Natural Compounds

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

6α-(4′-Hydroxy-benzoyloxy)-5α(H)-dauc-8(15)-ene-4β,9α-diol (Ferugin)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_891

CAS Registry Number: 109517-72-8 Open image in new window

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: 140°C (MeOH), colorless needles [1]

[α]D +15.0° (c 1.5, MeOH) [1]

UV (MeOH) 258 (3.98) [1]

IR (KBr): 3300, 2980, 2880, 1680, 1610, 1590, 1460, 1410, 1370, 1280, 1160, 1120, 1050, 920, 850 [1]

MS: 356 [M − H2O]+ (20), 338 [M − 2H2O]+ (5), 331 [M − C3H7]+ (6.5), 312 (40), 236 [M − C6H4(OH)COOH]+ (5.5), 218 (4.5), 200 (20), 193 [M − C6H4(OH)COOH − C3H7]+ (12), 175 (45), 157 (8), 132 (30), 121 [C6H4(OH)COOH − OH]+ (100), 93 (25), 83 (5), 77 (5), 71 (25), 65 (70) [1]

Found: C, 70.80; H, 8.10. Calc. for C22H30O5: C, 70.58; H, 8.02% [1]

1H NMR(400 MHz, TMS): 0.80 (3H, d, J = 7, H-12), 0.89 (3H, d, J = 7, H-13), 1.18 (3H, s, H-14), 1.3-1.65 (4H, m, H-2, H-3), 1.30 (1H, dd, J = 12, 12,...

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References

  1. 1.
    S.N. Garg, S.K. Agarwal, V.P. Mahajan, S.N. Rastogi, J. Nat. Prod. 50, 253 (1987)CrossRefGoogle Scholar
  2. 2.
    A.A. Ahmed, Phytochemistry 30(4), 1207 (1991)CrossRefGoogle Scholar

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