Natural Compounds

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

6α-Cinnamoyloxy-8α,9α-epoxy-5α(H)-dauc-4β-ol (Epoxy-jaeschkeanadiol t-Cinnamate)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_880

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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]

C24H32O4: 384.2301

Mp: colorless gum [1]

IR (NaCl): 3510, 2960, 1703, 1638, 1450, 1315, 1285, 1202, 1175, 980, 880, 768, 730, 710, 683 [1]

CI-MS: 385 [M + H]+ (4.3), 367 [M − H2O + H]+ (21.2), 237 [M − t-cinnamic acid + H]+ (5.8), 219 [M − t-cinnamic acid − H2O + H]+ (100), 201 [M − 2H2O + H]+ (12), 149 [t-cinnamic acid + H]+ (2.3), 131 [t-cinnamate acylium]+ (2) [1]

1H NMR (400 MHz, CDCl3, TMS): 0.90 (3H, d, J = 7, H-12), 0.91 (3H, d, J = 7, H-13), 1.20 (3H, s, H-14), 1.20 (1H, br ddd, J = 12; 9.5; 9.5, H-2β), 1.29 (1H, dd, J = 14.5; 7.0, H-10β), 1.48 (3H, s, H-15), 1.53 (1H, br dd, J = 12.0; 8.5, H-2α), 1.65 (1H, ddd, J = 15; 12; 8.5, H-3β), 1.80 (1H, d, J = 11, H-5), 1.88 (1H, ddd, J = 13.5; 11.0, H-7α), 1.95 (1H, dd, J = 15; 9.5, H-3α), 1.95 (1H, qq, J = 7; 7.0,...

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References

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

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