Natural Compounds

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

3α-[(Z)-3-Methylthioacryloyloxy]-11-hydroxyeremophila-9(10),6(7)-dien-8-one (S-Petasitin)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1064

CAS Registry Number: 211691-00-8 Open image in new window

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

Biological sources: Petasites formosanus Kitam. [1]

C19H26O4S: 350.1553

Mp: 143–144°C; colorless needles (from EtOH) [1]

[α]D25 −15° (c 1.0, MeOH) [1]

UV (MeOH) 240 (4.43) [1]

IR (KBr): 3520, 3020, 1705, 1660, 1620, 1575, 1210, 1160, 1010, 800 [1]

EI-MS: 350 [M]+ (8), 335 (45), 214 (100), 199 (38), 160 (35) [1]

HR-EI-MS: 350.1558 (calc. for C19H26O4S, 350.1553) [1]

1H NMR (300 MHz CDCl3): 0.94 (3H, d, J = 6.6, H-15), 1.08 (3H, s, H-14), 1.44 (3H, s, H-12), 1.44 (3H, s, H-13), 4.75(1H, br s, OH-11), 4.97 (1H, td, J = 11.1; 4.8, H-3), 6.07 (1H, d, J = 1.5, H-9), 6.88 (1H, s, H-6); acyl group: 2.41 (3H, s, S-Me), 5.79 (1H, d, J = 10.5, H-2′), 7.07 (1H, d, J = 10.5, H-3′); signals of H-1; H-2; H-4 – not resolved [1]

13 C NMR (75 MHz, CDCl 3) [ 1]

Table 1

C-1

30.1

C-8

187.6

C-15

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References

  1. 1.
    Y.-L. Lin, C.-H. Mei, S.-L. Huang, Y.-H. Kuo, J. Nat. Prod. 61, 887 (1998)CrossRefGoogle Scholar

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