Natural Compounds

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

3α-[(E)-4-Methylsenecioyloxy]-7βH-eremophila-9(10),11(12)-dien-8-one (Petasol-[3-methyl-pent-2E-enoate])

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1052

CAS Registry Number: 79331-13-8 Open image in new window

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

Biological sources: Hoehnephytum imbricatum (Gardner) Cabrera [1]

C21H30O3: 330.2195

Mp: colorless gum [1]

[α]24 (λ, nm): +37.2° (589), +38.6° (578), +44.1° (546), +68.6° (436) (c 0.29, CHCl3) [1]

IR (CCl4): 1715, 1680, 1650 [1]

MS: 330.220 [M]+ (1.6), 216 (100), 201 (56), 97 (80) [1]

1H NMR: 0.97 (3H, d, J = 6.5, H-15), 1.25 (3H, s, H-14), 1.49 (1H, m, J = 14; 11, H-2α), 1.62 (1H, m, J = 14; 4, H-2β), 1.69 (1H, m, J = 11; 6.5, H-4α), 1.75 (3H, br s, H-13), 1.90 (1H, dd, J = 13; 14, H-6α), 2.04 (1H, dd, J = 13, H-6β), 2.35 (1H, ddd, J = 14; 4; 2, H-1α), 2.53 (1H, dddd, J = 14; 14; 4; 1.5, H-1β), 3.12 (1H, dd, J = 14; 1, H-7β), 4.83 (1H, br s, H-12′), 4.92 (1H, ddd, J = 11; 11; 4, H-3β), 4.99 (1H, dq, J = 1, H-12), 5.79 (1H, d, J = 1.5, H-9); OtMeSen: 1.09 (3H, t, J =...

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References

  1. 1.
    F. Bohlmann, M. Ahmed, H. Robinson, R.M. King, Phytochemistry 20(5), 1157 (1981)CrossRefGoogle Scholar

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