Preparation, and analysis of 2-hydroxyarchaeol isomeric mixture prior to the determination of stereochemistry

抄録

A mixture of 2-hydroxyarchaeol isomers is chemically synthesized from commercially available racemic isophytol. In the gas chromatogram of TMS-derivative of the synthesized material, two peaks of equal intensity are observed, suggesting the occurrence of two stereoisomers at C-3 (hydroxylated carbon in the isoprenoid chain). The ¹³C NMR spectrum of the synthesized material is slightly different from that of 2-hydroxyarchaeol from microbial origin, which is also consistent with the occurrence of two isomers in the former. By contrast, natural 2-hydroxyarchaeol from microbes and sediments is inferred to consist of a single stereoisomer at C-3.