JPH02129113A - External preparation - Google Patents

Abstract

PURPOSE:To obtain an external preparation having skin color-lightening and stains and freckles-preventing effects with high safety without side-effects such as skin roughening and rashes by using an unsaturated straight-chain fatty acid or its derivative as an active ingredient. CONSTITUTION:The subject preparation is obtained by using an unsaturated straight-chain fatty acid of 4 to 17 carbon atoms having 1 to 4 unsaturated bonds distributing in arbitrary positions other than the chain terminal opposing to the carboxyl group on the alkyl chain or its derivative, as an active ingredient in combination with conventional base materials and auxiliary agents in a usual manner to give the subject preparation. At this time, the addition of an ultraviolet absorber and an antioxidant is preferred. The amount of the unsaturated fatty acid used is 0.001 to 5wt.% in cosmetics and 0.001 to 10wt.% in medicines. 10-Petandecenoic acid and 9-hexadecenoic acid are excluded from the unsaturated straight-chain fatty acid as an active ingredient.

Description

[Detailed Description of the Invention] [Field of Industrial Application] The present invention uses an unsaturated straight chain fatty acid or a derivative thereof as an active ingredient to effectively prevent skin pigmentation caused by melanin production such as age spots and freckles. , relates to an external preparation with an excellent skin-lightening effect.

[Conventional technology]

Conventionally, kojic acid and kojic acid derivatives are known as substances that suppress melanin production.

Various fairing cosmetics containing these substances as active ingredients have also been disclosed (for example, Japanese Patent Publication No. 56-1F1569).
No. 1, JP-A-56-7710, JP-A-56-7
776, JP-A-56-79616, etc.). Flavonol compounds are also known. For example, cosmetics and skin liniments containing quercetin as an active ingredient are disclosed in JP-A-55-92305 and JP-A-57-14.
There is one described in Publication No. 517. As a product containing quercetin fatty acid ester as an active ingredient,
There are those described in Japanese Patent Publication No. 34477, and those containing myricetin, fisetin, gutiscetin, rhamnetin, etc. as active ingredients are described in Japanese Patent Application Laid-open Nos. 111410-1982 and 35506-1987. . In addition, JP-A-55-111410 and JP-A-55-143908 disclose products containing 3-hydroxychromone compounds as active ingredients.

[Problem to be solved by the invention]

The present inventors searched for a new substance that has a safe and effective melanin production inhibiting effect and conducted various studies on its effectiveness as an external preparation. discovered that it was effective and invented an external preparation containing the same compound as an active ingredient (
(Japanese Patent Application No. 63-213255) The present invention has discovered that unsaturated straight chain fatty acids other than those mentioned above and their derivatives have an excellent melanin production inhibiting effect, and the object of the present invention is to provide an external preparation containing the same as an active ingredient. This is the purpose.

[Means to solve the problem]

The present inventors searched widely for melanin production inhibiting substances in unsaturated fatty acids, and found that
The present invention was completed based on the discovery that unsaturated straight fatty acids having 7 unsaturated bonds and 1 to 4 unsaturated bonds and derivatives thereof have an excellent melanin production inhibiting effect.

The present invention has 4 to 17 carbon atoms and 1 unsaturated bond.
This is an external preparation containing as an active ingredient an unsaturated straight chain fatty acid or a derivative thereof having 4 to 4 fatty acids present at any position other than the terminal position opposite to the carboxyl group of the alkyl chain.

The unsaturated straight fatty acid which is the active ingredient of the present invention has 4 to 17 carbon atoms and 1 to 4 unsaturated bonds,
It exists at any position of the alkyl chain except for the terminal position opposite to the carboxyl group, such as 2-butenoic acid (C,: 1Δ2).

6-octenoic acid (ca:tΔ6), 6-decenoic acid (C1
゜:lΔ6), 7-unzosylenic acid (C++:1Δ7)
, 9-dodecenoic acid (C+2:1Δ9), 6°9-dodecadienoic acid (C12: 2Δ6-9), 10-tridecenoic acid (C+3:1Δ10), 7.10-) lysocanoic acid (C
+3:2Δ7-10), 9-tetradecenoic acid (CI4:
1Δ9), 6.9-tetradecadienoic acid (C,,: 2
Δ6-9), 7.10-pentadecadienoic acid (C1s:
2Δ7-10), 10-heptadenoic acid (C+7:
1Δ10), 6.9-hexadecadienoic acid Cll1:
2Δ6-9), 6,9.12-hexadecatrienoic acid (
Cps: 3Δ6-9-12) [: The number after C in parentheses is the number of carbon atoms, the number after : is the number of unsaturated bonds, Δ
The next number is the number from the carbon atom of the carboxyl group bonded to the alkyl chain].

These unsaturated straight chain fatty acid derivatives of the present invention include:
The following compounds are included:

(1) A monoglyceride represented by formula (1) or (If) (R represents an aliphatic group of the above-mentioned unsaturated straight chain fatty acid) 2)
Diglyceride represented by formula (III) or (IV) (R1 and R2 are chain organic groups, at least one of which represents an aliphatic group of the unsaturated straight fatty acid) (3) Formula (V ) triglyceride CH20
CDRI = (R1, R2, R3 are chain organic groups, at least one of which represents an aliphatic group of the unsaturated straight chain fatty acid) (4) Metal salt represented by formula (VT) ( RCOO) pM (VI) (R is an aliphatic group of the above-mentioned unsaturated straight chain fatty acid, M is a metal atom, and p indicates the valence of M) (5) Ester RCOOR' (■) represented by formula (■) (R is an aliphatic group of the above-mentioned unsaturated straight chain fatty acid, R'' is a monovalent or divalent or more polyhydric alcohol residue, a polyoxyethylene residue, a sorbitan residue, or a sugar residue) (6) Formula Phospholipid (■) (R1 and R2 are chain organic groups, at least one of them is an aliphatic group of the above-mentioned unsaturated straight fatty acid, and X is choline, ethanolamine, serine, glycerol) , represents a phospholipid or inositol residue) (7) Phosphatidic acid represented by formula (IX) (8) Sterol ester represented by formula (X) (R represents an aliphatic group of the above unsaturated straight fatty acid) (9) Sphingolipid H represented by formula (XI) (R1 and R2 are chain organic groups, at least one of which represents an aliphatic group of the unsaturated straight chain fatty acid) (R is the unsaturated straight chain fatty acid group) αQ represents an aliphatic group of a saturated straight chain fatty acid, and X represents a sugar, phosphoric acid, or amine salt residue; αQ is a primary amide represented by formula (XI); and R' and Ro represent a hydrogen atom or an organic group)
Ql) The second niamide RIC represented by formula (XIII)
ONCOR2 R' (XI[[)(R1,R
2 is a chain organic group, at least one of which represents an aliphatic group of the unsaturated straight fatty acid, and Ro represents a hydrogen atom or an organic group) Amide RICONCOR2 COR3 (XIV) (R1, R2, R3 are chain organic groups, at least one of which represents an aliphatic group of the above-mentioned unsaturated straight fatty acid) Basic acids and their salts HO
OCRCOOH (XV) (R represents the aliphatic group of the above-mentioned unsaturated straight fatty acid) These derivatives include 1-mono-6-octenoin, 1-
Mono-9-dodecenoin, 1-monomyristolein, l
-Mono-10-pentatemonoin. 1-monopalmitolein, 1-mono-10-heftadecenoin, 2-mono-3-hexenoin.

2-mono-7-unzocenoin, 2-monopentademonoin. 2-monopalmitolein, 2-mono-10-hebutadecenoin, 1,2-di-9-dodecenoin, 1,2
- Similistrain, 1.2'; -10-Hentademonoin. 1,2-cibalmitolein, 1,3-cimilistolein, l,3-di-10-pentademonoin. 1.3
-Civalmitolein, 1,3-di-10-hebutadecenoin, trimyristolein, tri-Lopentademonoin.

Mono-, di-, and triglycerides such as tripalmitolein and tri-10-heptadecenoin, esters such as methyl 9-myristoleate, methyl lO-pentadecenoate, methyl palmitoleate, and methyl 10-hebutadecenoate, disodium dipalmitoleyl phosphatidate , G10
- Phosphatidic acids such as disodium pentadecenyl phosphatidate, sphingolipids such as N-palmitoleyl-D-sphingomyelin, N-10-pentadecenyl-D-sphingomyelin, palmitoleic acid amide, dibalmitolein Acid amides, amides such as tripalmitoleic acid amide, dibasic acids such as 9-hexadecenedicarboxylic acid, palmitooleyl cholesterol,
Examples include sterol esters such as myristoleyl cholesterol.

The external preparation of the present invention is used to include cosmetics such as creams, lotions, and packs, and quasi-drugs used for external use such as emulsions, lotions, and liniments.

The external preparation of the present invention contains the above-mentioned unsaturated straight chain fatty acid or its derivative as an active ingredient, in the case of cosmetics, 0.001 to 5%.
(weight), preferably 0.01 to 1% (weight), and in the case of quasi-drugs, 0.01 to 10% (weight), preferably 0.
．． Contains 01 to 2% (by weight).

When preparing the external preparation of the present invention, it can be prepared according to a conventional method using bases and auxiliary agents that are commonly used when preparing conventional cosmetics and external quasi-drugs. .

In addition, in this case, bendiphenone type and cinnamic acid type.

Salicylic acid, benzoic acid, ethyl urocanate.

Benzotriazole, other plant-based ultraviolet absorbers, vitamin E, BHA, BHT, nilinelupic acid,
It is recommended to add antioxidants such as phytic acid, nordihydroguaiaretic acid, and propyl gallate.

Next, examples of the present invention will be given and explained in more detail.

〔Example〕

Example 1 Cream 9-Tetradecenoic acid 0.05% Polyoxyethylene stearyl ether Polyoxyethylene cetyl ether Beeswax ethanol Isopropyl palmitate Liquid paraffin 2.0% 20% 6.0% 6.0% 10.0% 30.0% Polyethylene glycol monostearate 1.0% Methyl roseoxybenzoate 0.2% Make the total amount to 100% with purified water.

Example 2 Emulsion 7-10 Pentadecadienoic acid 0.1% Self-emulsifying glycerol monostearate Polyoxyethylene cetyl ether IC Stearate cetanol Isopropyl midistate Rose methyl benzoate Perfume The total volume is made up to 100% with purified water.

Example 3 Backing agent 10-hebutadecenoic acid ethanol p-oxybenzoic acid methylcarboxyvinyl polymer 0.5% 2.0% 2.0% 1.5% 10.0% 0.2% Trace amount 1.0% 6.0% 0.08% 1.0% Calcium carbonate 0.6% Titanium dioxide 0.02% Fragrance
Trace amount of li! Make the total amount to 100 by making ice.

Example 4 Lotion 6. 9-Hexadecadienoic acid paste posome solution (contains 1% 9-hexadecenoic acid) 0.5% roseoxybenzoic acid 0.08% citric acid
0.3% fragrance
Make the total volume 100 with a small amount of purified water.

Note that % in this example is % by weight.

The melanin production inhibiting effect of unsaturated fatty acids and their derivatives, which are the active ingredients of the present invention, will be clarified by the following tests.

Test Example Melanin production test of 816 cells B16 cells derived from mouse melanoma 1a4 x 10' cells were added to 10ml of fetal bovine serum.
Suspended in Eagle MEIJ medium containing 25 cal
Culture in a roux culture bottle at 37°C in the presence of 5% CO2.

On day 0 and day 3, the medium is replaced with a medium containing 80 μM/1 liter, and cultured for 5 days. After washing the cells with phosphate buffer (pH 7.2) containing 0.8 W/V saline,
Cells were harvested by detachment using a trypsin and EDTA containing solution and filtration. Cells collected on filter paper are
Reflected luminous intensity at 500 nm using a densitometer (
The degree of blackness) was determined.

The test results were as shown in Table 1 below.

Table 1-1 Table 1-3 Table 1-2 Table 1-4 Table 1-5 No change in procedural amendment note + Slightly thin + Quite obviously thin ++ Almost white [Effects of the invention] The external preparation of the present invention is It is an extremely useful invention that can be used safely without causing any injury such as rough skin or skin irritation, and has the effect of whitening the skin and preventing spots, freckles, etc.

1.Display of the incident 1986 Special 2. Name of the invention outside 3. Person who makes corrections Relationship with the incident 4゜ teenager Reason Man

Claims (1)

[Claims] 1. An unsaturated straight chain having 4 to 17 carbon atoms, 1 to 4 unsaturated bonds, and the position of the unsaturated bond is at any position other than the terminal position opposite to the carboxyl group of the alkyl chain. Chain fatty acids or derivatives thereof, provided that 10-pentadecenoic acid,
An external preparation characterized by containing as an active ingredient excluding 9-hexadecenoic acid.