Natural Compounds

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

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

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_927

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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, 3440, 3000, 2960, 2900, 1708, 1630, 1618, 1530, 1482, 1450, 1403, 1305, 1205, 1130, 1050, 975, 955, 930, 900 [1]

CI-MS: 403 [M − H]+ (0.4), 387 [M − H2O + H]+ (1.5), 369 [M − 2H2O + H]+ (6.8), 237 [M − vanillic acid + H]+ (4.9), 235 [M − vanillic acid − H]+ (6.1), 219 [M − vanillic acid − H2O + H]+ (45.1), 201 [M − vanillic acid − 2H2O + H]+ (100), 169 [vanillic acid + H]+ (11.3), 151 [vanillate acylium]+ (5.9) [1]

1H NMR (400 MHz, CDCl3, TMS): 0.86 (3H, d, J = 7, H-13), 0.90 (3H, d, J = 7, H-12), 1.25 (3H, s, H-14), 1.35 (3H, s, H-15), 1.44 (1H, m, H-2b), 1.59 (1H, m, H-11), 1.63 (1H, m, H-3b), 1.65 (1H, m, H-2a), 1.96 (1H, m, H-3a), 2.11 (1H, br ddd, J = 1.5; 1.5; 16, H-7b), 2.43 (1H, dd, J = 5.5; 16,...

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References

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

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