Natural Compounds

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

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

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_807

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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 [1]

Mp (Me ester): 104–105°C (hexane) [1]

[α]D (Me ester): −76° (c 1.65, CHCl3) [1]

IR (melted) (Me ester): 3400, 1740, 1725, 1630, 1445, 1380, 1250, 1120, 1040, 1030, 975, 940, 915, 880, 850, 825 [1]

MS (Me ester): 262 [M – AcOH]+ (18), 244 (15), 230 (14), 212 (31), 185 (37), 172 (67), 144 (70), 132 (100), 110 (33), 99 (74), 93 (96), 91 (98), 72 (44), 43 (55) [1]

1H NMR (200 MHz, CDCl3, TMS) (Me ester): 1.20 (3H, s, H-14), 1.34 (1H, dd, J = 8; 10, H-1ax), 1.34 (4H, m, H-7, H-8), 1.58 (3H, br s, H-15), 1.80 (1H, ddd, J = 2; 10; 10, H-10), 2.07 (3H, s, OAc), 2.30 (1H, m, H-6), 2.48 (1H, dd, J = 2; 6, H-1eq), 2.50 (1H, ddd, J = 1.5; 9; 10, H-5), 3.76 (3H, s, COOCH3),...

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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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