The absolute configuration of the four stereoisomers of trans-anethole diol (1-(4'-methoxyphenyl)-1,2-propanediol), a metabolite of anethole in the rat

被引:29
作者
Ishida, T
Bounds, SVJ
Caldwell, J
Drake, A
Takeshita, M
机构
[1] UNIV LONDON BIRKBECK COLL,DEPT CHEM,LONDON WC1E 0AJ,ENGLAND
[2] TOHOKU COLL PHARMACEUT SCI,SENDAI,MIYAGI 981,JAPAN
[3] ST MARYS HOSP,UNIV LONDON IMPERIAL COLL SCI TECHNOL & MED,SCH MED,LONDON W2 1PG,ENGLAND
关键词
D O I
10.1016/0957-4166(96)00411-9
中图分类号
O61 [无机化学];
学科分类号
070301 [无机化学]; 081704 [应用化学];
摘要
The four stereoisomers of anethole diol, one of the major neutral metabolites of trans-anethole in the rat, have been separated by HPLC of their camphanyl esters and characterized by H-1-NMR and CD spectroscopy. Their configurations were determined by comparison of their CD spectra with those of the 1-phenylpropane-1,2-diols. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:3113 / 3118
页数:6
相关论文
共 14 条
[1]
BOUNDS SVJ, 1994, THESIS IMPERIAL COLL
[2]
CALDWELL J, 1991, P TOX FOR ANN SUMM M, P613
[3]
CALDWELL J, 1993, PROGR REPORT TRANSAN
[4]
CRITTERIO H, 1983, J CHEM SOC PERK T, P891
[5]
VIBRONIC FINE STRUCTURE OF FORMALLY FORBIDDEN TRANSITIONS IN CIRCULAR DICHROISM [J].
GILLARD, RD ;
MITCHELL, PR .
TRANSACTIONS OF THE FARADAY SOCIETY, 1969, 65 (562P) :2611-&
[6]
OXIDATION BY COBALT(III) ACETATE .12. STEREOSELECTIVE FORMATION OF THREO-1-PHENYLPROPANE-1,2-DIOL MONOACETATE IN OXIDATION OF BETA-METHYLSTYRENES UNSUBSTITUTED AND SUBSTITUTED WITH ELECTRON-DONATING GROUPS BY COBALT(III) AND MANGANESE(III) ACETATE IN ACETIC-ACID [J].
HIRANO, M ;
HAMAGUCHI, T ;
ZHANG, XM ;
MORIMOTO, T .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1989, (12) :2141-2145
[7]
STUDIES ON THE SYNTHESES OF DRUGS ACTING ON CIRCULATORY-SYSTEM .3. SYNTHESIS OF 2-(4-BENZYLPIPERIDINO)-1-(4-HYDROXYPHENYL)PROPANOL AND THE DETERMINATION OF THE RELATIVE CONFIGURATION OF THESE DIASTEREOISOMERS (STUDIES ON THE SYNTHESES OF HETEROCYCLIC-COMPOUNDS .854. [J].
KAMETANI, T ;
KIGASAWA, K ;
HIIRAGI, M ;
WAGATSUMA, N ;
KOHAGIZAWA, T ;
INOUE, H .
YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1980, 100 (08) :844-854
[8]
Leung AY., 1980, ENCY COMMON NATURAL
[9]
STEREOCHEMISTRY AND REGIOCHEMISTRY OF THE ADDITION OF HYPOBROMOUS ACID TO BETA-METHYLSTYRENES [J].
MARPLES, BA ;
SAINT, CG .
SYNTHETIC COMMUNICATIONS, 1982, 12 (07) :545-555
[10]
INFLUENCE OF MODULATORS OF EPOXIDE METABOLISM ON THE CYTOTOXICITY OF TRANS-ANETHOLE IN FRESHLY ISOLATED RAT HEPATOCYTES [J].
MARSHALL, AD ;
CALDWELL, J .
FOOD AND CHEMICAL TOXICOLOGY, 1992, 30 (06) :467-473