Natural Compounds

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

6α-Vanilloyloxy-5α(H)-dauc-8-ene-2β,4β-diol (Jaeschferin; Yashferin)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_924

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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]

C23H32O6: 404.2199

[α]D +35° (c 1.0, CHCl3) [1]

UV (EtOH): 265 (3.78), 295 (3.51) [1]

IR: 3600–3200, 1690, 1590, 1520 [1]

MS: 361 [M − C3H7]+, 236 [M − C8H8O4]+, 193 [M − C3H7 − C8H8O4]+, 175 [M − C3H7 − C8H8O4 − H2O]+, 168 [C8H8O4]+ [1]

1H NMR: 0.91 and 1.01 (each 3H, d, J = 6.5, H-12, H-13), 1.12 (3H, s, H-15), 1.90 (3H, s, H-14), 3.52 (1H, t, J = 10, H-2), 5.42 (1H, sextet, J = 10.5: 10.5: 2.5, H-6), 5.62 (1H, m, H-9); OVan: 3.98 (3H, s, OCH3), 7.0 (1H, d, J = 8, H-5′), 7.60 (1H, d, J = 2, H-2′), 7.64 (1H, q, J = 10: 2.0, H-6′) [1]

References

  1. 1.
    K.B. Bijanova, A.I. Saidkhodzhaev, V.M. Malikov, Chem. Nat. Comp. 16, 127 (1980)Google Scholar

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