Natural Compounds

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

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

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1061

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

Biological sources: Petasites hybridus (L.) (= P. officinalis Moench) [1, 2, 3, 4]; P. formosanus Kitam. [5, 6, 7]

C19H26O3S: 334.2508

Mp: 128–130°C [1]

[α]D22 +41.9° (CHCl3) [1]

[α]58925 +9.15°, [α]54625 +4.88° (c 1.64, MeOH) [2]

UV (cyclohexane): 236.5, 283.5 [1]

IR (CCl4): 1700, 1664, 1628 [1]

MS: 334.2505 [M]+ (calc. for C19H26O3S: 334.2508) [1]

GC/EI-MS: 334.2 [M]+ (10), 281.1 (0.3), 253.1 (0.1), 233.2 (0.6), 216.1 [M – C5H8OS]+ (98), 201.2 (33), 187.1 (8), 173.1 (14), 161.1 (100), 160.1 (32), 147.1 (13), 133.1 (13), 119 (9), 105.1 (12), 101.0 (25), 91.0 (12), 73.0(7), 67.0 (4), 57.0 (6), 41.0 (18) [2]

HPLC-DAD/ESI-MS: 970.3 (1), 936.8 (1), 832.5 (1), 705.7 (1), 668.5 (1), 556.2 (1), 520.9 (1), 455.4 (1), 375.0 (2), 337.0 (8), 336.0 (25), 335.0 (100), 332.9 (1), 218.2 (2), 217.3 (7), 147.1 (2),...

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