JPS5984880A - 新規アイラントン誘導体及びその製造法 - Google Patents
新規アイラントン誘導体及びその製造法Info
- Publication number
- JPS5984880A JPS5984880A JP57196248A JP19624882A JPS5984880A JP S5984880 A JPS5984880 A JP S5984880A JP 57196248 A JP57196248 A JP 57196248A JP 19624882 A JP19624882 A JP 19624882A JP S5984880 A JPS5984880 A JP S5984880A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- acid residue
- general formula
- formula
- compound
- 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
- WBBVXGHSWZIJST-RLQYZCPESA-N Ailanthone Chemical class O1C(=O)C[C@H]2C(=C)[C@@H](O)[C@@]3(O)[C@@H]4[C@@]5(C)[C@H](O)C(=O)C=C(C)[C@@H]5C[C@@H]1[C@]42CO3 WBBVXGHSWZIJST-RLQYZCPESA-N 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- -1 triacetate carboxylic acid ester Chemical class 0.000 claims abstract description 24
- 125000002252 acyl group Chemical group 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims description 62
- 238000004519 manufacturing process Methods 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 230000007062 hydrolysis Effects 0.000 claims description 9
- 238000006460 hydrolysis reaction Methods 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 230000032050 esterification Effects 0.000 claims description 8
- 238000005886 esterification reaction Methods 0.000 claims description 8
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 4
- 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 4
- 235000007586 terpenes Nutrition 0.000 claims description 4
- 150000003648 triterpenes Chemical class 0.000 claims description 4
- WJHFZYAELPOJIV-IJFRVEDASA-N (2E,6E)-farnesoic acid Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\C(O)=O WJHFZYAELPOJIV-IJFRVEDASA-N 0.000 claims description 3
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 3
- 229930004069 diterpene Natural products 0.000 claims description 3
- 150000004141 diterpene derivatives Chemical class 0.000 claims description 3
- 229930003658 monoterpene Natural products 0.000 claims description 3
- 150000002773 monoterpene derivatives Chemical class 0.000 claims description 3
- 235000002577 monoterpenes Nutrition 0.000 claims description 3
- 229930002330 retinoic acid Natural products 0.000 claims description 3
- 229930004725 sesquiterpene Natural products 0.000 claims description 3
- 150000004354 sesquiterpene derivatives Chemical class 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 239000000932 sedative agent Substances 0.000 claims description 2
- 230000001624 sedative effect Effects 0.000 claims description 2
- 125000005472 straight-chain saturated fatty acid group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 10
- 238000000034 method Methods 0.000 abstract description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 7
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 abstract description 6
- 241001093963 Ailanthus Species 0.000 abstract description 5
- 229910000489 osmium tetroxide Inorganic materials 0.000 abstract description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract description 4
- 239000012279 sodium borohydride Substances 0.000 abstract description 4
- 241000196324 Embryophyta Species 0.000 abstract description 3
- 230000018044 dehydration Effects 0.000 abstract description 3
- 238000006297 dehydration reaction Methods 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 230000001590 oxidative effect Effects 0.000 abstract description 3
- 150000004671 saturated fatty acids Chemical group 0.000 abstract description 3
- 229910001923 silver oxide Inorganic materials 0.000 abstract description 3
- LZKVXMYVBSNXER-YZPKDWIXSA-N Glaucarubin Chemical compound O[C@@H]([C@]1(C)[C@@H]23)[C@@H](O)C=C(C)[C@@H]1C[C@@H]1[C@@]43CO[C@@]2(O)[C@H](O)[C@H](C)[C@@H]4[C@@H](OC(=O)[C@@](C)(O)CC)C(=O)O1 LZKVXMYVBSNXER-YZPKDWIXSA-N 0.000 abstract description 2
- LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 abstract description 2
- ZYKXSWCKEJLGFS-UHFFFAOYSA-N Ailanthone Natural products CC1=CC(=O)C(O)C2(C)C1CC3OC(=O)CC4C(=C)C(O)C5OCC34C25 ZYKXSWCKEJLGFS-UHFFFAOYSA-N 0.000 abstract 1
- 241001093951 Ailanthus altissima Species 0.000 abstract 1
- 230000003327 cancerostatic effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 150000003839 salts Chemical group 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- GVKGXDFZFAFBIW-MQQKCMAXSA-N (4e,6e)-octa-4,6-dienoic acid Chemical group C\C=C\C=C\CCC(O)=O GVKGXDFZFAFBIW-MQQKCMAXSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 208000008342 Leukemia P388 Diseases 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 239000002246 antineoplastic agent Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 229930014626 natural product Natural products 0.000 description 3
- 239000012285 osmium tetroxide Substances 0.000 description 3
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 3
- XRKBQVGBWJWJJJ-QGZVFWFLSA-N (2R)-2-aminooctadecanoic acid Chemical group CCCCCCCCCCCCCCCC[C@@H](N)C(O)=O XRKBQVGBWJWJJJ-QGZVFWFLSA-N 0.000 description 2
- MNRBGFKCVTVNBA-UHFFFAOYSA-N 2-Hydroxyundecanoate Chemical group CCCCCCCCCC(O)C(O)=O MNRBGFKCVTVNBA-UHFFFAOYSA-N 0.000 description 2
- JINGUCXQUOKWKH-UHFFFAOYSA-N 2-aminodecanoic acid Chemical group CCCCCCCCC(N)C(O)=O JINGUCXQUOKWKH-UHFFFAOYSA-N 0.000 description 2
- RDFMDVXONNIGBC-UHFFFAOYSA-N 2-aminoheptanoic acid Chemical group CCCCCC(N)C(O)=O RDFMDVXONNIGBC-UHFFFAOYSA-N 0.000 description 2
- SNDPXSYFESPGGJ-UHFFFAOYSA-N 2-aminopentanoic acid Chemical group CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001529936 Murinae Species 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical group NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
- 125000001976 hemiacetal group Chemical group 0.000 description 2
- VHVMWCWIYITOLN-UHFFFAOYSA-N heptadec-2-ynoic acid Chemical group CCCCCCCCCCCCCCC#CC(O)=O VHVMWCWIYITOLN-UHFFFAOYSA-N 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 125000001909 leucine group Chemical group [H]N(*)C(C(*)=O)C([H])([H])C(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical group CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000003505 terpenes Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- NTWSIWWJPQHFTO-AATRIKPKSA-N (2E)-3-methylhex-2-enoic acid Chemical group CCC\C(C)=C\C(O)=O NTWSIWWJPQHFTO-AATRIKPKSA-N 0.000 description 1
- RDFMDVXONNIGBC-ZCFIWIBFSA-N (2R)-aminoheptanoic acid Chemical group CCCCC[C@@H](N)C(O)=O RDFMDVXONNIGBC-ZCFIWIBFSA-N 0.000 description 1
- XRKBQVGBWJWJJJ-KRWDZBQOSA-N (2S)-2-aminooctadecanoic acid Chemical group CCCCCCCCCCCCCCCC[C@H](N)C(O)=O XRKBQVGBWJWJJJ-KRWDZBQOSA-N 0.000 description 1
- QUBNFZFTFXTLKH-LLVKDONJSA-N (2r)-2-aminododecanoic acid Chemical group CCCCCCCCCC[C@@H](N)C(O)=O QUBNFZFTFXTLKH-LLVKDONJSA-N 0.000 description 1
- BVXKPGXJOLWHFI-CYBMUJFWSA-N (2r)-2-aminotetradecanoic acid Chemical group CCCCCCCCCCCC[C@@H](N)C(O)=O BVXKPGXJOLWHFI-CYBMUJFWSA-N 0.000 description 1
- HASUJDLTAYUWCO-SNVBAGLBSA-N (2r)-2-aminoundecanoic acid Chemical group CCCCCCCCC[C@@H](N)C(O)=O HASUJDLTAYUWCO-SNVBAGLBSA-N 0.000 description 1
- JVPFOKXICYJJSC-MRVPVSSYSA-N (2r)-2-azaniumylnonanoate Chemical group CCCCCCC[C@@H]([NH3+])C([O-])=O JVPFOKXICYJJSC-MRVPVSSYSA-N 0.000 description 1
- AKVBCGQVQXPRLD-SSDOTTSWSA-N (2r)-2-azaniumyloctanoate Chemical group CCCCCC[C@@H]([NH3+])C([O-])=O AKVBCGQVQXPRLD-SSDOTTSWSA-N 0.000 description 1
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical group CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- JINGUCXQUOKWKH-VIFPVBQESA-N (2s)-2-aminodecanoic acid Chemical group CCCCCCCC[C@H](N)C(O)=O JINGUCXQUOKWKH-VIFPVBQESA-N 0.000 description 1
- CRJWOABTAHMMSA-INIZCTEOSA-N (2s)-2-aminoheptadecanoic acid Chemical group CCCCCCCCCCCCCCC[C@H](N)C(O)=O CRJWOABTAHMMSA-INIZCTEOSA-N 0.000 description 1
- BVXKPGXJOLWHFI-ZDUSSCGKSA-N (2s)-2-aminotetradecanoic acid Chemical group CCCCCCCCCCCC[C@H](N)C(O)=O BVXKPGXJOLWHFI-ZDUSSCGKSA-N 0.000 description 1
- JVPFOKXICYJJSC-QMMMGPOBSA-N (2s)-2-azaniumylnonanoate Chemical group CCCCCCC[C@H]([NH3+])C([O-])=O JVPFOKXICYJJSC-QMMMGPOBSA-N 0.000 description 1
- AKVBCGQVQXPRLD-ZETCQYMHSA-N (2s)-2-azaniumyloctanoate Chemical group CCCCCC[C@H]([NH3+])C([O-])=O AKVBCGQVQXPRLD-ZETCQYMHSA-N 0.000 description 1
- BLROLNSSBGCUAD-GQCTYLIASA-N (e)-3,4-dimethylpent-2-enoic acid Chemical group CC(C)C(\C)=C\C(O)=O BLROLNSSBGCUAD-GQCTYLIASA-N 0.000 description 1
- WJUCVNVYISECTJ-BQYQJAHWSA-N (e)-3-methyloct-2-enoic acid Chemical group CCCCC\C(C)=C\C(O)=O WJUCVNVYISECTJ-BQYQJAHWSA-N 0.000 description 1
- HSIUQCHVPSGZKT-UHFFFAOYSA-N 2-(methoxymethoxy)hexanoic acid Chemical group CCCCC(C(=O)O)OCOC HSIUQCHVPSGZKT-UHFFFAOYSA-N 0.000 description 1
- UNVRQZCTYCROLZ-UHFFFAOYSA-N 2-(methoxymethoxy)octadecanoic acid Chemical group CCCCCCCCCCCCCCCCC(C(O)=O)OCOC UNVRQZCTYCROLZ-UHFFFAOYSA-N 0.000 description 1
- SCDDPXCTSGNPLZ-UHFFFAOYSA-N 2-(methoxymethoxy)propanoic acid Chemical group COCOC(C)C(O)=O SCDDPXCTSGNPLZ-UHFFFAOYSA-N 0.000 description 1
- QUBNFZFTFXTLKH-UHFFFAOYSA-N 2-aminododecanoic acid Chemical group CCCCCCCCCCC(N)C(O)=O QUBNFZFTFXTLKH-UHFFFAOYSA-N 0.000 description 1
- LRQKBLKVPFOOQJ-UHFFFAOYSA-N 2-aminohexanoic acid Chemical group CCCCC(N)C(O)=O LRQKBLKVPFOOQJ-UHFFFAOYSA-N 0.000 description 1
- JVPFOKXICYJJSC-UHFFFAOYSA-N 2-azaniumylnonanoate Chemical group CCCCCCCC(N)C(O)=O JVPFOKXICYJJSC-UHFFFAOYSA-N 0.000 description 1
- KWNGIKVZXFFZNN-UHFFFAOYSA-M 2-chloro-1-methylpyridin-1-ium;4-methylbenzenesulfonate Chemical compound C[N+]1=CC=CC=C1Cl.CC1=CC=C(S([O-])(=O)=O)C=C1 KWNGIKVZXFFZNN-UHFFFAOYSA-M 0.000 description 1
- AFENDNXGAFYKQO-UHFFFAOYSA-N 2-hydroxybutyric acid Chemical group CCC(O)C(O)=O AFENDNXGAFYKQO-UHFFFAOYSA-N 0.000 description 1
- GHPVDCPCKSNJDR-UHFFFAOYSA-N 2-hydroxydecanoic acid Chemical group CCCCCCCCC(O)C(O)=O GHPVDCPCKSNJDR-UHFFFAOYSA-N 0.000 description 1
- YDZIJQXINJLRLL-UHFFFAOYSA-N 2-hydroxydodecanoic acid Chemical group CCCCCCCCCCC(O)C(O)=O YDZIJQXINJLRLL-UHFFFAOYSA-N 0.000 description 1
- KUZABABLVHWUGR-UHFFFAOYSA-N 2-hydroxyheptadecanoic acid Chemical group CCCCCCCCCCCCCCCC(O)C(O)=O KUZABABLVHWUGR-UHFFFAOYSA-N 0.000 description 1
- RGMMREBHCYXQMA-UHFFFAOYSA-N 2-hydroxyheptanoic acid Chemical group CCCCCC(O)C(O)=O RGMMREBHCYXQMA-UHFFFAOYSA-N 0.000 description 1
- JGHSBPIZNUXPLA-UHFFFAOYSA-N 2-hydroxyhexadecanoic acid Chemical group CCCCCCCCCCCCCCC(O)C(O)=O JGHSBPIZNUXPLA-UHFFFAOYSA-N 0.000 description 1
- NYHNVHGFPZAZGA-UHFFFAOYSA-N 2-hydroxyhexanoic acid Chemical group CCCCC(O)C(O)=O NYHNVHGFPZAZGA-UHFFFAOYSA-N 0.000 description 1
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 1
- BTJFTHOOADNOOS-UHFFFAOYSA-N 2-hydroxynonanoic acid Chemical group CCCCCCCC(O)C(O)=O BTJFTHOOADNOOS-UHFFFAOYSA-N 0.000 description 1
- KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-hydroxyoctadecanoic acid Chemical group CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 description 1
- JKRDADVRIYVCCY-UHFFFAOYSA-N 2-hydroxyoctanoic acid Chemical group CCCCCCC(O)C(O)=O JKRDADVRIYVCCY-UHFFFAOYSA-N 0.000 description 1
- NKASEPJANRVKDD-UHFFFAOYSA-N 2-hydroxypentadecanoic acid Chemical group CCCCCCCCCCCCCC(O)C(O)=O NKASEPJANRVKDD-UHFFFAOYSA-N 0.000 description 1
- JRHWHSJDIILJAT-UHFFFAOYSA-N 2-hydroxypentanoic acid Chemical group CCCC(O)C(O)=O JRHWHSJDIILJAT-UHFFFAOYSA-N 0.000 description 1
- KCEUZVYQPROALO-UHFFFAOYSA-N 2-hydroxytridecanoic acid Chemical group CCCCCCCCCCCC(O)C(O)=O KCEUZVYQPROALO-UHFFFAOYSA-N 0.000 description 1
- BQDKCWCMDBMLEH-UHFFFAOYSA-N 2-octynoic acid Chemical group CCCCCC#CC(O)=O BQDKCWCMDBMLEH-UHFFFAOYSA-N 0.000 description 1
- JZXHUPALAOUFMA-LBPRGKRZSA-N 2S-Amino-tridecanoic acid Chemical group CCCCCCCCCCC[C@H](N)C(O)=O JZXHUPALAOUFMA-LBPRGKRZSA-N 0.000 description 1
- XELWBYCKQCNAGY-HNNXBMFYSA-N 2S-aminohexadecanoic acid Chemical group CCCCCCCCCCCCCC[C@H](N)C(O)=O XELWBYCKQCNAGY-HNNXBMFYSA-N 0.000 description 1
- ZQJKMKZHAZNKAP-UHFFFAOYSA-N 3,4-dimethyldec-2-enoic acid Chemical group CCCCCCC(C)C(C)=CC(O)=O ZQJKMKZHAZNKAP-UHFFFAOYSA-N 0.000 description 1
- RADVBAWYLMSDOB-UHFFFAOYSA-N 3,4-dimethylnon-2-enoic acid Chemical group CCCCCC(C)C(C)=CC(O)=O RADVBAWYLMSDOB-UHFFFAOYSA-N 0.000 description 1
- SUQSTZBQEOQTEF-UHFFFAOYSA-N 3,4-dimethyloct-2-enoic acid Chemical group CCCCC(C)C(C)=CC(O)=O SUQSTZBQEOQTEF-UHFFFAOYSA-N 0.000 description 1
- UUSWYBUTZUWCOU-UHFFFAOYSA-N 3,4-dimethyltridec-2-enoic acid Chemical group CCCCCCCCCC(C)C(C)=CC(O)=O UUSWYBUTZUWCOU-UHFFFAOYSA-N 0.000 description 1
- KWQCCGWSFMZMBP-UHFFFAOYSA-N 3,4-dimethylundec-2-enoic acid Chemical group CCCCCCCC(C)C(C)=CC(O)=O KWQCCGWSFMZMBP-UHFFFAOYSA-N 0.000 description 1
- OILUAKBAMVLXGF-UHFFFAOYSA-N 3,5,5-trimethyl-hexanoic acid Chemical group OC(=O)CC(C)CC(C)(C)C OILUAKBAMVLXGF-UHFFFAOYSA-N 0.000 description 1
- ZEVJCQGYCJIXPB-UHFFFAOYSA-N 3-methyldec-2-enoic acid Chemical group CCCCCCCC(C)=CC(O)=O ZEVJCQGYCJIXPB-UHFFFAOYSA-N 0.000 description 1
- YKUOQEJKIPNUEA-UHFFFAOYSA-N 3-methyldodec-2-enoic acid Chemical group CCCCCCCCCC(C)=CC(O)=O YKUOQEJKIPNUEA-UHFFFAOYSA-N 0.000 description 1
- HSIBOIAYNONIBX-UHFFFAOYSA-N 3-methylhexadec-2-enoic acid Chemical group CCCCCCCCCCCCCC(C)=CC(O)=O HSIBOIAYNONIBX-UHFFFAOYSA-N 0.000 description 1
- RCXDKHZXABUNCU-UHFFFAOYSA-N 3-methyloctadec-2-enoic acid Chemical group CCCCCCCCCCCCCCCC(C)=CC(O)=O RCXDKHZXABUNCU-UHFFFAOYSA-N 0.000 description 1
- HGWFAESNFQJDRB-UHFFFAOYSA-N 3-methyltridec-2-enoic acid Chemical group CCCCCCCCCCC(C)=CC(O)=O HGWFAESNFQJDRB-UHFFFAOYSA-N 0.000 description 1
- MWKLFHTYBDIXBW-UHFFFAOYSA-N 3-methylundec-2-enoic acid Chemical group CCCCCCCCC(C)=CC(O)=O MWKLFHTYBDIXBW-UHFFFAOYSA-N 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical group NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
- 235000011274 Benincasa cerifera Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- JCBUETSSSYXCJP-UHFFFAOYSA-N COCOC(C(=O)O)CCCCCCCCCC Chemical group COCOC(C(=O)O)CCCCCCCCCC JCBUETSSSYXCJP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- TUHAVHITGNHKCB-UHFFFAOYSA-M Cl[N+]1=CC=CC=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 Chemical compound Cl[N+]1=CC=CC=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 TUHAVHITGNHKCB-UHFFFAOYSA-M 0.000 description 1
- 235000015001 Cucumis melo var inodorus Nutrition 0.000 description 1
- 240000002495 Cucumis melo var. inodorus Species 0.000 description 1
- 240000007235 Cyanthillium patulum Species 0.000 description 1
- SNDPXSYFESPGGJ-SCSAIBSYSA-N D-2-aminopentanoic acid Chemical group CCC[C@@H](N)C(O)=O SNDPXSYFESPGGJ-SCSAIBSYSA-N 0.000 description 1
- 125000000030 D-alanine group Chemical group [H]N([H])[C@](C([H])([H])[H])(C(=O)[*])[H] 0.000 description 1
- QWCKQJZIFLGMSD-GSVOUGTGSA-N D-alpha-aminobutyric acid Chemical group CC[C@@H](N)C(O)=O QWCKQJZIFLGMSD-GSVOUGTGSA-N 0.000 description 1
- 125000003301 D-leucyl group Chemical group N[C@@H](C(=O)*)CC(C)C 0.000 description 1
- LRQKBLKVPFOOQJ-RXMQYKEDSA-N D-norleucine Chemical group CCCC[C@@H](N)C(O)=O LRQKBLKVPFOOQJ-RXMQYKEDSA-N 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- RDFMDVXONNIGBC-LURJTMIESA-N L-2-aminoheptanoic acid Chemical group CCCCC[C@H](N)C(O)=O RDFMDVXONNIGBC-LURJTMIESA-N 0.000 description 1
- SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid Chemical group CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 description 1
- 125000003412 L-alanyl group Chemical group [H]N([H])[C@@](C([H])([H])[H])(C(=O)[*])[H] 0.000 description 1
- QWCKQJZIFLGMSD-VKHMYHEASA-N L-alpha-aminobutyric acid Chemical group CC[C@H](N)C(O)=O QWCKQJZIFLGMSD-VKHMYHEASA-N 0.000 description 1
- 125000003440 L-leucyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C(C([H])([H])[H])([H])C([H])([H])[H] 0.000 description 1
- LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-norleucine Chemical group CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical group CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 108010021119 Trichosanthin Proteins 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000003855 acyl compounds Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000000539 amino acid group Chemical group 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical group CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical group CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- ZHYZQXUYZJNEHD-VQHVLOKHSA-N geranic acid Chemical compound CC(C)=CCC\C(C)=C\C(O)=O ZHYZQXUYZJNEHD-VQHVLOKHSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- CKDDRHZIAZRDBW-UHFFFAOYSA-N henicosanoic acid Chemical group CCCCCCCCCCCCCCCCCCCCC(O)=O CKDDRHZIAZRDBW-UHFFFAOYSA-N 0.000 description 1
- KEMQGTRYUADPNZ-GZXVCZRGSA-N heptadecanoic acid Chemical group CCCCCCCCCCCCCCCC[14C](O)=O KEMQGTRYUADPNZ-GZXVCZRGSA-N 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid group Chemical group C(CCCCCC)(=O)O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- AKYAUBWOTZJUBI-UHFFFAOYSA-N hex-2-ynoic acid Chemical group CCCC#CC(O)=O AKYAUBWOTZJUBI-UHFFFAOYSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical group CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid group Chemical group C(CCCCC)(=O)O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical group CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical group CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- ISYWECDDZWTKFF-UHFFFAOYSA-N nonadecanoic acid Chemical group CCCCCCCCCCCCCCCCCCC(O)=O ISYWECDDZWTKFF-UHFFFAOYSA-N 0.000 description 1
- WEAGGGHXTMXZQA-UHFFFAOYSA-N octadec-2-ynoic acid Chemical group CCCCCCCCCCCCCCCC#CC(O)=O WEAGGGHXTMXZQA-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-GTFORLLLSA-N octadecanoic acid Chemical group CCCCCCCCCCCCCCCCC[14C](O)=O QIQXTHQIDYTFRH-GTFORLLLSA-N 0.000 description 1
- 125000005473 octanoic acid group Chemical group 0.000 description 1
- 150000004880 oxines Chemical class 0.000 description 1
- OTCVAHKKMMUFAY-UHFFFAOYSA-N oxosilver Chemical class [Ag]=O OTCVAHKKMMUFAY-UHFFFAOYSA-N 0.000 description 1
- MINRDQDGBLQBGD-UHFFFAOYSA-N pent-2-ynoic acid Chemical group CCC#CC(O)=O MINRDQDGBLQBGD-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N pentadecanoic acid Chemical group CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical group OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical group CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical group CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical group CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
Landscapes
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57196248A JPS5984880A (ja) | 1982-11-08 | 1982-11-08 | 新規アイラントン誘導体及びその製造法 |
| EP83306797A EP0108645B1 (en) | 1982-11-08 | 1983-11-08 | Novel ailanthone derivative |
| AT83306797T ATE27163T1 (de) | 1982-11-08 | 1983-11-08 | Aillanthonderivat. |
| DE8383306797T DE3371517D1 (de) | 1982-11-08 | 1983-11-08 | Novel ailanthone derivative |
| US06/794,331 US4774342A (en) | 1982-11-08 | 1985-11-04 | Novel ailanthone derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57196248A JPS5984880A (ja) | 1982-11-08 | 1982-11-08 | 新規アイラントン誘導体及びその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5984880A true JPS5984880A (ja) | 1984-05-16 |
| JPH0354666B2 JPH0354666B2 (enrdf_load_stackoverflow) | 1991-08-20 |
Family
ID=16354645
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57196248A Granted JPS5984880A (ja) | 1982-11-08 | 1982-11-08 | 新規アイラントン誘導体及びその製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5984880A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6072882A (ja) * | 1983-09-29 | 1985-04-24 | Suntory Ltd | 新規アイラントン誘導体 |
| KR100872588B1 (ko) * | 2007-04-18 | 2008-12-08 | 대구한의대학교산학협력단 | 항산화 효과를 갖는 가죽나무 추출물을 유효성분으로함유하는 조성물 |
-
1982
- 1982-11-08 JP JP57196248A patent/JPS5984880A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6072882A (ja) * | 1983-09-29 | 1985-04-24 | Suntory Ltd | 新規アイラントン誘導体 |
| KR100872588B1 (ko) * | 2007-04-18 | 2008-12-08 | 대구한의대학교산학협력단 | 항산화 효과를 갖는 가죽나무 추출물을 유효성분으로함유하는 조성물 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0354666B2 (enrdf_load_stackoverflow) | 1991-08-20 |
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