Natural Compounds

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

2α,10α-Diacetoxy-6α-angeloyloxy-8α,9α-epoxy-5α(H)-dauc-4β-ol (Lapidolin)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_977

CAS Registry Number: 85179-08-4 Open image in new window

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

Biological sources: Ferula lapidosa Korov. [1]

C24H36O8: 452.2410

Mp: 187–189°C [1]

[α]D 27.7° (c 1.3, CHCl3) [1]

UV 218 (3.72) [1]

IR: 3500, 1755, 1720, 1650, 1240, 970 [1]

MS: 409 [M − 43]+, 349, 309, 249, 266, 232 [1]

1H NMR: 0.83 and 0.85 (each 3H, d, J = 7, H-12, H-13), 1.25 (3H, s, H-14), 1.41 (3H, s, H-15), 2.8 (1H, d, J = 5, H-9), 4.87 (1H, d, J = 6, H-2), 5.2 (1H, d, J = 5, H-10), 5.32 (1H, m, Σ1/2 = 24, H-6), 2.04 (6H, s, 2 × OAc); OAng: 6.0 (1H, s, H-3″) [1]

X-ray [2]

Pharm./Biol.: estrogenic activity [3]

References

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    L.A. Golovina, A.I. Saidkhodzjaev, V.M. Malikov, S. Melibaev, Chem. Nat. Comp. 18, 755 (1982)CrossRefGoogle Scholar
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    B. Tashkhodzhaev, M.K. Makhmudov, L.A. Golovina, A.I. Saidkhodzjaev, M.R. Yagudaev, V. M. Malikov, Chem. Nat. Compd. 20, 287 (1984)CrossRefGoogle Scholar
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    S.S. Nazrullaev, Z.A. Khushbaktova, V.N. Syrov, K.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

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