Natural Compounds

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

3α-[(Z)-3-Methoxyacryloyloxy]-eremophila-9(10),7(11)-dien-8-one (Petasinone C)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1067

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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]

C19H26O4: 318.1831

Mp: colorless oil [1]

[α]D25 +36° (c 0.7, MeOH) [1]

UV (MeOH): 234 (4.82), 275 (3.95) [1]

IR (film): 3020, 1700, 1660, 1615, 1200, 1150, 1100, 1020, 980, 880 [1]

EI-MS: 318 [M]+ (12). 216 (70), 201 (52), 161 (88), 148 (100), 105 (44), 85 (88) [1]

HR-MS: 318.1828 [M]+ (calc. for C19H26O4: 3l8.1832) [1]

1H NMR (300 MHz, CDCl3): 0.94 (3H, d, J = 6.6, H-15), 1.00 (3H, s, H-14), 1.85 (3H, s, H-13), 2.06 (3H, d, J = 1.5, H-12), 2.16 (1H, d, dq, J = 13.5; 1.5, H-6b), 2.87 (1H, d, J = 13.5, H-6a), 3.84 (3H, s, OCH3), 4.82 (1H, d, J = 7.0, H-2′), 4.83 (1H, td, J = 11.1; 4.5, H-3), 5.73 (1H, d, J = 1.5, H-9), 6.43 (1H, d, J = 7.0, H-3′) [1]

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

Table 1

C-1

30.2

C-8

191.7

C-14

17.1

2

31.6

9

126.5

15

10.6

3

72.5

10

165.5...

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References

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

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