activity inhibition rate 4% or more and less than 5%
  • the tyrosinase activity inhibition rate is highest when the component (A) is ascorbic acid, followed by ascorbyl phosphate and 3-O-ethylascorbic acid. , Ascorbic glucoside was shown in that order.
  • the compounding agents 1 and 2 of the component (B) having the group (ii) of the component (B) and the formula (III) are found.
  • the tyrosinase activity inhibition rate tended to be higher than that of the combination agents 3, 4, 13, and 14.
  • the compounding agents 13 and 14 showed a high inhibition rate of tyrosinase activity.
  • ascorbic acid compounding agent 5 (Example 5) in which the component (A) is 3-O-ethylascorbic acid compounding agent 6 (Example 6) as compared with compounding agent 9 (Comparative Example 3).
  • the ascorbyl glucoside (combination agent 11) and the combination agent 12 in which the component (B) was combined had excellent stability, but the effect of inhibiting the tyrosinase activity was very small.
  • the combination of the component (A) and the component (B) of the present invention can both stabilize the component (A) and inhibit the tyrosinase activity (melanin production inhibitory effect).
  • the compounding agent of the combination of the component (A) and the component (B) of the present invention has good conductivity of the coated surface due to the effect of lowering the resistance value, and has the effects of suppressing static electricity and preventing static electricity, and is particularly targeted.
  • the liquid and non-volatile compounding agent of the present invention which is uniformly coated on an object and has a low resistance value, can be uniformly coated on, for example, skin and hair even after a solvent such as water has volatilized, and various ascorbic acid compounds are used. It was suggested that the effect could be expressed more efficiently for a long period of time.
  • the compounding composition in the form of a product also shows the same tendency as the result obtained in the evaluation of the state of the compounding agent (1) above, and the compounding agent of the present invention is excellent in stability and deteriorates even in the composition. It was suggested that it did not retain the various effects of ascorbic acid.

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Abstract

L'invention concerne une préparation ou une composition et un procédé de stabilisation permettant de stabiliser un composé d'acide ascorbique sur une longue période indépendamment de la présence ou de l'absence d'eau, la préparation ou la composition étant excellente en termes d'effets du composé d'acide ascorbique et pouvant conserver les effets sur une longue période.　La préparation ou la composition contient les ingrédients (A) et (B) suivants. (A) Un acide ascorbique ou un dérivé de celui-ci qui est représenté par la formule (I) ou un sel de l'un ou l'autre. (Dans la formule, R1 à R3' représentent chacun indépendamment un groupe hydroxyle, etc.) (B) Un composé amine ou ammonium qui (i) présente au moins un groupe hydroxyalkyle et au moins deux groupes hydroxyles au total ou qui (ii) présente au moins un groupe hydroxyalkyle ramifié, ou qui (iii) présente au moins un groupe hydroxyalkyle linéaire et au moins deux atomes d'oxygène au total ou présente au moins un groupe hydroxyalkyle linéaire, dans lequel le groupe hydroxyle se trouve à la position égale ou supérieure à 2.
PCT/JP2021/029474 2020-08-11 2021-08-10 Préparation ou composition contenant un composé d'acide ascorbique et procédé de stabilisation d'un composé d'acide ascorbique WO2022034874A1 (fr)

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Citations (11)

* Cited by examiner, † Cited by third party
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JPS6150908A (ja) * 1984-08-20 1986-03-13 Kanebo Ltd 皮膚化粧料
JPS61100511A (ja) * 1984-10-22 1986-05-19 Kanebo Ltd 皮膚化粧料
JPH111487A (ja) * 1997-06-11 1999-01-06 Showa Denko Kk Ｌ−アスコルビン酸−２−リン酸亜鉛塩及びその製造方法
JPH11116423A (ja) * 1997-09-02 1999-04-27 L'oreal Sa リン酸誘導体とメタ二亜硫酸塩に基づくアスコルビン酸安定化のためのシステムとそれを含有する組成物
JP2001220336A (ja) * 2000-02-08 2001-08-14 Lion Corp 口腔用組成物
WO2005067867A1 (fr) * 2004-01-20 2005-07-28 Kose Corporation Produit cosmetique
JP2006111614A (ja) * 2004-09-15 2006-04-27 Nipro Corp 安定化された注射用水溶液製剤
KR20070025426A (ko) * 2005-09-02 2007-03-08 부광약품 주식회사 Ｄ-(+)-α-리포산 트로메타민염을 포함하는 간섬유화 억제 및 치료용 조성물
JP2012025746A (ja) * 2010-07-21 2012-02-09 Lvmh Recherche 特定の水を含有する化粧品用組成物と、脱色又は抗加齢剤としてのその使用
JP2014129278A (ja) * 2012-12-28 2014-07-10 Kao Corp 皮膚外用組成物
JP2021054724A (ja) * 2019-09-27 2021-04-08 株式会社ダリヤ 皮膚化粧料組成物

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6150908A (ja) * 1984-08-20 1986-03-13 Kanebo Ltd 皮膚化粧料
JPS61100511A (ja) * 1984-10-22 1986-05-19 Kanebo Ltd 皮膚化粧料
JPH111487A (ja) * 1997-06-11 1999-01-06 Showa Denko Kk Ｌ−アスコルビン酸−２−リン酸亜鉛塩及びその製造方法
JPH11116423A (ja) * 1997-09-02 1999-04-27 L'oreal Sa リン酸誘導体とメタ二亜硫酸塩に基づくアスコルビン酸安定化のためのシステムとそれを含有する組成物
JP2001220336A (ja) * 2000-02-08 2001-08-14 Lion Corp 口腔用組成物
WO2005067867A1 (fr) * 2004-01-20 2005-07-28 Kose Corporation Produit cosmetique
JP2006111614A (ja) * 2004-09-15 2006-04-27 Nipro Corp 安定化された注射用水溶液製剤
KR20070025426A (ko) * 2005-09-02 2007-03-08 부광약품 주식회사 Ｄ-(+)-α-리포산 트로메타민염을 포함하는 간섬유화 억제 및 치료용 조성물
JP2012025746A (ja) * 2010-07-21 2012-02-09 Lvmh Recherche 特定の水を含有する化粧品用組成物と、脱色又は抗加齢剤としてのその使用
JP2014129278A (ja) * 2012-12-28 2014-07-10 Kao Corp 皮膚外用組成物
JP2021054724A (ja) * 2019-09-27 2021-04-08 株式会社ダリヤ 皮膚化粧料組成物

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