Natural Compounds

2013 Edition
| Editors: Shakhnoza S. Azimova, Ashraf I. Saidkhodzhaev

3α-[(Z)-3-Methylthioacryloyloxy]-7αH-eremophila-9(10),7(11)-dien-8-one (S-Petasin)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1060

CAS Registry Number: 70238-51-6 Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Sesquiterpene Esters – The Bicyclic Sesquiterpene Esters – Eremophilanes – Eremophilanes – Monoesters

Biological sources: Petasites hybridus (= P. officinalis Moench) [1, 2, 3, 4]; P. fragrans (Vill.) C. Presl [5]; P. formosanus Kitam. [6, 7, 8]; P. japonicus (Sieb. et Zucc.) Maxim. [9]

C19H26O3S: 334.2508

Mp: 123–124°C [1]; 123–125°C [5]

[α]D22 +66.4° (CHCl3) [1]; [α]D +51.0° (c 1.03, CHCl3) [5]; [α]D24 +57.7° (c 1.5, CHCl3) [9]

UV (cyclohexane): 231.5, 285.5 [1]; (EtOH): 237 (ε 12500), 290 (ε 12400) [5]

IR (CCl4): 1700, 1678, 1647, 1626 [1]; (nujol): 1675, 1650, 1630, 1560, 1220, 890 [5]

MS: 334.2506 [M]+ (calc. for C19H26O3S: 334.2508) [1]

MS: 334 [M]+, 319, 216, 201, 148 (100), 105, 101 [5]

CI-MS: 335 [M + 1]+, 279, 245, 231, 217 (base), 201, 175, 161, 148, 137 [9]

CD (MeOH, c 4.8 × 10−5): [θ]340 −111, [θ]310 −4660 (negative max.), [θ]255 0, [θ]222+29600 (positive...

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