Natural Compounds

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

3α-Angeloyloxy-furanoeremophil-9-one

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1117

CAS Registry Number: 53820-26-1 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. trilobus Harv., E. chrysanthemoides (DC.) B. Nord. [2]; Senecio smithii DC. [3]; S. aureus L. [4]

C20H26O4: 330.1831

Mp: 162°C [1]; 158–160°C [4]

UV: 269 (ε 12100) [1]

UV (EtOH): 280 (ε 11300), 217 (ε 9615) [4]

IR: 1730 (C=O), 1645, 1690, 1610, 1540 [1]

MS: 330.184 [M]+ (25) (calc. for C20H26O4 330.183), 315 (1), 230 (100), 215 (50), 201 (10), 187 (12), 83 (45), 55 (40) [1]

1H NMR (CCl4): 0.89 (3H, s, H-14), 0.96 (3H, d, H-15), 1.99 (3H, d, H-13), 2.38 (1H, d, J = 16, H-6α), 2.72 (1H, d, J = 16, H-6β), 4.74 (1H, ddd, H-3β), 7.28 (1H, q, H-12); OAng: 1.98 (3H, dq, J = 1; 1, H-5′), 1.89 (3H, dq, J = 7; 1, H-4′), 5.95 (1H, qq, J = 7; 1, H-3′) [1]

1H NMR (60 MHz, CDCl3, TMS): 0.88 (3H, s), 1.00 (3H, d, J...

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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, R.M. King, H. Robinson, Phytochemistry 20(10), 2389 (1981)CrossRefGoogle Scholar
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    L.H. Zalkow, L.T. Gelbaum, D. Van Derveer, J. Chem. Soc., Perkin Trans. 1 1542 (1979)CrossRefGoogle Scholar

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