Natural Compounds

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

6α-(3′,4′-Dihydroxy-benzoyloxy)-5α(H)-dauc-8-en-4β-ol (Akiferidin; Ferutinianin)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_886

CAS Registry Number: 70284-22-9 Open image in new window

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

Biological sources: Ferula akitschkensis B. Fedtsch. ex K.-Pol. [1], F. jaeschkeana Vatke [2]

C22H30O5: 374.2093

Mp: 53–54°C [1], 193–195°C [2]

[α]D +28.5° [1]; [α]D +28.5° (c 1.4, CHCl3) [2]

UV (EtOH): 265 (3.9), 300 (3.6) [1]; (EtOH): 210, 240, 260, 275 [2]

IR: 3600–3200, 1690, 1610, 1530, 1240 [1]

IR (KBr): 3410, 2960, 2860, 1705, 1645, 1450, 1270, 1150, 940 [2]

MS: 374.1979 [M]+ (calc. for C22H30O5: 374.4782), 356 [M − H2O]+, 331 [M − C3H7]+, 313 [M − C3H7 − H2O]+, 237 [M − C7H5O3]+, 219 [M − C7H5O3 − H2O]+, 193 [M − C7H5O3 − C3H7]+, 153 [C7H5O4]+, 137 [C7H5O3]+, 109 [C7H5O2]+, 55, 43, 28 [2]

1H NMR: 0.73 and 0.89 (each 3H, d, J = 7.5, H-12, H-13), 1.05 (3H, s, H-14), 1.76 (3H, br s, H-15), 5.16 (1H, sextet, J = 10.5; 10.5; 2.5, H-6), 5.42 (1H, m, H-9); acyl group: 6.70 (1H,...

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References

  1. 1.
    A.Y. Kushmuradov, A.Sh. Qadirov, A.I. Saidkhodzhaev, V.M. Malikov, Chem. Nat. Comp. 14, 617 (1978)CrossRefGoogle Scholar
  2. 2.
    T.K. Razdan, B. Qadri, M.A. Qurishi, M.A. Khuroo, P.K. Kachroo, Phytochemistry 28(12), 3389 (1989)CrossRefGoogle Scholar

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