Natural Compounds

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

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

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_809

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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 epi-2-acetylledesmate) [1]

Mp (Me ester): oil [1]

[α]D (Me ester): −70.5° (c 1.9, CHCl3) [1]

IR (film) (Me ester): 1740, 1725, 1630, 1440, 1375, 1245, 1210, 1150, 1030, 970, 900, 855, 820 [1]

MS (Me ester): 262 [M – –CH2C=O]+ (2), 244 (3), 239 (4), 212 (8), 184 (18), 156 (21), 143 (23), 132 (100), 117 (32), 91 (62), 43 (48) [1]

1H NMR (200 MHz, CDCl3, TMS) (Me ester): 1.40 (1H, dd, J = 2; 5, H-1ax), 1.75 (3H, d, J = 1.5, H-15), 1.80 (3H, d, J = 1.5, H-14), 2.10 (3H, s, OAc), 2.20 (2H, m, H-7), 2.34 (1H, dd, J = 1.5; 2, H-1eq), 2.38 (1H, ddd, J = 5; 8; 10, H-5), 2.43 (1H, ddd, J = 5; 5; 8, H-6), 2.68 (1H, ddd, J = 2; 5; 10, H-10), 3.76 (3H, s, OCH3), 5.20...

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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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