Natural Compounds

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

3α-Senecioyloxy-eremophila-9(10),7(11)-dien-8-one (Senecioyloxy-isopetasol)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1072

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

Biological sources: Petasites hybridus (L.) (= P. officinalis Moench) [1]

C20H28O3: 316.2038

Mp: mix. with the methylacryloyloxy-isopetasol [1]

UV (cyclohexane) (mix.) 268 [1]

IR (CCl4) (mix.): 1708, 1663, 1627 [1]

MS (mix.): 316.2049 [M]+ (calc. for C20H28O3: 316.2038) [1]

HPLC: [1]

1H NMR (360 MHz, CDCl3, TMS) (mix.): 0.99 (3H, d, J = 7, H-15), 1.04 (3H, s, H-14), 1.48 (1H, ddd, J = 4.5; 14; 11, H-2ax), 1.64 (1H, q, J = 11; 7, H-4ax), 1.86 (3H, s, H-13), 2.10 (3H, d, J = 2, H-12), 2.18 (1H, t, J = 14; 2, H-6ax), 2.2 (1H, q, J = 5; 2.5; 14; 4.5, H-2eq), 2.36 (1H, dq, J = 15; 2.5; 4.5, H-1eq), 2.48 (1H, qq, J = 15; 5; 1.8, H-1ax), 2.93 (1H, d, J = 14, H-6eq), 4.87 (1H, td, J = 11; 4.5; 11, H-3ax), 5.79 (1H, d, J = 1.8, H-9); OSen: 1.92 (3H, d), 2.18 (3H, d), 5.68 (1H, m, H-2′) [1]

13C NMR (CDCl3):...

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References

  1. 1.
    M. Neuenschwander, A. Neuenschwander, E. Steinegger, P. Engel, Helv. Chim. Acta 62, 609 (1979)CrossRefGoogle Scholar

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