Natural Compounds

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

3α-[4-(Hex-2E-enoyloxy)-hex-2E-enoyloxy]-9α-hydroxy-7β,10αH-eremophil-11(13)-en-8-one (3α-[4-(Pent-2′E-enoyloxy)-pent-2E-enoyloxy]-9α-hydroxy-7β,10αH-eremophil-11(13)-en-8-one)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1068

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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: 102°C, colorless crystals [1]

IR (CHCl3): 3480, 1730 [1]

MS: 460.283 [M]+ (2.5) (calc. for C27H40O6: 460.283), 442 (1), 346 (3), 235 (26), 234 (25), 97 (100), 69 (30) [1]

TLC: C6H6 – H2Cl2 – Et2O (3:3:1) [1]

HPLC: MeOH – H2O (4:1), Rt 15.2 min [1]

1H NMR (400 MHz, CDCl3, TMS): 0.91 (3H, d, J = 7, H-15), 1.14 (3H, s, H-14), 1.45 (1H, m, H-4), 1.60 (1H, dd, J = 14; 5.5, H-6b), 1.78 (3H, br s, H-13), 2.11 (1H, dd, J = 14; 14, H-6a), 3.24 (1H, dd, J = 14; 5.5, H-7), 3.49 (1H, d, J = 3.5, OH), 3.98 (1H, dd, J = 11; 3.5, H-9), 4.78 (1H, br s, H-12b), 4.87 (1H, ddd, J = 11; 11; 5, H-3), 5.00 (1H, br s, H-12a), H-10 – overlapped multiplets; acyl groups: 0.91 (3H, t, J = 7, H-6″), 0.95 (3H, t, J = 7, H-6′), 1.45 (2H,...

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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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