Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 22, 1992 - Issue 11
21
Views
3
CrossRef citations to date
0
Altmetric
Original Article

Enantioselective metabolism of cumene

&
Pages 1291-1298 | Received 17 Dec 1991, Accepted 20 May 1992, Published online: 23 Apr 2010

References

  • Asakawa Y., Ishida T., Toyota M., Tkemoto T. Terpenoid biotransformation in mammals IV. Biotransformation of (+)-longifolene, (−)-caryophyllene, (−)-caryophyllene oxide, (−)-cyclocolorenone, (+)-nootkatone, (−)-elemol, (−)-abietic acid, and (+)-dehydroabietic acid in rabbits. Xenobiotica 1986; 16: 753–767
  • Asakawa Y., Toyota M., Ishida T. Biotransformation of 1,4-cineole, a monoterpene ether. Xenobiotica 1988; 18: 1129–34
  • Dean A. V., Lan S. J., Kripalani K. J., Difazio L. T., Schreiber E. C. Metabolism of the (+)-, (±)-, and (−)-enantiomers of α-methylfluorene-2-acetic acid (cicloprofen) in rats. Xenobiotica 1977; 7: 549–560
  • Goenechea S., Olek K., Wardenbach P. Simultaneous gas chromatographic determination of the cumeme metabolites 2-phenylpropanol-1 and 2-phenyl-propanol-2 in urine. Journal of Chromatography 1978; 154: 282–284
  • Gerade H. W. Industrial Hygiene and Toxicology, F. A. Patty. Interscience, New York 1963; Vol. II: 1235, Toxicology, 2nd edn
  • Honda T., Fukada A., Kiyozumi M., Kojima S. Identification and determination of urinary metabolites of 2-isopropylnaphthalene in rabbits. European Journal of Drug Metabolism and Pharmacokinetics 1987; 12: 11–16
  • Inch T. D., Ley R. V., Rich P. Asymmetric Synthesis. Part III, Stereo specific synthesis of (R)-2-hydroxy-2-phenylpropionic acid, and (R)- and -(S)-cyclohexyl-2-hydroxy-2-phenylacetic acid. Configurational relationship between (R)-(−)-2-hydroxy-2-phenylpropionic acid and (S)-(+)-2-phenylpropionic acid. Journal of the Chemical Society (C) 1968; 1693–1699
  • Ishida T., Asakawa Y., Okano M., Aratani T. Biotransformation of terpenoids in mammals. 1. Biotransformation of 3-carene and related compounds in rabbits. Tetrahedron Letters 1977, 28: 2437–2440
  • Ishida T., Asakawa Y., Takemoto T., Aratani T. Terpenoids biotransformation in mammals III: Biotransformation of α-pinene, β-pinene, pinane, 3-carene, carane, myrcene, and p-cymene in rabbits. Journal of Pharmaceutical Science 1981; 70: 406–414
  • Ishida T., Toyota M., Asakawa Y. Terpenoid biotransformation in mammals. V. Metabolism of (+)-citronellal, (±)-7-hydroxycitronellal, citral, (−)-perillaldehyde, (−)-myrtenal, cuminaldehyde, thujone, and (±)-carvone in rabbits. Xenobiotica 1989a; 19: 843–855
  • Ishida T., Matsumoto T., Asakawa Y. Enantioselective metabolism of p-cymene in rabbits. Abstract of Third European Symposium on Foreign Compound Metabolism. 1989b, A32, No. 84
  • Kaiser D. G., Vangiessen G. J., Reischer R. J., Wechteh W. J. Isomeric inversion of ibuprofen (R)-enantiomer in humans. Journal of Pharmaceutical Sciences 1976; 65: 269–273
  • Lan S. J., Kripalani K. J., Dean A. V., Egli P., Difazio L. T., Schreiber E. C. Inversion of optical configuration of α-methylfluorene 2-acetic acid (cicloprofen) in rats and monkeys. Drug Metabolism and Disposition 1976; 4: 330–339
  • Matsumoto T., Hayashi N., Ishida T., Asakawa Y. Metabolites of (+)-dehydroabietic acid in rabbits. Journal of Pharmaceutical Sciences 1990; 79: 540–547
  • Matsumoto T., Ishida T., Yoshida T., Terao H., Takeda Y., Assakawa Y. Enantioselective Metabolism of p-Cymene in Rabbits. Chemical & Pharmaceutical Bulletin 1992; 40: 1721–1726
  • Nakamura Y., Yamaguchi T. Stereoselective metabolism of 2-phenylpropionic acid in rat. 1. In vitro studies on the stereoselective isomerization and glucuronidation of 2-phenylpropionic acid. Drug Metabolism and Disposition 1987; 15: 529–534
  • Robinson D., Smith J. N., Williams R. T. Studies in Detoxication. 60. The metabolism of alkylbenzenes. Isopropylbenzene (cumene) and derivatives of hydrotropic acid. Biochemical Journal 1955; 59: 153–159
  • Simmonds R. G., Woodage T. J., Duff S. M., Green J. N. Stereospecific inversion of (R)-(−)-benoxaprofen in rat and man. European Journal Drug Metabolism Pharmacokinetics 1980; 5: 169–172
  • Sugiyama K., Trager W. F. Prochiral selectivity and intramolecular isotope effects in the cytochrome p-450 catalyzed ω-hydroxylation of cumene. Biochemistry 1986; 15: 7336–7343
  • Sullivan H. R., MacMahon R. E., Hoffman D. G., Ridolfo A. S. (1977) Metabolite identification by GC-MS: species differences in the metabolic patterns of isopropylbiphenyl. Mass Spectrum Drug Metabolism. Proceedings of an International Symposium. 1976, F. Alberto. Plenum, 31–43
  • Walde, et al. p-Cymene metabolism in rats and guinea-pig. Xenobiotica 1983; 13: 503–512
  • Yamaguchi T., Nakamura Y. Stereoselective disposition of hydratropic acid in rats. Drug Metabolism and Disposition 1986; 13: 614–619
  • Yamaguchi T., Nakamura Y. Stereoselective metabolism of 2-phenylpropionic acid in rat. 2. Studies on the organs responsible for the optical isomerization of 2-phenylpropionic acid in rat in vivo. Drug Metabolism and Disposition 1987; 15: 535–539

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.