JP3435008B2 - Hair restoration cosmetics - Google Patents

Description

Description: BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention has a good blood circulation promoting effect, is highly safe for the skin, and has a hair growth effect, a hair loss preventing effect and a dandruff preventing effect. It relates to excellent hair nourishing cosmetics. 2. Description of the Related Art Hair growth cosmetics containing scalp blood circulation promoting substances such as pepper tincture, syrup extract, Korean ginseng extract, nicotinic acid and methyl nicotinate are well known. . However, in some cases, these blood circulation promoting substances are remarkably irritating to the skin, so that the amount of the substances is limited, and they cannot be added to obtain sufficient effects such as hair growth, hair loss prevention, and dandruff prevention. However, there has been no discovery of an effective substance which has little skin irritation and sufficiently exerts effects such as hair growth, hair loss prevention and dandruff. In recent years, it has been suggested that male hormones are involved in hair growth, transmit information at the DNA level, suppress keratin synthesis in hair, reduce hair growth, and ultimately promote hair loss. However, even when an antiandrogen compound is added, a mild effect of suppressing hair loss is recognized, but an effect of promoting hair growth is not sufficient. Capsaicin is an example of a blood circulation promoting substance that is effective when incorporated into a hair nourishing cosmetic. Capsaicin (Capsaicin, 8-methyl-N-vanillyl-6-
noneamide) is one of the components contained in the fruits of Capsicum belonging to the Solanaceae family (for example, hot chilli peppers, etc.) and is a fat-soluble substance having a molecular weight of about 300 (C ₁₈ H ₂₇ NO ₃ ). However, capsaicin has a problem in terms of safety in that it has a peculiar scent component, low stability, insolubility in aqueous solvents, and strong skin irritation and sensitization. Therefore, it could not be incorporated into the hair growth cosmetic to such an extent that sufficient effects such as hair growth, hair loss prevention and dandruff were obtained. In addition, it has been reported that minoxidil, a potassium channel opener that is currently receiving attention, has a hair growth-promoting action, and the effect of the drug is:
It is presumed to be caused by a weak blood circulation promoting effect.
Accordingly, a substance having a weak blood circulation promoting effect is expected to have a hair growth promoting effect. SUMMARY OF THE INVENTION The present inventors have conducted studies to maintain the blood circulation promoting effect of capsaicin and to solve the above-mentioned problems, and as a result, a specific vanillamide derivative which is a capsaicin analog Is a glycoside with saccharides such as glucose, galactose, xylose and maltose, thereby reducing the characteristic odor, increasing the stability and safety to human skin, and improving the solubility in aqueous solvents. Furthermore, the scalp resident bacteria are appropriately decomposed into an aglycone and a sugar moiety, which are vanillylamide derivatives, and found to have an effective blood circulation promoting action.
In addition, the present inventors have found that hair restoration cosmetics containing the glycoside have excellent effects on hair growth, hair loss prevention, dandruff prevention, and the like, and have completed the present invention. An object of the present invention is to provide a hair restoration cosmetic which is safe for the skin and has sufficient effects such as hair growth, hair loss prevention, and dandruff prevention. [0004] The above-mentioned object is achieved by a hair growth cosmetic containing at least one glycoside represented by the following general formula (I). Embedded image (Wherein, G represents a sugar residue selected from monosaccharides or oligosaccharides, and R represents a straight-chain or branched-chain saturated or unsaturated hydrocarbon group having 8 to 11 carbon atoms). DESCRIPTION OF THE PREFERRED EMBODIMENTS The glycoside used in the present invention can be easily synthesized by a known method. For example, a glycoside required as a mixture of α-form and β-form can be obtained according to the method for synthesizing arbutin described in US Pat. No. 3,201,385. Also, Flavor and Fragrance
Journal (Vol. 4, 163-167, 19)
According to the method for synthesizing glucovanillin described in 89), β
-It is possible to synthesize only the body. [0006] In the glycoside used in the present invention, as the saccharide to be combined with the vanillylamide derivative, any saccharide can be used as long as it forms a glycoside. Glucose, galactose, xylose, mannose, N-
Monosaccharides such as acetylglucosamine and oligosaccharides such as disaccharides such as maltose, cellobiose, gentibiose and lactose are preferred. Further, monosaccharides, particularly glucose, are preferable from the viewpoint of the manifestation of the effect. As the glycoside used in the present invention, a glucose glycoside is particularly preferable from the above, and specifically, capsaicin β-D-glucoside, nonylate vanillylamide β
-D-glucoside is preferred. In this case, the β-form is particularly preferred from the viewpoint of synthesis, availability from natural products, and ease of decomposition by bacteria resident in the scalp. However, even if the α-form is contained, there is no particular problem in the effect. In the glycoside used in the present invention, typical vanillylamide derivatives combined with saccharides include capsaicin, dihydrocapsaicin, nordihydrocapsaicin, vanillylamide n-undecylenate,
Nonyl acid vanillylamide and the like. In the chemical formula (I), the hydrocarbon group represented by R has 8 to 11 carbon atoms.
When it is less than 8 or more than 11, sufficient blood circulation promoting effect, hair growth effect, hair loss preventing effect and dandruff preventing effect cannot be obtained. [0009] The amount of the glycoside used in the present invention is 0.1 to 10% based on the total weight of the composition for hair restoration cosmetics of the present invention.
It is preferably 0% by weight (hereinafter abbreviated as wt%), more preferably 0.1 to 8.0 wt%. The blending amount is 0.
If the amount is less than 1 wt%, the intended effect of the present invention is not sufficient. On the other hand, if the amount exceeds 10.0 wt%, improvement of the effect corresponding to the increase may not be expected. The hair nourishing cosmetic of the present invention can be manufactured and used in general dosage forms as hair nourishing cosmetics, for example, hair tonic, hair lotion, hair cream, hair mist, hair mousse and the like. it can. The hair restoration cosmetic of the present invention is appropriately blended with a pigment, a fragrance, a bactericide, a preservative, a keratolytic agent, an antiandrogen, a hair restorer, an antioxidant and the like within a range that achieves the object of the present invention. be able to. The present invention will be described below in detail based on examples and comparative examples. The test methods for promoting the hair growth of C3H mice, the test methods for promoting the growth of human scalp hair, and the practical test methods described in the Examples are shown below. (1) C3H Mouse Hair Growth Promoting Effect Test Method The back skin (2 cm × 4 cm) of a C3H mouse (8 weeks old, male, average weight 35 g) was cut with an electric clipper and a shaver, and from the next day, Examples and Comparative Examples Each sample was applied to the skin of the test portion twice a day in the morning and evening, and 0.2 ml per animal was applied continuously for two weeks. A group of 10 animals was used for one sample. On the 14th day from the start of application, the skin of the test portion of each sample was photographed with a video camera, and the areas of the shaved portion and the hair growth portion were measured with an image analyzer. The hair growth effect was determined by calculating the hair growth rate (%) shown below. Hair growth rate (%) = (Area of hair growth part / Area of shaved part) × 1
The determination of the hair growth effect was made by dividing the average value of the hair growth rate of each group of the Examples or Comparative Examples by the average value of the control group (no application) as the degree of mouse hair growth promotion. (2) Test Method for Promoting Human Scalp Hair Growth The hair of a subject, who is a male pattern baldness patient, at a position 5 cm above the ears of the head at two places on the left and right is circular in shape with a diameter of 1 cm. Approximately 3 ml of each sample of Example and Comparative Example was applied to the left side of the test site twice daily in the morning and evening, and compared with the untreated right side. The effect was determined on the 28th day after the start of the test.
Twenty hairs at each of the left and right test sites were shaved, and the degree of human hair growth promotion was evaluated by the value obtained by the following equation. Degree of hair growth promotion = (B) / (A) (A): average value of length of 20 right-hand (untreated) hairs (B): left-hand hair (samples of Examples and Comparative Examples are applied) 2
(3) Practical test method The effect of application to the heads of 10 test subjects who have male pattern baldness twice daily in the morning and evening for 6 consecutive months was evaluated. . The test results show that for each item of hair growth effect, hair loss prevention effect, and anti-dandruff effect, “hair was bristle or hair growth increased”, “hair loss was reduced”, and “hair loss was reduced. "And the number of respondents. Example 1 (Synthesis of nonylate vanillylamide glucoside) A method for synthesizing nonylate vanillylamide glucoside is described below, but the method for synthesizing the glycoside used in the present invention is not limited thereto. Absent. 4.93 g in 100 ml of dehydrated toluene
(16.8 mmol) nonylate vanillylamide, 8 g
(20 mmol) of glucose pentaacetate and 5 g of molecular sieves were added, and the mixture was stirred at room temperature for about 1 hour. Then, 1 ml of boron trifluoride diethyl ether solution was added, and the mixture was further stirred for 3 hours. After adding 20 ml of water, the molecular sieves were filtered off. The organic layer was extracted from the filtrate with ethyl acetate, and the obtained ethyl acetate layer was washed with 1N sodium hydroxide to remove unreacted nonylate vanillylamide. The ethyl acetate layer was washed with purified water and dried over magnesium sulfate. After removing the magnesium sulfate, the organic solvent was removed under reduced pressure to obtain vanillylamide nonylate tetraacetylglucoside.
The resulting nonylate vanillylamide tetraacetylglucoside was deacetylated by a conventional method using sodium methoxide, and then neutralized using an ion exchange resin (trade name: Amberlite). After filtering off the ion exchange resin,
The solvent was removed under reduced pressure to obtain 2.1 g of nonylate vanillylamide glucoside (β form). The structure is ¹³ C-NMR,
^It was confirmed by ¹ H-NMR. Various glycosides used in the present invention can be synthesized according to the above method. Example 2 (Skin irritation test) A skin irritation test was carried out using the glycoside used in the present invention, and capsaicin and nonylate vanillylamide, which were incorporated in a hair growth cosmetic as a control. 0.3g each dissolved 2
10 ml of a 0% aqueous ethanol solution was prepared. For 3 panels, 3 ml of each aqueous ethanol solution was applied to the inner part of the forearm.
The irritability after uniform application in a section of 5 cm was evaluated. The evaluation was performed according to the evaluation criteria shown in Table 1 immediately after application and 4 hours after application. [Table 1] Table 2 shows the test results. [Table 2] As shown in Table 2, it is apparent that the skin irritating feeling of the glycoside used in the present invention is significantly weaker than that of capsaicin or nonylate vanillylamide which has been conventionally used in hair-growth cosmetics. As a result, blending into various preparations such as pharmaceuticals, quasi-drugs, and cosmetics has become easy. Example 3 (oily hair tonic) In the raw material compositions shown in Tables 3, 4, and 5, various hair growth-promoting substances were blended to prepare oily hair tonics. Carried out. The results of conducting various tests on each oily hair art tonic are also shown in Tables 4 and 5 below. [Table 3] [Table 4] [Table 5] (2) Preparation method In Table 3 above, among the components (B), nicotinic acid and methyl nicotinate are dissolved in the component (A), and red pepper tincture and various glycosides are contained in the component (C). After dissolving in (A)
The component and the component (C) were mixed and dispersed by stirring, and then charged into a container. At the time of use, the contents were uniformly shaken and used. (3) Properties As shown in the above Tables 4 and 5, the hair restoration cosmetics of Examples 1 to 17, which are the hair restoration cosmetics of the present invention, have a higher hair restoring effect as compared with Comparative Examples 1 to 13. It exhibits a hair loss preventing effect and an anti-dandruff effect, and can sufficiently achieve the object of the present invention. still,
In Comparative Examples 1 to 9, the test using humans was not possible because of the strong skin irritation of the hair growth promoting substance. As described above, the present invention is excellent in effects such as hair growth, hair loss prevention and dandruff, and has a blood circulation-promoting effect by capsaicin, which releases scalp resident bacteria.
Further, it is apparent that the present invention provides a hair nourishing cosmetic with low skin irritation.

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Claims (1)

(57) [Claims 1] The following general formula (I): (Where G represents a sugar residue selected from monosaccharides or oligosaccharides, and R represents a straight-chain or branched-chain saturated or unsaturated hydrocarbon group having 8 to 11 carbon atoms). A hair restoration cosmetic comprising at least one body.