Natural Compounds

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

2β-Acetoxy-cadina-3,8,11(13)-trien-12-oic Acid (2-Acetylledesmane)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_805

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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]

C17H22O4: 290.1518

Isolated as its methyl ester (methyl 2-acetylledesmate) [1]

Mp (Me ester): colorless oil [1]

[α]D (Me ester): −11.7° (c 5.6, CHCl3) [1]

IR (film) (Me ester): 3080, 1740, 1725, 1630, 1440, 1375, 1245, 1150, 1100, 1025, 1000, 970, 825 [1]

MS (Me ester): 244 [M – AcOH]+ (8), 243 (13), 229 (6), 211 (18), 183 (20), 169 (21), 156 (21), 143 (23), 132 (100), 115 (38), 91 (50), 43 (38) [1]

1H NMR (200 MHz, CDCl3, TMS) (Me ester): 1.45 (1H, dd, J = 8; 10, H-1ax), 1.65 (6H, s, H-14, H-15), 2.02 (3H, s, OAc), 2.35 (1H, dd, J = 2; 5, H-1eq), 2.50 (1H, m, H-6), 2.60 (2H, m, H-7), 2.76 (1H, ddd, J = 2; 6; 9, H-5), 2.95 (1H, ddd, J = 2; 9; 10, H-10), 3.70 (3H, s, OCH3), 5.32 (1H, br s, H-4), 5.32 (1H, br s,...

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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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