Natural Compounds

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

3α-Tigloyloxy-9β-hydroxy-10βH-eremophil-7(11)-en-8-one

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1079

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

Biological sources: Senecio ochoanus Cuatrec. [1]

C20H30O4: 334.2140

Mp: colorless gum [1]

[α]24 (λ, nm): −85° (589), −88° (578), −103° (546), −193° (436) (c 0.35, CHCl3) [1]

IR (CCl4): 3460, 1705, 1680, 1650 [1]

MS: 334.214 [M]+ (28) (C20H30O4), 234 (7), 216 (8), 206 (40), 191 (37), 83 (100), 55 (20) [1]

1H NMR (400 MHz, CDCl3, TMS): 0.96 (3H, d, J = 6.5, H-15), 0.98 (3H, s, H-14), 1.38 (1H, ddd, J = ∼3; 13; 11, H-2α), 1.50 (1H, m, H-1β), 1.56 (1H, dq, J = 10.5; 6.5, H-4), 1.57 (1H, ddd, J = 11; ∼3; 10, H-10β), 1.82 (3H, s, H-12), 1.87 (1H, d, J = 13.5, H-6α), 1.94 (3H, s, H-13), 2.08 (1H, ddd, J = 12; ∼3; ∼3, H-1α), 2.17 (1H, ddd, J = 13; 4.5; ∼3, H-2β), 2.92 (1H, d, J = 13.5, H-6β), 3.77 (1H, d, J = 2.5, OH), 3.84 (1H, dd, J = 11; 2.5, H-9α), 4.80 (1H, ddd, J = 11; 4.5; 10.5, H-3); OTigl: 1.81 (3H,...

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References

  1. 1.
    F. Bohlmann, N. Ates (Goren), R.M. King, H. Robinson, Phytochemistry 22 (7), 1675 (1983)CrossRefGoogle Scholar

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