Natural Compounds

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

6β-Propionyloxy-furanoeremophil-1(10)-en-9-one

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1266

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

Biological sources: Senecio lanceus Aiton [1]; S. olivaceobracteatus Ric. et Mart. [2]; S. conrathii N.E. Br. [3]; Cacalia adenostyloides (Maxim.) Matsumura et Koidz. [4]

C18H22O4: 302.1518

Mp: 96°C [1]

[α]24 (λ, nm): −61° (589), −64° (578), −71.5° (546), −72° (436) (c 0.4) [1]

IR: 1740, 1180, 1680, 1630, 1600, 1520 [1]

MS: 302.153 [M]+ (0.5) (calc. for C18H22O4: 302.152), 246 (24), 228 (100), 213 (63), 57 (46) [1]

1H NMR (270 MHz, CDCl3, TMS): 0.98 (3H, d, H-15), 1.12 (3H, s, H-14), 1.4–1.6 (2H, m, J3α,4 = 4, J3β,4 = 10, H-3), 1.92 (3H, d, H-13), 1.96 (1H, ddq, J4,15 = 6.5, H-4), 2.24 (2H, m, H-2), 6.36 (1H, s, H-6), 7.01 (1H, t, J1,2 = 4, H-1), 7.40 (1H, q, J11,13 = 1, H-12); OProp: 1.24 (3H, t, J = 7, H-3′), 2.50 (2H, q, J = 7, H-2′) [1]

References

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    F. Bohlmann, C. Zdero, M. Grenz, Chem. Ber. 110, 474 (1977)CrossRefGoogle Scholar
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    J. Jakupovic, M. Grenz, F. Bohlman, H.M. Niemeyer, Phytochemistry 30(8), 2691 (1991)CrossRefGoogle Scholar
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    F. Bohlmann, N. Ates (Gören), R. M. King, H. Robinson, Phytochemistry 22(7), 1675 (1983)CrossRefGoogle Scholar
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    M. Kuroyanagi, H. Naito, T. Noro, A. Ueno, S. Fukushima, Chem. Pharm. Bull. 33, 4792 (1985)CrossRefGoogle Scholar

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