Natural Compounds

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

6α-Angeloyloxy-4β-hydroxy-5α(H)-dauc-8-en-10-one (Lapidin; 10-Oxo-jaeschkeanadiol Angelate)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_857

CAS Registry Number: 79863-24-4 Open image in new window

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

Biological sources: Ferula lapidosa Korov. [1]; F. latipinna A. Santos [2]; Heliopsis helianthoides (L.) Sweet [3]; Ferula communis L. subsp. communis [4]

C20H30O4: 334.2144

Mp: 80–81°C (hexane) [1]; colorless oil [3]; 79°C (hexane) (mix. with the 10-oxojaeschkeanadiol isovalerate, ca 4:1) [4]

[α]D20 +166.1° (c 1.5, CHCl3) [1]; (mix.): [α]D25 +97.5° (c 1.2, CHCl2) [4]

UV (EtOH): 218 (4.3), 230 (4.8) [1]; (mix.): 252 [4]

IR (KBr): 3550, 1640, 1710, 1230 [1]; (CCl4): 3460, 1710, 1660 [3]; (mix.): 3400, 1710, 1635, 1335, 1380, 1260, 1230, 1165, 1040 [4]

MS: 334 [M]+, 291, 251, 234, 216, 191, 173 [1]; 334.214 [M]+ (0.3), 291 (9), 234 (14), 191 (21), 83 (100) [3]

EI-MS (mix.): 334 [M]+ (1), 291 (25), 234 (50), 191 (82), 149 (90), 83 (100) [4]

HPLC: [3]

1H NMR (100 MHz, CDCl3, HMDS):...

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References

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    J. Jakupovic, A. Schuster, T.V. Chau-Thi, F. Bohlmann, X.A. Dominguez, Phytochemistry 27(7), 2235 (1988)CrossRefGoogle Scholar
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    G. Appendino, S. Tagliapietra, L. Paglino, G.M. Nano, D. Monti, V. Picci, Phytochemistry 29(5), 1481 (1990)CrossRefGoogle Scholar

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