Natural Compounds

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

6α-Isovanilloyloxy-5α(H)-dauc-8-en-4β-ol (Ferutin)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_915

CAS Registry Number: 41744-35-8 Open image in new window

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

Biological sources: Ferula tenuisecta Korov. [1]; F. kuhistanica Korov. [2]; F. pallida Korov. [3]; F. akitschkensis B. Fedtsch.ex K.-Pol. [4]; F. ovina Boiss. [5]; F. jaeschkeana Vatke [6]

C23H32O5: 388.2250

Mp: 130–131°C [1, 4, 5, 6]

[α]D +101.8° (c 1.08, MeOH) [1]; [α]D22 +100.1° (c 1.00, EtOH) [5]

UV: 260 (4.05) [1, 5]; (95% EtOH): 260 (4.07); (HOAc): 260 (4.08) [7]; 260 (4.38) [8]

IR: 3600–3300, 1710, 1610, 1595, 1515 [1, 5]

TLC: CHCl3 – EtOAc (30:1), Rf 0.42 ± 0.05 [7]; petrol – EtOAc (3:1), Rf 0.25 [8]

1H NMR: 0.79 and 0.89 (each 3H, d, J = 7.5, H-12, H-13), 1.05 (3H, s, H-15) 1.77 (3H, s, H-14), 5.22 (1H, sextet, J = 10.5; 10.5; 2.5, H-6), 5.50 (1H, m, H-9); OiVan: 3.90 (3H, s, OCH3), 6.93 (1H, d, J = 10.0, H-5′), 7.51 (1H, d, J = 2.5, H-2′), 7.54 (1H, d, J = 10.0; H-6′)...

This is a preview of subscription content, log in to check access.

References

  1. 1.
    A.I. Saidkhodzhaev, G.K. Nikonov, Chem. Nat. Comp. 8, 544 (1972)CrossRefGoogle Scholar
  2. 2.
    A.I. Babekov, A.I. Saidkhodzhaev, B.M. Keneshov, Chem. Nat. Comp. 36, 219 (2000)CrossRefGoogle Scholar
  3. 3.
    V.M. Potapov, G.K. Nikonov, Chem. Nat. Comp. 12, 739 (1976)CrossRefGoogle Scholar
  4. 4.
    A.Sh. Kadyrov, A.I. Saidkhodzhaev, G.K. Nikonov, U. Rakhmankulov, J. Chem. Nat. Comp. 13, 247 (1977)CrossRefGoogle Scholar
  5. 5.
    A.I. Saidkhodzhaev, G.K. Nikonov, Chem. Nat. Comp. 10, 539 (1974)CrossRefGoogle Scholar
  6. 6.
    E.Kh. Khalilova, A.I. Saidkhodzhaev, Chem. Nat. Comp. 34, 516 (1998)CrossRefGoogle Scholar
  7. 7.
    Y.I. Eidler, G.L. Genkina, T.T. Shakirov, Chem. Nat. Comp. 12, 551 (1976)CrossRefGoogle Scholar
  8. 8.
    M.P. Nurmukhamedova, G.K. Nikonov, Chem. Nat. Comp. 10, 749 (1974)CrossRefGoogle Scholar
  9. 9.
    S.S. Nazrullaev, Z.A. Khushbaktova, V.N. Syrov, Kh.S. Akhmedkhodzhaeva, A.I. Saidkhodzhaev, The chemistry and biological activity of synthetic and natural compounds, in Oxygen- and Sulfur-Containing Heterocycles, ed. by Prof. V.G. Kartsev, vol. 1 (IBS PRESS, Moscow, 2003), p. 329Google Scholar

Copyright information

© Springer Science+Business Media New York 2013