New monoterpene glucoside from the aerial parts of thyme (Thymus vulgaris L.)

A new monoterpene glucoside (1) was isolated from a methanol extract of the dried aerial parts of thyme (Thymus vulgaris L.), together with known 2- and 5-beta-D-glucopyranosylthymoquinols (2 and 3, respectively), and (-)-angelicoidenol-beta-D-glucopyranoside (4). The structure of 1 was elucidated to be (R)-p-cymen-9-yl beta-D-glucopyranoside by spectral evidence and enantioselective synthesis from (R)- and (S)-p-cymen-9-ol derived from p-cymen-8-ol.