JPH1129563A - New substance of heteromonocyclic carboxylic acid esters, hair tonic composition using the same and hair tonic composition containing analogic compounds of the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject new substance, heteromonocyclic carboxylic acid esters, manifesting excellent hair growing effects, usable as the active ingredients in hair tonic composition. SOLUTION: The new substances are n-Pentadecyl-2-furoates of formula I, n-Pentadecyl-2-thenoates of formula II and Pentadecyltetrahydro-2-furoate of formula III. The substance of formula I has a molecular weight of 322, melting point of 36-37 deg.C and brown colored crystal at normal temperature. The compound of formula II is a new substance having a molecular weight of 338, a transparent oily substance at normal temperature. The new substance of formula III has a molecular weight of 326, a transparent oily substance at normal temperature. The new substances of formulae I to III are obtained by an esterification of n-pentadecanol with either one of 2-furoic acid of formula IV, thenoic acid of formula V, tetrahydro-2-furoic acid of formula VI.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a new group of heteromonocyclic carboxylic acid ester-based substances, and a hair restorer composition containing these novel substances and analogous substances thereof. Another object of the present invention is to provide a hair restorative composition which exhibits an excellent hair restoring effect by incorporating these novel substances or their similar substances. Incidentally, the hair restorer composition according to the present invention, pharmaceuticals under the Pharmaceutical Affairs Law, quasi-drugs,
It may belong to any of cosmetics and the like.

[0002]

2. Description of the Related Art Conventionally, as a hair nourishing agent, JP-A No. 1-2
No. 50310: What is described in the title of the invention "hair restorer" is disclosed. However, Japanese Patent Laid-Open No. 1-25
The nicotinic acid ester of n-pentadecanol disclosed in Japanese Patent No. 0310 does not have a sufficient hair-growth effect, and a hair restorer containing these as an active ingredient was not effective enough for practical use. Therefore, creation of a compound having a further excellent hair restoring action and a hair restoring agent composition having an excellent hair restoring effect have been desired.

[0003]

In view of the above circumstances, an object of the present invention is to provide a novel substance having an excellent hair-growth action and a hair-growing composition containing these novel substances and having an excellent hair-growth effect. Aim.

[0004]

Means for Solving the Problems The invention according to claim 1 is a novel substance n-Pentad represented by the following formula (Formula 5).
ecyl-2-furoate.

[Formula 5] The invention according to claim 2 provides a novel substance n-pentadecyl-2-thenoate represented by the following formula (Formula 6).
It is.

[Formula 6] The invention according to claim 3 provides a novel substance n-pentadecyl tetrahydro represented by the following formula (Formula 7).
-2-furoate.

[Formula 7] The invention according to claim 4 is a novel substance n-Pentade
cyl-2-furoate, a new substance n-Penta
decyl-2-thenoate, a new substance n-Pe
ntadecyl tetrahydro-2-fur
It is a hair restorer composition comprising at least one selected from the group consisting of oat and oate. According to a fifth aspect of the present invention, there is provided the following formula (wherein R is a saturated or unsaturated heteromonocyclic carboxylic acid residue, and the heteroatom of the heteromonocyclic is selected from oxygen and sulfur. The hair restorer composition comprises 0.01 to 10% of the heteromonocyclic carboxylic acid ester represented by the formula (1).

[Formula 8] The invention according to claim 6 is the hair restorer composition according to claim 5, wherein the heteromonocyclic ring is a 5-membered ring or a 6-membered ring. By providing these inventions, the above problems are completely solved. The hair-growth effect of carboxylate esters in which the heteroatom of the heterocyclic ring is nitrogen is known, but it is the first time that a carboxylate ester in which the heteroatom is oxygen or sulfur has a hair-growth effect. .

[0005]

Embodiments of the present invention will be described below in detail. The novel heteromonocyclic carboxylic acid ester-based substance according to claim 1 is n-Pen represented by the following formula (Formula 9).
tadecyl-2-furoate.

[Formula 9] n-Pentadecyl-2-furoate has a molecular weight of 322, a melting point of 36 to 37 ° C, and is a brown crystal at normal temperature. The novel heteromonocyclic carboxylic acid ester-based substance according to claim 2 is n-Penta represented by the following formula (Formula 10).
decyl-2-thenoate.

Embedded image n-Pentadecyl-2-thenoate has a molecular weight of 338 and is a colorless oil at normal temperature. Claim 3
The novel heteromonocyclic carboxylic acid ester-based substance described in (1) is an n-pentadecyl te represented by the following formula (Formula 11).
Trahydro-2-furoate.

Embedded image n-Pentadecyl tetrahydro-2
-Furoate is a colorless oil at room temperature with a molecular weight of 326.

Hereinafter, a method for synthesizing the novel heteromonocyclic carboxylic acid ester-based substance of the present invention will be described. The novel substance of the present invention comprises n-pentadecanol (Chem. 12) and a heteromonocyclic carboxylic acid 2-furoic acid (Chem. 13),
2-thenoic acid (Chem. 14), tetra
It is synthesized by esterifying hydro-2-furoic acid (Formula 15).

Embedded image

Embedded image

Embedded image

Embedded image The method of esterification may be in accordance with a conventional method, and is not particularly limited. However, these n-pentadecanol and heteromonocyclic carboxylic acid are dissolved in a solvent capable of dissolving both n-pentadecanol and heteromonocyclic carboxylic acid. For example, a method of dissolving, adding a catalyst, heating to a predetermined temperature and condensing can be exemplified.

The hair restorer composition according to claim 5 is a hair restorer composition comprising 0.01 to 10% of a heteromonocyclic carboxylic acid ester represented by the following formula (Formula 16).

Embedded image In Formula 16, R is a saturated or unsaturated heterocyclic monocyclic ring, and a hetero atom of the heterocyclic ring is oxygen or sulfur. Further, the heterocyclic ring is preferably a 5-membered ring or a 6-membered ring. Specific examples of the heteromonocyclic carboxylate include n-pentadecyl-2-furoate, which is a novel substance described above.
(Formula 17), n-Pentadecyl-2-then
oate (Formula 18), n-Pentadecyl te
Of course, trahydro-2-furoate (Chemical Formula 19) can be exemplified, and all other similar substances are heteromonocyclic carboxylic acid ester compounds usable in the present invention.

Embedded image

Embedded image

Embedded image

Hereinafter, a method for synthesizing a heteromonocyclic carboxylate compound which is a similar substance to the novel substance used in the present invention will be described. The heteromonocyclic carboxylic acid ester compound used in the present invention is synthesized by esterifying n-pentadecanol (Chem. 20) and a heteromonocyclic carboxylic acid (Chem. 21).

Embedded image

Embedded image In addition, in Chemical formula 21, R is a saturated or unsaturated heterocyclic monocyclic ring, and a hetero atom of this heterocyclic ring is oxygen or sulfur. Specific examples of the heterocyclic monocyclic carboxylic acid used in the present invention include 2-furic acid (Formula 22) and 2-th
enoic acid (chemical formula 23), tetrahydror
o-2-Furoic acid (Formula 24) is preferably used, but other tetrahydro-2-thene is preferred.
noic acid (Formula 25), 3-thenoic
acid (chemical formula 26), tetrahydro-3-th
enoic acid (Chemical Formula 27), 5-methyl-
2-furoic acid (Formula 28), 2,5-di
methyl-3-furoic acid
9), 2,5-furandicarboxylic
acid (Chemical Formula 30), 4-butanolide-3-
Carboxylic acid (Formula 31), 2-py
lone-6-carboxylic acid
2), 4-pyrone-2-carboxylic
acid (Formula 33), 5-hydroxy-4-py
lone-2-carboxylic acid
4), 4-pyrone-2,6-dicarboxy
liic acid (Formula 35), 3-hydroxy
-4-pyrone-2,6-dicarboxyli
C acid (Formula 36) or the like may be used.

Embedded image

Embedded image

Embedded image

Embedded image

Embedded image

Embedded image

Embedded image

Embedded image

Embedded image

Embedded image

Embedded image

Embedded image

Embedded image

Embedded image

Embedded image

The novel substance n synthesized by the above method
-Pentadecyl-2-furoate, n-P
entadecyl-2-thenoate, n-Pe
ntadecyl tetrahydro-2-fur
Oate-containing heteromonocyclic carboxylate compounds each have a hair-growth effect, so that when one or more of these heteromonocyclic carboxylate compounds are blended as an active ingredient, a suitable hair restorer can be obtained. In this case, the amount is preferably about 0.01 to 10%. If the amount is less than 0.01%, the hair growth effect may not be obtained, and even if the amount exceeds 10%, a significant improvement in the hair growth effect cannot be expected. The hair restorer of the present invention may contain a blood circulation enhancer, a local stimulant and the like in addition to the above-mentioned active ingredients. Specifically, vitamin E and its derivatives, assembly extract, garlic extract, cepharanthin, carpronium chloride, acetylcholine, etc. Blood circulation enhancer, pepper agar tincture, cantaris tincture, ginger tincture, local stimulants such as vanillamide nonylate, keratolytic agents such as salicylic acid, resorcinol, lactic acid, placenta extract, glyceride pentadecanoate, pantothenyl ethyl ether, biotin, Hinokitiol, metabolic activators such as allantoin, glycyrrhizic acid, anti-inflammatory agents such as glycyrrhetinic acid,
Fungicides such as isopropylmethylphenol, triclosan, zinc pyrithione, hinokitiol, menthol,
A cooling agent such as camphor and other female hormones can be appropriately combined and compounded. Further, in the present invention, in addition to the above, other components that are usual, such as alcohol, polyhydric alcohol, water-soluble polymer, antioxidant, pH adjuster, as long as the effects and system of the present invention are not impaired, Normal cosmetic ingredients such as UV inhibitors, sequestering agents, thickeners, surfactants, purified water, fragrances, preservatives, antibacterial agents, oils, higher fatty acids, fatty acid esters, humectants, fresheners, pigments, etc. Or hormones, vitamins, amino acids, astringents and placenta extracts, elastin, collagen, mucopolysaccharide, aloe extract, loofah water, royal jelly, birch, carrot extract, chamomile extract, licorice extract, salvia extract, altea extract, Specially formulated components such as animal and plant extracts, including crude drug components such as Yarrow Extract, may be appropriately blended according to the purpose.

[0010]

EXAMPLES A method for synthesizing a novel heteromonocyclic carboxylic acid ester-based substance of the present invention will be described below with reference to Synthesis Examples 1 to 4.

<Synthesis Example 1> Synthesis of n-Pentadecyl-2-furoate
Success. Attach an H tube in a 300 ml flask and add 2-fu
roic acid 17.9 g (0.16 mol), n
-Pentadecanol 30.0g (0.13m
ol), 1 g of tosyl alcohol monohydrate, and tolue
200 ml was charged. Leave this solution at 115 ° C for 5 hours
It was azeotroped to remove water. The distillate at this point
The volume was about 1.0 ml. Then add tosyl alcohol to the solution
2 g of urea monohydrate was added and azeotroped for another 8 hours.
Was removed. The total amount of distillate at this time is about 2.3.
ml. After azeotrope, the solution is cooled and saturated
After pouring into 200 ml of thorium aqueous solution,
Then, the toluene layer was taken out. Saturate the removed toluene layer
Wash once with 200 ml of aqueous sodium bicarbonate solution.
After washing once with 200 ml of underground water, toluene is evaporated
And concentrated to give 42.0 g of crude oil. 95 of this crude oil
Recrystallized with 80 ml of ethanol, melting point 36-37 ° C
To obtain 36.0 g of brown crystals. The yield was 86%.
Was. Identification of the substance obtained¹H nuclear magnetic resonance spectrum
,¹³C nuclear magnetic resonance spectrum, mass spectrometry, infrared absorption
The spectra were determined by gas chromatography.
¹H nuclear magnetic resonance spectrum [(CDCl_Three) Δ_Hpp
m] is CDCl as a solvent_ThreeWith TM as the reference material
S (27 ° C), sample concentration 1%
0.88 (3H, t, -CH 3), 1.26 (24
H,-(CH 2)₁₂-), 1.70 (2H, m, -CO
O-CH 2−CH Two−), 4.30 (2H, t, —COO)
-CH 2--), 6.49 (1H, dd, -CH-4),
7.16 (1H, dd, -CH-3), 7.57 (1
H, dd, -CH-5).¹³C nuclear magnetic resonance spec
Coutle [(CDCl_Three) Δ_Cppm] is C
DCI_ThreeUsing TMS (27 ° C.) as a reference substance,
When performed at a sample concentration of 3%, 14.2 (q), 2
2.8 (t), 26.0 (t), 28.8 (t), 2
9.3 (t), 29.4 (t), 29.4 (t × 7),
32.0 (t), 65.1 (t), 111.8 (d),
117.7 (d), 145.0 (s), 146.2
(D), 158.9 (s). Mass spectrometry [EIM
S (%)] is 322 (M⁺, 38), 277
(4), 210 (14), 113 (100), 95 (4
2). Infrared absorption spectrum [IRνmax
(KBr) cm^-1Is 3100, 2920, 2
850, 1720, 1705, 1580, 1475, 1
300, 1130, 1020, and 770. In addition,
Of the substance obtained¹H nuclear magnetic resonance spectrum chart
In FIG.¹³FIG. 2 shows a chart of the C nuclear magnetic resonance spectrum.
FIG. 3 shows a chart of the mass spectrometry results, and FIG.
Figure 4 shows the chart of the gas chromatography.
The chart is shown in FIG.

<Synthesis Example 2> Synthesis of n-pentadecyl-2-thenoate Attach an H tube in a 300 ml flask and place 2-Th
enoic acid 20.5 g (0.16 mol),
n-Pentadecanol 30.0 g (0.13
mol), 1 g of tosyl alcohol monohydrate, and 200 ml of toluene. The solution was azeotroped at 115 ° C. for 5 hours to remove water. The amount of distillate at this time was about 1.0 ml. Thereafter, 2 g of tosyl alcohol monohydrate was added to the solution, and azeotropic distillation was performed for further 8 hours to remove water. At this point, the total amount of distillate is about 2.
It was 2 ml. After azeotropic distillation, the solution was cooled and poured into 200 ml of a saturated aqueous solution of sodium carbonate, and a toluene layer was taken out of the solution. The extracted toluene layer was washed once with 200 ml of a saturated aqueous solution of sodium carbonate and once with 200 ml of underground water, and then evaporated and concentrated to obtain 50.0 g of crude oil, which was further distilled in a distillation column. did. Table 1 shows the distillation conditions and yields.

[Table 1]As described in Table 1, n-Pentadecyl-2-t
The yield of henoate (fraction 2) was 41.0 g,
The yield was 93%. Identification of the substance obtained¹H nuclear magnetism
Air resonance spectrum,¹³C nuclear magnetic resonance spectrum, mass fraction
Analysis, infrared absorption spectrum, gas chromatography
I did it.¹H nuclear magnetic resonance spectrum [(CDCl
_Three) Δ_Hppm] is CDCl as a solvent._ThreeThe reference
Using TMS (27 ° C) as quality, sample 1% concentration
When performed, 0.88 (3H, t, -CH 3), 1.
26 (24H,-(CH 2)₁₂−), 1.73 (2H,
m, -COO-CH 2−CH ₂ −), 4.28 (2H,
t, -COO-CH 2−), 7.07 (1H, dd, −
CH-4), 7.52 (1H, dd, -CH-3),
7.78 (1H, dd, -CH-5).¹³C nucleus
Magnetic resonance spectrum [(CDCl_Three) Δ_Cppm)
CDCl as solvent_ThreeWith TMS (27
° C) at a sample concentration of 3%.
2 (q), 22.8 (t), 26.0 (t), 28.7
(T), 29.3 (t), 29.4 (t), 29.8
(T × 7), 32.0 (t), 65.3 (t), 12
7.6 (d), 132.1 (d), 133.2 (d),
134.2 (s) and 162.3 (s). Mass
The result of the precipitation [EIMS (%)] was 338 (M⁺, 6
1), 305 (5), 210 (32), 129 (10
0), 111 (66). Infrared absorption spectrum
[IRνmax (KBr) cm^-1] Is 292
0,2850,1710,1520,1470,127
It was 0.1100. In addition, of the obtained substance¹H nuclear magnetism
The chart of the air resonance spectrum is shown in FIG.¹³C nuclear magnetic resonance
Fig. 7 shows the spectrum chart, and the chart of the mass spectrometry results.
FIG. 8 shows an infrared absorption spectrum and FIG.
FIG. 10 shows a chart of gas chromatography.
You.

<Synthesis Example 3> n-Pentadecyl tetrahydro-2
-Synthesis of furoate. Attach an H tube in a 300 ml flask, and add
ahydro-2-furoic acid 18.6
g (0.16 mol), n-Pentadecanol
30.0 g (0.13 mol), tosyl alcohol 1
1 g of hydrate and 200 ml of toluene were charged. The solution was azeotroped at 115 ° C. for 5 hours to remove water.
The amount of distillate at this time was about 2.3 ml.
After azeotropic distillation, the solution was cooled and poured into 200 ml of a saturated aqueous solution of sodium carbonate, and a toluene layer was taken out of the solution. The removed toluene layer was washed once with 200 ml of a saturated sodium carbonate aqueous solution, and further washed with underground water 20 ml.
After washing once with 0 ml, the toluene was evaporated and concentrated to obtain 48.0 g of crude oil, which was further distilled in a distillation column. Table 2 shows the distillation conditions and yield.

[Table 2]As described in Table 2, n-Pentadecyl tet
The yield of rahydro-2-furoate (fraction 2)
Was 38.0 g, and the yield was 90%. Got
Substance identification¹H nuclear magnetic resonance spectrum,¹³C nuclear magnetic
Sounding spectrum, mass spectrometry, infrared absorption spectrum, gas
Performed by chromatography.¹H nuclear magnetic resonance
Vector [(CDCl_Three) Δ_Hppm) as a solvent
CDCl_ThreeUsing TMS (27 ° C) as reference material
When the sample was run at a 1% concentration, 0.88 (3
H, t, -CH 3), 1.26 (26H,-(CH 2)₁₃
−), 1.60 (2H, m, —CH_Two -4), 1.94
(2H, m, -CH_Two -3), 3.93 (2H, m,-)
CH 2-5), 4.13 (2H, t, -COO-CH Two
-), 4.44 (1H, dd, -CH-2).
¹³C nuclear magnetic resonance spectrum [(CDCl_Three) Δ_Cpp
m] is CDCl as a solvent_ThreeWith TM as the reference material
S (27 ° C), sample concentration 3%
14.0 (q), 22.6 (t), 25.1
(T), 25.7 (t), 28.5 (t), 29.1
(T), 29.2 (t), 29.6 (t × 7), 30.
1 (t), 31.8 (t), 64.8 (t), 69.1
(T), 76.7 (d) and 173.3 (s).
The result of mass spectrometry [EIMS (%)] was 326 (M⁺,
2), 225 (3), 210 (3), 71 (100),
43 (22). Infrared absorption spectrum [IRν
max (KBr) cm^-1] Are 2920, 286
0, 1750, 1730, 1460, 1200, 109
It was 0. In addition, of the obtained substance¹H nuclear magnetic resonance spec
Fig. 11 shows the chart of Khutor.¹³C nuclear magnetic resonance spectrum
Fig. 12 shows the mass spectrometry chart and Fig. 12 shows the mass analysis chart.
13 shows a chart of an infrared absorption spectrum in FIG.
FIG. 15 shows a chart of gas chromatography.

The novel heteromonocyclic carboxylic acid ester synthesized as described above has an excellent hair-growth effect.
Hair growth agents containing these novel substances exhibit excellent hair growth effects. Hereinafter, the effects of the present invention will be clarified by describing Examples and Test Examples of the present invention. <Example 1> n-Pentadecyl-2-then
5% -1,3-butylene glycol in ethanol was added to 1.25 g of oate to make the total volume 25 ml.
The sample of Example 1 was used. <Example 2> n-Pentadecyl-2-furo
A sample of Example 2 was prepared by adding an ethanol solution of 5% -1,3-butylene glycol to 1.25 g of ate to make the total volume 25 ml. <Embodiment 3> n-Pentadecyl tetrah
ydro-2-furoate 1.25g 5%-
A sample of Example 3 was prepared by adding an ethanol solution of 1,3-butylene glycol to a total volume of 25 ml. <Control Example> A 25% ethanol solution of 5% -1,3-butylene glycol was used as a control sample.

Comparative Example A sample of a comparative example was prepared by adding an ethanol solution of 5% -1,3-butylene glycol to 1.25 g of n-pentadecyl nicotinate to make the total volume 25 ml.

Using the samples of Examples 1 to 3, the control example, and the comparative example, the following tests were respectively performed. C3H
/ HeN Crj mice (8 weeks old, body weight 21-26 g)
After acclimatization and breeding for at least one week, the hair on the back was shaved with an electric clipper in the area of 2 cm × 4 cm for the one that had no abnormality, and then the electric clipper (0.05 m
The hair was removed with an m-blade) and used as a sample administration site. Three days after the hair was removed, 100 μl of each of the samples of Examples 1 to 3, the control example and the comparative example was added to each of the 10 mice for 19 consecutive days.
It was applied once a day in the morning. During the test period, C3H / He
The N Crj mice had a temperature of 22 ± 2 ° C. and a relative humidity of 55 ±
15%, ventilation rate 20 times / hour, irradiation time from 6 hours to 1
In a breeding room set for 8 hours, a plastic gauge (1
(5 × 23 × 15.5) (cm). The hair growth effect was evaluated as follows. The skin has a pink color (1 point). Skin changed to gray (appearance rate less than 30%) ---- 2 points. Skin changes to gray (appearance rate 30% or more, less than 60%),
And hair elongation is observed (appearance rate is less than 30%).
3 points. Skin changes to gray (appearance rate 60% or more) and hair elongation is observed (appearance rate 30% or more, less than 60%)
4 points. Hair growth is observed (appearance rate of 60% or more) ---- 5
point.

In Examples 1 to 3, the control example and the comparative example, Table 3 shows an average value of 10 animals in a hair-growing state as scores.

[Table 3]

As shown in Table 3 above, the novel heteromonocyclic carboxylic acid ester-based substance of the present invention has an excellent hair-growth effect as compared with known hair-growth components. Tables 4 to 7 below show Formulation Examples 1 to 4 of the hair restorer composition containing the novel heteromonocyclic carboxylic acid ester-based substance. <Prescription example 1>

[Table 4] <Prescription example 2>

[Table 5] <Prescription example 3>

[Table 6] <Prescription example 4>

[Table 7]

[0019]

Industrial Applicability The novel heteromonocyclic carboxylic acid ester-based substance of the present invention has an excellent hair-growth effect, and the hair-growing agent composition containing this heteromonocyclic carboxylic acid ester-based novel substance or a compound similar thereto is excellent. Has a hair-growth effect.

[Brief description of the drawings]

Fig. 1 New substance n-Pentadecyl-2-f
It is a chart of ¹ H nuclear magnetic resonance spectrum of uroate.

FIG. 2: New substance n-Pentadecyl-2-f
It is a chart of ¹³ C nuclear magnetic resonance spectrum of uroate.

Fig. 3 New substance n-Pentadecyl-2-f
It is a chart of the mass analysis result of uroate.

FIG. 4. New substance n-Pentadecyl-2-f
It is a chart of the infrared absorption spectrum of uroate.

FIG. 5: New substance n-Pentadecyl-2-f
It is a chart of gas chromatography of uroate.

FIG. 6: New substance n-Pentadecyl-2-t
3 is a chart of ¹ H nuclear magnetic resonance spectrum of henoate.

FIG. 7: New substance n-Pentadecyl-2-t
3 is a chart of ¹³ C nuclear magnetic resonance spectrum of henoate.

FIG. 8: New substance n-Pentadecyl-2-t
6 is a chart of the results of mass analysis of henoate.

FIG. 9: New substance n-Pentadecyl-2-t
It is a chart of the infrared absorption spectrum of henoate.

FIG. 10: New substance n-Pentadecyl-2-t
It is a chart of the gas chromatography of henoate.

FIG. 11: New substance n-Pentadecyl tet
It is a chart of < ¹ > H nuclear magnetic resonance spectrum of rahydro-2-furoate.

FIG. 12: New substance n-Pentadecyl tet
It is a chart of ¹³ C nuclear magnetic resonance spectrum of rahydro-2-furoate.

FIG. 13: New substance n-Pentadecyl tet
It is a chart of the mass spectrometry result of rahydro-2-furoate.

FIG. 14: New substance n-Pentadecyl tet
It is a chart of the infrared absorption spectrum of rahydro-2-furoate.

FIG. 15: New substance n-Pentadecyl tet
It is a chart of the gas chromatography of rahydro-2-furoate.

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁶ Identification symbol FI C07D 333/24 C07D 333/24 (72) Inventor Toshihiro Sakano 5-12, Jungen-cho, Chuo-ku, Osaka-shi Mandom Chuo Kenkyu Co., Ltd. Inside

Claims (6)

[Claims] 1. A novel substance nP represented by the following formula (Formula 1)
entadecyl-2-furoate. [Formula 1] 2. A novel substance n-P represented by the following formula (Formula 2)
entadecyl-2-thenoate. [Formula 2] 3. A new substance nP represented by the following formula (Formula 3)
entadecyltetrahydro-2-fur
oate. [Formula 3] 4. A new substance, n-pentadecyl-2
-Furoate, a new substance n-Pentadecyl
-2-thenoate, a new substance n-Pentade
A hair restorer composition comprising at least one selected from cyl tetrahydro-2-furoate. 5. The following formula (wherein, R is a saturated or unsaturated heteromonocyclic carboxylic acid residue, and the heteroatom of the heteromonocyclic is selected from oxygen and sulfur). A hair restorer composition comprising 0.01 to 10% of the indicated heteromonocyclic carboxylic acid ester. [Formula 4] 6. The hair restorer composition according to claim 5, wherein the heterocyclic monocyclic ring is a 5-membered ring or a 6-membered ring.