Natural Compounds

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

3α-Isobutyroyloxy-1α-hydroxy-1αH-furanoeremophil-9-one (1α-Hydroxyeuryopsonol Isobutyrate)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1170

Open image in new window

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

Biological sources: Senecio smithii DC. [1]

C19H26O5: 334.1780

Mp: colorless gum [1]

IR (CHCl3): 3520, 1730, 1665, 1540 (α-furan-ketone) [1]

MS: 334.178 [M]+ (2), 246 [M – C3H7COOH]+ (4), 228 [246 – H2O]+ (14), 213 [228 – CH3]+ (21), 163 [C10H11O2]+ (100), 71 [C3H7CO]+ (8) [1]

1H NMR (400 MHz, CDCl3): 0.86 (3H, s, H-14), 0.95 (3H, d, J = 7, H-15), 1.45 (1H, ddd, J = 11.5; 12, H-2α), 1.81 (1H, dq, J = 7, H-4), 2.01 (3H, br s, H-13), 2.40 (1H, ddd, J = 5; 12; 5, H-2β), 2.42 (1H, d, J = 11, H-10), 2.52 (1H, d, J = 17, H-6a), 2.71 (1H, d, J = 17, H-6b), 4.24 (1H, br ddd, J = 11.5; 5; 10, H-1β), 4.80 (1H, ddd, J = 11; 5, H-3β), 7.42 (1H, br s, H-12); OiBu: 1.17 (3H, d, H-4′), 1.18 (3H, d, H-3′), 2.56 (1H, qq, H-2′) [1]

References

  1. 1.
    F. Bohlmann, C. Zdero, R.M. King, H. Robinson, Phytochemistry 20(10), 2389 (1981)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2013