Natural Compounds

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

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

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_986

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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]

C17H22O7: 338.1366

C18H24O7: 352.1522 (methyl ester: 2-Acetoxy-10β-hydroperoxy-7αH-eremophila-1(2),11(13)-dien-3-on-12-oic acid methyl ester)

Mp: isolated as its methyl ester [1]

IR (CCl4) (methyl ester): 3600, 1780, 1730, 1705 [1]

MS (methyl ester): 319 (2), 277 (80), 245 (28), 55 (100) [1]

1H NMR (400 MHz, CDCl3) (methyl ester): 0.90 (3H, s, H-14), 1.16 (3H, d, J = 7, H-15), 1.42 (1H, dd, J = 14; 12, H-6a), 1.58 (1H, m, J = 3, H-8a), 1.70 (1H, m, J = 14; 3, H-6b), 1.75 (1H, m, J = 12; 3; 15, H-8b), 2.23 (3H, s, OAc), 2.55 and 1.88 (2H, dt × 2, J = 15; 15, H-9), 2.71 (1H, t, J = 12; 12; 3, H-7), 3.05 (1H, q, J = 7, H-4), 3.77 (3H, s, OCH3), 5.60 (1H, br s, H-13a), 6.23 (1H, br s, H-13b), 6.69 (1H, s, H-1), 7.59 (s, OOH) [1]

References

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

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