Natural Compounds

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

6α-Vanilloyloxy-4β-hydroxy-5α(H)-dauc-7-en-9-one (Lancerodiol Vanillate)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_931

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 orientalis L. var. orientalis [1]; F. rigidula DC. [2]

C23H30O6: 402.2042

UV: 263, 292 [1]

IR: 3380, 3080, 2960, 1710, 1690, 1655, 1610, 1598, 1516, 1450, 1385, 1275, 1100, 875, 850, 780, 760, 738 [1]

MS: 402 [M]+ (0.2), 329 (0.6), 234 (10.9), 216 (2.5), 191 (32.2), 168 (201), 163 (17.9), 151 (100), 148 (45.9) [1]

1H NMR: 0.85 (3H, d, J = 6.8, H-13), 0.97 (3H, d, J = 6.8, H-12), 1.26 (3H, s, H-14), 1.89 (3H, t, J = 1.7, H-15), 2.48 (1H, d, J = 11, H-5), 2.74 and 2.62 (2H, d, J = 15.6, H-10), 6.09 (1H, ddd, J = 2; 2.4; 11, H-6), 6.19 (1H, dd, J = 2; 2.4, H-7); OVan: 3.95 (3H, s, OCH3), 6.96 (1H, d, J = 8.4, H-5′), 7.58 (1H, d, J = 1.9, H-2′), 7.69 (1H, dd, J = 1.9; 8.4, H-6′) [1]

References

  1. 1.
    M. Miski, T.J. Mabry, J. Nat. Prod. 50, 829 (1987)CrossRefGoogle Scholar
  2. 2.
    M. Miski, J. Jakupovic, Phytochemistry 29(1), 173 (1990)CrossRefGoogle Scholar

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