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The progenitors of damascenone (1), the most intensive C13-norisoprenoid volatile aroma constituent of rose essential oil, were surveyed in the flowers of Rosa damascena Mill. Besides 9-O-beta-D-glucopyranosyl-3-hydroxy-7,8-didehydro-beta-ionol (4b), a stable progenitor already isolated from the residual water after steam distillation of flowers of R. damascena Mill., two labile progenitors were identified to be (3S, 9R)- and (3S, 9S)-megastigma-6,7-dien-3,5,9-triol 9-O-beta-D-glucopyranosides (2b) based on their synthesis and HPLC-MS analytical data. Compound 2b gave damascenone (1), 3-hydroxy-beta-damascone (3) and 4b upon heating under acidic conditions.

bioscience, biotechnology, and biochemistry

Identification of (3S, 9R)- and (3S, 9S)-Megastigma-6,7-dien-3,5,9-triol 9-O-β-<scp>D</scp>-glucopyranosides as Damascenone Progenitors in the…

Identification of (3S, 9R)- and (3S, 9S)-Megastigma-6,7-dien-3,5,9-triol 9-O-β-D-glucopyranosides as Damascenone Progenitors in the…