Natural Compounds

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

6α-Coumaroyloxy-4β-hydroxy-5α(H)-dauc-7-en-9-one (Lancerodiol p-Coumarate)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_885

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Taxonomy: Physicochemical and Pharmacological Properties of Sesquiterpene Esters – The Bicyclic Sesquiterpene Esters – Daucanes (Carotanes) – Monoesters

Biological sources: Ferula rigidula DC. [1]

C24H30O5: 398.2093

Mp: colorless gum [1]

IR (NaCl): 3590, 2970, 1715, 1660, 1640, 1600, 1595, 1520, 1315, 1280, 1170, 980, 950, 905 [1]

CI-MS: 399 [M + H]+ (1.6), 381 [M − H2O + H]+ (7.6), 357 [M − C3H7 + H]+ (3.5), 235 [M − p-coumaric acid + H]+ (64.7), 219 [M − C9H8O + H]+ (89.4), 217 [M − p-coumaric acid − H2O + H]+ (56), 201 (11.5), 165 [p-coumaric acid + H]+ (12.5), 147 [p-coumarate acylium]+ (9.2) [1]

1H NMR (400 MHz, CDCl3, TMS): 0.92 (3H, d, J = 7, H-12), 0.95 (3H, d, J = 7, H-13), 1.22 (3H, s, H-15), 1.36 (1H, m, H-2α), 1.65 (1H, m, H-2β), 1.65 (1H, m, H-3α), 1.80 (1H, qq, J = 7; 7.0, H-11), 1.90 (3H, dd, J = 1.5; 1.5, H-14), 2.00 (1H, m, H-3β), 2.41 (1H, d, J = 11, H-5), 2.60 (1H, br d, J = 15.5, H-10α), 2.72 (1H, d, J = 15.5, H-10β), 5.96 (1H, ddq, J =...

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References

  1. 1.
    M. Miski, J. Jakupovic, Phytochemistry 29(1), 173 (1990)CrossRefGoogle Scholar

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