Natural Compounds

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

2β-Acetoxy-9α-ethoxy-5β,6α,10α(H)-cadina-3,11(13)-dien-12-oic Acid

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_806

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Taxonomy: Physicochemical and Pharmacological Properties of Sesquiterpene Esters – The Bicyclic Sesquiterpene Esters – Cadinanes – Cadalenes – Monoesters

Biological sources: Leucanthemopsis pulverulenta (Lag.) Heywood (=Pyrethrum hispanicum Willk.) [1]

C19H28O5: 336.1937

Isolated as its methyl ester [1]

Mp (Me ester): oil (hexane – ether 9:1) [1]

[α]D (Me ester): −71° (c 1.97, CHCl3) [1]

IR (film) (Me ester): 1740, 1725, 1630, 1445, 1380, 1240, 1200, 1150, 1070, 1030, 950, 820 [1]

MS (Me ester): 350 [M]+ (−), 262 (8), 244 (7), 230 (7), 212 (13), 185 (18), 132 (52), 99 (100), 91 (48), 86 (52), 71 (60), 43 (59) [1]

1H NMR (200 MHz, CDCl3, TMS) (Me ester): 1.11 (3H, t, J = 7, H-2′), 1.13 (3H, s, H-14), 1.55 (3H, br s, H-15), 2.05 (3H, s, OAc), 3.40 (1H, q, J = 7, H-6), 3.75 (3H, s, COOCH3), 5.35 (1H, m, H-4), 5.40 (1H, s, H-13a), 6.25 (1H, s, H-13b) [1]

References

  1. 1.
    J.P. de Teresa, V.M.A. Moreno, M.S. Gonzalez, I.S. Bellido, Tetrahedron 40, 2189 (1984)CrossRefGoogle Scholar

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© Springer Science+Business Media New York 2013