Natural Compounds

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

6α-Vanilloyloxy-5α(H)-dauc-7-ene-4β,9α-diol (Lancerotriol 6-Vanillate)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_923

CAS Registry Number: 112501-46-9 Open image in new window

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): 3530, 3440, 2980, 2940, 2880, 1700, 1615, 1605, 1515, 1470, 1435, 1390, 1292, 1200, 1120, 1045, 945, 900 [1]

CI-MS: 387 [M − H2O + H]+ (1.1), 237 [M − vanillic acid + H]+ (1), 219 [M − vanillic acid − H2O + H]+ (74.2), 201 [M − vanillic acid − 2H2O + H]+ (100), 175 [M − vanillic acid − H2O – C3H7]+ (4.2), 169 (1.2), 151 (3.4) [1]

1H NMR (400 MHz, CDCl3, TMS): 0.85 (3H, d, J = 7, H-12), 0.92 (3H, d, J = 7, H-13), 1.19 (3H, s, H-14), 1.32 (1H, m, H-2α), 1.62 (1H, m, H-2β), 1.62 (1H, m, H-10α), 1.62 (1H, m, H-3α), 1.80 (1H, qq, J = 7; 7.0, H-11), 1.88 (3H, dd, J = 2.0; 2.0, H-15), 1.92 (1H, m, H-3β), 2.12 (1H, dd, J = 13.5; 5.0, H-10β), 2.19 (1H, d, J = 11, H-5), 4.30 (1H, br m, H-9),...

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References

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

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