Natural Compounds

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

3α-[4-(Hex-2E-enoyloxy)-hex-2E-enoyloxy]-8α,9α-dihydroxy-7β,10αH-eremophil-11(12)-ene (3α-[4-(Pent-2′E-enoyloxy)-pent-2E-enoyloxy]-8α,9α-dihydroxy-7β,10αH-eremophil-11(12)-ene)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1070

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

Biological sources: Senecio erubescens Aiton var. crepidifolius DC. [1]

C27H42O6: 462.2980

Mp: colorless oil [1]

[α]D −75° (c 0.34, CHCl3) [1]

IR (CCl4): 3570, 1725, 1640 [1]

MS: 462.298 [M]+ (1) (calc. for C27H42O6: 462.298), 444 (0.5), 426 (0.3), 236 (30), 218 (15), 97 (100) [1]

TLC: Et2O – petrol (9:1) [1]

HPLC: MeOH – H2O (4:1), Rt 5.8 min [1]

1H NMR (400 MHz, CDCl3, TMS): 0.79 (3H, s, H-14), 0.84 (3H, d, J = 7, H-15), 1.43 (1H, m, H-4), 1.48 (1H, ddd, J = 11; 3.5; 11, H-10), 1.50 (1H, dd, J = 13; 13, H-6b), 1.81 (3H, br s, H-13), 2.00 (1H, br d, J = 13; 3, H-6a), 2.25 (1H, br dd, J = 3; 13; ∼2; ∼2, H-7), 3.48 (1H, br dd, J = 11; ∼2, H-9), 3.98 (1H, br s, H-8), 4.82 (1H, br s, H-12b), 4.83 (1H, ddd, J = 11; 11; 5, H-3), 4.99 (1H, br s, H-12a); acyl groups: 0.91 (3H, t, J = 7, H-6″), 0.95 (3H, t, J...

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References

  1. 1.
    F. Bohlmann, C. Zdero, J. Jakupovic, L.N. Misra, S. Banerjee, P. Singh, R.N. Baruah, M.A. Metwally, G. Schmeda-Hirschmann, L.P.D. Vincent, R.M. King, H. Robinson, Phytochemistry 24(6), 1249 (1985)CrossRefGoogle Scholar

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