Natural Compounds

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

8α-Tigloyloxy-1β,10β-epoxy-7αH-eremophil-11(13)-ene

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1080

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

Biological sources: Senecio portalesianus Remy [1]

C20H30O3: 318.2190

IR (CCl4): 1720 [1]

MS: 318.219 [M]+ (0.5) (calc. for C20H30O3: 318.219), 218 (12), 203 (8), 200 (9), 83 (100) [1]

TLC: Et2O – petrol (1:1), Rf 0.75 [1]

1H NMR (400 MHz, CDCl3): 0.74 (3H, d, J = 7, H-15), 1.00 (3H, s, H-14), 1.21 (1H, dd, J = 5; 15, H-9b), 1.61 (1H, dd, J = 14; ∼2, H-6b), 1.72 (2H, br s, H-13), 1.76 (1H, m, H-4), 1.78 (1H, m, H-6a), 2.80 (1H, ddd, J = ∼2; 8.5; 9, H-7), 2.84 (1H, br d, J = 4, H-1), 2.84 (1H, dd, J = 7; 15, H-9a), 4.82 (3H, br s, H-12), 5.25 (1H, ddd, J = 9; 7; 5, H-8); OTigl: 1.76 (3H, dq, J = ∼1.5; ∼1.5, H-5′), 1.80 (3H, dq, J = 7; ∼1.5, H-4′), 6.86 (1H, qq, J = 7; ∼1.5, H-3′) [1]

References

  1. 1.
    J. Jakupovic, M. Grenz, F. Bohlmann, H.M. Niemeyer, Phytochemistry 30(8), 2691 (1991)CrossRefGoogle Scholar

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