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… | Zendy

Masayuki Suzuki | Zendy; Shigetaka Matsumoto | Zendy; Masaya Mizoguchi | Zendy; Satoshi Hirata | Zendy; Kazuteru Takagi | Zendy; Ikue Hashimoto | Zendy; Yumiko Yamano | Zendy; Masayoshi Ito | Zendy; Peter Fleischmann | Zendy; Peter Winterhalter | Zendy; Tetuichiro MORITA | Zendy; Naoharu Watanabe | Zendy

Open Access

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…

Author(s) -

Masayuki Suzuki,

Shigetaka Matsumoto,

Masaya Mizoguchi,

Satoshi Hirata,

Kazuteru Takagi,

Ikue Hashimoto,

Yumiko Yamano,

Masayoshi Ito,

Peter Fleischmann,

Peter Winterhalter,

Tetuichiro MORITA,

Naoharu Watanabe

Publication year - 2002

Publication title -

bioscience biotechnology and biochemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.509

H-Index - 116

eISSN - 1347-6947

pISSN - 0916-8451

DOI - 10.1271/bbb.66.2692

Subject(s) - triol , rosa × damascena , aroma , chemistry , steam distillation , terpene , distillation , chromatography , stereochemistry , organic chemistry , essential oil , food science , diol

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.

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