JPH0238565B2 - - Google Patents
Info
- Publication number
- JPH0238565B2 JPH0238565B2 JP61118900A JP11890086A JPH0238565B2 JP H0238565 B2 JPH0238565 B2 JP H0238565B2 JP 61118900 A JP61118900 A JP 61118900A JP 11890086 A JP11890086 A JP 11890086A JP H0238565 B2 JPH0238565 B2 JP H0238565B2
- Authority
- JP
- Japan
- Prior art keywords
- hair
- carvone
- growth
- piperitenone
- isopiperitenone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- SEZLYIWMVRUIKT-UHFFFAOYSA-N isopiperitenone Natural products CC(=C)C1CCC(C)=CC1=O SEZLYIWMVRUIKT-UHFFFAOYSA-N 0.000 claims description 56
- HKZQJZIFODOLFR-UHFFFAOYSA-N piperitenone Chemical compound CC(C)=C1CCC(C)=CC1=O HKZQJZIFODOLFR-UHFFFAOYSA-N 0.000 claims description 56
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 claims description 49
- SEZLYIWMVRUIKT-VIFPVBQESA-N (+)-isopiperitenone Chemical compound CC(=C)[C@@H]1CCC(C)=CC1=O SEZLYIWMVRUIKT-VIFPVBQESA-N 0.000 claims description 28
- 239000005973 Carvone Substances 0.000 claims description 24
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 239000004480 active ingredient Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- -1 monocyclic monoterpene ketones Chemical class 0.000 claims description 11
- 229930003647 monocyclic monoterpene Natural products 0.000 claims description 2
- 230000003779 hair growth Effects 0.000 description 37
- 230000000694 effects Effects 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 241000196324 Embryophyta Species 0.000 description 17
- ULDHMXUKGWMISQ-SECBINFHSA-N (-)-carvone Chemical compound CC(=C)[C@@H]1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-SECBINFHSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- 239000004615 ingredient Substances 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 239000000341 volatile oil Substances 0.000 description 8
- 108010029908 3-oxo-5-alpha-steroid 4-dehydrogenase Proteins 0.000 description 7
- 102000001779 3-oxo-5-alpha-steroid 4-dehydrogenase Human genes 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 239000003205 fragrance Substances 0.000 description 7
- 230000003450 growing effect Effects 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 201000004384 Alopecia Diseases 0.000 description 6
- 239000005556 hormone Substances 0.000 description 6
- 229940088597 hormone Drugs 0.000 description 6
- 241000207923 Lamiaceae Species 0.000 description 5
- 239000002537 cosmetic Substances 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- 230000003676 hair loss Effects 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 244000184734 Pyrus japonica Species 0.000 description 4
- 208000024963 hair loss Diseases 0.000 description 4
- 230000001766 physiological effect Effects 0.000 description 4
- 239000003755 preservative agent Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 240000000467 Carum carvi Species 0.000 description 3
- 235000005747 Carum carvi Nutrition 0.000 description 3
- 241001183967 Isodon Species 0.000 description 3
- 235000014435 Mentha Nutrition 0.000 description 3
- 241001072983 Mentha Species 0.000 description 3
- 244000246386 Mentha pulegium Species 0.000 description 3
- 235000016257 Mentha pulegium Nutrition 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 231100000957 no side effect Toxicity 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000007586 terpenes Nutrition 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 description 2
- RSJDCIZTVMASEO-UHFFFAOYSA-N 4,8-dimethyl-2-propan-2-ylidene-3,3a,4,5,6,7-hexahydroazulen-1-one Chemical compound CC1CCCC(C)=C2C(=O)C(=C(C)C)CC12 RSJDCIZTVMASEO-UHFFFAOYSA-N 0.000 description 2
- 239000002677 5-alpha reductase inhibitor Substances 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 240000008790 Musa x paradisiaca Species 0.000 description 2
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 2
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
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- 239000003098 androgen Substances 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
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- 235000009508 confectionery Nutrition 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
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- 239000003814 drug Substances 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
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- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 241000411851 herbal medicine Species 0.000 description 2
- 239000003906 humectant Substances 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000457 mentha pulegium l. herb oil Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical group COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 description 2
- 235000016788 valerian Nutrition 0.000 description 2
- CUNWUEBNSZSNRX-RKGWDQTMSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;(z)-octadec-9-enoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O CUNWUEBNSZSNRX-RKGWDQTMSA-N 0.000 description 1
- ODFCWXVQZAQDSO-CMKODMSKSA-N (2s,4as,10ar)-1,1,4a-trimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-2,6-diol Chemical compound CC([C@@H]1CC2)(C)[C@@H](O)CC[C@]1(C)C1=C2C=C(C(C)C)C(O)=C1 ODFCWXVQZAQDSO-CMKODMSKSA-N 0.000 description 1
- FDCJDKXCCYFOCV-UHFFFAOYSA-N 1-hexadecoxyhexadecane Chemical compound CCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCC FDCJDKXCCYFOCV-UHFFFAOYSA-N 0.000 description 1
- CIVCELMLGDGMKZ-UHFFFAOYSA-N 2,4-dichloro-6-methylpyridine-3-carboxylic acid Chemical compound CC1=CC(Cl)=C(C(O)=O)C(Cl)=N1 CIVCELMLGDGMKZ-UHFFFAOYSA-N 0.000 description 1
- MCEJNMNAUVHZAJ-UHFFFAOYSA-N 2-methyl-5-propan-2-ylbicyclo[3.1.0]hex-1-en-3-one Chemical compound CC=1C(CC2(CC=12)C(C)C)=O MCEJNMNAUVHZAJ-UHFFFAOYSA-N 0.000 description 1
- 229940113178 5 Alpha reductase inhibitor Drugs 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 235000003840 Amygdalus nana Nutrition 0.000 description 1
- 244000296825 Amygdalus nana Species 0.000 description 1
- 241000125205 Anethum Species 0.000 description 1
- 240000000662 Anethum graveolens Species 0.000 description 1
- 235000007227 Anethum graveolens Nutrition 0.000 description 1
- 235000017311 Anethum sowa Nutrition 0.000 description 1
- 241000208173 Apiaceae Species 0.000 description 1
- 244000080767 Areca catechu Species 0.000 description 1
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- 206010003694 Atrophy Diseases 0.000 description 1
- 208000012219 Autonomic Nervous System disease Diseases 0.000 description 1
- 241001131796 Botaurus stellaris Species 0.000 description 1
- 240000001548 Camellia japonica Species 0.000 description 1
- 240000007524 Camellia sinensis var. sinensis Species 0.000 description 1
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 1
- 241000132536 Cirsium Species 0.000 description 1
- 208000001840 Dandruff Diseases 0.000 description 1
- 241000212314 Foeniculum Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 235000008418 Hedeoma Nutrition 0.000 description 1
- BYTORXDZJWWIKR-UHFFFAOYSA-N Hinokiol Natural products CC(C)c1cc2CCC3C(C)(CO)C(O)CCC3(C)c2cc1O BYTORXDZJWWIKR-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241001365031 Isodon japonicus Species 0.000 description 1
- 241001365032 Isodon trichocarpus Species 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 244000024873 Mentha crispa Species 0.000 description 1
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- 244000182807 Mentha suaveolens Species 0.000 description 1
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- 241000283977 Oryctolagus Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
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- 244000299790 Rheum rhabarbarum Species 0.000 description 1
- 235000009411 Rheum rhabarbarum Nutrition 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
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- 150000001413 amino acids Chemical class 0.000 description 1
- 206010068168 androgenetic alopecia Diseases 0.000 description 1
- 229940030486 androgens Drugs 0.000 description 1
- 229940011037 anethole Drugs 0.000 description 1
- 239000001264 anethum graveolens Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
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- 239000003963 antioxidant agent Substances 0.000 description 1
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- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 1
- 229960002685 biotin Drugs 0.000 description 1
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- 239000011616 biotin Substances 0.000 description 1
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- 239000003240 coconut oil Substances 0.000 description 1
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- 238000007796 conventional method Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
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- 229960000525 diphenhydramine hydrochloride Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000031774 hair cycle Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 230000005722 itchiness Effects 0.000 description 1
- 239000003410 keratolytic agent Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
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- 229930003658 monoterpene Natural products 0.000 description 1
- 235000002577 monoterpenes Nutrition 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
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- RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
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- 108090000765 processed proteins & peptides Proteins 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
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- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
- A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q7/00—Preparations for affecting hair growth
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Cosmetics (AREA)
Description
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<Industrial Application Field> The present invention relates to a novel hair nourishing and hair growing agent that has no side effects and has remarkable hair nourishing and hair growing effects. <Prior Art> There are many unknown aspects of the medical science related to hair loss and hair growth, and there are many unknown points regarding the physiological mechanisms of action of hair nourishing ingredients used for this purpose. At present, causes of hair loss are considered to include endocrine abnormalities, hair cycle abnormalities, autonomic nervous system disorders, poor blood circulation, nutritional disorders, and others (genetics, aging, etc.). Conventional hair tonic ingredients include hormones such as follicle hormone (Japanese Patent Application Laid-Open No. 60-38313), vitamin E,
B 2 , B 6 , biotin, vitamins such as pantothenic acid, and other amino acids (peptide substances:
Japanese Patent Publication No. 61-7209), herbal medicine extracts such as Oriental japonica extract, anti-inflammatory agents such as diphenhydramine hydrochloride, keratolytic agents such as Photosensor No. 301, hinokiol, lactic acid, etc.
There are humectants such as glycerin, other scalp irritants, disinfectants, and cooling agents. In addition, among the plants of the Lamiaceae family, especially Hikiokoshi (Isodon japonicus),
H ARA ), Isodon
trichocarpus K UDO ), Isodon
There are precedents for the use of extracts (crystalline substances) in water or organic solvents of plants belonging to the genus Isodon, such as Kameda O KUYAMA ), in hair-growth cosmetics. (Special Publication No. 38-8500, Special Publication No. 41-2197) Hair nourishing and hair growth agents are used with the expectation of local efficacy by combining the above-mentioned hair nourishing ingredients alone or in combination. It promotes hair growth, prevents dandruff, itchiness, and inflammation, and prevents thinning hair and hair loss, with the aim of achieving comprehensive hair growth and growth effects. Recently, there has been a tendency to focus on the properties of substances, such as their ability to inhibit testosterone-5α-reductase and to activate cells and skin, and to use these substances as hair nourishing agents. According to one theory, the reason why the above-mentioned testosterone-5α-reductase inhibitor is used as a hair growth agent is to treat male-pattern baldness, coarse hair, acne vulgaris,
Physiological symptoms such as seborrhea are thought to be caused by increased stimulation of androgens caused by excessive accumulation of androgen (5α-dihydrotestosterone) in the vicarious ejaculatory system. In other words, this male hormone (5α-dihydrotestosterone)
is produced by reducing testosterone by the action of testosterone-5α-reductase. It is believed that the male hormone is produced and accumulated in various organs such as hair roots and sebaceous glands under the action of testosterone-5α-reductase, resulting in atrophy of hair roots and inducing hair loss and baldness. For example, examples of substances that have testosterone-5α-reductase inhibiting properties include bicyclic fused ring compounds such as bicyclic terpenes (described later), carboxylic acids such as higher fatty acids (Japanese Patent Application Laid-Open No. 59-152308, No. 59-172410, JP-A No. 59-172411, JP-A No. 61
-5007, JP-A-61-5014, JP-A-61-7205, etc.), aromatic alcohols, aromatic carboxylic acids (JP-A-57-53401, etc.), and other natural extracts [e.g., testosterone- Examples of 5α-reductase inhibitors that exist in the natural world include Acacia japonica, Ukiyo, Kengoshi, Gobaishi, Shiyakuyaku, Syazenshi, Senso, Rhubarb, Chiyoji,
Solvent extracts of herbal medicines of betel nut, rosin, katsuko thistle, gennosyouko, kagosou, saiko, inchin, eijitsu, yokuinin, soybean, bittern, japonica, japonica, valerian and valerian (Japanese Patent Application Laid-open No. 146829/1982)], and compounds (special (Japanese Patent Publication No. 59-59606, Japanese Patent Application Publication No. 59-59607, etc.). Examples of bicyclic fused ring compounds (examples of bicyclic terpene derivatives) having enzyme inhibiting properties include:
5,6-dimethyl-8-isopropenyl-bicyclo[4,4,0]decen-1-one-3 (JP-A-Sho
59-53417), 4,8-dimethyl-2-isopropylidene-1,2,3a, 4,5,6-hexahydro-azulenone (6) or 3,6,8,-tetramethyl-1,2, 4,7,8,8a-hexahydro-azulenone (JP-A No. 59-53418, JP-A No. 59-59)
-55813), 4-methyl-1-isopropyl-bicyclo[3,1,0]hexen-3-one 2 and 4,6,6-trimethyl-bicyclo[3,1,
1] Heptene-3-one-2 (JP-A-59-53419
No. 59-55812). Thus, the reason why there is a wide range and variety of substances that are said to have testosterone-5α-reductase inhibitory properties and/or hair-growth/hair-growth effects is due to the enzymatic activity of the testosterone-5α-reductase and the hair-growth/hair-growth effects. The specificity of physiological activity related to hair growth etc. is thought to be due to the correlation with the molecular structure of the chemical substance. Even if the chemically similar compounds are the same or homologous, the presence or absence and potency of the enzymatic activity and physiological activity vary greatly depending on the isomer (positional isomer, structural isomer, geometric isomer). Therefore, it is extremely difficult to predict the presence or absence and magnitude of the properties related to the enzyme activity and physiological activity. In particular, the physiological activities of various substances, such as their hair-nurturing and hair-growth properties, differ significantly in their specificity, and it is currently impossible to distinguish between them unless the hair-nurturing and hair-growth effects of each substance are directly measured and searched one by one. Thus, there are a wide variety of substances that have hair nourishing and hair growing effects, and these conventional hair nourishing and hair growing agents (particularly hormones) may have side effects.
Furthermore, the hair nourishing and hair growing effects are not necessarily sufficient, and the development of new hair nourishing and hair growing agents is desired. By the way, it is preferable that the active ingredients having various effects (for example, hair nourishing/hair growing effects) are originally specified as substances. Various effects of extracts derived from natural products such as crude drugs or medicinal plants (hair nourishing/growth effects, etc.)
When determining the presence or absence of hair growth, it is necessary to determine which active ingredients in the extract produce the desired effect (hair growth/growth effect, etc.), and whether the effect (hair growth/hair growth effect, etc.) is achieved only through the synergistic action of two or more active ingredients. It must be said that it is extremely important to elucidate whether or not the product has the desired effect (e.g., effectiveness, etc.). In particular, it is a well-known fact that the active ingredients contained in crude drugs and medicinal plants are completely different depending on the "family", "genus", "species", and "subspecies" to which the raw material plants belong. Temporarily, the above âdepartmentâ,
Even if plants are the same in terms of "genus", "species", etc. (they are simply variants of each other), there may be differences in the production areas of the plants, or differences between cultivated species and wild species. It is also a well-known fact that the types and contents of active ingredients contained in plants are completely different. Therefore, from this point of view, there has been a strong desire to identify substances that have hair-nurturing and hair-growth effects among compounds that exist in the natural world. <Problems to be Solved by the Invention> This invention is intended to meet the above requirements, and as a result of searching and testing the hair-nurturing and hair-growth effects of terpenes and their derivatives, it was discovered that monocyclic monoterpene ketones This product was developed based on the discovery that piperitenone, isopiperitenone, and carvone have excellent hair-nourishing and hair-growth effects, thereby providing a hair-nourishing and hair-growth agent that is safe and has no side effects and has remarkable hair-nourishing and hair-growth effects. The purpose is to <Means for Solving the Problems> In order to achieve the above object, the present invention uses piperitenone (IUPAC name: 1,4(8)-paramentadiene-3) as an active ingredient of a hair growth agent. -on) (hereinafter referred to as "piperitenone"), isopiperitenone (isopiperitenone,
IUPAC name: 1,8-paramentadien-3-one) (hereinafter referred to as "isopiperitenone"), carvone (IUPAC name: 5,8-paramentadien-2-one) (hereinafter referred to as "carvone")
At least one of the three types of monoterpene ketones is contained as an active ingredient. By the way, in the natural world, for example, the piperitenone is found in Mentha pulegium L.var. of the Lamiaceae family.
eriantha), and a variety of the pennyroyal hatsuka (Mentha
present in the essential oil of L. var. villona Benth. In nature, isopiperitenone is present in the essential oils of Mentha pulegium L. var. eriantha and Mentha rotundifolia varieties of the Lamiaceae family. Piperitenone and isopiperitenone are both contained in the essential oil ("pennyroyal oil") of the above-mentioned pennyroyal oil, and are isolated and purified by a known method described below. Further, the carvone has optical isomers of d-form and l-form. And the d-isomer carvone is
In nature, Carum is a member of the Umbelliferae family.
It is present in the essential oil of the seeds of Anethum graveolens (carvi L.) and anethum oil. on the other hand,
L-carvone can be found in various spearmints (Menthaspicate), for example, Mentha in the Lamiaceae family.
Present in the essential oil of viridis L. (spearmint oil). The piperitenone, isopiperitenone, and carvone are obtained by adding a sodium sulfite (Na 2 SO 3 ) solution to the various essential oils and shaking them on a hot bath to add and dissolve them and separate the oil layer and the aqueous layer. It can be prepared by applying a caustic soda aqueous solution to the part and regenerating and separating it. In addition, the identity of each compound and its purity can be confirmed by measuring the physical constants of the prepared piperitenone, isopiperitenone, and carvone. Of course, any of the piperitenone, isopiperitenone, and carvone can be chemically synthesized by known methods, and the chemically synthesized piperitenone, isopiperitenone, and carvone can be used as the hair growth agent according to the present invention. Needless to say. Moreover, as mentioned above, the raw material plants for the piperitenone and isopiperitenone, which are the active ingredients of the hair nourishing/growth agent of this invention, belong to the genus Mentha of the Labiatae family, as mentioned above. On the other hand, the raw material plants (Hikiokoshi, Black Banana Hikiokoshi, and Camellia Hikiokoshi) according to the above documents (Japanese Patent Publication Nos. 38-8500 and 41-2197) are plants belonging to the ``genus Isodon'' of the ``Lamiaceae'' family. The "genus" to which the raw material plants of both the raw material plants according to the above and the raw material plants described in the above-mentioned literature belong are completely different. On the other hand, there is no literature that states that plants belonging to the ``Isodon genus'' (Hikiokoshi, Black Banana kiokoshi, Camellia chinensis) contain piperitenone and isopiperitenone. Furthermore, the raw material plant for the carvone used as the active ingredient of the hair nourishing/hair growth agent according to the present invention (Prunus japonicus) belongs to the ``genus Carum'' of the ``Umbelliferae''; â146829)
One of the raw material plants for this, ``Foeniculum'', belongs to the ``genus Foeniculum'' in the ``Umbelliferae'' family, and the genus to which ``Foeniculum'' belongs is completely different from the genus to which ``Foeniculum'' belongs. In addition, while the main component of the essential oil (caraway oil) is "carvone," the main component of the essential oil (sweet) of the fenugreek is anethole, etc. It is clear from the literature that carvone is not contained in oil (sweet oil). ïŒAnalysis of
Essentia Oils by Gas Chromatography and
Mass Spectrometry ~ Gas chromatography
Analysis of natural fragrances using mass spectra ~p83~
85, p92-95, Yoshiro Shoda, October 1, 1975, Co., Ltd.
(Published by Hirokawa Shoten) Piperitenone, isopiperitenone, and carvone are recognized to exhibit hair nourishing and hair growth effects at a single concentration of each of them at a concentration of 0.001% or more (0.001 to 30%). This piperitenon,
The test method for the hair-nourishing and hair-growth effects of isopiperitenone and carvone is to shave the hair from the back of a domestic rabbit (10 weeks old), and apply a diluted solution of each compound at a predetermined concentration (solvent example: 99.5%) to the shaved area. It can be detected by repeatedly applying ethanol) over a certain period of time and measuring the elongated hair. In addition, piperitenone, isopiperitenone, and carvone are both nontoxic and irritating to the skin (by the Patchist method, etc.), and have no side effects such as those of hormones. The hair growth agent of the present invention is prepared by containing at least one selected from piperitenone, isopiperitenone, and carvone as an active ingredient. The amount of piperitenone, isopiperitenone and/or carvone in the hair growth agent of the present invention is not particularly limited as it can be varied depending on the form of use. In principle, it is sufficient that it exists in an effective amount, but in general, the content (single amount or combined total amount) is 0.001 to 30% by weight based on the total amount of the hair growth product as a final product. %,
Preferably 0.01 to 15% by weight (more preferably 0.1 to 10% by weight) can exhibit hair nourishing and hair growth effects. In addition, the hair growth agent of the present invention is prepared by blending at least one kind selected from the group of compounds consisting of piperitenone, isopiperitenone, and carvone into various known (cosmetic) bases by a conventional method. It can be applied to creams, milky lotions, hair liquids, hair lotions, hair rinses, hair tricks, pomades, shampoos and other cosmetics. Further, the cosmetic can be applied in various forms such as a solution, sol, gel, emulsion, ointment, oil, wax, and spray (aerosol). Furthermore, the hair growth/growth agent of this invention can be applied to other hair growth/growth agents.
It goes without saying that it can be used in combination with a hair restorer, and an excellent synergistic effect can be achieved. Furthermore, the hair growth agent of the present invention is stable against various surfactants, solvents, pigments, fragrances, preservatives, antioxidants, humectants, and other additives and various cosmetic base materials. Therefore, it can be used in combination with these various additives. <Example> Next, a description will be given based on a specific example. (1) About piperitenon. The physical constants of piperitenone used in this invention are as follows. Boiling point = 106-107°C/10mmHg, d 20 4 = 0.977, n 20 D = 1.525 (2) Regarding isopiperitenone. The physical constants of isopiperitenone used in this invention are as follows. Boiling point = 83-86°C/2 mmHg, d 25 25 = 0.964, n 20 D = 1.5054 (3) Regarding l-carvone. The physical constants of l-carvone used in this invention are as follows. Boiling point = 230-231°C, d 15 15 = 0.9652, n 20 D = 1.4998, [α] 20 D â62.46° (4) Piperitenone, isopiperitenone and l-
Test method for carvone's hair growth and hair growth effects. The hair on the back of a male rabbit (10 weeks old) was shaved.
0.2% each of piperitenone, isopiperitenone, and l-carvone once a day in this area.
1 ethanol solution (solvent: 99.5% ethanol)
Apply 1 ml each and measure the length of the elongated hair on the 6th day. As a control, 1 ml of 99.5% ethanol, which does not contain any of the above-mentioned compounds, is similarly applied to a comparatively close control position on the back once a day, and the length of the elongated hair on the 6th day is similarly measured. . The test results are shown in Table 1. In addition, in the table, A = average value ± standard deviation of the hair on the control side (mm) AⲠ= average value ± standard deviation (mm) of the hair on the test side B = (average value of the hair on the test example) - (average value of the hair on the control side hair average value) (mm) *=means the average of each average value of the control side and the test side, respectively. All units are mm.
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è¶ããå¹æãå¥ãããA significant difference is observed in [Table].
(3) Prescription example of shampoo [Ingredients] [Content/weight%] â Sodium polyoxyethylene alkyl ether sulfate (EO 2 mol) ...15 â Coconut oil fatty acid diethanolamide ...5 â Glycerin ...3 â Piperitenone, l -Carvone or/and piperitenone...0.2 âFragrances and preservatives...Appropriate amount âIon exchange water...The total is 100. (4) Hair cream formulation example [Ingredients] [Content/weight%] âLiquid paraffin...20 âSolid paraffin...3 âPolyoxyethylene cetyl ether (EO
15 moles)...2 âSorbitan sesquioleate...1 âPiperitenone, l-carvone or/and isopiperitenone...0.5 âPotassium hydroxide...0.1 âGlycerin...3 âFragrances and preservatives...Appropriate amount âIon exchange Water: Set the total to 100. (5) Example of hair lotion formulation [Ingredients] [Content/Weight%] â95% ethanol...20 âGlycerin...3 âPolyoxyethylene sorbitan monolaurate (EO 20 mol)...1 âPiperitenone, l- Carvone or/and isopiperitenone...0.5 âFragrances and preservatives...Appropriate amount âIon-exchanged water...The total is 100. (6) Hair Tonik formulation example [Ingredients] [Content/Weight%] â95% ethanol...60 âPolyoxyethylene hydrogenated castor oil (EO 60
Mol)...0.5 âGlycerin...3 âPiperitenone, l-carvone or/and isopiperitenone...0.1 âFragrances and pigments...appropriate amount âIon-exchanged water...The total is 100. (7) Prescription example of pomade [Ingredients] [Content/weight%] âJapanese blackberry...13 âCastor oil...85.8 âPiperitenone, l-carvone or/and isopiperitenone...1 âFragrance...0.2 <Action of the invention Effects> The hair nourishing agent of the present invention has excellent hair nourishing and hair growing effects that are safe and have excellent hair nourishing and hair growing effects due to the excellent hair nourishing and hair growing effects of piperitenone, isopiperitenone, and carvone. be effective.
Claims (1)
ã³ïŒpiperitenoneïŒãã€ãœãããªããã³ïŒisoâ
piperitenoneïŒããã³ã«ã«ãã³ïŒcarvoneïŒãã
ãªãååç©çŸ€ããéžæãããå°ãªããšãïŒçš®ä»¥äž
ã®ååç©ãæå¹æåãšããŠå«æããé€æ¯ã»è²æ¯
å€ã1 Among monocyclic monoterpene ketones, piperitenone and isopiperitenone (iso-
A hair nourishing agent containing as an active ingredient at least one compound selected from the compound group consisting of piperitenone and carvone.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11890086A JPS62273909A (en) | 1986-05-23 | 1986-05-23 | Agent for nourishing and growing hair |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11890086A JPS62273909A (en) | 1986-05-23 | 1986-05-23 | Agent for nourishing and growing hair |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS62273909A JPS62273909A (en) | 1987-11-28 |
JPH0238565B2 true JPH0238565B2 (en) | 1990-08-31 |
Family
ID=14747948
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP11890086A Granted JPS62273909A (en) | 1986-05-23 | 1986-05-23 | Agent for nourishing and growing hair |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS62273909A (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2671721B1 (en) * | 1991-01-17 | 1993-08-27 | Morier Jean Pierre | PRODUCT FOR THE NATURAL REPIGMENTATION OF HAIR AND HAIR AND THE IMPROVEMENT OF CALVITIS. |
JP5946232B2 (en) * | 2008-12-10 | 2016-07-05 | ã¢ã¢ã³ã¹ã¡ãã£ãã¯ã¹æ ªåŒäŒç€Ÿ | Cyclooxygenase-2 inhibitor and cosmetics |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS60146829A (en) * | 1984-01-05 | 1985-08-02 | Rooto Seiyaku Kk | Testosterone 5alpha-reductase inhibitor |
-
1986
- 1986-05-23 JP JP11890086A patent/JPS62273909A/en active Granted
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS60146829A (en) * | 1984-01-05 | 1985-08-02 | Rooto Seiyaku Kk | Testosterone 5alpha-reductase inhibitor |
Also Published As
Publication number | Publication date |
---|---|
JPS62273909A (en) | 1987-11-28 |
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