JPH08291044A - Cosmetic - Google Patents

Abstract

PURPOSE: To obtain a cosmetic which contains a hydroxybenzamide derivative, has high skin-lightening action and is effective for roughened skin. CONSTITUTION: This cosmetic contains a compound of the formula (R, is H, methyl; (n) is 1-2) as an active ingredient. The compound of the formula is typically 2-hydroxybenzamide, 4-hydroxybenzamide, 2,6-dihydroxybenzamide, 2,5-dihydroxybenzamide or 4-methoxybenzamide. In addition, oil, a variety of activating agents, a moisturizer and a variety of medicines are properly formulated to give lotion, cream, milk (emulsion), pack or the like. The cosmetic containing the compound of the formula has not only strong skin-lightening action but also strong inhibiting action on active oxygen.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a cosmetic product which has a high whitening effect and is effective against rough skin.

[0002]

Various substances are known as substances having a whitening effect that can be used as a raw material for cosmetics, but there are problems in effectiveness and safety. A substance having a strong whitening effect and also having other effects on the skin has been desired.

[0004]

The object of the present invention is to be applied to the skin to be safe and to have a large whitening effect, and
It is another object of the present invention to provide a cosmetic containing an ingredient effective for rough skin.

[0005]

Means for Solving the Problems In order to solve the above-mentioned problems, the present inventors have screened and investigated and examined what has a utility value as a cosmetic product. As a result, the general formula

[0006]

[Chemical 1]

(In the formula, R is hydrogen or a methyl group, and n is 1
It has been found that the substance represented by the formula (2) is very effective as a raw material for cosmetics or as a quasi drug.

This substance is commercially available and may be synthesized as needed. The synthetic method can be prepared using a known method. This substance is used as a raw material for other cosmetics such as liquid oils such as squalane and jojoba oil, solid oils such as beeswax and cetyl alcohol, various active agents, glycerin, 1,
Cosmetics of various dosage forms can be prepared by adding moisturizing agents such as 3-butylene glycol and various chemicals. For example, a lotion, a cream, a milky lotion, a pack, or the like may be used depending on the purpose.

As described above, the effect of the substance of the present invention is, firstly, the whitening effect on the skin.

Secondly, it has an effect of suppressing active oxygen. There is oxygen in the air, and without it, living things (except anaerobic ones) cannot exist. However, oxygen becomes active oxygen under the influence of ultraviolet rays and enzymes. Active oxygen oxidizes fatty acids and produces peroxides. It also oxidizes and damages the phospholipids of biological membranes in the body. Furthermore, it is said that the generated peroxide and active oxygen damage DNA and accelerate aging. This active oxygen also influences the mechanism of making melanin from tyrosine and is also involved in the blackening of the skin. Suppressing this active oxygen is an important factor for the skin, in other words, an important factor required for cosmetics. The substance of the present invention also has this active oxygen suppressing action.

The production examples and examples of the method of producing a substance, which is the actual utilization method, are described below, but the present invention is not limited to these production examples and examples.

Production Example 1 2,6-Dihydroxybenzamide 2,6 Dihydroxybenzonitrile (Lancaste)
(manufactured by r company) was dissolved in 100 ml of a 1.0 M sodium hydroxide / dimethyl sulfoxide mixed solution, and the internal temperature was 75
The mixture was heated and stirred at ± 2 ° C for 14 hours. After the reaction was completed, the oil was extracted with ether. The yield was 54%

Production Example 2 2,5-dihydroxybenzamide 5.0 g of 5-chlorosalicylamide (manufactured by Tokyo Chemical Industry Co., Ltd.) was dissolved in 200 ml of a 0.65 M aqueous sodium hydroxide solution, and the mixture was put into a flask and mercury was added under a nitrogen stream. Lamp (10W-low-pressure mercury
The mixture was stirred with a magnetic stirrer for 5 hours while irradiating with (lamp 254 nm). After completion of the reaction, dilute hydrochloric acid was added to acidify, and the mixture was collected with ether. The obtained oil was purified by silica gel gel column chromatography using a mixed solvent of hexane: ether = 9: 1 as a developing solvent.
The yield was 53%.

Production Example 3 4-Methoxybenzamide 2.0 g of 4-hydroxybenzamide (manufactured by Lancaster) was placed in a four-necked flask equipped with a stirrer, a reflux condenser and a dropping funnel and dissolved in 80 ml of 10% sodium hydroxide aqueous solution. After that, 3.68 g of dimethylsulfate was added dropwise over 30 minutes while keeping the internal temperature at 0 ° C. After completion of the dropping, the mixture was heated to reflux at an internal temperature of 100 to 105 ° C for 30 minutes. After the reaction was completed, the oil was extracted with ether. The obtained oil was purified by silica gel gel column chromatography using a mixed solvent of hexane: ether = 9: 1 as a developing solvent.
The yield was 23%.

Example-1 Lotion Olive oil 0.5 2-Hydroxybenzamide 0.3 Polyoxyethylene (20EO) sorbitan monostearate 2.0 Polyoxyethylene (60EO) hydrogenated castor oil 2.0 Ethanol 10 0.0 1.0% sodium hyaluronate aqueous solution 5.0 Purified water 80.2

Example-2 Cream A Squalane 20.0 Olive Oil 2.0 Mink Oil 1.0 Jojoba Oil 5.0 Beeswax 5.0 Cetostearyl Alcohol 2.0 Glycerin Monostearate 1.0 Sorbitan Monostearate 2. 0 4-hydroxybenzamide 0.5 B Purified water 48.4 Polyoxyethylene (20 EO) sorbitan monostearate 2.0 Polyoxyethylene (60 EO) hydrogenated castor oil 1.0 Glycerin 5.0 1.0 % Aqueous sodium hyaluronate solution 5.0 Methyl paraoxybenzoate 0.1 A and B are each weighed and heated to 70 ° C., A is slowly added to B while stirring, and then 30 while slowly stirring.
Cooled to ° C.

Example 3 was prepared by replacing the 2-hydroxybenzamide of Example 1 with the hydroxybenzamide of Production Example 1.

Example 4 was prepared by replacing the 4-hydroxybenzamide of Example-2 with the 2,5-dihydroxybenzamide of Production Example 2.

Example-5 was prepared by replacing the 2-hydroxybenzamide of Example-1 with the 4-methoxybenzamide of Production Example3.

Inhibition of tyrosinase activity (Test method) 1.8 ml of matsuvalbaln buffer solution, 0.05% dopa solution 1.
0 ml and 0.1 ml of the 15 mM dimethyl sulfoxide solution of Preparation Example were placed in a screw vial and left in a constant temperature water bath at 25 ° C. for 5 minutes or more. Tyrosinase solution (Sigma
A company, derived from Massroom, 2 minutes after tyrosinase was added by the following measurement, the absorbance of the control was 0.3 to 0.5.
0.1 ml (diluted so that
The cells were transferred to a cell and the absorbance was measured at 475 nm every 15 seconds from 30 seconds after the addition of tyrosinase while keeping the temperature at 25 ° C. As a control, 0.1 ml of dimethyl sulfoxide was added instead of the above sample solution, and the same measurement was performed. In this test, the final concentration of the sample is 0.5 mM. (Calculation formula) Tyrosinase activity inhibition rate (%) = (B−A) / B × 10
0 where A: slope of absorbance of sample specimen B: slope of absorbance of control

[0021]

[Table 1]

(Effect of Active Oxygen Suppression Test) There are various methods for measuring the effect of suppressing active oxygen, but this time an experiment was performed using SOD Test Wako of Wako Pure Chemical. Use the coloring reagent 1.
0 ml and 0.1 ml of the sample (15 mM dimethylsulfoxide solution of the preparation example) were taken and kept at 37 ° C. to a constant temperature, 1.0 ml of enzyme solution was added and stirred, and after leaving at 37 ° C. for 20 minutes, the reaction stop solution was added to 2 ml. 0.0 ml was added and the absorbance was measured at 560 nm. In this test, the final concentration of the sample is 0.3
It becomes 75 mM.

[0023]

[Table 2]

[0024]

[Effect] General formula

(In the formula, R is hydrogen or a methyl group, and n is 1-2.
The cosmetics containing, for example, 2-hydroxybenzamide, 4-hydroxybenzamide, 2,6-dihydroxybenzamide, 2,5-dihydroxybenzamide, 4-methoxybenzamide have not only a strong whitening effect, It has a strong inhibitory effect on active oxygen and is most suitable as a raw material for cosmetics.

Claims (2)

[Claims] 1. A compound of the general formula (R in the formula is hydrogen or a methyl group, and n is 1 to 2)
Cosmetics containing the substance represented by 2. The cosmetic product according to claim 1, which is 2-hydroxybenzamide, 4-hydroxybenzamide, 2,6-dihydroxybenzamide, 2,5-dihydroxybenzamide, or 4-methoxybenzamide.