Natural Compounds

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

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

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1042

CAS Registry Number: 70238-50-5 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.) (= P. officinalis Moench) [1, 2]

C19H26O3: 302.1882

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

UV (cyclohexane) (mix.): 225 [1]

IR (CCl4) (mix.): 1713, 1676, 1648, 1627 [1]

MS (mix.): 302.1880 [M]+ (calc. for C19H26O3: 302.1882) [1]

HPLC [1, 2]

1H NMR (360 MHz, CDCl3, TMS) (mix.): 0.97 (3H, d, J = 7, H-15), 1.25 (3H, s, H-14), 1.51 (1H, dtd, J = 5; 14; 11, H-2ax), 1.69 (1H, dq, J = 11; 7, H-4ax), 1.75 (3H, s, H-13), 1.87 (1H, dd, J = 13; 14.5, H-6ax), 2.04 (1H, dd, J = 13; 4.5, H-6eq), 2.24 (1H, dd, J = 14; 4.5, H-2eq), 2.38 (1H, dd, J = 14; 5, H-1eq), 2.54 (1H, tdd, J = 14; 1.8, H-1ax), 3.15 (1H, dd, J = 14.5; 4.5, H-7ax), 4.86 (1H, d, J = <1, H-12-trans), 4.92 (1H, td, J = 11; 4.5; 11, H-3ax), 5.01 (1H, d, J = 1.3, H-12-cis),...

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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.
    B. Debrunner, M. Neuenschwander, R. Brenneisen, Pharm. Acta Helv. 70, 167 (1995)CrossRefGoogle Scholar

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