Natural Compounds

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

6α-(4′-Hydroxy-benzoyloxy)-5α(H)-dauc-8-ene-2β,4β-diol (6α-p-Hydroxybenzoyl Akichenol; 2β-Hydroxy-6-p-hydroxybenzoyl-jaeschkeanadiol)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_889

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

Biological sources: Ferula jaeschkeana Vatke [1], F. sinaica Boiss. [2]

C22H30O5: 374.2093

Mp: 125–126°C (MeOH), needles [1]

[α]D30 +31° (c 2.0, CHCl3) [1], [α]D24 +14° (c 1.75, CHCl3) [2]

UV (MeOH) 256 (4.35); UV (MeOH/KOH) 294 (4.10) [1]

IR (KBr): 3300, 2980, 1690, 1600, 1590, 1510, 1440, 1365, 1110, 1090, 940, 825 [1]

IR (CHCl3): 3660, 3610, 1720 [2]

MS: 356 [M − H2O]+ (1.7), 338 (1.30), 331 [M − 43]+ (47.2), 313 (6.7), 236 (7), 217 (3), 193 [M − C3H7 − C6H4(OH)COOH]+ (6), 191 (7), 175 (7), 157 (7.6), 149 (20), 138 (100), 133 (37), 121 (100), 119 (55), 83 (22), 81 (36) [1]

TLC: CHCl3 – MeOH (47:3), Rf 0.42 [1]

1H NMR (400 MHz, CDCl3, TMS): 0.88 (3H, d, J = 7, H-12), 0.92 (3H, d, J = 7, H-13), 1.19 (3H, s, H-14), 1.81 (3H, s, H-15), 1.62 (1H, m, H-7a), 1.99 (1H, dd, J = 14; 10, H-10α), 2.30 (1H, dd, J = 14;...

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References

  1. 1.
    S.N. Garg, K. Vishwapaul, S.N. Rastogi, Phytochemistry 29(2), 531 (1990)CrossRefGoogle Scholar
  2. 2.
    A.A. Ahmed, Phytochemistry 30(4), 1207 (1991)CrossRefGoogle Scholar

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