Natural Compounds

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

2α-Angeloyloxy-6α-(4″-hydroxy-benzoyloxy)-5α(H)-dauc-8-en-4β-ol (Akichenin)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_955

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

Biological sources: Ferula akitschkensis B. Fedtsch. [1]; F. soongarica Pall. ex Spreng. [2]; F. jaeschkeana Vatke [3]

C27H36O6: 456.2461

Mp: 162–163°C [1]

[α]D −8.3° (c 0.9, CHCl3) [1]

UV 260 (4.16) [1]

IR: 3600–3200, 1710–1695, 1625, 1590, 1520 [1]

MS: 438 [M − H2O]+, 413, 318, 275, 235, 203, 200, 175 [1]

1H NMR (100 MHz, CDCl3, TMS): 0.72 and 0.90 (each 3H, d, J = 7.0, H-12, H-13), 1.11 (3H, s, H-14), 1.7 (3H, s, H-15), 2.4 (2H, m, H-3), 4.5 (1H, t, J = 7, H-2), 5.30 (1H, t J = 10.0; 2, H-6), 7.52 (1H, s, OH), 7.6 (1H, s, OH); OAng: 1.85 (3H, s, H-5′), 1.92 (3H, s, H-4′), 6.08 (1H, q, J = 7; 1.5, H-3′); Op-HOBz: 6.9 (2H, d, J = 10, H-3″, H-5″), 7.9 (2H, d, J = 10, H-2″, H-6″) [1]

1H NMR (100 MHz, CDCl3, TMS): 0.72 and 0.90 (each 3H, d, J = 7.0, H-12, H-13), 1.12 (3H, s, H-14), 1.76 (3H, br s, H-15), 4.6 (1H,...

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References

  1. 1.
    A.Sh. Qadirov, A.I. Saidkhodzhaev, G.K. Nikonov, Chem. Nat. Comp. 12, 93 (1976)CrossRefGoogle Scholar
  2. 2.
    N.N. Najmitdinova, A.I. Saidkhodzjaev, Chem. Nat. Comp. 29, 804 (1993)CrossRefGoogle Scholar
  3. 3.
    E.Kh. Khalilova, A.I. Saidkhodzhaev, Chem. Nat. Comp. 34, 516 (1998)CrossRefGoogle Scholar

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