Natural Compounds

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

6α-Isobutyroyloxy-furanoeremophil-9(10)-en-1-one

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1171

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

Biological sources: Senecio pseudoorientalis Schischk. [1]

C19H24O4: 316.1675

Mp: colorless gum [1]

[α]24 (λ, nm): +100.0° (589), +101.8° (578), +120.0° (546), +209.4° (436) (c 0.17) [1]

IR (CCl4): 1735, 1680, 1575, 1535 [1]

MS: 316.167 [M]+ (17), 301 [M – Me]+ (4), 246 [M – O = C = CMe2]+ (24), 229 [M – C3H7COO]+ (100), 71 [C3H7CO]+ (26) [1]

1H NMR (270 MHz, CDCl3): 1.02 (3H, d, J = 7, H-15), 1.02 (3H, s, H-14), 1.83 (2H, m, J = 2; 3.5; 10; 7, H-3), 2.07 (3H, br s, H-13), 2.28 (1H, m, J = 7, H-4), 2.40 (1H, dd, J = 17; 10; 7, H-2′), 2.65 (2H, ddd, J = 17; 2, H-2), 5.84 (1H, s, H-6), 7.25 (1H, br s, H-12), 7.43 (1H, s, H-9); OiBu: 1.09 (3H, d, H-4′), 1.14 (3H, d, H-3′), 2.46 (1H, qq, H-2′) [1]

References

  1. 1.
    F. Bohlmann, J. Ziesche, Phytochemistry 19(8), 1851 (1980)CrossRefGoogle Scholar

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