Natural Compounds

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

6β-Isobutyroyloxy-1β,10β-epoxy-furanoeremophil-2(3)-en-9-one (Senmauricinolisobutyrate)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1182

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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]

C19H22O5: 330.1467

Mp: 118°C (ether–petrol) [1]

[α]24 (λ, nm): +430° (589), +453° (578), +535° (546), +1156° (436), +2951° (365) (c 0.6, CHCl3) [1]

CD: Δε364 +0.8, Δε346 +1.2, Δε331 +0.8, Δε370 +0.5, Δε278 +26.0, Δε235 −21.2 [1]

IR (CCl4): 3050, 1740, 1705, 1665, 1535 [1]

MS: 330.147 [M]+ (0.5) (C19H22O5), 260 (10), 242 (10), 177 (100) [1]

1H NMR (270 MHz, CDCl3, TMS): 1.15 (H, d, J = 7, H-15), 1.39 (3H, s, H-14), 1.92 (3H, d, J = 1, H-13), 2.15 (1H, m, H-4), 3.22 (1H, dd, H-1), 6.05 (2H, m, H-2, H-3), 6.44 (1H, s, H-6), 7.47 (1H, q, J = 1, H-12); OiBu: 1.27 (3H, d, J = 7, H-4′), 1.29 (3H, d, J = 7, H-3′), 2.73 (1H, qq, J = 7; 7, H-2′) [1]

1H NMR (270 MHz, C6D6, TMS): 1.08 (3H, d, J = 7, H-15), 1.24 (3H, s, H-14), 1.55 (3H, d, J = 1,...

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References

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

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