Natural Compounds

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

6α-Cinnamoyloxy-5α(H)-dauc-8-en-4β-ol (Jaeschkeanadiol t-Cinnamate)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_879

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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]

C24H32O3: 368.2351

Mp: colorless gum [1]

IR (NaCl): 3520, 2965, 1703, 1640, 1450, 1312, 1285, 1205, 1180, 978, 770, 710, 683 [1]

CI-MS: 367 [M − H]+ (2.3), 351 [M − H2O + H]+ (100), 222 [M − t-cinnamic acid + 2 H]+ (25), 219 [M − t-cinnamic acid − H]+ (23.8), 203 [M − t-cinnamic acid − H2O + H]+ (42.6), 149 [t-cinnamic acid + H]+ (6.2), 131 [t-cinnamate acylium]+ (5.2) [1]

1H NMR (400 MHz, CDCl3): 0.91 (3H, d, J = 7, H-13), 0.94 (3H, d, J = 7, H-12), 1.07 (3H, s, H-14), 1.22 (1H, br ddd, J = 12, 11, 8.5, H-2β), 1.50 (1H, br dd, J = 12, 11, H-2α), 1.60 (1H, ddd, J = 14, 11, 8.5, H-3β), 1.82 (3H, br s, H-15), 1.93 (1H, d, J = 10.5, H-5), 1.94 (1H, m, H-10β), 1.94 (1H, m, H-11), 1.94 (1H, m, H-3α), 2.05 (1H, dd, J = 15, 8.5, H-10α), 2.27 (1H, dd, J = 14,3H-7β), 2.48...

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References

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

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