Natural Compounds

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

2α-Acetoxy-6α,10α-diangeloyloxy-5α(H)-dauc-8-en-4β-ol (Acetoxy Tingitanol)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_975

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

Biological sources: Ferula tingitana L. [1, 2]

C27H40O7: 476.2774

MP: 141–143°C [1]

IR: 3510, 2960, 1730, 1710, 1650, 1460, 1440, 1375, 1360, 1260, 1230, 1150, 1095, 1085, 1040, 990 [1]

MS: 476 [M]+ (0.2), 393 [M − C5H7O]+ (8), 333 [M − C8H15O2]+ (25.3), 317 [M − C7H11O4]+ (6.4), 293 [M − C10H15O3]+ (59.2), 234 [M − C12H18O5]+ (81.3), 216 (82.4), 191 (63.7), 173 (94.4), 83 (93.3), 43 (100) [2]

1H NMR (200 MHz, CDCl3): 0.90 (3H, d, J = 7, H-12), 0.94 (3H, d, J = 7, H-13), 1.20 (3H, s, H-14), 1.55 (1H, dd, J = 10; 14, H-2β), 1.84 (3H, br s, H-15), 2.05 (3H, s, OAc), 2.15 (1H, dd, J = 2; 14, H-7α), 2.42 (1H, dd, J = 8; 14, H-2α), 2.70 (1H, d, J = 10, H-9), 2.72 (1H, d. t, J = 10, H-7β), 4.72 (1H, t, J = 9, H-3), 4.82 (1H, dd, J = 8, H-4), 5.38 (1H, d, t, J = 2; 10; 10, H-8), 5.8 (1H, dd, J = 8, H-5); 2 × OAng: 1.9...

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References

  1. 1.
    M. Miski, A. Ulubelen, T.J. Mabry, W.H. Watson, I. Vickovic, M. Holub, Tetrahedron 40, 5197 (1984)CrossRefGoogle Scholar
  2. 2.
    M. Miski, T.J. Mabry, J. Nat. Prod. 49, 637 (1986)Google Scholar

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