Natural Compounds

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

6α-Vanilloyloxy-5α(H)-dauc-8(15)-ene-4β,9α-diol (Isolancerotriol 6-Vanillate)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_925

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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): 3525, 3460, 3000, 2960, 2900, 1715, 1625, 1615, 1525, 1480, 1445, 1400, 1300, 1210, 1125, 1055, 970, 950, 900 [1]

CI-MS: 403 [M − H]+ (1.2), 387 [M − H2O + H]+ (8.7), 369 [M − 2H2O + H]+ (1.8), 235 [M − vanillic acid − H]+ (8.3), 219 [M − vanillic acid − H2O + H]+ (47.8), 201 [M − vanillic acid − 2H2O + H]+ (100), 169 [vanillic acid + H]+ (11.8), 151 [vanillate acylium]+ (8.4) [1]

1H NMR (400 MHz, CDCl3, TMS): 0.84 (3H, d, J = 7, H-12), 0.88 (3H, d, J = 7, H-13), 1.20 (3H, s, H-14), 1.66 (1H, qq, J = 7; 7, H-11), 1.37 (1H, dd, J = 13; 10.5, H-10α), 2.24 (1H, dd, J = 13; 6, H-10β), 4.28 (1H, dd, J = 10.5; 6, H-9), 2.61 (1H, dd, J = 9.5; 4.0, H-7α), 2.65 (1H, dd, J = 9.5; 5, H-7β), 5.50 (1H, ddd, J = 10.5; 5; 4.5,...

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References

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

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