ENANTIOSELECTIVE METABOLISM OF CUMENE

被引：10

作者：

ISHIDA, T ^{[1
]}

MATSUMOTO, T ^{[1
]}

机构：

[1] UNIV TOKUSHIMA,FAC INTEGRATED ARTS & SCI,DEPT APPL MAT SCI,TOKUSHIMA 770,JAPAN

来源：

XENOBIOTICA | 1992年 / 22卷 / 11期

关键词：

D O I：

10.3109/00498259209053157

中图分类号：

R9 [药学];

学科分类号：

1007 ;

摘要：

1. The enantioselective metabolism of cumene (isopropylbenzene) was studied in intact rabbits. 2. Of the total 2-phenyl-1-propanol formed metabolically, 90.3% was shown by h.p.l.c. to be (R)-(+)-2-phenyl-1-propanol. The corresponding values for (S)-(+)-2-phenylpropanoic acid and (R)-(-)-2-hydroxy-2-phenylpropanoic acid were 99.0 and 81.0%, respectively. 3. These results imply that firstly, preferential omega-hydroxylation occurs at the pro-S methyl group and secondly, the oxidation is followed by stereochemical inversion of (R)-(-)-2-phenylpropanol to the corresponding (S)-(+)-acid.

引用

页码：1291 / 1298

页数：8

共 23 条

[1] BIOTRANSFORMATION OF 1,4-CINEOLE, A MONOTERPENE ETHER [J].

ASAKAWA, Y ;

TOYOTA, M ;

ISHIDA, T .

XENOBIOTICA, 1988, 18 (10) :1129-1134

[2] TERPENOID BIOTRANSFORMATION IN MAMMALS .4. BIOTRANSFORMATION OF (+)-LONGIFOLENE, (-)-CARYOPHYLLENE, (-)-CARYOPHYLLENE OXIDE, (-)-CYCLOCOLORENONE, (+)-NOOTKATONE, (-)-ELEMOL, (-)-ABIETIC ACID AND (+)-DEHYDROABIETIC ACID IN RABBITS [J].

ASAKAWA, Y ;

ISHIDA, T ;

TOYOTA, M ;

TAKEMOTO, T .

XENOBIOTICA, 1986, 16 (08) :753-767

[3] METABOLISM OF (+)-ENANTIOMER, (+/-)-ENANTIOMER AND (-)-ENANTIOMER OF ALPHA-METHYLFLUORENE-2-ACETIC ACID (CICLOPROFEN) IN RATS [J].

DEAN, AV ;

LAN, SJ ;

KRIPALANI, KJ ;

DIFAZIO, LT ;

SCHREIBER, EC .

XENOBIOTICA, 1977, 7 (09) :549-560

[4]

GERADE HW, 1963, IND HYGIENE TOXICOLO, V2, P1235

[5] SIMULTANEOUS GAS-CHROMATOGRAPHIC DETERMINATION OF CUMENE METABOLITES 2-PHENYLPROPANOL-1 AND 2-PHENYLPROPANOL-2 IN URINE [J].

GOENECHEA, S ;

OLEK, K ;

WARDENBACH, P .

JOURNAL OF CHROMATOGRAPHY, 1978, 154 (02) :282-284

[6] IDENTIFICATION AND DETERMINATION OF URINARY METABOLITES OF 2-ISOPROPYLNAPHTHALENE IN RABBITS [J].

HONDA, T ;

FUKADA, A ;

KIYOZUMI, M ;

KOJIMA, S .

EUROPEAN JOURNAL OF DRUG METABOLISM AND PHARMACOKINETICS, 1987, 12 (01) :11-16

[7] ASYMMETRIC SYNTHESIS .3. STEREOSPECIFIC SYNTHESIS OF (R)-2-HYDROXY-2-PHENYLPROPIONIC ACID AND (R)- AND (S)-2-CYCLOHEXYL-2-HYDROXY-2-PHENYLACETIC ACID . CONFIGURATIONAL RELATIONSHIP BETWEEN (R)[-)-2-HYDROXY-2-PHENYLPROPIONIC ACID AND (S)(+)-2-PHENYLPROPIONIC ACID [J].

INCH, TD ;

LEY, RV ;

RICH, P .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (13) :1693-&

[8]

ISHIDA T, 1977, TETRAHEDRON LETT, P2437

[9] TERPENOID BIOTRANSFORMATION IN MAMMALS .5. METABOLISM OF (+)-CITRONELLAL, (+/-)-7-HYDROXYCITRONELLAL, CITRAL, (-)-PERILLALDEHYDE, (-)-MYRTENAL, CUMINALDEHYDE, THUJONE, AND (+/-)-CARVONE IN RABBITS [J].

ISHIDA, T ;

TOYOTA, M ;

ASAKAWA, Y .

XENOBIOTICA, 1989, 19 (08) :843-855

[10] TERPENOIDS BIOTRANSFORMATION IN MAMMALS .3. BIOTRANSFORMATION OF ALPHA-PINENE, BETA-PINENE, PINANE, 3-CARENE, CARANE, MYRCENE, AND RHO-CYMENE IN RABBITS [J].

ISHIDA, T ;

ASAKAWA, Y ;

TAKEMOTO, T ;

ARATANI, T .

JOURNAL OF PHARMACEUTICAL SCIENCES, 1981, 70 (04) :406-415

← 1 2 3 →