Natural Compounds

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

6α-Coumaroyloxy-5α(H)-dauc-8-en-4β-ol (Jaeschkeanadiol p-Coumarate)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_884

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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

Isolated as 6α-[4-acetoxy-coumaroyloxy]-5α(H)-dauc-8-en-4β-ol [1]:

Mp (its Coum(OAc) deriv.): colorless gum [1]

IR (NaCl) (its Coum(OAc) deriv.): 3520, 2962, 1769, 1702, 1635, 1600, 1505, 1370, 1318, 1203, 1167, 980, 835 [1]

CI-MS (its Coum(OAc) deriv.): 427 [M + H]+ (0.9), 409 [M − H2O + H]+ (100), 367 [M − H2O − acetate acylum + H]+ (12.8), 237 [M − p-acetylcoumarate acylium]+ (3.7), 221 [M − p-acetylcoumaric acid + H]+ (13.4), 219 [M − p-acetylcoumaric acid − H]+ (42.5), 203 [M − p-acetylcoumaric acid − H2O + H]+ (52.5), 189 [p-acetylcoumarate acylium]+ (4.6) [1]

1H NMR (400 MHz, CDCl3, TMS) (its Coum(OAc) deriv.): 0.89 (3H, d, J = 7, H-13), 0.93 (3H, d, J = 7.0, H-12), 1.06 (3H, s, H-15), 1.22 (1H, br ddd, J = 8.5; 11; 12, H-2β), 1.53 (1H, br...

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References

  1. 1.
    M. Miski, J. Jakupovic, Phytochemistry 29(1), 170 (1990)CrossRefGoogle Scholar

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