JPH1179948A - Hair tonic and hair cosmetic, and preparation for external use for skin for suppressing sebum secretion - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a hair tonic excellent in stability and safety, and useful for treating and improving alopecia and dermatoses by including specific plant extract(s) and specific terpene(s). SOLUTION: This hair tonic is obtained by including at least one kind of extract selected from those from Salvia officinalis L., Humulus lupulus L., Rosmarinus officinalis L., Hypericum erectum Thunb., Mentha arvensis L. var. piperascens Malinv., Mentha piperita L., Matricaria chamomilla L., Arnica montana L. and Thymus vulgaris L. and at least one kind of compound selected from cis-jasmone of formula I, methyl dihydroisojasmonate of formulae, methyl dihydrojasmonate of formula III and dihydrojasmone of formula IV.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a hair restorer and a cosmetic for hair in which the effect of preventing and ameliorating male pattern baldness is synergistically enhanced by synergistically improving the anti-androgen action, and the effect of inhibiting sebum secretion. The present invention relates to an external preparation for skin which is synergistically enhanced and is very effective for treating and improving acne vulgaris, seborrhea and the like.

[0002] More specifically, sage ( Salvia officin)
alis L.), hops ( Humulus lupulus L.), rosemary ( Rosmarinus officinalis L.), hypericum ( H.
ypericum erectum Thunb.), Mentha ( Mentha arvensis )
L. var. Piperascens Malinv.), Mentha ( Me )
ntha piperita L.), chamomile ( Matricaria chamomill )
a L.), Arnica ( Arnica montana L.), Thyme ( Thy
mus vulgaris L.), and one or more cis-jasmon (cis-j) terpenes.
asmone), methyldihydroisojasmonate (methyl
dihydroisojasmonate, methyl dihydrojasmonate and one or more selected from dihydrojasmone, a synergistically enhanced hair restorer and cosmetic for hair, and sebum The present invention relates to a skin external preparation for secretion suppression.

[0003]

2. Description of the Related Art Drugs having an antiandrogenic effect have been used for skin diseases such as acne vulgaris and seborrhea which are dependent on the male hormone testosterone. A typical example of such an anti-androgen is cyproterone acetate. This cyproterone acetate is said to competitively inhibit the binding of dihydrotestosterone, an active form of testosterone, to the receptor.

[0004] In addition, to improve and prevent testosterone-dependent androgenetic alopecia, 2,4-diamino-6-piperidinopyrimidine-3-oxide (minoxidil), cepharanthin, vitamin E derivatives, carpronium chloride, etc. Adenosine triphosphate, which has a blood circulation promoting action,
Those having hair matrix activation such as urogastron, baicalein, pantethein-S-sulfonic acid, and odd-chain fatty acid derivatives have been mainly used.

[0005] Furthermore, since male pattern baldness is testosterone-dependent, testosterone, an enzyme that converts testosterone to active dihydrotestosterone, is used.
Investigations have mainly been made on substances that inhibit 5α-reductase. Examples of such inhibitors include androstanone derivatives, bicycloheptenone derivatives, phenoxybutane derivatives, tocopherylquinone, tropolone derivatives, ubiquinone, etc., as well as extracts of many plants including Lamiaceae and Asteraceae. I have.

[0006] However, the above-mentioned antiandrogen,
Blood circulation promoter, hair matrix activator or testosterone 5α-
Many reductase inhibitors have sufficient antiandrogenic activity and sufficient stability and safety due to concerns about the occurrence of side effects, poor stability in the formulation base, or insufficient action. There was not much to do. In addition, it is difficult to obtain a plant-based product having a certain quality, and many of the products have an unfavorable color or odor at the time of formulation.

[0007]

Accordingly, the present invention has a high antiandrogenic effect, and can effectively treat and improve testosterone-dependent alopecia and skin diseases by using a low concentration of the compound, and is stable. An object of the present invention is to provide a hair nourishing agent and a cosmetic for hair having good properties, no side effects and excellent safety, and a skin external preparation for suppressing sebum secretion.

[0008]

Means for Solving the Problems The present inventors have focused on terpenes in plant essential oils and have studied the terpenes contained in jasmine essential oil.
We have found that certain terpenes have very good antiandrogenic activity and filed a patent application (Japanese Patent Application No. 8-20).
3045). This time, when one or more of these were used in combination with one or more selected from extracts of specific plants such as sage ( Salvia officinalis L.) having testosterone 5α-reductase inhibitory activity, The present inventors have found that an unexpected enhancement of antiandrogen action can be obtained, and have completed the present invention.

That is, in the present invention, the chemical formula (1)
Cis-jasmone represented by the formula, methyldihydroisojasmonate represented by the chemical formula (2), methyldihydrojasmonate represented by the chemical formula (3)
smonate) and one or more selected from dihydrojasmone represented by the chemical formula (4), sage ( Salvia officinalis L.), hop ( Humul )
us lupulus L.), rosemary ( Rosmarinus officina)
lis L.), Hypericum erectum Thun
b.), mint ( Mentha arvensis L. var. piperascens
Malinv.), Mentha Piperita L.,
Chamomile ( Matricaria chamomilla L.), Arnica ( Ar
nica montana L.) and thyme ( Thymus vulgaris L.) are contained in a hair restorer, a hair cosmetic or a skin external preparation base.

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[0010]

In the present invention, cis used as an active ingredient is used.
-4 types of terpenes such as jasmon or sage ( Salvi
a officinalis L.), etc., compared with the case where each of them is contained alone in a hair nourishing agent, etc., a much higher improvement effect of male pattern baldness and suppression of sebum secretion can be achieved with a lower concentration of each. Admitted. The effect of improving male pattern baldness and the effect of suppressing sebum secretion are competitive inhibition of the binding of the active androgen dihydrotestosterone to the receptor, and inhibition of the conversion of testosterone to dihydrotestosterone by inhibiting testosterone 5α-reductase. It is considered that the anti-androgen effect was synergistically improved through

[0011]

DESCRIPTION OF THE PREFERRED EMBODIMENTS Terpenes such as cis-jasmon may be added as they are, but ethanol, propylene glycol, dipropylene glycol, glycerin,
It is dissolved or dispersed in a liquid carrier such as 3-butylene glycol or squalane, a semi-solid carrier such as liquid paraffin, or a solid carrier such as petrolatum, or encapsulated in microcapsules or liposomes to prepare a hair restorer, hair cosmetic or skin It can also be contained in an external preparation base.

[0012] Sage ( Salvia officinalis L.)
Such plant extracts are obtained by immersing these plants in an extraction solvent. For the extraction, each part such as a flower, a leaf, a stem and the like of each plant and the whole plant can be used. These plants may be subjected to an extraction treatment as it is, but in order to increase the extraction efficiency, it is preferable to extract after shredding, pulverizing or the like, or to homogenate in an extraction solvent. As the extraction solvent, a polar solvent is preferable. In addition to water, methanol, ethanol, propanol,
Lower alcohols such as isopropanol and butanol,
Propylene glycol, dipropylene glycol, 1,3-
Preferred are polyhydric alcohols such as butylene glycol and glycerin, ethers such as ethyl ether and propyl ether, esters such as ethyl acetate and butyl acetate, and ketones such as acetone and ethyl methyl ketone. One or two or more are selected and used. Further, a phosphate buffer or a physiological saline can also be used favorably. Extraction with ethanol is particularly preferred from the viewpoint of testosterone 5α-reductase inhibitory activity. An appropriate extraction temperature is about 5 to 50 ° C., and an appropriate extraction time is about 4 hours to 1 week.

The above-mentioned plant extract may be added to a base such as a hair tonic as it is, but the concentrated and dried one may be redissolved in water or a polar solvent, or subjected to purification such as decolorization, deodorization and desalination. It may be added after the treatment. Further, after concentration and drying, or after performing a purification treatment, it may be freeze-dried and added as a powder.

The present invention can be provided in the form of a lotion, emulsion, gel, cream, ointment or the like as an external preparation for skin for suppressing sebum. Further, it can be provided as a hair restorer and a hair cosmetic in the form of a hair lotion, a hair tonic, a hair milk, a hair gel, a hair cream, a hair pack, a hair treatment, a hair shampoo, and a hair rinse. The amount of the terpene, such as cis-jasmon, added to the external preparation for skin, the hair tonic or the cosmetic base for hair is 1.0 × 10 ^-5 % by weight or more.
0.1% by weight, sage ( Salvia officinalis L.)
As an extract obtained by homogenizing 500 g of each plant in 1.0 liter of an extraction solvent, 0.1 g of each plant extract is used.
About 001 to 20% by weight is appropriate.

The hair nourishing agent, the hair cosmetic and the skin external preparation for inhibiting sebum secretion according to the present invention include oils and fats, lower alcohols, polyhydric alcohols, and surface active agents as long as the characteristics of the present invention are not impaired. Agents, moisturizers, cell activators, fungicides,
Raw materials and additives usually used in cosmetics and skin external preparations, such as preservatives, ultraviolet absorbers, and fragrances, can be contained.

[0016]

EXAMPLES Further, the features of the present invention will be described in detail with reference to examples.

Example 1 Hair Nourishing Lotion (1) Ethanol 60.000 (% by weight) (2) Tocopherol acetate 0.500 (3) Propylene glycol 2.000 (4) Purified water 36.498 (5) Cis -Jasmon 0.002 (6) Hop ethanol extract 1.000 Production method: (1) to (3) are added to (4) sequentially to solubilize, and then
Add and dissolve (5) and (6). The hop ethanol extract of (6) was prepared by slicing 500 g of hops, immersing them in 1.0 liter of ethanol, allowing them to stand at 15 ° C. for 3 days, centrifuging and filtering to collect the filtrate.

Example 2 Hair rinse (1) Silicone oil 3.000 (% by weight) (2) Liquid paraffin 1.000 (3) Cetanol 1.500 (4) Stearyl alcohol 1.000 (5) Stearyl chloride Trimethylammonium 0.700 (6) Glycerin 3.000 (7) Methyl paraoxybenzoate 0.200 (8) Green No. 3 0.002 (9) Purified water 89.088 (10) 1.0% by weight methyldihydroiso 0.010 Jasmonate ethanol solution (11) Sage 50% by volume 1,3-butylene glycol 0.250 extract (12) Thyme 50% by volume 1,3-butylene glycol 0.250 extract Production method: (5) ~ The aqueous phase component of (9) is mixed and dissolved and heated to 70 ° C. On the other hand, the oil phase components (1) to (4) are mixed and heated to 70 ° C. The oil phase is added to the aqueous phase and emulsified by a homomixer. After cooling, (10) to (12) are added and mixed at 40 ° C.
The 1,3-butylene glycol extract of sage or thyme in (11) and (12) is obtained by adding 500 g of sage or thyme to 5 g each.
Immersed in 1.0 liter of 0 volume% 1,3-butylene glycol,
The mixture was homogenized at 5 ° C. for 24 hours, centrifuged, filtered, and the filtrate was recovered to prepare a filtrate.

[Example 3] Hair foam (stock solution formulation) (1) Cationic cellulose 3.000 (% by weight) (2) Polyoxyethylene (50E.O.) hydrogenated castor oil 1.000 (3) Silicone oil 5.000 (4) Dipropylene glycol 7.000 (5) Ethanol 15,000 (6) Methyl parahydroxybenzoate 0.150 (7) Purified water 68.395 (8) 1.0% by weight methyl dihydrojasmonate 0.005 Ethanol solution (9) Rosemary 50% by volume ethanol extract 0.150 (10) Mint 50% by volume ethanol extract 0.150 (11) Chamomile 30% by volume glycerin extract 0.150 (filling formulation) Stock solution 90.0 Liquefied petroleum gas 10.0 Production method: (3) is added to the melt of (2) and (4) and homogenized with a homomixer. This is added to the solutions (1), (5) to (11). For filling, a can is filled with a stock solution, and after mounting a valve, liquefied petroleum gas is filled. The rosemary and peppermint ethanol extracts of (9) and (10) or the chamomile glycerin extract of (11) were prepared by adding 500 g of each of these plants to 1.0 liter of 50% by volume of ethanol or 1.0% of 30% by volume of glycerin, respectively. It was immersed, homogenized at 10 ° C. for 24 hours, filtered after centrifugation, and collected by filtration to prepare a filtrate.

Example 4 Hair Treatment (1) Liquid paraffin 15,000 (% by weight) (2) Vaseline 15.000 (3) Beeswax 2.000 (4) Polyoxyethylene (50E.O.) cured castor Oil 3.000 (5) Glycerin 5.000 (6) Carboxyvinyl polymer 0.100 (7) Xanthan gum 0.100 (8) Disodium ethylenediaminetetraacetate 0.100 (9) Purified water 59.395 (10) Water Sodium oxide 0.050 (11) 2.0 wt% cis-jasmon ethanol solution 0.003 (12) 2.0 wt% dihydrojasmon ethanol 0.002 solution (13) 10.0 wt% Hypericum extract glycerin 0. 250 solution Production method: The oil phase components (1) to (3) are dissolved by heating to 80 ° C. On the other hand, the aqueous phase components (4) to (9) were mixed and dissolved by heating.
° C. The oil phase is added thereto with stirring, and the mixture is uniformly emulsified by a homogenizer. 30 ° C after cooling (10) ~
(13) is added and mixed. The glycerin solution of the hypericum extract of (13) was prepared by adding 500 g of hypericum to ethanol 1.
Ethanol was evaporated to dryness from the extract obtained by immersing in 0 l at 20 ° C. for 5 days, and it was dissolved and dissolved in glycerin so as to be 10.0% by weight.

Example 5 Acne Treatment Cream (1) Beeswax 6.00 (% by weight) (2) Cetanol 5.00 (3) Reduced Lanolin 8.00 (4) Squalane 15.50 (5) Glyceryl Fatty acid ester 4.00 (6) Lipophilic glyceryl monostearate 1.50 (7) Polyoxyethylene (20E.O.) sorbitan 4.00 Monolaurate (8) Propylene glycol 5.00 (9) Methyl paraoxybenzoate 0.10 (10) Purified water 50.48 (11) 2.0% by weight cis-jasmon ethanol solution 0.01 (12) 2.0% by weight methyl dihydroiso 0.01 Jasmonate ethanol solution (13) Arnica phosphate buffer extract 0.15 (14) Mentha phosphate buffer extract 0.25 Production method: Mix and dissolve the oil phase components of (1) to (7) and heat to 75 ° C I do. On the other hand, the aqueous phase components (8) to (10) are mixed and dissolved, and heated to 75 ° C. Next, the oil phase component is added to the water phase component and pre-emulsified, and then uniformly emulsified by a homomixer. After cooling, (11) to (14) are added at 40 ° C. (13), (1
4) The phosphate buffer extract of Arnica or peppermint is obtained by adding 750 g of Arnica or peppermint to 20 mM each.
The solution was homogenized in a phosphate buffer (pH 7.0) at 10 ° C. for 24 hours, centrifuged, filtered, and the filtrate was collected to prepare a filtrate.

Example 6 Antiseborrheic agent (1) Dipropylene glycol 10.000 (% by weight) (2) Carboxyvinyl polymer 0.500 (3) Potassium hydroxide 0.100 (4) Methyl paraoxybenzoate 0.100 (5) Purified water 88.250 (6) 1.0% by weight methyl dihydrojasmonate 0.025 ethanol solution (7) 1.0% by weight dihydrojasmon ethanol 0.025 solution (8) Hop physiological saline Water extract 1.000 Production method: After dissolving (2) uniformly in (5), dissolve (4) in (1) and then add (3) to increase the viscosity by adding (3). ) ~ (8)
Is added. The hop extract of (8) was prepared by homogenizing 600 g of hops in 1.0 liter of physiological saline at 10 ° C. for 48 hours, centrifuging and filtering to collect a filtrate.

Of the above embodiments, Embodiment 1, Embodiment 5,
For Example 6, the effect of improving male pattern baldness, the effect of treating acne, and the effect of preventing dandruff and itch were evaluated, respectively.

First, in Example 1, the hop ethanol extract in the formulation was replaced with ethanol, and Comparative Example 1 was used.
Comparative Example 2 in which cis-jasmon was replaced with purified water,
The cis-jasmon and hop ethanol extracts were replaced with 2.0 wt% of the ethanol extract of the assembly, and the total amount was 100.0 wt% with purified water as Comparative Example 3,
A use test was conducted in male pattern baldness patients. The use test consisted of 20 male pattern bald patients as one group, each group was allowed to use the examples and comparative examples twice a day for 6 months with a blind, and photographed the degree of hair growth after 6 months. The evaluation was performed according to The evaluation was performed according to the criteria shown in Table 1.
Table 2 shows the number of panelists who obtained each evaluation score.

[Table 1]

[0025]

[Table 2] As shown in Table 2, in the use group of Example 1 of the present invention, overall hair growth was observed in all patients, and 70% of the patients had ingrown hair. On the other hand, in the group using Comparative Example 1 containing only cis-jasmon as an active ingredient, 85% of the patients showed overall hair growth, but 30% of them showed hard hair. It was not too much. Even in the group using Comparative Example 2 containing only the ethanol extract of hops as an active ingredient, 75% of the patients showed overall hair growth, but only 15% of the patients showed hair growth. I was staying. Further, in the group using Comparative Example 3 containing the ethanol extract of the assembly as an active ingredient, although the occurrence of partial hair growth was observed, few patients showed overall hair growth. In addition, there was no patient that showed the occurrence of ingrown hair.

Next, in Example 5, Comparative Example 4 in which the phosphate buffer extract was substituted for each of the phosphate buffer extracts of Arnica and Mentha in the formulation, cis-jasmon and methyldihydroisojasmonate were used. Comparative Example 5 was obtained by replacing the ethanol solution with ethanol, and each ethanol solution of cis-jasmon and methyldihydroisojasmonate and the phosphate buffer extract of Arnica and peppermint were replaced by 1.0% by weight of pyridoxine hydrochloride. The total amount was adjusted to 100.0% by weight with purified water as Comparative Example 6,
A use test in acne patients was performed. In the use test, 20 groups of acne patients were used as a group, and each group was allowed to use the examples and the comparative examples twice a day for one month with a blind, and the improvement of symptoms was observed. The symptom improvement status was evaluated in three stages of “improvement”, “slight improvement”, and “improvement was not observed”. Table 3 shows the number of patients who obtained each evaluation.

[Table 3]

As is clear from Table 3, 19 out of 20 patients in the group using Example 5 of the present invention showed a clear improvement, and no patients showed no improvement tendency. In contrast, in the group using Comparative Example 4 containing only a terpene such as cis-jasmon as an active ingredient, no patient showed any improvement tendency, but only 8 patients showed a clear improvement. . Even in the group using Comparative Example 5 containing only a plant extract such as arnica as an active ingredient, an improvement tendency was observed, but only 5 people showed a clear improvement. Further, in the group using Comparative Example 6 containing pyridoxine hydrochloride as an active ingredient, only one person showed a clear improvement, and no improvement was observed in three persons.

Next, in Example 6, Comparative Example 7 was obtained by replacing the physiological saline extract of hop in the formulation with physiological saline, and Example 6 was obtained by replacing each ethanol solution of methyldihydrojasmonate and dihydrojasmon with ethanol. Comparative Example 8, comparison was made between a solution of methyldihydrojasmonate, an ethanol solution of dihydrojasmon and a physiological saline extract of hops replaced with 1.0% by weight of pyridoxine hydrochloride and a total amount of 100.0% by weight with purified water. Example 9
A use test was conducted in a dandruff patient with hypersebum secretion. The use test consisted of 20 dandruff patients as a group, and each group was blinded with the examples and comparative examples 2 days a day.
It was used for one month, and the improvement status of each symptom of dandruff and itch was evaluated. The improvement status of each symptom was evaluated in three stages of “improvement”, “slight improvement”, and “improvement was not recognized”. Table 4 shows the number of patients who obtained each evaluation.

[0029]

[Table 4] In Table 4, in the group using Example 6 of the present invention, improvement tendency of dandruff symptoms was observed in all patients, and clear improvement was observed in 19 patients. In addition, all patients showed a clear improvement in itch. On the other hand, in the group using Comparative Example 7 containing only terpene such as methyldihydrojasmonate as an active ingredient, although there was a tendency for improvement for each symptom, 10 people for dandruff showed clear improvement, and itching was observed. In the group using Comparative Example 8 containing only a hop physiological saline extract as an active ingredient, only 9 people showed a clear improvement in dandruff and 7 people showed itching in itching. Further, in the group using Comparative Example 9 containing pyridoxine hydrochloride as an active ingredient, 4 people showed clear improvement, and 3 people showed itching.
Did not see any improvement in the names.

The above evaluation results show that the examples of the present invention show that the terpenes such as cis-jasmon and the plant extract such as hops, which are the constituents of the present invention, are used in comparison with the case where the plant extracts such as hops are used alone. It is shown that the synergistic improvement of is significantly enhanced the hair growth promoting effect in male pattern baldness patients, and the acne treatment effect and dandruff improving effect by suppressing excessive secretion of sebum.

In the above use test, no irritation or sensitization to the skin or scalp was observed at all, and no other side effects were observed by using the examples of the present invention. Further, regarding Examples 1 to 6 of the present invention,
All showed good storage stability.

[0032]

As described above in detail, according to the present invention, a hair restorer and a hair cosmetic wherein the preventive and ameliorating effects of androgenetic alopecia are synergistically enhanced by synergistically improving the antiandrogenic action, and In addition, the effect of inhibiting sebum secretion was synergistically enhanced, and an external preparation for skin which was very effective for treating and improving acne vulgaris, seborrhea and the like was obtained.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification code FI A61K 35/78 A61K 35/78 W

Claims (3)

[Claims] 1. Sage ( Salvia officinalis L.), hop ( Humulus lupulus L.), rosemary ( Rosmarin )
us officinalis L.), Hypericum erect
um Thunb.), Mentha ( Mentha arvensis L. var. piper)
ascens Malinv.), Mentha piperita
L.), chamomile ( Matricaria chamomilla L.), arnica ( Arnica montana L.), thyme ( Thymus vulgaris )
L.) and cis-jasmon (cis-jasmon) represented by the chemical formula (1).
e), methyl dihydroisojasmonate represented by the chemical formula (2), methyl dihydroisojasmonate represented by the chemical formula (3) (meth)
yl dihydrojasmonate) and 1 selected from dihydrojasmone represented by chemical formula (4)
A hair tonic comprising at least one species or two or more species. 2. Sage ( Salvia officinalis L.), hop ( Humulus lupulus L.), rosemary ( Rosmarin )
us officinalis L.), Hypericum erect
um Thunb.), Mentha ( Mentha arvensis L. var. piper)
ascens Malinv.), Mentha piperita
L.), chamomile ( Matricaria chamomilla L.), arnica ( Arnica montana L.), thyme ( Thymus vulgaris )
L.) and cis-jasmon (cis-jasmon) represented by the chemical formula (1).
e), methyl dihydroisojasmonate represented by the chemical formula (2), methyl dihydroisojasmonate represented by the chemical formula (3) (meth)
yl dihydrojasmonate) and 1 selected from dihydrojasmone represented by chemical formula (4)
A hair cosmetic, characterized by comprising a seed or two or more kinds. 3. Sage ( Salvia officinalis L.), hop ( Humulus lupulus L.), rosemary ( Rosmarin )
us officinalis L.), Hypericum erect
um Thunb.), Mentha ( Mentha arvensis L. var. piper)
ascens Malinv.), Mentha piperita
L.), chamomile ( Matricaria chamomil la L.), arnica ( Arnica montana L.), thyme ( Thymus vulgaris )
L.) and cis-jasmon (cis-jasmon) represented by the chemical formula (1).
e), methyl dihydroisojasmonate represented by the chemical formula (2), methyl dihydroisojasmonate represented by the chemical formula (3) (meth)
yl dihydrojasmonate) and 1 selected from dihydrojasmone represented by chemical formula (4)
A skin external preparation for inhibiting sebum secretion, comprising a seed or two or more kinds. Embedded image Embedded image Embedded image Embedded image