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6α-(4′-Hydroxy-benzoyloxy)-8α,9α-epoxy-5α(H)-dauc-4β-ol (p-Oxybenzoyl-epoxy-jaeschkeanadiol; Tenuferidin; Epoxyjaeschkeanadiol p-Hydroxybenzoate; Jaeskeanin)

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Natural Compounds
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CAS Registry Number: 66559-24-8

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

Biological sources: Ferula tenuisecta Korov. [1, 2]; F. lancerottensis Parl. ex Hartung [3]; F. jaeschkeana Vatke [4]

C22H30O5: 374.2093

Mp: 164–165°C [1]

[α]D +75° (c 1.2, CHCl3) [1]

UV 263 (4.15) [1]

IR: 3550–3200, 1690, 1600, 1580, 1520 [1]; IR (CHCl3): 3600, 3350, 2970, 2890, 1695, 1620, 1590, 1515, 1450, 1385, 1310, 1270, 1170, 1120, 1100, 960, 920, 880, 850 [3]

EI-MS: 331 [M − C3H7]+, 234, 207, 191, 163, 151, 148 [3]

1 H NMR: 0.80 and 0.86 (6H, d, J = 6.5, H-12, H-13), 1.24 (3H, s, H-14), 1.45 (3H, s, H-15), 2.82 (1H, t, J = 6.5, H-9), 5.37(1H, sextet, J = 10.5; 10.5; 2.5, H-6); Op-HOBz: 6.72 (2H, d, J = 9.5, H-3′, H-5′), 7.75 (2H, d, J = 9.5, H-2′, H-6′) [1]

1 H NMR (90 MHz, CDCl3): 0.88 (6H, t, J = 8), 1.26 (3H, s, H-14), 1.48 (3H, s, H-15), 2.93 (1H, t, J = 8), 5.48 (1H, t, J = 11, H-6), 6.90...

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References

  1. A.I. Saidkhodzhaev Terpenoids from plants of the Ferula L. genus, Author’s Abstract of a Doctoral Dissertation in Chemical Sciences, Tashkent (1984)

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  2. A.I. Saidkhodzhaev, Chem. Nat. Comp. 14, 55 (1978)

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  3. B.M. Fraga, A.G. Gonzalez, P. Gonzalez, M.G. Hernandez, C.L. Larruga, Phytochemistry 24(3), 501 (1985)

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  4. T.K. Razdan, B. Qadri, M.A. Qurishi, M.A. Khuroo, P.K. Kachroo, Phytochemistry 28(12), 3389 (1989)

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(2013). 6α-(4′-Hydroxy-benzoyloxy)-8α,9α-epoxy-5α(H)-dauc-4β-ol (p-Oxybenzoyl-epoxy-jaeschkeanadiol; Tenuferidin; Epoxyjaeschkeanadiol p-Hydroxybenzoate; Jaeskeanin). In: Azimova, S.S., Saidkhodzhaev, A.I. (eds) Natural Compounds. Springer, New York, NY. https://doi.org/10.1007/978-1-4614-0539-9_900

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