Natural Compounds

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

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

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1038

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

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

C19H28O3: 304.2038

UV (cyclohexane): 224.5, 267 [1]

IR (CCl4): 1729, 1663, 1625 [1]

MS: 304.2040 [M]+ (calc. for C19H28O3: 304.2038 [1]

HPLC: [1]

1H NMR (360 MHz, CDCl3, TMS): 0.97 (3H, d, J = 7, H-15), 1.03 (3H, s, H-14), 1.45 (1H, ddd, J = 4.5; 14; 11, H-2ax), 1.65 (1H, q, J = 11; 7, H-4ax), 1.85 (3H, s, H-13), 2.10 (3H, d, J = 2, H-12), 2.14 (1H, q, J = 5; 2.5; 4; 4.5, H-2eq), 2.18 (1H, t, J = 14; 2, H-6ax), 2.33 (1H, dq, J = 15; 2.5; 4.5, H-1eq), 2.46 (1H, qq, J = 15; 5; 1.8, H-1ax), 2.92 (1H, d, J = 14, H-6eq), 4.81 (1H, td, J = 11; 4.5; 11, H-3ax), 5.78 (1H, d, J = 1.8, H-9); OiBu: 1.17 (3H, d, J = 7, H-4′), 1.19 (3H, d, J = 7, H-3′), 2.55 (1H, septuplett, J = 7, H-2′) [1]

13 C NMR (CDCl 3): [ 1]

Table 1

191.4

46.2

 

17.1

170.1

42.2

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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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