Natural Compounds

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

6α-(4′-Hydroxy-benzoyloxy)-dauc-8(15)-ene-4β,9β-diol (4β,9β-Dihydroxy-6α-p-hydroxybenzoyloxy-dauc-8(15)-ene; 9-epi-6-p-Hydroxybenzoyl-isolancerotriol)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_892

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Taxonomy: Physicochemical and Pharmacological Properties of Sesquiterpene Esters – The Bicyclic Sesquiterpene Esters – Daucanes (Carotanes) – Monoesters

Biological sources: Ferula sinaica Boiss. [1]

C22H30O5: 374.2093

[α]D20 +21.9° (c 0.57, MeOH) [1]

IR (CHCl3): 3550, 3460, 1750, 1620 [1]

EI-MS: 331 [M − 43]+ (4), 313 [331 − 18]+ (0.6), 236 [M − 138]+ (7), 138 [p-hydroxy-benzoic acid]+ (3), 121 [p-hydroxybenzoyl acylium]+ (100) [1]

1H NMR (400 MHz, CDCl3): 0.83 (3H, d, J = 6.5, H-12), 0.86 (3H, d, J = 6.5, H-13), 1.33 (3H, s, H-14), 1.62 (1H, m, J = 6.5, H-11), 1.75 (1H, dd, J = 12; 14.5, H-10b), 2.03 (1H, dd, J = 6; 14.5, H-10a), 2.04 (1H, d, J = 10, H-5), 2.31 (1H, dd, J = 5, H-7b), 3.14 (1H, dd, J = 5, H-7a), 4.50 (1H, br s, H-9), 5.21 and 5.07 (each 1H, br s, H-15), 5.58 (1H, ddd, J = 10; 5; 5, H-6); Op-HOBz: 6.88 (2H, d, J = 7.5, H-3′, H-5′), 7.95 (2H, d, J = 7.5, H-2′, H-6′)

References

  1. 1.
    A.A. Ahmed, Phytochemistry 30(4), 1207 (1991)CrossRefGoogle Scholar

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