JPH05932A - Agent for artificial suntan - Google Patents

Abstract

PURPOSE:To provide the subject agent for artificial suntan, showing an effect on coloration of skin to be remarkably natural cocoa brown wlar same as in suntan by sunbathing, etc., when applied to the skin, and free from side effects such as inflammation of the skin or excessive generation of chloasmas or freckles. CONSTITUTION:Hydroquinone-O-alpha-D-glycopyranoside is blended as the active component in an amount of 0.0001-30wt.%, preferably 0.01-20wt.%. The above- mentioned compound can be obtained by reacting hydroquinone with starch in the presence of CGT-ase and a phosphate buffer solution and shows an effect on promotion of the activity of tyrosinase as an oxygenase producing melanin pigments. The suntan effect of this agent is based on the same mechanism as in suntan due to actual sunbathing, etc., caused by promotion of generating melanin pigments. A suntanned color free from irregular fading due to washing, etc., can be uniformly developed therefor.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a tanning agent which changes the color of the skin so-called "tan color" without being exposed to sunlight or ultraviolet rays.

[0002]

2. Description of the Related Art Burning the skin to a brown color by sunbathing or the like is one of the fashion factors accompanied by a healthy image.
It is especially popular among the younger generation, but there is a problem that excessive ultraviolet irradiation causes not only skin inflammation but also liver spots and freckles.

As a solution to such a problem, a skin colorant has been provided which imparts a tan color to the skin irrespective of exposure to sunlight (see JP-A-62-270512).
However, in this case, after continuous use in order to utilize the skin-staining reaction between the intermediate product derived from hydroxyacetone and the skin lightening component, different shades are obtained depending on the degree of keratinization of the skin. Not only is it developed, but there is also the drawback that the color tone disappears irregularly due to washing, etc., and it is not sufficient as a sunburn agent.

[0004]

DISCLOSURE OF THE INVENTION The present invention solves the above problems, and evens out a tan color whose color tone does not disappear irregularly by washing or the like on the skin without being exposed to sunlight or ultraviolet rays. It was made in order to provide a tanning agent to be expressed in.

[0005]

That is, the present invention relates to a tanning agent containing hydroquinone-O-α-D-glucopyranoside as an active ingredient.

Hydroquinone-O-D-glucopyranoside (arbutin) has α-isomers and β-isomers, and these isomers are obtained as a mixture according to a conventional general production method and are highly selective. It is difficult to prepare. For example, glucose and hydroquinone were added to DMSO in p-
Depending on the method of reacting in the presence of an acid catalyst such as toluenesulfonic acid, the α-isomer and the β-isomer are 75:
Obtained in a ratio of 25 (Chemistry Letters (Chemi Letters)
stry Letters), 1983, pp. 1487-14.
(See page 88).

Among these isomers, the β-isomer is known to exert a remarkable skin whitening effect by suppressing the activity of the oxidative enzyme tyrosinase which produces a melanin pigment (Japanese Patent Laid-Open Publication No. Sho. 60-56912).

However, the present inventors have surprisingly found that
By reacting hydroquinone with starch in the presence of CGTase and a phosphate buffer, not only is the α-isomer pure, but the α-isomer has the opposite characteristics to the β-isomer, ie , And has the property of promoting the activity of tyrosinase, an oxidase that produces melanin pigment.

Therefore, by applying a tanning agent containing hydroquinone-O-α-D-glucopyranoside as an active ingredient to the skin, the melanin pigment-forming activity of tyrosinase is promoted, the skin color changes to a wheat color, and sunburn The effect is obtained. This tanning effect is based on the same mechanism as in the case of actual tanning due to the accelerated production of melanin pigment and is a very natural skin discoloration effect. Moreover, in this case, unlike the case of actual sunbathing, since irradiation of high-energy ultraviolet rays is not required, side effects such as skin inflammation and excessive occurrence of liver spots and freckles do not pose a problem. ..

The blending amount of hydroquinone-O-α-D-glucopyranoside depends on the dosage form and the like and is not particularly limited, but is usually 0.0001 to 30% by weight, preferably 0.01 to 20% by weight. Yes, 0.0001% by weight
In the following cases, it is difficult to obtain a sufficient tanning effect, and even if it is blended in an amount of 30% by weight or more, an increase in tanning effect cannot be expected.

The tanning agent according to the present invention may be prepared according to a conventional formulation for external preparation for skin, and in addition to the above-mentioned active ingredients, various ingredients commonly used in cosmetics and pharmaceuticals, such as ion exchange. Water, alcohol, powdery components, surfactants, moisturizing properties, fragrances, colorants, ultraviolet absorbers, preservatives, viscosity modifiers and the like can be appropriately added.

The dosage form of the tanning agent according to the present invention may be arbitrarily selected, and is not particularly limited, and examples thereof include lotion, cream, emulsion, ointment, dispersion liquid, spray liquid and the like.

[0013]

【Example】Example 1  Hydroquinone 2.5% (w / v), starch 2% (w / v), phosphoric acid
Buffer (pH 6.5) 10 mM and CGTase (Bacillus
・ Macerans origin) 50m reaction liquid consisting of 100 units / ml
Add l to Erlenmeyer flask (200ml) and keep at 37 ℃ for 90 hours.
Perform the reaction and add 100 ml of ethanol to the reaction mixture.
After adding the reaction to stop the reaction, centrifuge the insoluble matter.
Removed by. Residual liquid is rotary evaporator
After vacuum concentration and drying treatment using
Dissolve the aqueous solution and perform column chromatography under the following conditions.
The reaction product was subjected to a chromatographic treatment and the eluent volume was 480
Elution with ~ 540 ml: column: inner diameter 2.6 cm x length 91 cm packing material: biogel p-2 (400 mesh) eluent: 5% (v / v) aqueous ethanol solution The obtained fractions were filtered on a rotary evaporator. Reduced by
After pressure concentrating to dryness, it is further dried using a vacuum dryer.
Then, 39 mg of the product was obtained as a white powder.
The product was subjected to thin layer chromatography under the following conditions:
(Rf value: 0.61): Thin layer: Silica gel 60F254 Developing solvent: Ethyl acetate / acetic acid / water (3: 1: 1) Detection: UV irradiation or sulfuric acid / methanol (1: 2) blend
After spraying, the color is developed by heating at 110 to 120 ° C.

The product (hydroquinone-O-α-D-
Glucopyranoside) of ^{1 H-NMR (ppm; CH} 3 OH-d 4)
Data are as follows: 3.31 (1H, dd), 3.45 (1H, t), 3.57 (1H, d)
d), 3.76 (2H, dd, H-6), 3.88 (1H, t), 5.
34 (1H, d, J = 3.7Hz, anomer H), 6.72 (4
H, s, aromatic H)

[0015]Example 2  The hydroquinone-O-α-D-obtained in Example 1 above
The sunburn effect of glucopyranoside was evaluated by the following method.
I paid. As a measure of the sunburn effect, melanin pigment is produced.
At a rate that promotes the activity of the oxidative enzyme tyrosinase
The method described was used. Promotion of tyrosinase activity: Promotion of tyrosinase activity is L
-Dopa was used as a substrate according to the following procedure. Sample solution: Hydroquinone-α-D-glucopyranoside
Of 150, 300 and 600 mM aqueous solutions
did. Enzyme solution: Tyrosinase (manufactured by Sigma) 2000 units / m
It was prepared by dissolving it in water so as to have a volume of l. Measurement: 0.05 ml sample to 0.5 ml substrate solution and phosphoric acid
Add 0.9 ml of buffer solution (20 mM: pH 6.5) and add 5 ml at 25 ° C.
Incubate for minutes. Add this to 25 ° C beforehand.
Incubate 0.05 ml of enzyme solution for 1.5 minutes
The reaction was carried out and the absorbance at 475 nm was measured. Activity promotion rate
Was calculated by the following formula. Acceleration rate = ((TT ′) / (CC ′) − 1) × 100 (%) T: Absorbance when a promoter is added T ′: When a promoter is added and a substrate is not added Absorbance C: Absorbance without addition of promoter C ': Absorbance without addition of promoter or substrate The results obtained are as follows.

[0016]

[0017]

By applying the tanning agent according to the present invention to the skin, as in the case of tanning by sunbathing, etc.,
An extremely natural color change to the skin is obtained. Moreover, in this case, unlike the case of actual sunbathing, since it does not require the irradiation of ultraviolet rays, it is based on a healthy image without causing side effects such as skin inflammation and excessive occurrence of liver spots and freckles. It can respond to fashion orientation.

Claims (1)

What is claimed is: 1. A tanning agent comprising hydroquinone-O-α-D-glucopyranoside as an active ingredient.