Natural Compounds

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

2β-Acetoxy-9β-hydroxy-5,6,10α(H)-muurola-3,11(13)-dien-12-oic Acid (9(S)2-Acetylepizafrone)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_808

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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]

C17H24O5: 308.1624

Isolated as its methyl ester (methyl 9(S)2-acetylepizafronate) [1]

Mp (Me ester): 99–101°C [1]

[α]D (Me ester): −113° (c 2.1, CHCl3) [1]

IR (melted) (Me ester): 3400, 1740, 1725, 1640, 1450, 1380, 1250, 1200, 1150, 1070, 1030, 990, 960, 950, 890, 860 [1]

MS (Me ester): 280 [M – –CH2C=O]+ (3), 262 (11), 244 (4), 230 (8), 212 (11), 185 (16), 132 (85), 113 (33), 110 (32), 93 (67), 91 (100), 77 (56), 43 (78) [1]

1H NMR (200 MHz, CDCl3, TMS) (Me ester): 1.20 (3H, s, H-14), 1.38 (1H, dd, J = 2; 6, H-1ax), 1.50 (4H, m, H-7, H-8), 1.68 (3H, d, J = 1.5, H-15), 1.85 (1H, ddd, J = 2; 6; 10, H-10), 2.08 (3H, s, OAc), 2.45 (1H, ddd, J = 5; 10; 12, H-5), 2.65 (1H, dd, J = 1.5; 2, H-1eq), 2.70 (1H, ddd, J =...

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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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