Natural Compounds

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

13-Vanilloyloxy-5β,8β-epoxy-4α(H)-dauc-9-ol (13-Vanilloyloxydaucol)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_933

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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, 3470, 3010, 2975, 2920, 1720, 1630, 1620, 1530, 1450, 1410, 1310, 1220, 1135, 1070, 950 [1]

EI-MS: 404.21987 [M]+ (1.4) (calc. for C23H32O6: 404.21989), 253 [M − vanillate acylium]+ (0.4), 236 [M − vanillic acid]+ (1.8), 221 [M − vanillic acid − Me]+ (3.3), 219 [M − vanillic acid − H2O]+ (3.4), 192 (42), 168 [vanillic acid]+ (2), 151 [vanillate acylium]+ (38) [1]

1H NMR (400 MHz, C6D6, TMS): 1.07 (3H, s, H-14), 1.12 (1H, dd, J = 10.5; 12, H-10b), 1.15 (1H, m, H-3a), 1.31 (1H, m, H-7b), 1.38 (3H, s, H-15), 1.46 (1H, ddd, J = 3; 12; 12, H-6b), 1.47 (3H, d, J = 6.7, H-12), 1.50 (1H, dd, J = 5.5; 12, H-10a), 1.62 (2H, m, H-2), 1.72 (1H, ddd, J = 6; 9; 10, H-4), 1.80 (1H, m, H-3b), 1.90 (1H, ddd, J = 3; 10; 12,...

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References

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

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