Natural Compounds

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

3β-Acetoxy-7αH-eremophila-1(10),11(13)-dien-2-on-12-oic Acid

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_991

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

Biological sources: Haeckeria pholidota (F. Muell.) J. H. Willis [1]

C17H22O5: 306.1467

C18H24O5: 320.1624 (methyl ester: 3β-Acetoxy-7αH-eremophila-1(10),11(13)-dien-2-on-12-oic acid methyl ester)

Mp: isolated as its methyl ester [1]

IR (CCl4) (methyl ester): 1745, 1730, 1680 [1]

MS (methyl ester): 320.162 [M]+ (18) (calc. for C18H24O5: 320.162), 289 (7), 260 (11), 220 (100), 188 (32), 165 (96), 149 (95), 108 (94) [1]

CD (MeOH) (methyl ester): Δε325 −0.46 [1]

TLC (methyl ester): CHCl3 – C6H6 – Et2O (9:9:2), Rf 0.50 min [1]

1H NMR (400 MHz, CDCl3, TMS) (methyl ester): 1.00 (3H, d, J = 7, H-15), 1.24 (3H, s, H-14), 1.56 (1H, dd, J = 14; 10, H-6b), 1.90 (1H, m, H-9b), 1.93 (1H, m, J = 4, H-8b), 1.95 (1H, br d, J = 14, H-6a), 2.12 (3H, s, OAc), 2.22 (1H, dq, J = 5; 7, H-4), 2.35 (1H, ddd, J = 8; 4; 14,...

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References

  1. 1.
    C. Zdero, F. Bohlmann, A. Anderberg, R.M. King, Phytochemistry 30(8), 2643 (1991)CrossRefGoogle Scholar

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