Natural Compounds

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

2α-Acetoxy-6α-benzoyloxy-5α(H)-dauc-8-en-4β-ol (2-Acetoxy-6-benzoyl Jaeschkeanadiol)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_943

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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]; F. communis L. [2]

C24H32O5: 400.2250

Mp: gum [1]

Mp: 116–118°C [2]

[α]D +12.5° (c 0.08, CHCl3) [2]

UV (CHCl3): 285 (ε 1230), 273 (ε 1730), 246 (ε 6550) [1]

IR (CHCl3): 3480, 2980, 2940, 2882, 1720, 1710, 1608, 1582, 1510, 1450, 1380, 1320, 1300, 1260, 1120, 1075, 1032, 732 [1]

MS: 357 [M − iso-Pr]+ (20.4), 297 [M − iso-Pr − HOAc]+ (29.1), 218 [M − C6H5CO2H − HOAc]+ (46.2), 175 [M − C6H5CO2H − HOAc − iso-Pr]+ (46.2), 157 [M − C6H5CO2H − HOAc − H2O]+ (29.5), 147 (67.8), 122 [C6H5COOH]+ (20.9), 105 [benzoate]+ (95), 43 (64.6) [1]

1H NMR: 0.81 (3H, d, J = 6.5, H-13), 0.96 (3H, d, J = 6.5, H-12), 1.13 (3H, s, H-14), 1.84 (3H, br s, H-15), 2.07 (3H, s, OAc), 2.28 (1H, dd, J = 2.1; 15, H-7β), 2.53 (1H d, J = 10.5, H-5), 4.89 (1H, d, J = 5.1, H-2), 5.47 (1H,...

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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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