Natural Compounds

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

3α-(2′-Methylacryloyloxy)-eremophila-9(10),7(11)-dien-8-one (Methylacryloyloxy-isopetasol)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1040

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

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

C19H26O3: 302.1882

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

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

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

MS (mix.): 302 [M]+ [1]

HPLC [1]

1H NMR (360 MHz, CDCl3, TMS) (mix.): 1.00 (3H, d, J = 7, H-15), 1.05 (3H, s, H-14), 1.48 (1H, ddd, J = 4.5; 14; 11, H-2ax), 1.72 (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), 2.94 (1H, d, J = 14, H-6eq), 4.89 (1H, td, J = 11; 4.5; 11, H-3ax), 5.80 (1H, d, J = 1.8, H-9); OMeacr: 1.96 (3H, br s, H-4′), 5.59 (1H, m, H-3′a), 6.12 (1H, br s, H-3′b) [1]

13C NMR (CDCl3): OMeacr: 136.4...

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References

  1. 1.
    M. Neuenschwander, A. Neuenschwander, E. Steinegger, P. Engel, Helv. Chim. Acta 62, 609 (1979)CrossRefGoogle Scholar
  2. 2.
    F. Bohlmann, W. Otto, Liebigs Ann. Chem. 1982, 186 (1982)CrossRefGoogle Scholar

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