Natural Compounds

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

6β-Isobutyroyloxy-4α-hydroxy-furanoeremophil-1(10)-ene (4α-Hydroxy-6β-(isobutyryloxy)euryopsin)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1184

CAS Registry Number: 53820-29-4 Open image in new window

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

Biological sources: Euryops hebecarpus (DC.) B. Nord. [1, 2]; E. linearis Harv., E. chrysanthemoides (DC.) B. Nord. [2]; E. jacksonii S. Moore [3]; Senecio deppeanus Hemsl. [4]

C19H26O4: 318.1831

Mp: oil [1]

[α]D24: +42.2° (589), +44.6° (578), +50.6° (546), +98° (436) (c 1.64)

IR: 3580 (br), 1720, 1640 [1]

MS: 318.182 [M]+ (38%) (calc. for C19H26O4 318.183), 230 [M – C3H7COOH]+ (100), 215 [230 – CH3]+ (32), 212 [230 – H2O]+ (36), 71 [C3H7CO]+ (52) [1]

1H NMR: 1.11 (3H, s, H-15), 1.21 (3H, s, H-14), 1.3–1.7 (2H, H-3), 1.78 (3H, d, J = 1, H-13), 2.05 (2H, H-2), 2.92 (1H, d, J = 16, H-9α), 3.41 (1H, br d, J = 16, H-9β), 5.54 (1H, m, H-1), 6.25 (1H, br s, H-6), 6.91 (1H, br s, H-12) [1]

References

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    F. Bohlmann, C. Zdero, M. Grenz, Chem. Ber. 107, 2730 (1974)CrossRefGoogle Scholar
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    F. Bohlmann, C. Zdero, Phytochemistry 17(7), 1135 (1978)CrossRefGoogle Scholar
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    P. Gonser, J. Jakupovic, G.M. Mungali, Phytochemistry 30(3), 899 (1991)CrossRefGoogle Scholar
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    F. Bohlmann, K.-H. Knoll, C. Zdero, P.K. Mahanta, M. Grenz, A. Suwita, D. Ehlers, N.L. Van, W.-R. Abraham, A.A. Natu, Phytochemistry 16(7), 965 (1977)CrossRefGoogle Scholar

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