Natural Compounds

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

2α-Acetoxy-6α-anisoyloxy-5α(H)-dauc-8-en-4β-ol (2α-Acetoxy-6α-p-anisate-jaeschkeanadiol)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_941

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

Biological sources: Ferula communis L. subsp. communis [1], Ferula communis L. [2]

C25H34O6: 430.2355

Mp: gum [1]

UV (CHCl3) 261 (ε 16200) [1]

IR (CHCl3): 3480, 2980, 2960, 2890, 1725, 1710, 1610, 1585, 1515, 1382, 1308, 1260, 1175, 1108, 1038, 952, 938, 855 [1]

MS: 387 [M − iso-Pr]+ (13.9), 327 [M − HOAc − iso-Pr]+ (7.4), 218 [M − p-anisic acid − HOAc]+ (32.2), 203 [M − p-anisic acid − HOAc − CH3]+ (8), 175 [M − p-anisic acid − HOAc − iso-Pr]+ (91.5), 157 [M − p-anisic acid – HOAc − iso-Pr − H2O]+ (16.3), 152 [p-anisic acid]+ (45.2), 147 (53.1), 135 [p-anisate]+ (100), 132 (75.2), 121 (38.1), 105 (61.3), 92 (43.4) [1]

1H NMR: 0.81 (3H, d, J = 6.5, H-13*), 0.94 (3H, d, J = 6.5, H-12*), 1.13 (3H, s, H-14), 1.82 (3H, br s, H-15), 2.07 (3H, s, OAc), 2.27 (1H, dd, J = 2.5; 14.5, H-7), 2.51 (1H, d, J = 10.5, H-5),...

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References

  1. 1.
    M. Miski, T.J. Mabry, Phytochemistry 24(8), 1735 (1985)CrossRefGoogle Scholar
  2. 2.
    M.A. Al-Yahya, I. Muhammad, H.H. Mirza, F.S. El-Feraly, Phytother. Res. 12, 335 (1998)CrossRefGoogle Scholar

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