8-Hydroxygeraniol

Abstract: An operationally simple protocol for the conversion of geranyl acetate to 8-hydroxygeraniol is reported. The convenient two-step procedure relies on an efficient, chemo- and regioselective SeO2-promoted oxidation, followed by straightforward deacetylation. This facile means to prepare 8-hydroxygeraniol is expected to enable biosynthetic studies pertaining to thousands of monoterpene indole alkaloids.

Abstract: Despite being isomers having the same citrus-like, floral odor, geraniol, 1, and nerol, 3, show different odor thresholds To date, no systematic studies are at hand elucidating the structural features required for their specific odor properties Therefore, starting from these two basic structures and their corresponding esters, namely, geranyl acetate, 2, and neryl acetate, 4, a total of 12 oxygenated compounds were synthesized and characterized regarding retention indices (RI), mass spectrometric (MS), and nuclear magnetic resonance (NMR) data All compounds were individually tested for their odor qualities and odor thresholds in air (OT) Geraniol, the Z-isomer, with an OT of 14 ng/L, was found to be more potent than its E-isomer, nerol, which has an OT of 60 ng/L However, 8-oxoneryl acetate was the most potent derivative within this study, exhibiting an OT of 88 ng/L, whereas 8-oxonerol was the least potent with an OT of 493 ng/L Interestingly, the 8-oxo derivatives smell musty and fatty, whereas t