JPS61243099A - トリテルペンアルコール有機酸エステル - Google Patents
トリテルペンアルコール有機酸エステルInfo
- Publication number
- JPS61243099A JPS61243099A JP60085254A JP8525485A JPS61243099A JP S61243099 A JPS61243099 A JP S61243099A JP 60085254 A JP60085254 A JP 60085254A JP 8525485 A JP8525485 A JP 8525485A JP S61243099 A JPS61243099 A JP S61243099A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- group
- carbon atoms
- methoxy
- hydroxy
- 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.)
- Granted
Links
- -1 Triterpene alcohol organic acid ester Chemical class 0.000 title claims abstract description 145
- 238000004519 manufacturing process Methods 0.000 title claims description 39
- 239000002253 acid Substances 0.000 claims abstract description 73
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 48
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 43
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 28
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims abstract description 22
- 150000001555 benzenes Chemical class 0.000 claims abstract description 22
- 235000013985 cinnamic acid Nutrition 0.000 claims abstract description 21
- 229930016911 cinnamic acid Natural products 0.000 claims abstract description 21
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims abstract description 21
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 21
- 125000003277 amino group Chemical group 0.000 claims abstract description 18
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 17
- 150000003648 triterpenes Chemical class 0.000 claims abstract description 17
- 239000005711 Benzoic acid Substances 0.000 claims abstract description 15
- 235000010233 benzoic acid Nutrition 0.000 claims abstract description 15
- 125000001424 substituent group Chemical group 0.000 claims abstract description 15
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims abstract description 14
- RRTBTJPVUGMUNR-UHFFFAOYSA-N Cycloartanol Natural products C12CCC(C(C(O)CC3)(C)C)C3C2(CC)CCC2(C)C1(C)CCC2C(C)CCCC(C)C RRTBTJPVUGMUNR-UHFFFAOYSA-N 0.000 claims description 89
- YNBJLDSWFGUFRT-UHFFFAOYSA-N cycloartenol Natural products CC(CCC=C(C)C)C1CCC2(C)C1(C)CCC34CC35CCC(O)C(C)(C)C5CCC24C YNBJLDSWFGUFRT-UHFFFAOYSA-N 0.000 claims description 89
- XZEUYTKSAYNYPK-UHFFFAOYSA-N 3beta-29-Norcycloart-24-en-3-ol Natural products C1CC2(C)C(C(CCC=C(C)C)C)CCC2(C)C2CCC3C(C)C(O)CCC33C21C3 XZEUYTKSAYNYPK-UHFFFAOYSA-N 0.000 claims description 81
- HVXLSFNCWWWDPA-UHFFFAOYSA-N Isocycloartenol Natural products C1CC(O)C(C)(C)C2C31CC13CCC3(C)C(C(CCCC(C)=C)C)CCC3(C)C1CC2 HVXLSFNCWWWDPA-UHFFFAOYSA-N 0.000 claims description 81
- HXQRIQXPGMPSRW-UHZRDUGNSA-N Pollinastanol Natural products O[C@@H]1C[C@H]2[C@@]3([C@]4([C@H]([C@@]5(C)[C@@](C)([C@H]([C@H](CCCC(C)C)C)CC5)CC4)CC2)C3)CC1 HXQRIQXPGMPSRW-UHZRDUGNSA-N 0.000 claims description 81
- ONQRKEUAIJMULO-YBXTVTTCSA-N cycloartenol Chemical compound CC(C)([C@@H](O)CC1)[C@H]2[C@@]31C[C@@]13CC[C@]3(C)[C@@H]([C@@H](CCC=C(C)C)C)CC[C@@]3(C)[C@@H]1CC2 ONQRKEUAIJMULO-YBXTVTTCSA-N 0.000 claims description 81
- FODTZLFLDFKIQH-UHFFFAOYSA-N cycloartenol trans-ferulate Natural products C1=C(O)C(OC)=CC(C=CC(=O)OC2C(C3CCC4C5(C)CCC(C5(C)CCC54CC53CC2)C(C)CCC=C(C)C)(C)C)=C1 FODTZLFLDFKIQH-UHFFFAOYSA-N 0.000 claims description 81
- 125000004432 carbon atom Chemical group C* 0.000 claims description 74
- CIBNJPPYSPYHDB-UHFFFAOYSA-N Cyclobranol Natural products C1CC(O)C(C)(C)C2C31CC13CCC3(C)C(C(CCC(C)=C(C)C)C)CCC3(C)C1CC2 CIBNJPPYSPYHDB-UHFFFAOYSA-N 0.000 claims description 66
- CIBNJPPYSPYHDB-UEBIAWITSA-N cyclobranol Chemical compound CC(C)([C@@H](O)CC1)[C@H]2[C@@]31C[C@@]13CC[C@]3(C)[C@@H]([C@@H](CCC(C)=C(C)C)C)CC[C@@]3(C)[C@@H]1CC2 CIBNJPPYSPYHDB-UEBIAWITSA-N 0.000 claims description 65
- 150000002148 esters Chemical class 0.000 claims description 61
- KKSCKZFKHNHGEO-UHFFFAOYSA-N 24-methylenecycloartanol Natural products CC(CCC(=C)C(C)(C)O)C1CCC2C3CCC4C(C)(C)C(O)CCC45CC35CCC12C KKSCKZFKHNHGEO-UHFFFAOYSA-N 0.000 claims description 36
- BJZVHTWNCLKZGN-SPQNPFHSSA-N 24-methylidenecycloartanol Natural products CC(C)C(=C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C(C)(C)[C@@H](O)CC[C@@]45C[C@@]35CC[C@]12C BJZVHTWNCLKZGN-SPQNPFHSSA-N 0.000 claims description 35
- BDHQMRXFDYJGII-UEBIAWITSA-N 24-methylenecycloartanol Chemical compound CC(C)([C@@H](O)CC1)[C@H]2[C@@]31C[C@@]13CC[C@]3(C)[C@@H]([C@H](C)CCC(=C)C(C)C)CC[C@@]3(C)[C@@H]1CC2 BDHQMRXFDYJGII-UEBIAWITSA-N 0.000 claims description 33
- 150000007524 organic acids Chemical class 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000005157 alkyl carboxy group Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 claims description 11
- 150000004820 halides Chemical class 0.000 claims description 11
- CAHGCLMLTWQZNJ-UHFFFAOYSA-N Nerifoliol Natural products CC12CCC(O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C CAHGCLMLTWQZNJ-UHFFFAOYSA-N 0.000 claims description 10
- BQPPJGMMIYJVBR-UHFFFAOYSA-N (10S)-3c-Acetoxy-4.4.10r.13c.14t-pentamethyl-17c-((R)-1.5-dimethyl-hexen-(4)-yl)-(5tH)-Delta8-tetradecahydro-1H-cyclopenta[a]phenanthren Natural products CC12CCC(OC(C)=O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C BQPPJGMMIYJVBR-UHFFFAOYSA-N 0.000 claims description 9
- CHGIKSSZNBCNDW-UHFFFAOYSA-N (3beta,5alpha)-4,4-Dimethylcholesta-8,24-dien-3-ol Natural products CC12CCC(O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21 CHGIKSSZNBCNDW-UHFFFAOYSA-N 0.000 claims description 9
- XYTLYKGXLMKYMV-UHFFFAOYSA-N 14alpha-methylzymosterol Natural products CC12CCC(O)CC1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C XYTLYKGXLMKYMV-UHFFFAOYSA-N 0.000 claims description 9
- FPTJELQXIUUCEY-UHFFFAOYSA-N 3beta-Hydroxy-lanostan Natural products C1CC2C(C)(C)C(O)CCC2(C)C2C1C1(C)CCC(C(C)CCCC(C)C)C1(C)CC2 FPTJELQXIUUCEY-UHFFFAOYSA-N 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- BKLIAINBCQPSOV-UHFFFAOYSA-N Gluanol Natural products CC(C)CC=CC(C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(O)C(C)(C)C4CC3 BKLIAINBCQPSOV-UHFFFAOYSA-N 0.000 claims description 9
- LOPKHWOTGJIQLC-UHFFFAOYSA-N Lanosterol Natural products CC(CCC=C(C)C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(C)(O)C(C)(C)C4CC3 LOPKHWOTGJIQLC-UHFFFAOYSA-N 0.000 claims description 9
- QBSJHOGDIUQWTH-UHFFFAOYSA-N dihydrolanosterol Natural products CC(C)CCCC(C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(C)(O)C(C)(C)C4CC3 QBSJHOGDIUQWTH-UHFFFAOYSA-N 0.000 claims description 9
- CAHGCLMLTWQZNJ-RGEKOYMOSA-N lanosterol Chemical compound C([C@]12C)C[C@@H](O)C(C)(C)[C@H]1CCC1=C2CC[C@]2(C)[C@H]([C@H](CCC=C(C)C)C)CC[C@@]21C CAHGCLMLTWQZNJ-RGEKOYMOSA-N 0.000 claims description 9
- 229940058690 lanosterol Drugs 0.000 claims description 9
- YABASAWVVRQMEU-YBXTVTTCSA-N cycloartanol Chemical compound CC(C)([C@@H](O)CC1)[C@H]2[C@@]31C[C@@]13CC[C@]3(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@@]3(C)[C@@H]1CC2 YABASAWVVRQMEU-YBXTVTTCSA-N 0.000 claims description 8
- IXHACUTUTOCSJE-UHFFFAOYSA-N Cyclolaudenol Natural products C1CC(O)C(C)(C)C2C31CC13CCC3(C)C(C(CCC(C)C(C)=C)C)CCC3(C)C1CC2 IXHACUTUTOCSJE-UHFFFAOYSA-N 0.000 claims description 6
- IXHACUTUTOCSJE-HWTFXIFRSA-N cyclolaudenol Chemical compound CC(C)([C@@H](O)CC1)[C@H]2[C@@]31C[C@@]13CC[C@]3(C)[C@@H]([C@@H](CC[C@H](C)C(C)=C)C)CC[C@@]3(C)[C@@H]1CC2 IXHACUTUTOCSJE-HWTFXIFRSA-N 0.000 claims description 6
- BTLJUKNIXFTSMI-DFWJFPTDSA-N (23e) cyclosadol Chemical compound CC(C)([C@@H](O)CC1)[C@H]2[C@@]31C[C@@]13CC[C@]3(C)[C@@H]([C@H](C)C/C=C(\C)C(C)C)CC[C@@]3(C)[C@@H]1CC2 BTLJUKNIXFTSMI-DFWJFPTDSA-N 0.000 claims description 5
- ZBFPGLKEWSMWSG-BQNIITSRSA-N (3S,5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-3-ol Chemical compound CC1(C)[C@@H](O)CC[C@]2(C)C3=CC[C@]4(C)[C@@H]([C@@H](CCC=C(C)C)C)CC[C@@]4(C)C3=CC[C@H]21 ZBFPGLKEWSMWSG-BQNIITSRSA-N 0.000 claims description 5
- DICCPNLDOZNSML-XGKJEQFASA-N (3S,5R,9R,10R,13S,14S,17S)-4,4,10,13,14-pentamethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol Chemical compound C[C@H](CCC=C(C)C)[C@@H]1CC[C@]2(C)C3=CC[C@H]4C(C)(C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]12C DICCPNLDOZNSML-XGKJEQFASA-N 0.000 claims description 5
- CIUWDTKQGZYEEE-UHFFFAOYSA-N Butyrospermol Natural products C12CCC3(C)C(C(CCC=C(C)C)C)CCC3(C)C2=CCC2C1CCC(O)C2(C)C CIUWDTKQGZYEEE-UHFFFAOYSA-N 0.000 claims description 5
- BTLJUKNIXFTSMI-IHLDJTSYSA-N Cyclosadol Natural products CC(C)C(=CC[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4C(C)(C)[C@@H](O)CC[C@@]45C[C@]35CC[C@]12C)C BTLJUKNIXFTSMI-IHLDJTSYSA-N 0.000 claims description 5
- DICCPNLDOZNSML-UHFFFAOYSA-N Delta7-tirucallol Natural products CC1(C)C(O)CCC2(C)C(CCC3(C(C(CCC=C(C)C)C)CCC33C)C)C3=CCC21 DICCPNLDOZNSML-UHFFFAOYSA-N 0.000 claims description 5
- ZBFPGLKEWSMWSG-UHFFFAOYSA-N agnosterone Natural products CC1(C)C(O)CCC2(C)C3=CCC4(C)C(C(CCC=C(C)C)C)CCC4(C)C3=CCC21 ZBFPGLKEWSMWSG-UHFFFAOYSA-N 0.000 claims description 5
- ZCBDFGFNCFLBOL-BQNIITSRSA-N (3S,5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-3-ol Chemical compound CC1(C)[C@@H](O)CC[C@]2(C)C3=CC[C@]4(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@@]4(C)C3=CC[C@H]21 ZCBDFGFNCFLBOL-BQNIITSRSA-N 0.000 claims description 4
- CBFHVQNQZFSQRM-UHFFFAOYSA-N 2-[(4-butanoyloxy-3-methoxyphenyl)methylidene]butanoic acid Chemical compound CCCC(=O)OC1=CC=C(C=C(CC)C(O)=O)C=C1OC CBFHVQNQZFSQRM-UHFFFAOYSA-N 0.000 claims description 4
- JPOSRBNQHFELCB-UHFFFAOYSA-N 2-methyl-3-(4-propanoyloxyphenyl)prop-2-enoic acid Chemical compound CCC(=O)OC1=CC=C(C=C(C)C(O)=O)C=C1 JPOSRBNQHFELCB-UHFFFAOYSA-N 0.000 claims description 4
- INMUZOBPSGXABB-OJIQHVHUSA-N Cycloeucalenol Natural products CC(C)C(=C)CC[C@@H](C)[C@H]1CCC[C@@]2(C)[C@@H]3CC[C@H]4[C@H](C)[C@@H](O)CC[C@@]45C[C@@]35CC[C@]12C INMUZOBPSGXABB-OJIQHVHUSA-N 0.000 claims description 4
- HUNLTIZKNQDZEI-PGFZVWMDSA-N cycloeucalenol Chemical compound C[C@@H]([C@@H]1CC[C@H]2[C@]3(C)CC[C@@H]([C@]3(CC3)C)[C@H](C)CCC(=C)C(C)C)[C@@H](O)CC[C@]11[C@@]23C1 HUNLTIZKNQDZEI-PGFZVWMDSA-N 0.000 claims description 4
- ZCBDFGFNCFLBOL-UHFFFAOYSA-N gamma-Lanostadienol Natural products CC1(C)C(O)CCC2(C)C3=CCC4(C)C(C(C)CCCC(C)C)CCC4(C)C3=CCC21 ZCBDFGFNCFLBOL-UHFFFAOYSA-N 0.000 claims description 4
- XJLZCPIILZRCPS-CKCUNPICSA-N (3s,5r,10s,13s,14s,17s)-4,4,10,13,14-pentamethyl-17-[(2s)-6-methyl-5-methylideneheptan-2-yl]-2,3,5,6,7,11,12,15,16,17-decahydro-1h-cyclopenta[a]phenanthren-3-ol Chemical compound C([C@@]12C)C[C@H](O)C(C)(C)[C@@H]1CCC1=C2CC[C@@]2(C)[C@H]([C@@H](C)CCC(=C)C(C)C)CC[C@@]21C XJLZCPIILZRCPS-CKCUNPICSA-N 0.000 claims description 3
- REJOBCUTAMAPIS-HWKANZROSA-N (e)-3-(3-methoxy-4-nitrophenyl)prop-2-enoic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1[N+]([O-])=O REJOBCUTAMAPIS-HWKANZROSA-N 0.000 claims description 3
- OHJGKUKNHMWTCP-UHFFFAOYSA-N 2-[(4-butanoyloxyphenyl)methylidene]butanoic acid Chemical compound CCCC(=O)OC1=CC=C(C=C(CC)C(O)=O)C=C1 OHJGKUKNHMWTCP-UHFFFAOYSA-N 0.000 claims description 3
- AWWVCUPVXCDDHS-UHFFFAOYSA-N 2-methyl-3-(4-nitrophenyl)prop-2-enoic acid Chemical compound OC(=O)C(C)=CC1=CC=C([N+]([O-])=O)C=C1 AWWVCUPVXCDDHS-UHFFFAOYSA-N 0.000 claims description 3
- AHHAVYVFUHKHHQ-UHFFFAOYSA-N 2-methyl-3-(5-nitro-2-propoxyphenyl)prop-2-enoic acid Chemical compound CCCOC1=CC=C([N+]([O-])=O)C=C1C=C(C)C(O)=O AHHAVYVFUHKHHQ-UHFFFAOYSA-N 0.000 claims description 3
- IBXDEDGIXFRCCW-UHFFFAOYSA-N 3-(3-methoxy-4-nitrophenyl)-2-methylprop-2-enoic acid Chemical compound COC1=CC(C=C(C)C(O)=O)=CC=C1[N+]([O-])=O IBXDEDGIXFRCCW-UHFFFAOYSA-N 0.000 claims description 3
- LLQXKNWGEYFOIG-UHFFFAOYSA-N 3-(3-methoxy-4-propanoyloxyphenyl)-2-methylprop-2-enoic acid Chemical compound CCC(=O)OC1=CC=C(C=C(C)C(O)=O)C=C1OC LLQXKNWGEYFOIG-UHFFFAOYSA-N 0.000 claims description 3
- MUYUDVPKJZCBOA-UHFFFAOYSA-N 3-(4-aminophenyl)-2-methylprop-2-enoic acid Chemical compound OC(=O)C(C)=CC1=CC=C(N)C=C1 MUYUDVPKJZCBOA-UHFFFAOYSA-N 0.000 claims description 3
- YHOAZFMXZXWRHC-UHFFFAOYSA-N 3-(4-hydroxy-3-methoxyphenyl)-2-methylprop-2-enoic acid Chemical compound COC1=CC(C=C(C)C(O)=O)=CC=C1O YHOAZFMXZXWRHC-UHFFFAOYSA-N 0.000 claims description 3
- PWURRRRGLCVBMX-UHFFFAOYSA-N 3-methoxy-4-nitrobenzoic acid Chemical compound COC1=CC(C(O)=O)=CC=C1[N+]([O-])=O PWURRRRGLCVBMX-UHFFFAOYSA-N 0.000 claims description 3
- XNCRUNXWPDJHGV-UHFFFAOYSA-N alpha-Methyl-cinnamic acid Chemical compound OC(=O)C(C)=CC1=CC=CC=C1 XNCRUNXWPDJHGV-UHFFFAOYSA-N 0.000 claims description 3
- VOKLEOFNMAVWIU-UHFFFAOYSA-N euphorbol Natural products CC(C)C(=C)CCC(C)C1CCC2(C)C3=C(CCC12C)C4CCC(O)C(C)(C)C4CC3 VOKLEOFNMAVWIU-UHFFFAOYSA-N 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- WZAMDSBJONFHAO-UHFFFAOYSA-N quercetin 3-alpha-L-rhamnofuranoside Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC(C(=C)CCC=C(C)C)C4CCC3C21C WZAMDSBJONFHAO-UHFFFAOYSA-N 0.000 claims description 3
- PPVBATUJIOGJMW-UHFFFAOYSA-N 2-[(3-butanoyloxyphenyl)methylidene]butanoic acid Chemical compound CCCC(=O)OC1=CC=CC(C=C(CC)C(O)=O)=C1 PPVBATUJIOGJMW-UHFFFAOYSA-N 0.000 claims description 2
- VKKJXDLVEHTPOQ-UHFFFAOYSA-N 2-[(3-methoxy-4-pentanoyloxyphenyl)methylidene]pentanoic acid Chemical compound CCCCC(=O)OC1=CC=C(C=C(CCC)C(O)=O)C=C1OC VKKJXDLVEHTPOQ-UHFFFAOYSA-N 0.000 claims description 2
- XIXMPQYDAHJQNN-UHFFFAOYSA-N 2-[(4-nitrophenyl)methylidene]butanoic acid Chemical compound CCC(C(O)=O)=CC1=CC=C([N+]([O-])=O)C=C1 XIXMPQYDAHJQNN-UHFFFAOYSA-N 0.000 claims description 2
- CVZUPRDSNNBZLH-UHFFFAOYSA-N 2-methoxy-5-nitrobenzoic acid Chemical compound COC1=CC=C([N+]([O-])=O)C=C1C(O)=O CVZUPRDSNNBZLH-UHFFFAOYSA-N 0.000 claims description 2
- NGZYZOOMYKRLPT-UHFFFAOYSA-N 3-(3-ethoxy-4-hydroxyphenyl)-2-methylprop-2-enoic acid Chemical compound CCOC1=CC(C=C(C)C(O)=O)=CC=C1O NGZYZOOMYKRLPT-UHFFFAOYSA-N 0.000 claims description 2
- LWWPSEIFAKNPKQ-UHFFFAOYSA-N 5-amino-2-methoxybenzoic acid Chemical compound COC1=CC=C(N)C=C1C(O)=O LWWPSEIFAKNPKQ-UHFFFAOYSA-N 0.000 claims description 2
- CZJBMPUIZBEHSZ-UHFFFAOYSA-N CCCCCCCC(=O)OC1=CC=C(C=C(CCCC)C(O)=O)C=C1OC Chemical compound CCCCCCCC(=O)OC1=CC=C(C=C(CCCC)C(O)=O)C=C1OC CZJBMPUIZBEHSZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000005947 deacylation reaction Methods 0.000 claims description 2
- GQBVUGXINLMDTO-UHFFFAOYSA-N 2-[(4-hydroxy-3-methoxyphenyl)methylidene]butanoic acid Chemical compound CCC(C(O)=O)=CC1=CC=C(O)C(OC)=C1 GQBVUGXINLMDTO-UHFFFAOYSA-N 0.000 claims 2
- BJXDOISSZUSFMH-UHFFFAOYSA-N 2-[(4-hydroxy-3-methoxyphenyl)methylidene]hexanoic acid Chemical compound CCCCC(C(O)=O)=CC1=CC=C(O)C(OC)=C1 BJXDOISSZUSFMH-UHFFFAOYSA-N 0.000 claims 2
- VUGVHRGTLSPHJV-UHFFFAOYSA-N 3-(4-amino-3-methoxyphenyl)-2-methylprop-2-enoic acid Chemical compound COC1=CC(C=C(C)C(O)=O)=CC=C1N VUGVHRGTLSPHJV-UHFFFAOYSA-N 0.000 claims 2
- QGMNUFDKFDEQRV-UHFFFAOYSA-N 3-(4-amino-3-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC(C=CC(O)=O)=CC=C1N QGMNUFDKFDEQRV-UHFFFAOYSA-N 0.000 claims 2
- YNMMLKQHOGURNL-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-2-methylprop-2-enoic acid Chemical compound OC(=O)C(C)=CC1=CC=C(O)C=C1 YNMMLKQHOGURNL-UHFFFAOYSA-N 0.000 claims 2
- JZINNAKNHHQBOS-AATRIKPKSA-N 3-methylcinnamic acid Chemical compound CC1=CC=CC(\C=C\C(O)=O)=C1 JZINNAKNHHQBOS-AATRIKPKSA-N 0.000 claims 2
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 description 1
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 description 1
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- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 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 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60085254A JPS61243099A (ja) | 1985-04-19 | 1985-04-19 | トリテルペンアルコール有機酸エステル |
| CA000481808A CA1265785A (en) | 1984-06-04 | 1985-05-17 | Triterpenyl esters of organic acids, process for their production, and hypolipidemic agents composed of them |
| EP85303839A EP0166542B1 (en) | 1984-06-04 | 1985-05-30 | Triterpenyl esters of organic acids, process for their production, and hypolipidemic agents composed of them |
| DE8585303839T DE3579064D1 (de) | 1984-06-04 | 1985-05-30 | Triterpene ester von organischer saeure, verfahren zu ihrer herstellung und hypolipeinische zusammenstellungen die sie enthalten. |
| US06/739,183 US4748161A (en) | 1984-06-04 | 1985-05-30 | Triterpenyl esters of organic acids and hypolipidemic agents composed of them |
| KR1019850003819A KR920007235B1 (ko) | 1984-06-04 | 1985-05-31 | 유기산의 트리테르페닐 에스테르의 제조방법 |
| NO85852246A NO852246L (no) | 1984-06-04 | 1985-06-03 | Fremgangsmaate ved fremstilling av terapeutisk aktive triterpenylestere av organiske syrer. |
| FI852216A FI852216A7 (fi) | 1984-06-04 | 1985-06-03 | Menetelmä terapeuttisesti aktiivisten orgaanisten happojen triterpenyyliesterien valmistamiseksi. |
| DK246985A DK246985A (da) | 1984-06-04 | 1985-06-03 | Triterpenylestere af organiske syrer, fremgangsmaade til fremstilling deraf samt farmaceutiske praeparater indeholdende saadanne triterpenylestere |
| SU853913136A SU1538892A3 (ru) | 1984-06-04 | 1985-06-03 | Способ получени тритерпениловых эфиров органических кислот |
| ES544466A ES8708125A1 (es) | 1984-06-04 | 1985-06-04 | Procedimiento para la fabricacion de esteres de triterpenilode acidos organicos |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60085254A JPS61243099A (ja) | 1985-04-19 | 1985-04-19 | トリテルペンアルコール有機酸エステル |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61243099A true JPS61243099A (ja) | 1986-10-29 |
| JPH0533713B2 JPH0533713B2 (https=) | 1993-05-20 |
Family
ID=13853435
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60085254A Granted JPS61243099A (ja) | 1984-06-04 | 1985-04-19 | トリテルペンアルコール有機酸エステル |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61243099A (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000063328A (ja) * | 1998-02-13 | 2000-02-29 | Givaudan Roure Internatl Sa | アリ―ル―アクリル酸エステル |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2742947C (en) | 2008-11-19 | 2013-12-17 | Morinaga Milk Industry Co., Ltd. | Antioxidant |
-
1985
- 1985-04-19 JP JP60085254A patent/JPS61243099A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000063328A (ja) * | 1998-02-13 | 2000-02-29 | Givaudan Roure Internatl Sa | アリ―ル―アクリル酸エステル |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0533713B2 (https=) | 1993-05-20 |
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