Natural Compounds

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

3α-(2′-Methylacryloyloxy)-7αH-eremophila-9(10),11(12)-dien-8-one (Methylacryloyloxy-neopetasol)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1041

CAS Registry Number: 70238-52-7 Open image in new window

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-neopetasol [1]

UV (cyclohexane) (mix.): 226 [1]

IR (CCl4) (mix.): 1712, 1679, 1629 [1]

MS (mix.): 302.1887 [M]+ (calc. for C19H26O3: 302.1882) [1]

HPLC [1]

1H NMR (360 MHz, CDCl3, TMS) (mix.): 0.99 (3H, d, J = 7, H-15), 1.17 (3H, s, H-14), 1.41 (1H, q, J = 5; 11, H-2ax), 1.78 (3H, s, H-13), 1.92 (1H, t, J = 11; 7, H-4ax), 1.97 (1H, t, J = 14; 12.5, H-6ax), 2.03 (1H, t, J = 14; 5, H-6eq), 2.26 (1H, dd, J = 14; 5; 2.5, H-1eq), 2.36 (1H, td, J = 5; 2.5; 5, H-2eq), 2.59 (1H, dd, J = 14; 5; ≤ 3, H-1ax), 3.07 (1H, dd, J = 12.5; 5, H-7ax), 4.75 (1H, s, H-12-trans), 4.95 (1H, s, H-12-cis), 4.97 (1H, J = 11; 5; 11, H-3ax), 5.85 (1H, d, J = ≤ 3,...

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References

  1. 1.
    M. Neuenschwander, A. Neuenschwander, E. Steinegger, Helv. Chim. Acta 62, 627 (1979)CrossRefGoogle Scholar

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