Natural Compounds

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

10α-(4′-Hydroxy-benzoyloxy)-5β-hydroxy-4α(H)-dauc-8-en-2-one

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_905

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

Biological sources: Ferula communis L. [1]

C22H28O5: 372.1937

Isolated as its p-methoxybenzoate after conversion with CH2N2:

Mp (its 4′-OCH3 deriv.): colorless needles [1]

[α]D25 (its 4′-OCH3 deriv.): −217° (c 1.2, CHCl3) [1]

UV (EtOH) (its 4′-OCH3 deriv.): 256 (4.3), 210 (4.4) [1]

IR (KBr) (its 4′-OCH3 deriv.): 3520, 1730, 1710, 1670, 1610, 1170, 1100, 1000, 850, 775 [1]

EI-MS (its 4′-OCH3 deriv.): 386 [M]+ (C23H30O5) (34), 251 [M − ArCO]+ (97), 233 [M − ArCO − H2O]+ (27), 135 [ArCO]+ (100), 107 [Ar]+ (46) [1]

CD (MeOH) (its 4′-OCH3 deriv.): Δε305 +1.2, Δε256 −3.9 [1]

ΔTAI (CDCl3) (its 4′-OCH3 deriv.): H-10: −0.18; H-9: −0.04; H-13: +0.08; H-14: +0.12 [1]

1H NMR (200 MHz, CDCl3, TMS) (its OCH3deriv.): 1.00 (3H, d, J = 7.2, H-12), 1.09 (3H, s, H-14), 1.12 (3H, d, J = 7.2, H-13), 1.74 (3H, s, H-15), 5.50 (1H,...

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References

  1. 1.
    M.G. Valle, G. Appendino, G.M. Nano, V. Picci, Phytochemistry 26(1), 253 (1987)CrossRefGoogle Scholar

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