Natural Compounds

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

3α-[(E)-3-Methylthioacryloyloxy]-eremophila-9(10),7(11)-dien-8-one (Petasinone D)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1063

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

Biological sources: Petasites formosanus Kitam. [1]

C19H26O3S: 334.1603

Mp: 135–137°C (from EtOH) [1]

[α]D25 +42° (c 1.0, MeOH) [1]

UV (MeOH): 243 (4.10), 276 (4.40) [1]

IR (KBr): 3040, 3020, 1690, 1665, 1620, 1570, 1210, 1150, 1000, 860, 690 [1]

EI-MS: 334 [M]+ (16), 218 (100), 161 (90), 148 (25) [1]

HR-MS: 334.1597 [M]+ (calc. for C19H26O3S: 334.1604) [1]

1H NMR (300 MHz, CDCl3): 0.96 (3H, d, J = 6.6, H-15), 1.02 (3H, s, H-14), 1.82 (3H, s, H-13), 2.06 (3H, d, J = 1.5, H-12), 2.12 (1H, dq, J = 12.6; 1.5, H-6b), 2.90 (1H, d, J = 12.6, H-6a), 4.91 (1H, td, J = 11.0; 4.8, H-3), 5.76 (1H, d, J = 1.5, H-9); acyl group: 2.32 (3H, s, S-CH3), 5.64 (1H, d, J = 14.7, H-2′), 7.74 (1H, d, J = 14.7, H-3′) [1]

13 C NMR (300 MHz, CDCl 3): [ 1]

Table 1

C-1

30.1

C-8

191.6

C-14

17.1

2

31.7

9

126.7

15

10.7

3

73.3

10

164.8

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References

  1. 1.
    Y.-L. Lin, J.-C. Ou, C.-F. Chen, Y.-H. Kuo, Chem. Pharm. Bull. 46, 1807 (1998)CrossRefGoogle Scholar

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