Natural Compounds

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

6β-Isobutyroyloxy-9β-hydroxy-1β,10β-epoxy-furanoeremophilane

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1195

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

Biological sources: Senecio candollii Wedd. [1]

C19H26O5: 334.1780

Mp: gum [1]

IR (CCl4): 3600, 1740

MS: 334.178 [M]+ (6) (calc. for C19H26O5: 334.178), 246 [M – C3H7COOH]+ (44), 231 [246 – Me]+ (24), 217 [246 – CHO]+ (46), 189 [217 – CO]+ (96), 109 (60), 71 [C3H7CO]+ (100) [1]

1H NMR (400 MHz, CDCl3): 1.06 (3H, d, H-15), 1.30 (3H, s, H-14), 1.46 (1H, ddq, J = 3.5; 7, H-4), 1.70 (2H, m, J = 3.5, H-3), 1.70 (2H, m, J = 4; 5, H-2a, H-2b), 1.88 (3H, br s, H-13), 2.46 (1H, d, OH-10), 3.24 (1H, br d, J = 4; 5, H-1), 4.04 (1H, d, J = 2.5, H-9), 6.33 (1H, s, H-6), 7.19 (1H, br s, H-12); OiBu: 1.23 (3H, d, J = 7, H-4′), 1.26 (3H, d, J = 7, H-3′), 2.66 (1H, qq, J = 7, H-2′) [1]

References

  1. 1.
    S. Dupre, M. Grenz, J. Jakupovic, F. Bohlmann, H.M. Niemeyer, Phytochemistry 30(4), 1211 (1991)CrossRefGoogle Scholar

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