JPH11302127A - Hair tonic - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain hair tonic having excellent depilation-preventing effect and hair growth-promoting effect in mammal including human by including a specific ketol fatty acid. SOLUTION: This hair tonic contains a ketol fatty acid in which either one of different two carbons selected from carbons located at some positions among 2 to (n) positions of carbon is carbon constituting carbonyl group and the other is carbon in which hydroxyl group is bound and (n) is 4-24, e.g. 9-hydroxy-10- oxo-12(Z) of formula I, 15(Z)-octadecadienoic acid, 12-oxo-13-hydroxy-9(Z) of formula II or 15(Z)-octadecadienoic acid as an active ingredient. In the above hair tonic, the formulating amount of the active ingredient is preferably 0.000005 to 10.0 wt.%.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to the field of hair restoration. More specifically, the present invention relates to a hair restorer containing a ketol fatty acid having a specific structure as an active ingredient, and specifically to a hair restorer used in the fields of pharmaceuticals, quasi-drugs, and cosmetics.

[0002]

2. Description of the Related Art Conventionally, causes of baldness and hair loss include activation of androgens in organs such as hair roots and sebaceous glands, decreased blood flow to hair follicles, excessive secretion of sebum, and generation of peroxide. Abnormalities of the scalp are considered. For this reason, a compound having an action of removing or reducing the above-mentioned causes is generally added to conventional hair restorations.

Examples of such compounds include vitamins such as vitamin B and vitamin E, amino acids such as serine and methionine, vasodilators such as assembly extracts and acetylcholine derivatives, and anti-inflammatory agents such as purple root extract and hinokitiol. It contains a female hormone such as estradiol, a skin function enhancer such as cepharanthin, and the like, and is used for prevention and treatment of alopecia and the like.

[0004]

However, in spite of various attempts as described above, conventional hair restorations do not always have sufficient hair restoration effects such as prevention of hair loss and promotion of hair growth. Did not. This is probably due to a variety of causes of hair loss and the very complex mechanism of hair growth. In view of the variety of causes of such hair loss, it is desired to provide a further new hair restoration.

[0005] Accordingly, an object of the present invention is to provide a hair restorer having an excellent hair loss preventing effect and a hair growth promoting effect in order to address the various causes of hair loss.

[0006] From the above viewpoints, the present inventors have sought to search for effective substances widely and have studied them. as a result,
It has been found that ketol fatty acids having a specific structure exhibit an excellent hair-growing action.

[0007]

That is, the present invention provides the following hair restorer in the present application.

In claim 1, one of two different carbon atoms selected from carbon atoms located at any of the 2-position to the n-position is a carbon atom constituting a carbonyl group, and the other is a carbon atom having a hydroxyl group bonded thereto. Provided is a hair restorer comprising, as an active ingredient, a ketol fatty acid in which n, which is the number of carbon atoms, is 4 or more and 2 or less.

In claim 2, the carbon atom located at any one of the 2-position to the n-position of the ketol fatty acid which is an active ingredient of the hair restorer according to claim 1 is a carbon atom constituting a carbonyl group in its carbon chain. And a hair restorer comprising, as an active ingredient, a ketol fatty acid in which any one carbon atom other than the carbon atom to which a hydroxyl group is bonded is a carbon atom to which a hydroperoxy group is bonded.

[0010] In claim 3, the carbon atom forming one carbonyl group of the ketol fatty acid as the active ingredient of the hair restorer according to the first or second aspect and the carbon atom bonded to the other hydroxyl group are α. And a hair tonic comprising as an active ingredient a ketol fatty acid located at the γ-position or the γ-position.

[0011] In Claim 4, the double bond is present in one or more and six or less places with respect to the bonding form of the carbon atoms. Provided is a hair nourishing composition comprising ketol fatty acid, which is an active ingredient of hair, as an active ingredient.

[0012] In claim 5, the number of carbon atoms is 18
And ketol which is an active ingredient of the hair restorer of the hair restorer according to any one of claims 1 to 4, wherein a double bond is present at two places with respect to the bonding form between the carbon atoms. Provided is a hair restorer containing a fatty acid as an active ingredient.

[0013]

Embodiments of the present invention will be described below.

The hair restorer of the present invention is a hair restorer containing a specific ketol fatty acid as an active ingredient. In this ketol fatty acid, as described above, one of two different carbon atoms selected from the carbon atoms located at any of the 2-position to the n-position is a carbon atom constituting a carbonyl group, and the other is a carbon atom constituting a carbonyl group. It is a ketol fatty acid in which the number of carbon atoms, which is a carbon atom, is 4 or more and 24 or less (hereinafter, this ketol fatty acid may be referred to as “the ketol fatty acid related to the present invention”).

That is, one feature of the ketol fatty acid related to the present invention is that it has a ketol structure in which a carbon atom constituting a carbonyl group and a carbon atom to which a hydroxyl group is bonded are present in the carbon skeleton.

It is desired that the carbon atom constituting the carbonyl group and the carbon atom to which the hydroxyl group is bonded in the ketol structure be in the α-position or the γ-position in the carbon skeleton of the ketol fatty acid. From the viewpoint of exhibiting the activity, the α-position is particularly preferable from this viewpoint.

Further, the ketol fatty acid related to the present invention is an unsaturated ketol fatty acid having one or more and no more than six double bonds with respect to the bonding form between its carbon atoms. It is preferable to exhibit

The ketol fatty acid of the present invention preferably has 18 carbon atoms. Further, in this case, it is preferable that there are two double bonds in the bonding form between carbon atoms of the ketol fatty acid related to the present invention.

The ketol fatty acid related to the present invention has a carbon atom having a hydroperoxy group bonded to any one of the carbon atoms other than the carbon atom forming the carbonyl group and the carbon atom having the hydroxyl group bonded thereto. Is also good.

Specific examples of the above-mentioned ketol fatty acids related to the present invention include, for example, 9-hydroxy-10-oxo-1
2 (Z), 15 (Z) -octadecadienoic acid [hereinafter sometimes referred to as ketol fatty acid (I) related to the present invention], 1
2-oxo-13-hydroxy-9 (Z), 15 (Z)
-Octadecadienoic acid [hereinafter sometimes referred to as ketol fatty acid (II) related to the present invention], 10-oxo-13-
Hydroxy-11 (E), 15 (Z) -octadecadienoic acid [hereinafter sometimes referred to as ketol fatty acid (III) related to the present invention], 9-hydroxy-12-oxo-10
(E), 15 (Z) -octadecadienoic acid [hereinafter sometimes referred to as ketol fatty acid (IV) related to the present invention] and the like.

The ketol fatty acids (I) related to the present invention are described below.
-Chemical formula of (IV) is described.

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Further, ketol fatty acids related to the present invention having a carbon atom having a hydroperoxy group bonded to any one of the carbon atoms other than the carbon atom forming the carbonyl group and the carbon atom having the hydroxyl group bonded thereto include: ,
For example, 9-hydroperoxy-12-oxo-13
Hydroxy-10 (E), 15 (Z) -octadecadienoic acid [hereinafter sometimes referred to as ketol fatty acid (V) related to the present invention], 9-hydroxy-10-oxo-13-hydroperoxy-11 (E) , 15 (Z) -octadecadienoic acid [hereinafter sometimes referred to as ketol fatty acid (VI) related to the present invention] and the like.

The ketol fatty acids (V) related to the present invention are described below.
And the chemical structural formula (VI).

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The method for producing the ketol fatty acid related to the present invention is described in Japanese Patent Application No. 9-348678 filed by the present applicant.

The amount of the ketol compound related to the present invention to be added to the hair restorer of the present invention is not specified because it can vary depending on the dosage form, form or application method of the hair restorer. However, when used for a hair restoration obtained according to the method described in Examples described later, the ketol compound of the present invention is usually 0.000005 to 10.0 with respect to the total amount of the hair restoration.
% By weight, preferably 0.0001 to 5.0% by weight. If it is less than 0.000005% by weight, the hair-growing effect is not sufficiently exhibited, which is not preferable. 10.
If it exceeds 0% by weight, it is not preferable in terms of formulation.

The dosage form of the hair nourishing composition of the present invention is arbitrary, and may be any liquid, emulsion, ointment or any other properties applicable to the scalp. Accordingly, within a range that does not impair the effects of the present invention,
Various ingredients generally used in cosmetics, quasi-drugs, pharmaceuticals, etc., such as oils, humectants, thickeners, preservatives, antioxidants, fragrances, coloring agents, drugs, and other active ingredients,
It can be manufactured according to a conventional method.

In preparing the hair restorer of the present invention, specific examples of the above-mentioned components which can be added to the hair restorer of the present invention as an auxiliary component of the hair restorer composition include the following. Oils, for example, higher fatty acids, solid paraffin, liquid paraffin, silicone oil, squalane, olive oil, isopropyl myristate, higher alcohols, etc .; humectants, such as hyaluronic acid, propylene glycol, maltitol, atelocollagen, sodium lactate, etc. Agents such as quince, carboxyvinyl polymer, xanthan gum and the like; other active ingredients such as oils such as glyceryl monooleate, nicotinamide, benzyl nicotinate, vitamin E acetate,
Carpronium chloride, assembly extract, vasodilators such as acetylcholine derivatives, amino acids such as serine, methionine, vitamin B ₆ , vitamin E and its derivatives, vitamins such as biotin, pantothenic acid and its derivatives, glycyrrhetinic acid and its derivatives, Nicotinic acid esters such as nicotinic acid, methyl nicotinate, and tocopherol nicotinate, skin function enhancers such as cepharanthin, female hormones such as estradiol, and the like may be simultaneously added. Further, additives usually used for hair restoration, for example, hinokitiol, hexachlorophen, benzalkonium chloride, cetylpyridinium chloride, undecylenic acid, antibacterial agents such as trichlorocarbanilide and bitionol, refreshing agents such as menthol, salicylic acid, Drugs such as zinc and its derivatives, lactic acid and its alkyl esters, organic acids such as citric acid, amino acids such as arginine, polyhydric alcohols such as glycerin and propylene glycol, ultraviolet absorbers, ethanol, and water are the effects of the present invention. Can be appropriately compounded within a range that does not impair.

Further, the form of the hair refining agent of the present invention is arbitrary, and in the field of medicines, quasi-drugs and cosmetics, for example, it can be in the form of products such as tonics, hair creams, hair foams, shampoos and rinses. .

[0029]

EXAMPLES The present invention will be described below more specifically with reference to examples. The present invention is not limited to only these examples.

The hair growth effect of the ketol compound related to the present invention, which is an essential component of the hair restorer of the present invention, was confirmed by performing the following hair growth test.

"Hair Growth Test" Using a C3H / HeNCrj mouse in the telogen phase of the hair cycle as an experimental animal, the method of Ogawa et al. [Normal and Abnormal Epidural Differentiation (Normal and
Abnormal EpidermalDiffer
entry), M.E. Seiji and I.S. A.
Bernstein, pages 159-170, 1
982, University of Tokyo Press].

That is, each group consisted of 10 mice, and each test substance (0.01 ketol fatty acid related to the present invention,
A 70% ethanol solution containing 0.002 and 0.04% by weight), a control sample (70% ethanol solution), and a control (0.1% by weight croton oil 75% ethanol solution)
And the back of the mouse was shaved with a clipper and a shaver, and 0.1 ml of each sample was applied once a day. After 17 days and 30 days, the regenerated area of the hair was measured, and the ratio of the regenerated area to the shaved area was determined as a percentage. The results are shown in Table 1.

[0033]

[Table 1] ---------------------------------------------- ------------------------- Sample concentration 17 days 30 days Judgment (% by weight) (%) (%) -------- -------------------------------------------------- ------------- Ketol fatty acid (I) related to the present invention 0.001 17 55 Effective ---------------------- ------------------------------------------------- Book Invention-related ketol fatty acid (II) 0.002 23 64 Effective ------------------------------------ ----------------------------------- Ketol fatty acid (III) related to the present invention 0.04 31 71 Effective -------------------------------------------------- --------------------- Ketol fatty acid (IV) related to the present invention 0.01 21 60 Effective -------------- -------------------------------------------------- ------- Ketol fatty acid (V) related to the present invention 0.02 25 68 Effective ---------------------------- -------------------- ----------------------- Ketol fatty acid (VI) related to the present invention 0.04 29 76 Effective ------------ -------------------------------------------------- --------- Control 0 0 No effect ------------------------------------ ----------------------------------- Comparison 28 63 Effective --------- -------------------------------------------------- ------------

Table 1 shows that the ketol fatty acid of the present invention, which is an essential component of the present invention, shows an excellent hair growth effect in a mouse hair growth test.

"Example 1" (1) Ketol fatty acid (II) related to the present invention 0.001% by weight (2) 70% ethanol 90.0 (3) Sodium oleate 0.01 (4) Dodecylbenzene sulfone oxygen 0 .49 (5) hydrogenated castor oil ethylene oxide (40 mol) adduct 0.5 (6) ion-exchanged water residue (production method) ketol fatty acid (II) related to the present invention was 70%
It was mixed with ethanol, sodium oleate, dodecylbenzenesulfonic acid, adduct of hydrogenated castor oil ethylene oxide (40 mol) and a part of ion-exchanged water, and dissolved by stirring. Further, ion-exchanged water (10%) was added and mixed to obtain a liquid hair restorative.

Example 2 (A phase) Ketol fatty acid (II) related to the present invention 0.002% by weight Polyoxyethylene (6 mol) addition-hardened castor oil 2.0 Glycerin 10.0 Dipropylene glycol 10.0 1 , 3-butylene glycol 5.0 polyethylene glycol 1500 5.0 (phase B) cetyl isooctanoate 10.0 squalane 5.0 petrolatum 2.0 propylparaben 2.0 (phase C) 1% aqueous solution of carboxyvinyl polymer 30. 0 Sodium hexametaphosphate 0.03 Ion-exchanged water 8.35 (D-phase) Ion-exchanged water 4.5 (E-phase) Caustic potash 0.12 Ion-exchanged water 5.0 (Production method) Heat, dissolve, mix and homogenize to form a gel. Phase D is gradually added to this and dispersed with a homomixer. Next, the dissolved C phase was added thereto, and finally the dissolved E phase was added, and the mixture was emulsified with a homomixer to obtain an oil-in-water emulsion type hair restorer.

Example 3 (Phase A) Liquid paraffin 5.0% by weight Cetostearyl alcohol 5.5 Glyceryl monostearate 3.0 EO (20 mol) -2-octyldodecyl ether 8.0 Propylparaben 3 Fragrance 0.1 (Phase B) Ketol fatty acid (III) related to the present invention 0.04 Glycerin 8.0 Dipropylene glycol 20.0 Polyethylene glycol 4000 5.0 Sodium dodecyl sulfate 0.1 Sodium hexametaphosphate 0.005 Ion exchange Water 45.095 (Preparation method) The phases A and B were each dissolved by heating, mixed, and emulsified with a homomixer to obtain a creamy hair restorer.

Example 4 (1) 0.005% by weight of ketol fatty acid (III) related to the present invention (2) 70% ethanol 90.0 (3) Sodium oleate 0.01 (4) Dodecylbenzenesulfonic acid 0 .49 (5) Hardened castor oil ethylene oxide (40 mol) adduct 0.5 (6) Ion-exchanged water residue (Preparation method) 70% ethanol, sodium oleate, dodecylbenzenesulfonic acid, The mixture was mixed with a hydrogenated castor oil ethylene oxide (40 mol) adduct and a part of ion-exchanged water with stirring to dissolve. Further, ion-exchanged water (10%) was added and mixed to obtain a liquid hair restorative.

"Comparative Example 1" A liquid hair restorer of Comparative Example was obtained by removing the ketol fatty acid (I) related to the present invention in Example 1.

Using each of the hair nourishing compositions of Examples 1 to 4 and Comparative Example 1 obtained above, the following methods were applied to humans in order to examine their hair nourishing effects such as hair loss prevention and hair growth. A trigram test was performed. The control sample is 70% ethanol.

"Trichogram test" The hair roots of the extracted hair before and after use of the hair restoration were observed under a microscope, the number of telogens in the telogen was counted from the form of the hair root, and the hair growth of the hair restoration was determined by increasing or decreasing the ratio. The effects were compared. The telogen follicles are the hair follicles that have stopped growing, and it has been recognized that those who report hair loss have a higher percentage of these telogen follicles than normal people.

Each of the hair tonics of the test sample and the control sample of Examples 1 to 4 and Comparative Example 1 was applied to the scalp of 10 male subjects twice a day, 2 ml at a time, for 6 consecutive months, and immediately before application. Immediately after the application for 6 months, 100 hairs were removed from each subject, and the roots of each hair were examined, and a practical use test was performed. The results are shown in "Table 2".

----------------------------------------------- ------------------------ Sample Percentage of resting roots (%) Evaluation of hair restoration effect Reduced by 20% or more Less than ± 20% Increased by 20% or more -------------------------------------------------- --------------------- Example 1 55 35 10 Valid ---------------------- ------------------------------------------------- Implementation Example 2 50 40 10 Valid -------------------------------------------- --------------------------- Example 3 60 30 10 Effective ---------------- -------------------------------------------------- ----- Example 4 60 25 15 Valid -------------------------------------- --------------------------------- Comparative Example 1 15 60 40 Invalid ---------- -------------------------------------------------- ----------- Control 10 50 40 Invalid ---------------------------------- -------------------------------------

From Table 2, it can be seen that the hair restorer of the present invention exhibits an excellent hair restorer effect.

[0045]

As described above, according to the present invention,
Provided is a hair restorer having an excellent hair loss preventing effect and a hair growth promoting effect in mammals including humans.

Claims (5)

[Claims] 1. One of two different carbon atoms selected from carbon atoms located at any of the 2-position to n-position is a carbon atom constituting a carbonyl group, and the other is a carbon atom to which a hydroxyl group is bonded. , The number of its carbon atoms, n
A hair tonic containing a ketol fatty acid having an active ingredient of 4 or more and 24 or less. 2. The ketol fatty acid as the active ingredient according to claim 1, wherein the carbon atom located at any of the 2-position to the n-position has a carbon atom to which a carbon atom constituting a carbonyl group in the carbon chain and a hydroxyl group are bonded. A hair restorer comprising, as an active ingredient, a ketol fatty acid in which any one carbon atom other than an atom is a carbon atom to which a hydroperoxy group is bonded. 3. A carbon atom constituting one carbonyl group of a ketol fatty acid which is an active ingredient of the hair restorer according to claim 1 or 2, and a carbon atom to which the other hydroxyl group is bonded is in α-position or γ-position. Hair restoration containing ketol fatty acid as an active ingredient. 4. A method for bonding carbon atoms to each other,
4. A hair restorer comprising ketol fatty acid as an active ingredient of the hair restorer according to any one of claims 1 to 3, wherein a heavy bond is present in one or more places and six or less places. 5. The method according to claim 1, wherein the number of carbon atoms is 18, and two types of double bonds are present in the bonding form of the carbon atoms. Hair restoration containing ketol fatty acid as an active ingredient of hair as an active ingredient.