Natural Compounds

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

6β-Isobutyroyloxy-10β-hydroxy-furanoeremophil-2(3)-en-9-one

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1190

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

Biological sources: Senecio mauricei Hilliard et Burtt [1]

C19H22O6: 346.1416

Mp: 215°C (CHCl3 – ether) [1]

[α]24 (λ, nm): −106° (589), −113° (578), −130° (546), −260° (436), −382° (365) (c 0.1, CHCl3) [1]

CD: Δε302 −9.9, Δε279 +1.8, Δε233 −22.3 [1]

IR (CCl4): 3460, 1735, 1705, 1690, 1615, 1540 [1]

MS: 346.142 [M]+ (3), 318 (5), 258 (21), 177 (100) [1]

1H NMR (270 MHz, C6D6, 80°C, TMS): 0.88 (H, d, J = 7, H-15), 0.96 (3H, s, H-14), 1.68 (3H, d, J = 1, H-13), 2.30 (1H, ddq, J = 7; 10; 10.5, H-4), 4.74 (1H, s, OH), 5.89 (1H, br dd, J = 10; 10.5, H-3), 5.99 (1H, dd, J = 10; 10; 2.5, H-2), 6.35 (1H, br s, H-6), 6.81 (1H, br s, H-12); OiBu: 1.11 (3H, d, J = 7, H-4′), 1.13 (3H, d, J = 7, H-3′), 2.47 (1H, qq, J = 7; 7, H-2′) [1]

References

  1. 1.
    F. Bohlmann, C. Zdero, Phytochemistry 17(8), 1333 (1978)CrossRefGoogle Scholar

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