Natural Compounds

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

6α-Anisoyloxy-5α(H)-dauca-3,8-dien-2-one

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_864

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

Biological sources: Ferula communis L. subsp. communis [1]

C23H28O4: 368.1988

Mp: gum [1]

UV (CHCl3): 314 (sh) (ε 3100), 261 (ε 12840) [1]

IR (CHCl3): 2990, 2940, 2895, 1720, 1710, 1660, 1610, 1585, 1518, 1260, 1175, 1120, 1100, 1040, 938, 853 [1]

MS: 368 [M]+ (1.7), 340 [M − CO]+ (1.75), 300 [C18H12O4]+ (5.9), 290 (8.3), 234 [M − p-anisate + H]+ (2.9), 216 [M − p-anisic acid]+ (25.3), 201 (9.3), 191 [M − p-anisate − iso-Pr + H]+ (8.3), 173 [M − p-anisic acid − iso-Pr]+ (20.9), 159 (9.2), 152 [p-anisic acid]+ (11.5), 135 [p-anisate]+ (100), 83 (60.5) [1]

1H NMR (200 MHz, CDCl3): 1.1 (3H, d, J = 6.5, H-12*), 1.06 (3H, d, J = 6.5, H-13*), 1.26 (3H, s, H-14), 1.78 (3H, d, J = 2, H-15), 2.29 (1H, dd, J = 3.2; 15, H-7β), 2.57 (1H, septet, H-11), 2.92 (1H, br dd, J = 14.6; 15, H-7α), 3.35 (1H, dd, J = 2; 10.5, H-5),...

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References

  1. 1.
    M. Miski, T.J. Mabry, Phytochemistry 24(8), 1735 (1985)CrossRefGoogle Scholar

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