Natural Compounds

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

6α-Vanilloyloxy-5α(H)-dauc-9-ene-4β,8β-diol

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_928

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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]

C23H32O6: 404.2199

Mp: colorless gum [1]

IR (CHCl3): 3560, 3450, 3000, 2970, 2910, 1715, 1630, 1620, 1530, 1485, 1450, 1405, 1310, 1210, 1130, 1055, 1030, 955, 900 [1]

CI-MS: 387 [M − H2O + H]+ (21.8), 369 [M − 2H2O + H]+ (5.1), 237 [M − vanillic acid + H]+ (0.9), 219 [M − vanillic acid − H2O + H]+ (100), 201 [M − vanillic acid − 2H2O + H]+ (24.2), 175 [M − vanillic acid − H2O − C3H7]+ (1.8), 169 [vanillic acid + H]+ (2.3), 151 [vanillate acylium]+ (2.2), 127 (18) [1]

1H NMR (400 MHz, CDCl3, TMS): 0.85 (1H, d, J = 7, H-13), 0.87 (3H, d, J = 7, H-12), 1.29 (3H, s, H-14), 1.39 (1H, m, H-2b), 1.58 (1H, qq, J = 7; 7, H-11), 1.62 (3H, s, H-15), 1.63 (1H, m, H-3b), 1.65 (1H, m, H-2a), 1.95 (1H, m, H-3a), 2.11 (1H, br td, J = 2; 15.5, H-7b), 2.47 (1H, d, J = 11, H-5), 2.51...

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References

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

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