Natural Compounds

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

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

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1066

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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 +18° (c 1.0, MeOH) [1]

UV (MeOH): 235 (4.45), 273 (3.76) [1]

IR (film): 3020, 1700, 1665, 1620, 1210, 1120, 1015 [1]

EI-MS: 318 [M]+ (15), 278 (15), 216 (100), 201 (60), 161 (100), 148 (38), 85 (64) [1]

HR-MS: 318.1826 [M]+ (calc. for C19H26O4: 318.1830) [1]

1H NMR (300 MHz, CDCl3): 0.96 (3H, d, J = 6.6, H-15), 1.01 (3H, s, H-14), 1.82 (3H, s, H-13), 2.06 (3H, d, J = 1.5, H-12), 2.16 (1H, dq, J = 13.6; 1.5, H-6b), 2.89 (1H, d, J = 13.6, H-6a), 3.68 (3H, s, OCH3), 4.87 (1H, td, J = 11.0; 4.8, H-3), 5.17 (1H, d, J = 12.6, H-2′), 5.75 (1H, d, J = 1.5, H-9), 7.61 (1H, d, J = 12.6, H-3′) [1]

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

Table 1

C-1

30.1

C-8

191.7

C-14

17.2

2

31.7

9

126.7

15

10.7

3

72.8

10

167.3

1′

165.3

4

46.3...

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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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