Natural Compounds

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

3α,9α-di(Hex-2′E-enoyloxy)-8α-hydroxy-7β,10αH-eremophil-11(12)-ene (3α,9α-di(Pent-2′E-enoyloxy)-8α-hydroxy-7β,10αH-eremophil-11(12)-ene)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1095

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

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

C27H42O5: 446.3032

Mp: colorless oil [1]

IR (CCl4): 3570, 1720 [1]

MS: 446.303 [M]+ (8) (calc. for C27H42O5: 446.303), 332 (4), 218 (100), 200 (8), 97 (73) [1]

TLC: C6H6–CH2Cl2 (1:1) [1]

HPLC: MeOH – H2O (4:1), Rt 7.5 min [1]

1H NMR (400 MHz, CDCl3, TMS): 0.84 (3H, d, J = 7, H-15), 0.87 (3H, s, H-14), 1.45 (1H, m, H-4), 1.50 (1H, m, H-10), 1.81 (3H, br s, H-13), 2.12 (1H, br d, J = 13; 3, H-6a), 2.30 (1H, br d, J = 3; 13; ∼2; ∼2, H-7), 4.07 (1H, br s, H-8β), 4.81 (1H, dd, J = 11; 11; 5, H-3), 4.88 (1H, br s, H-12b), 4.95 (1H, dd, J = 11; 2.5, H-9), 4.98 (1H, br s, H-12a), H-6b – overlapped multiplets; acyl group at C-3: 0.91 (3H, t, J = 7, H-6′), 1.5 (2H, m, H-5′), 2.61 (2H, ddt, J = 1.5; 7.5; 7, H-4′), 5.71 (1H, dt, J = 11; 1.5,...

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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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