2 Scopus citations

Abstract

Benzo[c]chrysene (B[c]C), a weakly carcinogenic polycyclic aromatic hydrocarbon (PAH), has been detected in coal tar and crude oil. Its structure is intriguing in that it has a bay region and a fjord region in the same molecule. To study in vitro metabolism of B[c]C and to identify the metabolites of this compound, synthetic standards were needed. In this communication, we report the synthesis of B[c]C and its three proximate carcinogenic metabolites; namely, (±)-trans-1,2-dihydro-1,2-dihydroxyB[c]C (B[c]C-1,2-diol), (±)-trans-7,8-dihydro-7,8-dihydroxyB[c]C (B[c]C-7,8-diol), and (±)-trans-9, 10-dihydro-9,10-dihydroxyB[c]C (B[c]C-9,10-diol) from methoxy-substituted dinaphthylethylenes by photochemical cyclization. Major and minor phenolic metabolites of B[c]C were also synthesized.

Original languageEnglish (US)
Pages (from-to)301-312
Number of pages12
JournalPolycyclic Aromatic Compounds
Volume13
Issue number3
DOIs
StatePublished - Jan 1 1999

All Science Journal Classification (ASJC) codes

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

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