JPH01268623A - Hair tonic - Google Patents

Abstract

PURPOSE:To obtain a hair tonic, containing 1-O-(4-O-alpha-L-arabinofuranosyl-beta-D- glucopyranosyl)-1,2,3-propanetriol or a safflower extract solution containing the above- mentioned compound as an active ingredient and having preventive action on alopecia. CONSTITUTION:The objective substance, containing a novel compound expressed by the formula or a safflower extract solution containing the afore-mentioned compound and obtained by mixing a commonly used additive with a drug and preparing a pharma ceutical according to a conventional method. The hair tonic can be prepared in the form of a solution for external use, such an lotion, liniment or milky lotion, or semi solid agent for external use, such as cream, ointment, pasta, jelly or spray. The amount of the blended ingredient is 0.001-10wt.% compound expressed by the formula or 0.001-100wt.% safflower extract solution containing the above-mentioned compound. The percutaneous dose thereof is 0.0001-20mg/kg per day administered in 1-4 portions. The compound expressed by the formula is obtained by adding a water-soluble organic solvent to a hot water extract concentrate of safflower, fractionally precipitat ing the concentrate, passing the resultant supernatant through a chromatographic column and evaporation the obtained fraction to dryness under reduced pressure.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to 1-0-(4-0-α-arabinofuranosyl-β-D-glucopyranosyl)-1°2,3-propanetriol or This invention relates to a novel hair tonic containing safflower extract as an active ingredient.

[Prior Art] Traditionally, the causes of baldness and hair loss include activation of male hormones in organs such as hair roots and sebaceous glands, decreased blood flow to hair follicles, excessive secretion of sebum, production of peroxides, and bacterial growth. Scalp abnormalities due to breeding etc., genetic factors, neurosis due to stress, etc.
It is thought to be secondary to disease and aging.

For this reason, conventional hair growth agents generally contain compounds that have the effect of eliminating or alleviating the above-mentioned causes.

[Problems to be solved by the invention] However, the mechanism of hair removal and hair growth is extremely complex;
Simply inhibiting the activation of male hormones or increasing blood flow to hair follicles cannot sufficiently prevent baldness and hair loss.

In view of the above circumstances, the present inventors have conducted intensive research to obtain a substance that has an effective preventive effect against hair loss, and as a result,
1-0- (4-0-α-L-arapinofuranosyl-β
-D-glucopyranosyl)-1,2,3-propanetriol or a safflower extract containing it has discovered a novel fact that it has an excellent hair-nourishing effect, and based on this knowledge, they have completed the present invention. .

[Means and effects for solving the problems] That is, the present invention provides 1-0-(4-0-α-L-arabinofuranosyl-β-D-glucopyranosyl)-1゜2 represented by the following structural formula. .3-propanetriol or a safflower extract containing the same as an active ingredient.

The present invention will be explained in more detail below.

1-0-(4-0-α-L-arabinofuranosyl-β-D-glucopyranosyl)-1,2,3-
Propanetriol is a new substance and one of the components contained in the water-soluble extract of safflower. There has been no description of the method for producing this compound, and it is of course not known that it has a hair-nourishing effect.

As used herein, "hair nourishing effect" or "hair nourishing effect" means prevention of hair loss, promotion of caterpillars and hair growth, and hair growth.

The compound can be produced by a method using high performance liquid chromatography or the like.

Examples of manufacturing the compounds according to the present invention are shown below. Note that the present invention is not limited to this.

Fragment 1■ A water-soluble organic solvent is added to a concentrated solution of hot water extraction of safflower to obtain a supernatant by fractional precipitation according to a known method [JP-A-62-875
23].

When the concentrate of the hysteresis was redissolved in water and injected into a column for reversed-phase liquid chromatography, and water, etc. with a weak elution power was passed through as the mobile phase, the concentration was mainly at k' = 0.5 to 20. Collect only the fractions in which a peak is observed.

Next, both concentrates were injected into an NH2-125NI-column, and when a 70% acetonitrile solution was passed through, k'
The main peak seen at =0.5 to 8 was collected and dried under reduced pressure to yield 1-0-(4-0-α-L-arabinofuranosyl-β-D-glucopyranosyl)-1゜2.3-propane. triol is obtained. The compound obtained according to this production method is l-0-(4-0-α-L) from the following measurement data.
-Arabinofuranosyl-β-D-glucopyranosyl)-
It was identified as 1,2,3-propanetriol.

l-0-(4-0-α-L-arabinofuranosyl-β-
D-glucopyranosyl)-1,2,3-propanetriol: ClηH-4I2 Mass spectrum; Molecular weight: 386 Nuclear magnetic resonance spectrum (deuterated dimedyl sulfoxide) σ: ppm, 3.32 (LH, multiplet), 3.34
(IH1 multiple line), 3.4H11-1, triple cotton), 3
．． 43 (IH1 double line), 3.46-3.52 (7H
, multiplet) 3.54 (I H, doublet), 3.64-3
．． 66 (3H, multiplet) 3.74 (IH, doublet),
3.81 (IH, multiplet) 3.93 (IH, quartet)
, 4.16 (IH, double line), 5-01 (IH5 double line).

Stereospecificity of each sugar moiety: Binding constant (1'C-nuclear magnetic resonance spectrum); 176
Hz (arabinose), 160Hz (glucose)
.

Specific rotation (acid decomposition); [α]p'= + 52.94
(arabinose), [α] = + 45.45
(glucose).

Next, 1-0-(4-0-α-L-arabinofuranosyl-β-D-glucopyranosyl)-1,2°3-propanetriol and the safflower extract containing the same were applied as a hair tonic. The formulation will be described. In this specification, the safflower extract refers to a supernatant obtained by adding a water-soluble organic solvent to a safflower hot water extract concentrate and precipitating the fraction by a known method as described above. The hair tonic of the present invention is 1-〇-
In addition to (4-0-α-L-arabinofuranosyl-β-D-glucopyranosyl)-1,2,3-brobandoliol and a safflower extract containing the same, pharmaceutically acceptable additions It is used in the form of a mixture with drugs and other drugs. Examples of the additives include antibacterial agents such as hinokitiol, hexachlorophene, phenol, benzalkonium chloride, cetylpyridinium chloride, unticilenic acid, trichlorocarbanilide, and bithionol, derivatives such as glycyrrhizic acid and its ammonium salt, allantoin, etc. , anti-inflammatory or refreshing agents such as menthol, salicylic acid, zinc and its compounds, drugs such as lactic acid and its alkyl esters, animal and vegetable oils such as olive oil, macadamia nut oil, and squalane, hydrocarbon oils such as liquid paraffin, isopropyl milli Ester oils such as state, cetyl isooctanoate and 2-ethylhexyl palmitate, waxes such as beeswax, oils such as higher fatty acids and higher alcohols, water, derivatives such as lactic acid and its ethyl ester, poly J-1 Non-glycol,
Moisturizing agents such as polyhydric alcohols such as glycerin and sorbitol, lower alcohols such as ethanol, mucopolysaccharides, and pyrrolidone carboxylates.

Examples include surfactants, fragrances [1], antioxidants, ultraviolet absorbers, pigments, etc., and these may be used alone or in combination of two or more.

The dosage form of the hair tonic of the present invention may be any form as long as it can be used externally, such as external liquid preparations such as lotions, liniments, and milky lotions, and external semisolid preparations such as creams, ointments, pasta, jelly, and sprays. can be mentioned.

The hair tonic of the present invention contains 1-O-(4-O-
-α-L-arabinofuranosyl-β-D-glucobylanosyl)-1,2,3-propanetriol 0.001
-10% by weight, preferably 0.01-5% by weight, or a safflower extract containing the compound is
．． The content ranges from 0.01 to 100% by weight, preferably from 0.01 to 50% by weight. The hair growth agent of the present invention is administered by transdermal administration, in which it is directly applied or sprayed onto the skin.

In addition, the dosage of the hair tonic of the present invention cannot be clearly defined as it varies depending on age, individual differences, medical conditions, etc., but in general when it is used for humans, it is 1-0-(4,-0-α-L −
Arabinofuranosyl-β-D-glucopyranosyl)-1
, 2,3-propanetriol transdermal dosage is based on body weight I
Kg and 0.0001 to 20 mg per day, preferably 0.001 to 2 mg, and this amount can be administered once or in 2 to 4 divided doses per day. I will explain in detail. Note that the present invention is not limited to this.

Kourikan-ko-ko- A lotion having the following composition was prepared.

(Weight%) 95% ethanol 80.0l-0-(
4-0-α-ri-1-arabinofuranosyl-β-D-glucopyranosyl)-1,0,1 2,3-propanetriol hinokitiol 0.01 Ethylene oxide 0.5 (40 mol) adduct purification of hydrogenated castor oil Water 19.0 Fragrances and Colors Appropriate amount of 95% ethanol, 1
-0- (4-0-α-L-arabinofuranosyl-β-
D-glucopyranosyl)-1,2,3-propanetriol, hinokitiol, hydrogenated castor oil adduct with ethylene oxide (40 mol), fragrance and pigment were added and dissolved with stirring, and then purified water was added to obtain a transparent liquid lotion. Ta.

Suka 1L-2- An emulsion was prepared from Phase A and Phase B having the following composition.

(Phase A) (Weight%) Whale wax
0.5 cetanol
2.0 Vaseline
5.0 Squalane 10.
0 Polyoxyethylene (10 mol) 2.0 Monostearate Sorbitan monooleate 1.0 (B phase) 1-0- (4-0-α-L- Arabinofuranosyl-β-D 0.5- Glucopyranosyl-1,2゜3-propanetriol glycerin 10.0 Purified water
69. .

Aroma rice, pigment, and preservative Appropriate amounts of phase A and phase B are dissolved by heating and kept at 80°C. Both phases were mixed and emulsified, and cooled to room temperature while stirring to obtain a milky lotion.

XJLfL-3-,- A cream was prepared from Phase A and Phase B having the following composition.

(Phase A) (% by weight) Liquid paraffin 5.0 Cetostearyl alcohol 5.5 Vaseline
5.5 Glycerin Monostearate 3. .

Polyoxyethylene (20 mol) 3.0 2-octyldodecyl ether probilbaraben 0.3 (B phase) Safflower extract 1.0 Glycerin 7.0 Dipropylene glycol 20.0 Polyethylene glycol 4000
5.0 Sodium hexametaphosphate o,
oos Purified water Dissolve an appropriate amount of phase A by heating and keep at 70°C. Separately, heat and melt the 8 phases and
Keep at ℃. Phase B was added to phase A and stirred, and the resulting emulsion was cooled to obtain a cream.

In order to investigate the hair growth effect of the hair growth agent of the present invention, a tricogram test and a garrison conversion rate test were conducted. In both tests, 20 male subjects were divided into two groups of 10 subjects each, and two different test solutions were given to the subjects in each group for comparison.

Two types of test solutions are shown in Table 1.

Table 1 - 2 ml of each test solution was applied twice a day to the scalp of the test subject.

(1) Trichogram Observe the removed hair roots under a microscope before and after using both test solutions, calculate the number of telogen hair roots from the morphology of the hair roots, and determine the growth rate of both test solutions by increasing or decreasing the ratio. The hair effect was compared. A telogen hair root is a hair root that has stopped growing. People who complain of hair loss have more telogen hair roots than normal people, so the hair-nourishing effect was evaluated based on the decrease in telogen hair roots. The application of each test solution to the scalp was continued for 3 months, and 60 hair roots were removed for each test subject immediately before and immediately after the application. The results are shown in Table 2.

Head hair region 3 of each of 40 subjects with androgenetic alopecia
The conversion rate from downy hair to garrison was compared before and after application of each test solution.

Garrison refers to hair other than downy hair, that is, hair with a length of 14 mm or more, and the conversion from downy hair to downy hair means a hair-nourishing effect. Immediately after application of each test solution and immediately after completion of the 4-month application, close-up photographs of the above-mentioned upper part of the head were taken to measure the conversion rate. The conversion rate to fluff is expressed as a percentage of the average of the three locations. The results are shown in Table 3.

■-U On-road conversion rate test results As is clear from the above results, 1-0- (4-0-α
It has been found that -L-arabinofuranosyl-β-D-glucopyranosyl)-1,2,3-butantriol and a safflower extract containing the same exhibit excellent hair-nourishing effects.

Claims (1)

[Claims] 1-O-(4-O-α-L-arabinofuranosyl-β-D-glucopyranosyl)-1,2 represented by the following structural formula ▲ Numerical formulas, chemical formulas, tables, etc. ▼ , 3-propanetriol, or a safflower extract containing the compound as an active ingredient.