Natural Compounds

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

3α-[4-(Hex-2E-enoyloxy)-hex-2E-enoyloxy]-9α-hydroxy-10αH-eremophil-7(11)-en-8-one (3α-[4-(Pent-2′E-enoyloxy)-pent-2E-enoyloxy]-9α-hydroxy-10αH-eremophil-7(11)-en-8-one)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1069

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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]

C27H40O6: 460.2825

Mp: colorless oil [1]

IR (CCl4): 3500, 1720 [1]

MS: 460.282 [M]+ (1) (calc. for C27H40O6: 460.282), 442 (0.5), 414 (2.5), 346 (1.5), 235 (26), 234 (32), 206 (30), 97 (100), 55 (87) [1]

TLC: C6H6 – CH2Cl2 – Et2O (3:3:1) [1]

HPLC: MeOH – H2O (4:1), Rt 7.1 min [1]

1H NMR (400 MHz, CDCl3, TMS): 0.92 (3H, s, H-14), 0.93 (3H, d, J = 7, H-15), 1.45 (1H, m, H-4), 1.48 (1H, ddd, J = 11, H-10), 1.81 (3H, d, H-13), 1.93 (3H, d, H-12), 2.91 (1H, d, J = 14, H-6a), 3.81 (1H, d, J = 11; 2.5, H-9), 4.83 (1H, ddd, J = 11; 11; 5, H-3), H-6b – overlapped multiplets; acyl groups: 0.91 (3H, t, J = 7, H-6″), 0.95 (3H, t, J = 7, H-6′), 1.45 (2H, tq, J = 7; 7, H-5″), 1.75 (2H, m, H-5′), 2.60 (2H, br dt, J = 7; 7, H-4″), 5.76 (1H, dt, 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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