Natural Compounds

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

6α-Cinnamoyloxy-4β-hydroxy-5α(H)-dauc-7-en-9-one (Lancerodiol t-Cinnamate)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_881

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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]

C24H30O4: 382.2144

Mp: colorless gum [1]

IR (NaCl): 3525, 2965, 1710, 1660, 1640, 1580, 1500, 1450, 1340, 1310, 1280, 1202, 1170, 1045, 980, 862, 770, 753, 710, 683 [1]

CI-MS: 383 [M + H]+ (1.9), 365 [M − H2O + H]+ (9.2), 341 [M − C3H7 + H]+ (3.8), 235 [M − t-cinnamic acid + H]+ (62.7), 219 [M − C9H8O3 + H]+ (100), 217 [M − t-cinnamic acid − H2O + H]+ (50), 201 (13.2), 149 [t-cinnamic acid + H]+ (13.6), 131 [t-cinnamate acyllium]+ (8.5) [1]

1H NMR(400 MHz): 0.91 (3H, d, J = 7, H-12), 0.94 (3H, d, J = 7, H-13), 1.21 (3H, s, H-14), 1.89 (3H, dd, J = 1.5; 1.5, H-15), 1.82 (1H, qq, J = 7; 7.0, H-11), 2.59 (1H, br d, J = 15.5, H-10α), 2.71 (1H, d, J = 15.5, H-10 β), 6.15 (1H, dq, J = 1.5; 3, H-7), 5.96 (1H, ddq, J = 11.5; 11.5; 3.0, H-6), 2.42 (1H, d, J = 11.5, H-5),...

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References

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

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