JPH02200614A - Hair tonic - Google Patents

Abstract

PURPOSE:To obtain a hair tonic showing excellent hair growing effects on alopecia free from side effects, comprising a specific noncyclic branched higher aliphatic hydrocarbon containing a specific substituent group or noncyclic branched acyl compound containing a specific substituent group as an active ingredient. CONSTITUTION:A hair tonic base is blended with usually 0.1-10wt.%, preferably 0.5-5wt.% based on total amounts of hair tonic of a compound shown by the formula R<1> and R<2> (R<1> and R<2> are that R<1> is 20C noncyclic branched higher aliphatic hydrocarbon group and R<2> is alkoxy, alkylthio, alkylsulfinyl, alkylsufonyl or carbanmoyloxy which may be replaced or R<1> is 20C noncyclic branched acyl group and R<2> is OH or alkoxy which may be replaced) or a salt thereof as an active ingredient to give a hair tonic showing excellent hair growing effects.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a novel hair nourishing agent. In more detail, the general formula [■R'-R2[I] [In the formula, when R1 is an acyclic branched higher aliphatic hydrocarbon group having 20 carbon atoms, R2 may be substituted. It represents an alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or carbamoyloxy group, and when R1 is an acyclic branched acyl group having 20 carbon atoms, R2 represents a hydroxyl group or an optionally substituted alkoxy group. The present invention relates to a hair tonic containing a compound represented by the following or a salt thereof as an active ingredient.

[Conventional technology] Conventionally, various active ingredients have been used in hair nourishing agents.
Amino acids such as serine and methionine;
Vasodilators such as acetylcholine derivatives; anti-inflammatory agents such as salicylic acid and purple root extract; hormonal agents such as estradiol; vitamins such as vitamin E; keratolytic agents: humectants: fragrances: anti-dandruff agents; cooling agents; crude drug extracts ; and hair nourishing agents containing fatty acids and the like are known.

Moreover, in JP-A Sho-e, o-41i3@, alcohols or derivatives thereof having odd-numbered carbon chain lengths are described as active ingredients of hair tonics. Furthermore, JP-A-61-20
No. 7321 contains 22 carbon atoms as an active ingredient of a hair growth agent.
~34 higher aliphatic alcohols have been described.

[Problems to be Solved by the Invention] However, the reality is that none of the hair growth agents that have been used so far can be said to have a sufficient hair growth effect.

[Means for Solving the Problems] In view of the above-mentioned circumstances, the present inventors conducted extensive research on substances that exhibit excellent hair growth effects against alopecia without causing side effects, and as a result, the general formula [engineering] The present inventors have discovered that the compound represented by or a salt thereof exhibits an excellent hair growth effect, and has completed the present invention.

An object of the present invention is to provide a hair tonic containing as an active ingredient a compound or a salt thereof that exhibits an excellent hair growth effect.

The present invention will be explained in detail below.

In the compound of general formula [I], the number of carbon atoms in R1 is 2
Examples of the acyclic branched higher aliphatic hydrocarbon group of 0 include phytyl group (3,7,11,15-te1-ramethyl-2-hexadecen-1-yl group), isophyl group (3,7, 11,15-tetramethyl-1-hexadecen-3-yl group), geranyl linalyl group (3,7,11
, 15-ti~ramethylhexadecane-1.6,10.
14-tetraen-3-yl group) and 7-hydroxymethyl-3,11,15-trimethylhexadecane-2
, 6,10,14-tetraen-1-yl group, etc.; In addition, examples of the acyclic branched acyl group having 20 carbon atoms include groups such as 3,7,11.15-tetramethyl-2-hexadecenoyl group, etc. can be mentioned.

Further, as the alkoxy group in R2, for example,
Cal 1-8 koxy groups such as methoxy, ethoxy, n-propoxy, isopropoxy and butoxy; examples of alkyldio groups include C 1-8 alkylthio groups such as methylthio, ethylthio, n-proprthio, isopropylthio and butyldio; ; As the alkylsulfinyl group, for example, methylsulfinyl, ethylsulfinyl, n-
C alkylsulfinyl groups such as propylsulfinyl, isopropylsulfinyl and butylsulfonyl;
Alkylsul 1-8 Honyl groups include, for example, C alkylsulfonyl groups such as methylsulfonyl, ethylsulfonyl, lowpropylsulfonyl, isopropylsulfonyl, and butylsulfonyl; carbamoyl 1-8 oxy groups, such as carbamoyloxy groups;
N-Ca 1-8 alkylcarbamoyloxy groups such as N-methylcarbamoyloxy and N-ethylcarbamoyloxy; N,N-dimethylcarbamoyloxy and N,N-diethylcarbamoyloxy 1-8 alkylcarbamoyloxy groups; and C alkyl groups such as N-phenylcarbamoyloxyloxytyl, ethyl, n-propyl and isopropyl; C 3-7 chloroalkyl groups such as cyclopropyl, Schif1-40 butyl and cyclohexyl; methoxy, 1-hexy, C alkoxy groups such as n-propoxy and isopropoxy; C alkyl groups such as methylthio, ethylthio, n-propylthio and isopropylthio; groups; C alkylenedioxy groups such as methylenedioxy and ethylenedioxy; hydroxyl-4 sil groups; aryl groups such as phenyl, 3-nitrophenyl a3 and naphthyl; carboxyl groups; C alkoxy such as methoxycarbonyl and ethoxycarbonyl Carbonyl group; Amino group; Me1-4 C a1-4 such as thylamino d5 and ethylamino
4 alkylamino group; selected from di-C1-4 alkylamino groups such as dimethylamino, diethylamino and methylsulfonyl; and 1-5C alkyl ammonio groups such as 1-limethylammonio and l-heliethylammonio. 1-4 May be substituted with one or more substituents.

These groups, hydroxyl groups, carboxyl groups, amino groups, alkylamino groups, etc., can be synthesized by, for example, Protective Groups in Organic
anic 5ynthesis) [Theodora W. Green
), John Wiley & Sons Incorporated (JohnWiley FA 5ons,
Inc., )], etc., and may be protected with a conventional protecting group.

In addition, salts of the compound of general formula [I] include salts with alkali metals such as sodium and potassium; salts with alkaline earth metals such as magnesium and calcium; salts with organic bases such as triethylamine and pyridine;
Examples include salts with mineral acids such as hydrochloric acid and sulfuric acid; and salts with sulfonic acids such as benzenesulfonic acid, toluenesulfonic acid and methanesulfonic acid.

Next, a method for producing the compound of general formula [I] or a salt thereof will be explained.

Production method (1) General formula [Ia] Rla-R2a [■a] "In the formula, Rla is the same acyclic branched higher aliphatic hydrocarbon group having 20 carbon atoms as mentioned for R1, and R2a is R
It represents the same optionally substituted alkoxy or alkylthio group as listed in 2. ” or a salt thereof has the general formula [n]R”
X [II] "In the formula, X represents a leaving group, and Rla has the same meaning as described above." R2a has the same meaning as described above. It can be obtained by reacting a salt of a compound represented by

In the compound of general formula [II], the leaving group in X is, for example, a halogen atom such as fluorine, chlorine, bromine, and iodine; Examples include 7 lanesulfonyloxy groups such as 4-lanesulfonyloxy and benzenesulfonyloxy.

Examples of the salts of the compound of general formula [111] include salts with alkali metals such as sodium and potassium, and salts with organic bases such as triethylamine and pyridine.

This reaction may be carried out in a solvent, and the solvent used is not particularly limited as long as it does not adversely affect the reaction, but examples include aromatic hydrocarbons such as benzene and toluene; methylene chloride and halogenated hydrocarbons such as chloroform; ethers such as tetrahydrofuran and dioxane; pyridine; amides such as hexamethylphosphoric triamide, N,N-dimethylformamide and N,N-dimethylacetamide; and sulfoxides such as dimethylsulfoxide. These solvents may be used alone or in combination of two or more.

In this reaction, the amount of the salt of the compound of general formula [111] to be used is at least equimolar to the compound of general formula [n].

This reaction may normally be carried out at 0 to 80'C for 10 minutes to 10 hours.

Production method (2) General formula [Ib] Rla-R2b[Ib] [In the formula, R2b is the same optionally substituted alkylsulfinyl or alkylsulfonyl group as mentioned for R2, and Rla is the same as mentioned above. have meaning. A compound or a salt thereof represented by the general formula [] % formula % [] [wherein R20 is the same optionally substituted alkylthio group as mentioned for R2, and R18 has the same meaning as above] has. If the compound represented by " is reacted with an equivalent or two equivalents of an oxidizing agent, 1q of the corresponding sulfinyl compound (sulfoxide) or sulfonyl compound (sulfone) will be obtained.

This reaction may be carried out in a solvent, and the solvent used is not particularly limited as long as it does not adversely affect the reaction, but examples include aromatic hydrocarbons such as benzene and toluene; methylene chloride and Examples include halogenated hydrocarbons such as chloroform; pyridine; amides such as hexamethylphosphorus triamide, N,N-dimethylformamide and N,N-dimethylacetamide; and sulfoxides such as dimethylsulfoxide. You may use one kind or a mixture of two or more kinds of solvents.

Examples of the oxidizing agent used in this reaction include inorganic oxidizing agents such as potassium permanganate and potassium periodate; and organic oxidizing agents such as peracetic acid and benzoyl peroxide.

This reaction may normally be carried out at 0-80°C for 10 minutes to 10 hours.

Production method (3) General formula [Id] Rla-R2d[Id] "In the formula, R2d is the same optionally substituted carbamoyloxy group as mentioned for R2, and Rla has the same meaning as described above. ” or a salt thereof is a compound represented by the general formula [] % formula %] “In the formula, Rla has the same meaning as above.”
1 or substituted carbamoyl halides.

The cyanates used in this reaction are:
Examples include sodium cyanate and potassium cyanate.

Examples of the substituted isocyanes include C1-4 alkyl-substituted isocyanates such as methyl isocyanate, ethyl isocyanate and probyl isocyanate 1-, and aryl-substituted isocyanates such as phenyl isocyanate.

Furthermore, the substituted carbamoyl halides include, for example, C alkyl-substituted carbamoyl halides such as N-methylcarbamoyl chloride;
4 and N. N-dimethylcarbamoyl chloride, N-
Ethyl-N-methylcarbamoyl chloride and N,
G-C such as N-diethylcarpamoyl chlorite
Alkyl substitution power Rubamoyl ha 1-4 lite.

This reaction may be carried out in a solvent, and the solvent used is not particularly limited as long as it does not adversely affect the reaction, and examples thereof include those similar to those in production method (1).

In this reaction, the amount of cyanogen MFA, substituted isocyanates or substituted carbamoyl halides used is equal to or more than 2 molar relative to the compound of general formula [Ie].

This reaction may normally be carried out at 0 to 100°C for 10 minutes to 20 hours.

Production method (4) General formula [1': f] Rlb-R2e [Eng. The compound or its salt represented by the general formula [ ] % formula % [ ] "where n1b has the same meaning as defined above." The compound represented by the general formula [1■] R20-H [IV:] "In the formula, R2e has the same meaning as above." It can be obtained by reacting salts.

Examples of the salt of the compound of general formula [1v] include salts with alkali metals such as sodium and potassium.

Examples of the reactive derivatives at the carboxyl group of the compound of the general formula [E] include acid halides, active acid amides, active esters, acid anhydrides, and mixed acid anhydrides.

When using a compound of the general formula [Ig], it is preferable to use a common dehydration condensation agent such as dicyclohexylcarbodiimide, and when using a reactive derivative at the carboxyl group of the compound of the general formula [1g], sodium hydride Preference is given to using inorganic or organic bases such as , pyridine and triethylamine.

This reaction may be carried out in a solvent, and the solvent used is not particularly limited as long as it does not adversely affect the reaction, and examples thereof include those similar to those in production method (1).

In this reaction, the amount of the compound of general formula [Ig] or its reactive derivative in the carboxyl group used is at least equimolar to the compound of general formula [IV'] or its salt, and the dehydration condensation agent Alternatively, when a base is used, the amount of the dehydration condensing agent or the base used is at least equimolar to the compound of general formula [IV] or a salt thereof.

This reaction is usually carried out at -70 to 150°C for 10 to 20 minutes.
All you have to do is time it.

The compound obtained by the above production method can be purified by conventional means such as column separation and distillation after removing the protective group by a conventional method.

Furthermore, when isomers (e.g., optical isomers, geometric isomers, tautomers, etc.) exist in the compound of general formula [I] or a salt thereof, the present invention includes all such isomers. , and all crystal forms and solvates.

The content of the compound of general formula [I] or its salt in the hair growth agent (total weight) of the present invention is not particularly limited and can be selected within a wide range, but is usually 0.1 to 10% by weight.
, preferably 0.5 to 5% by weight.

The hair tonic of the present invention includes amino acids (serine, methionine, etc.), hormonal agents (progesterone, estradiol, etc.), anti-inflammatory agents (purple root extract, glycyrrhizinic acid, hydrocortisone acetate, etc.), vasodilators such as cotinic acid, minoxidil, etc.), herbal extracts (Japanese cabbage extract, carrot extract, etc.), anti-dandruff agents (hinokitiol, sulfur nato), cooling agents (1-menthol, camphor, etc.), Hygrometers (glycerin, mucopolysaccharides, pyrrolidone carboxylic acid, etc.), keratolytic agents (urea, resorcinol, etc.), fragrances (lavender oil, neroli, bergamot, etc.), vitamin A1 vitamin F or vitamin E derivatives, vitamin B6, vitamin H-lucitin, fatty acids, etc. can be used singly or in combination of two or more.

In addition, as a base, for example, purified water, -hydric alcohols (ethanol, isopropyl alcohol, etc.), polyhydric alcohols (glycerin, propylene glycol, etc.), higher fatty acids (palmitic acid, linoleic acid, etc.)
, fats and oils (fatty acid glycerides, olive oil, squalene, beeswax, etc.), liquid paraffin, surfactants (polyoxyethylene hydrogenated castor oil, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, sodium lauryl sulfate, etc.), emulsifiers (cetyl alcohol) ) and solubilizers, etc. can be used.

The hair tonic of the present invention can be prepared by a conventional method such as a hair tonic,
It can be prepared and used in various dosage forms such as hair cream, hair lotion, or hair spray.

Next, the effects of the hair tonic of the present invention will be explained.

(Hair growth promotion effect test) A group of 4 6-week-old BDF1 male mice were pricked from the back to the buttocks with a safety razor, and from the next day, 2% (weight ratio) was applied in order to suppress hair growth. An ethanol solution containing 0.2 d/mouse of testosterone was applied once a day for 1 week. From the 8th molar onwards, the same amount was applied twice/week for 3 weeks.

On the other hand, the test solution was applied at 0.2 d/mouse from the 8th molar of the hair once a day for 3 weeks (excluding Sundays).

In addition, for the control group, a solution (hereinafter abbreviated as mixture A) consisting of 85.5 parts by weight of ethanol, 10.0 parts by weight of glycerin, and 4.5 parts by weight of purified water (a) was added to each mouse. It was applied once a day for 3 weeks (excluding Sundays) starting from the 8th hair.

The hair growth promoting effect of the rr-regular hair growth agent of the present invention was determined by observing the degree of hair growth with the naked eye every day and measuring the number of mice that had hair growth on the entire surface of the stinging site.

In addition, in Table 1, the hair growth promoting effect observed 2 weeks and 3 weeks after administration of the test solution is shown below. Indicated by

In addition, the test solution is the compound shown in the reference example number in Table-1.
The mixture A was prepared by mixing it with the concentration shown in .

(The following is a blank space) Table 1 *1 - Weight ratio to pentadecanoylglycerol material mixture A As is clear from these results, the hair growth agent of the present invention exhibits an excellent hair growth promoting effect.

[Effects of the Invention] The general formula of the present invention is % [wherein R and R2 have the same meanings as described above]. The compound represented by `` or its salt can be used as a hair tonic.

Next, the method for producing the compound represented by the general formula [I] or a salt thereof of the present invention will be specifically explained by giving reference examples.

All mixing ratios of mixed solvents are volume ratios, and unless otherwise specified, the carrier in column chromatography is silica gel [Gieselglu 60.
Art 7734 (Kieselgel 60° Art,
7734)] was used.

Reference example 1 Methanol 701 containing 2.07 sodium methoxide
10.0 g of phytyl chloride is added dropwise to the Bl mixture, and the resulting mixture is stirred at 60°C for 4 hours. After the reaction is complete, the reaction mixture is concentrated under reduced pressure, and the resulting residue is dissolved in 30 d of ethyl acetate. This solution is washed with water and dried over anhydrous magnesium sulfate.

The solvent was distilled off under reduced pressure, and the resulting residue was distilled (148
~150'C, 1,55 lLJ) to obtain 9.49 g of oily methyl phytyl ether (95% yield).

IR) cm-1; 2920.2850.10
95NHR (CDCl2) δ value; 0, 86 (12H, d, J=5.5Hz), 1.
00-1.60 (19H, m).

1.74 (3N, S), 1.85-2.30 (2H, m
).

3.30 (3H, s), 3.92 (2H, d, J=8.
7Hz).

5.34 (1N, t, J=6.7Hz) Compounds in Table 2 are obtained in the same manner.

(The following is a blank space) Reference Example 5 0.0% sodium hydride was added to a mixed solution of 30ae of N,N-dimethylformamide containing 2.40g of ethyl mercaptan.
Add 84g. To this, neutyl chloride 10.00
g was added dropwise at 40°C, and the resulting mixture was stirred at the same temperature for 3 hours. After the reaction is complete, the reaction mixture is concentrated under reduced pressure, and the resulting residue is dissolved in 30 d of ethyl acetate. This solution is washed successively with 1N hydrochloric acid, 3% aqueous sodium bicarbonate solution and water, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography (eluent; n-hexane:ethyl acetate = 9:1) to obtain an oily ethyl-phytyl-
10.00 g (92% yield) of thioether are obtained.

IR) cm”; 2920.286ONHR
(CDCl2”) δ value; 0, 86 (12H, d, J=5.6H2), 1.0
0-1.60 (22H, m).

1.63 (3H, s), 1.80-2.20 (2H
, m).

2, 20-2.80 (2H, m), 3.14 (2H
, d, J=7.5Hz).

5°30 (1H, t, J=7.5Hz) Reference Example 6 5.1 m-chloroperbenzoic acid was added to a mixture of 30 d of methylene chloride containing 10.0 g of ethyl-phytyl-thioether.
g is added and the resulting mixture is stirred at room temperature for 2 hours.

After the reaction is completed, the reaction mixture is washed successively with a 2% aqueous sodium bisulfite solution, a 3% aqueous sodium bicarbonate solution, and water, and then dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure, and the resulting residue was subjected to column chromatography (eluent; n-hexane:ethyl acetate=
9:1) to obtain 9.4 g (90% yield) of oily ethyl phytyl sulfoxide.

IR) cm-1; 2910.2860.10
5ONHR (CDCl2) δ value; 0.86 (12H, d, J = 5.5Hz), 1.00 ~
1.60 (22H, ■).

1, 72 (3H, s), 1.84-2.30 (2H,
m).

2, 30-3.00 (2H, ml 3.45 (2H,
d, J=7.9Hz).

5, 27 (IH, t, J = 7.9 Hz) Reference Example 7 In a mixed solution of 50 ml of methylene chloride containing 10.0 g of ethyl hydrothioether...-chloroperbenzoic acid 10
．． 2=j is added and the resulting mixture is stirred at room temperature for 2 hours. After the reaction is completed, the reaction mixture is washed successively with a 2% aqueous sodium bisulfite solution, a 3% aqueous sodium bicarbonate solution, and water, and then dried over anhydrous magnesium sulfate.

Then, the solvent was distilled off under reduced pressure, and the resulting residue was purified by column chroma 1 to graphie (eluent: benzene) to obtain oily ethyl phenylene sulfone 10.09
(yield 91%).

IR) Cm-'; 2910.2850.1
305.112ON) fR (CDCl2>δ value; 0, 86 (12H, d, J=5.5H2), 1.0
0-1.60 (221 tm).

1.72 (31-Ls), 1.90-2.30 (2H,
m).

2, 30-3.20 (2N, m), 3.88 (2
1-1, d, J=7.9Hz15.30 (IH, t,
J=7.9+1Z) Reference Example 8 Phytol 5. Add 2.0 ml of methyl isocyanate to a mixture of 15 ml of methylene chloride containing Og. OJ is added and the resulting mixture is heated to reflux for 6 hours. After the reaction is completed, the reaction mixture is concentrated under reduced pressure, and the resulting residue is purified by column chromatography (eluent: benzene) to obtain an oily N
-phytyl methylcarbamate 5.59 (yield 99.2
%).

JR (knee t~) cm-'; 2910.2850
．． 1305.112ONMR (CDCl2) δ value; 0.86 (12H, d, J = 5.5H2), 1.00 ~
1.60 (1911, m) 1.72 (31Ls11.8
2-2.28 (2H, m).

3,65 (3H,S), 4.57(2H,d,
J=6.7H7).

5.34 (11-L t, J = 6.7117) Reference Example 9 115.0 g of 3,7.11.15-Te1-lamedel-2-hexadecenoic and 4-(N,N-dimethylamino ) A mixed solution of 50 d of methylene chloride containing 4,3 U of pyridine is cooled to -50 DEG C., and 1.8 g of methanesulfonyl chloride is added dropwise thereto. After the addition was completed, the resulting mixture was stirred at the same temperature for 1 hour, and 3.2 g of 2.2-dimethyl-1,3-dioxolane-4-methanol was added dropwise thereto at the same temperature. After the dropwise addition is completed, the temperature of the reaction mixture is raised to room temperature over a period of 6 hours. After the reaction is completed, the reaction mixture is washed successively with 1N hydrochloric acid, a 3% aqueous solution of mono-lium hydrogen carbonate, and water, and then the solvent is distilled off under reduced pressure, and the resulting residue is dissolved in 50 ml of acetonitrile. 115 ml of 2N salt are added to this solution and the resulting mixture is stirred at room temperature for 5 hours. After neutralizing the reaction mixture with triethylamine, it is concentrated under reduced pressure and the residue obtained is dissolved in 20 ml of ethyl acetate. Add this solution to 1N hydrochloric acid,
After sequentially washing with a 3% aqueous sodium bicarbonate solution and water, it is dried over anhydrous magnesium sulfate. Then, the solvent is distilled off under reduced pressure, and the resulting residue is purified by column chromatography (eluent: benzene) to obtain oily 3.
．． 7.11.15-Tetramethyl-2-hexadecenoic acid glycerol 6.09 (yield 96.7%) is obtained.

IR (knee h) cm-'; 3300.2920
．． 2860.1720°64O NHR (CDCl2 > δ value; 0.86 (12N, d, J = 5.5tfz), 0.99
~1.7'0 (21N, m).

2.25 (3H, S), 3.50-4.40 (7N,
m) 5,70(IH,s) Reference Example 10 Methylene chloride containing 115.09 g of 3.7,11.15-tetramethyl-2-hexadecenoic and 4.3 g of 4-(N,N-dimethylamino)pyridine 50 ml of the mixture was cooled to -50°C, and 1.87 g of methanesulfonyl chloride was added dropwise thereto. After the addition was completed, the resulting mixture was stirred at the same temperature for 1 hour, and then 2 parts of ethyl alcohol was added dropwise at the same temperature. After the dropwise addition is completed, the temperature of the reaction mixture is raised to room temperature over a period of 6 hours. After the reaction is complete,
The reaction mixture is washed successively with 1N hydrochloric acid, 3% aqueous sodium bicarbonate solution and water, and then dried over anhydrous magnesium sulfate. The solvent is distilled off under reduced pressure, and the resulting residue is distilled (163-165°C/0.5 mmH9) to obtain oily ethyl 3.7,11.15-tetramethyl-2-hexadecenoic acid. 5. Oq (yield 91.7%)
get.

IR) cm-'; 2930.2B70.1
722.165ONHR (CDCl2>δ value; 0.86 (1211, d, J=5.5Hz), 0.99
〜1.77(24H,m)2,25(3H,s),
4.15 (2H, q, J=7.0Hz).

5.65 (1N, s) [Example] Next, as an example of the present invention, various dosage forms of the hair tonic of the present invention are shown together with their compositions (% by weight), but the present invention is not limited to these. It's not a thing.

Example 1 Hair lotion) (Ingredients) Content (weight%) Example 3 (hair cream) (component) Content (wt%) Example 2 (hair lotion) (component) Content (wt%) Example 4 (hair rinse) (component) Content (wt%)

Claims (1)

[Claims] (1) General formula R^1-R^2 "In the formula, when R^1 is an acyclic branched higher aliphatic hydrocarbon group having 20 carbon atoms, R^2 is an optionally substituted alkoxy , alkylthio, alkylsulfinyl, alkylsulfonyl or carbamoyloxy group, and when R^1 is an acyclic branched acyl group having 20 carbon atoms, R^2 is a hydroxyl group or an optionally substituted alkoxy group. A hair tonic containing a compound or a salt thereof as an active ingredient.