JP2012001520A5 - - Google Patents

Info

Publication number

JP2012001520A5

JP2012001520A5 JP2010140429A JP2010140429A JP2012001520A5 JP 2012001520 A5 JP2012001520 A5 JP 2012001520A5 JP 2010140429 A JP2010140429 A JP 2010140429A JP 2010140429 A JP2010140429 A JP 2010140429A JP 2012001520 A5 JP2012001520 A5 JP 2012001520A5

Authority

JP

Japan

Prior art keywords

group

compound

general formula

methyl

composition according

Prior art date

2010-06-21

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.)

Granted

Links

• Espacenet
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• -1 benzyl ester Chemical class 0.000 claims description 432
• 150000001875 compounds Chemical class 0.000 claims description 123
• 239000000203 mixture Substances 0.000 claims description 91
• 125000004432 carbon atom Chemical group C* 0.000 claims description 69
• 239000000419 plant extract Substances 0.000 claims description 65
• 150000003839 salts Chemical class 0.000 claims description 65
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 64
• 239000003795 chemical substances by application Substances 0.000 claims description 50
• 230000001153 anti-wrinkle effect Effects 0.000 claims description 46
• 125000005842 heteroatom Chemical group 0.000 claims description 46
• 229910052799 carbon Inorganic materials 0.000 claims description 42
• FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 38
• 210000003491 skin Anatomy 0.000 claims description 38
• 125000003118 aryl group Chemical group 0.000 claims description 37
• 239000002253 acid Substances 0.000 claims description 35
• 230000009471 action Effects 0.000 claims description 31
• 229910052757 nitrogen Inorganic materials 0.000 claims description 30
• 125000001931 aliphatic group Chemical group 0.000 claims description 29
• 239000002537 cosmetic Substances 0.000 claims description 27
• 125000004122 cyclic group Chemical group 0.000 claims description 25
• FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 claims description 24
• 230000037373 wrinkle formation Effects 0.000 claims description 24
• 229960001727 tretinoin Drugs 0.000 claims description 22
• 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 20
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 19
• 229930002330 retinoic acid Natural products 0.000 claims description 18
• 102000008186 Collagen Human genes 0.000 claims description 17
• 108010035532 Collagen Proteins 0.000 claims description 17
• SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 claims description 17
• 229920001436 collagen Polymers 0.000 claims description 17
• 239000000835 fiber Substances 0.000 claims description 17
• 238000002360 preparation method Methods 0.000 claims description 17
• 239000011607 retinol Substances 0.000 claims description 17
• 229960003471 retinol Drugs 0.000 claims description 17
• 235000020944 retinol Nutrition 0.000 claims description 17
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
• IUCHRJJXIZKLTA-UHFFFAOYSA-N 2-trityloxyethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCCO)C1=CC=CC=C1 IUCHRJJXIZKLTA-UHFFFAOYSA-N 0.000 claims description 15
• GHSBJDZSBNDAGL-UHFFFAOYSA-N 2-(tritylamino)ethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(NCCO)C1=CC=CC=C1 GHSBJDZSBNDAGL-UHFFFAOYSA-N 0.000 claims description 13
• 230000002500 effect on skin Effects 0.000 claims description 12
• 230000006872 improvement Effects 0.000 claims description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
• 229910019142 PO4 Inorganic materials 0.000 claims description 10
• 229940126214 compound 3 Drugs 0.000 claims description 10
• 229940125898 compound 5 Drugs 0.000 claims description 10
• 239000010452 phosphate Substances 0.000 claims description 10
• GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims description 9
• TXLIAXQCAUHQEE-UHFFFAOYSA-N 2-trityloxyethanamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCCN)C1=CC=CC=C1 TXLIAXQCAUHQEE-UHFFFAOYSA-N 0.000 claims description 9
• 240000004385 Centaurea cyanus Species 0.000 claims description 9
• 241000207923 Lamiaceae Species 0.000 claims description 9
• 229940125904 compound 1 Drugs 0.000 claims description 9
• 229940125797 compound 12 Drugs 0.000 claims description 9
• 235000008995 european elder Nutrition 0.000 claims description 9
• 125000005039 triarylmethyl group Chemical group 0.000 claims description 9
• WCGUUGGRBIKTOS-GPOJBZKASA-N (3beta)-3-hydroxyurs-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C WCGUUGGRBIKTOS-GPOJBZKASA-N 0.000 claims description 8
• 241000219926 Myrtaceae Species 0.000 claims description 8
• VYGQUTWHTHXGQB-FFHKNEKCSA-N Retinol Palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C VYGQUTWHTHXGQB-FFHKNEKCSA-N 0.000 claims description 8
• 244000178231 Rosmarinus officinalis Species 0.000 claims description 8
• 241000208829 Sambucus Species 0.000 claims description 8
• 235000018735 Sambucus canadensis Nutrition 0.000 claims description 8
• 235000007123 blue elder Nutrition 0.000 claims description 8
• 229940125773 compound 10 Drugs 0.000 claims description 8
• 229940125782 compound 2 Drugs 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 8
• 235000007124 elderberry Nutrition 0.000 claims description 8
• ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims description 8
• 229940096998 ursolic acid Drugs 0.000 claims description 8
• PLSAJKYPRJGMHO-UHFFFAOYSA-N ursolic acid Natural products CC1CCC2(CCC3(C)C(C=CC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1C)C(=O)O PLSAJKYPRJGMHO-UHFFFAOYSA-N 0.000 claims description 8
• 229940045997 vitamin a Drugs 0.000 claims description 8
• QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 claims description 7
• MAZMHPQDNYKCOI-UHFFFAOYSA-N 1-benzhydrylimidazole Chemical compound C1=NC=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 MAZMHPQDNYKCOI-UHFFFAOYSA-N 0.000 claims description 7
• NPZDCTUDQYGYQD-UHFFFAOYSA-N 1-tritylimidazole Chemical compound C1=NC=CN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 NPZDCTUDQYGYQD-UHFFFAOYSA-N 0.000 claims description 7
• DAXRGSDCXVUHEW-UHFFFAOYSA-N 2-(benzhydrylamino)ethanol Chemical compound C=1C=CC=CC=1C(NCCO)C1=CC=CC=C1 DAXRGSDCXVUHEW-UHFFFAOYSA-N 0.000 claims description 7
• JSYRPEKHRQJXQK-UHFFFAOYSA-N 2-benzhydryloxyethanol Chemical compound C=1C=CC=CC=1C(OCCO)C1=CC=CC=C1 JSYRPEKHRQJXQK-UHFFFAOYSA-N 0.000 claims description 7
• FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 claims description 7
• 210000004207 dermis Anatomy 0.000 claims description 7
• 239000000284 extract Substances 0.000 claims description 7
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 7
• 230000002265 prevention Effects 0.000 claims description 7
• 235000019155 vitamin A Nutrition 0.000 claims description 7
• 239000011719 vitamin A Substances 0.000 claims description 7
• LLOQMFDCQPKSFB-UHFFFAOYSA-N 1-benzhydrylpiperidine Chemical compound C1CCCCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 LLOQMFDCQPKSFB-UHFFFAOYSA-N 0.000 claims description 6
• 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000001072 heteroaryl group Chemical group 0.000 claims description 6
• 230000002207 retinal effect Effects 0.000 claims description 6
• DJMXWKUBTGMKCG-UHFFFAOYSA-N 1-benzhydrylpyrrolidine Chemical compound C1CCCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 DJMXWKUBTGMKCG-UHFFFAOYSA-N 0.000 claims description 5
• ZDTBBCYZMFEIHU-UHFFFAOYSA-N 1-tritylpiperidine Chemical compound C1CCCCN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ZDTBBCYZMFEIHU-UHFFFAOYSA-N 0.000 claims description 5
• DVFDHIZVAQOEMX-UHFFFAOYSA-N 1-tritylpyrrolidine Chemical compound C1CCCN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 DVFDHIZVAQOEMX-UHFFFAOYSA-N 0.000 claims description 5
• 150000004347 all-trans-retinol derivatives Chemical class 0.000 claims description 5
• 229940079593 drug Drugs 0.000 claims description 5
• SHGAZHPCJJPHSC-NUEINMDLSA-N Isotretinoin Chemical compound OC(=O)C=C(C)/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-NUEINMDLSA-N 0.000 claims description 4
• GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 4
• 239000003995 emulsifying agent Substances 0.000 claims description 4
• 229960005280 isotretinoin Drugs 0.000 claims description 4
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
• 229960000342 retinol acetate Drugs 0.000 claims description 4
• QGNJRVVDBSJHIZ-QHLGVNSISA-N retinyl acetate Chemical compound CC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C QGNJRVVDBSJHIZ-QHLGVNSISA-N 0.000 claims description 4
• 235000019173 retinyl acetate Nutrition 0.000 claims description 4
• 239000011770 retinyl acetate Substances 0.000 claims description 4
• 229940108325 retinyl palmitate Drugs 0.000 claims description 4
• 235000019172 retinyl palmitate Nutrition 0.000 claims description 4
• 239000011769 retinyl palmitate Substances 0.000 claims description 4
• 241000894007 species Species 0.000 claims description 4
• GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims description 4
• QGJZLNKBHJESQX-UHFFFAOYSA-N 3-Epi-Betulin-Saeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C(=C)C)C5C4CCC3C21C QGJZLNKBHJESQX-UHFFFAOYSA-N 0.000 claims description 3
• CLOUCVRNYSHRCF-UHFFFAOYSA-N 3beta-Hydroxy-20(29)-Lupen-3,27-oic acid Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C(O)=O)CCC5(C)CCC(C(=C)C)C5C4CCC3C21C CLOUCVRNYSHRCF-UHFFFAOYSA-N 0.000 claims description 3
• DIZWSDNSTNAYHK-XGWVBXMLSA-N Betulinic acid Natural products CC(=C)[C@@H]1C[C@H]([C@H]2CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C(=O)O DIZWSDNSTNAYHK-XGWVBXMLSA-N 0.000 claims description 3
• 229930002945 all-trans-retinaldehyde Natural products 0.000 claims description 3
• QGJZLNKBHJESQX-FZFNOLFKSA-N betulinic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C QGJZLNKBHJESQX-FZFNOLFKSA-N 0.000 claims description 3
• PZXJOHSZQAEJFE-UHFFFAOYSA-N dihydrobetulinic acid Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C(C)C)C5C4CCC3C21C PZXJOHSZQAEJFE-UHFFFAOYSA-N 0.000 claims description 3
• MQYXUWHLBZFQQO-UHFFFAOYSA-N nepehinol Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C)CCC(C(=C)C)C5C4CCC3C21C MQYXUWHLBZFQQO-UHFFFAOYSA-N 0.000 claims description 3
• NCYCYZXNIZJOKI-OVSJKPMPSA-N retinal group Chemical group C\C(=C/C=O)\C=C\C=C(\C=C\C1=C(CCCC1(C)C)C)/C NCYCYZXNIZJOKI-OVSJKPMPSA-N 0.000 claims description 3
• NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 claims description 3
• 229960001295 tocopherol Drugs 0.000 claims description 2
• 229930003799 tocopherol Natural products 0.000 claims description 2
• 239000011732 tocopherol Substances 0.000 claims description 2
• 235000010384 tocopherol Nutrition 0.000 claims description 2
• 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
• 241000205585 Aquilegia canadensis Species 0.000 claims 1
• 238000003763 carbonization Methods 0.000 claims 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 74
• 239000000126 substance Substances 0.000 description 39
• 230000000694 effects Effects 0.000 description 35
• 238000004519 manufacturing process Methods 0.000 description 31
• 206010040954 Skin wrinkling Diseases 0.000 description 23
• 230000037303 wrinkles Effects 0.000 description 21
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 20
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
• 125000003944 tolyl group Chemical group 0.000 description 17
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 15
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
• GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 13
• 125000001624 naphthyl group Chemical group 0.000 description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• 238000000034 method Methods 0.000 description 12
• 229920002125 Sokalan® Polymers 0.000 description 11
• 125000003277 amino group Chemical group 0.000 description 11
• 235000014113 dietary fatty acids Nutrition 0.000 description 11
• 239000000194 fatty acid Substances 0.000 description 11
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• 125000001207 fluorophenyl group Chemical group 0.000 description 11
• 235000017309 Hypericum perforatum Nutrition 0.000 description 10
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
• 125000004464 hydroxyphenyl group Chemical group 0.000 description 10
• 230000002829 reductive effect Effects 0.000 description 10
• 241000196324 Embryophyta Species 0.000 description 9
• 125000006267 biphenyl group Chemical group 0.000 description 9
• 229920001296 polysiloxane Polymers 0.000 description 9
• 239000000047 product Substances 0.000 description 9
• 239000002904 solvent Substances 0.000 description 9
• JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 9
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
• 241000546188 Hypericum Species 0.000 description 8
• 150000007513 acids Chemical class 0.000 description 8
• 235000004347 Perilla Nutrition 0.000 description 7
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• 239000006096 absorbing agent Substances 0.000 description 7
• 239000004359 castor oil Substances 0.000 description 7
• 125000000068 chlorophenyl group Chemical group 0.000 description 7
• 241000228212 Aspergillus Species 0.000 description 6
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
• 125000003545 alkoxy group Chemical group 0.000 description 6
• 125000004799 bromophenyl group Chemical group 0.000 description 6
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• 238000006243 chemical reaction Methods 0.000 description 6
• 230000000052 comparative effect Effects 0.000 description 6
• 125000004212 difluorophenyl group Chemical group 0.000 description 6
• 238000009472 formulation Methods 0.000 description 6
• 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 6
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 6
• 239000012044 organic layer Substances 0.000 description 6
• 125000001424 substituent group Chemical group 0.000 description 6
• NFJFUDGBWGXTHS-UHFFFAOYSA-N 2-benzhydryloxyethanamine Chemical compound C=1C=CC=CC=1C(OCCN)C1=CC=CC=C1 NFJFUDGBWGXTHS-UHFFFAOYSA-N 0.000 description 5
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• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
• ZDVDCDLBOLSVGM-UHFFFAOYSA-N [chloro(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(Cl)C1=CC=CC=C1 ZDVDCDLBOLSVGM-UHFFFAOYSA-N 0.000 description 5
• 125000005002 aryl methyl group Chemical group 0.000 description 5
• 235000011187 glycerol Nutrition 0.000 description 5
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• 235000013402 health food Nutrition 0.000 description 5
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
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• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
• 230000003449 preventive effect Effects 0.000 description 5
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• 239000000243 solution Substances 0.000 description 5
• 238000012360 testing method Methods 0.000 description 5
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• 239000004166 Lanolin Substances 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
• 150000001298 alcohols Chemical class 0.000 description 4
• 239000007864 aqueous solution Substances 0.000 description 4
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• 239000000287 crude extract Substances 0.000 description 4
• POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
• 150000002170 ethers Chemical class 0.000 description 4
• 239000000706 filtrate Substances 0.000 description 4
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