Natural Compounds

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

13-Acetoxy-14-hydroxy-caryophyllen-7-one

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_832

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

Biological sources: Pulicaria dysenterica Gaertn. [1]

C17H24O4: 292.1675

Mp: colorless gum [1]

IR (CCl4): 3610, 3520, 3070, 1740, 1670, 1250, 900 [1]

MS: 292.167 [M]+ (1) (C17H24O4), 261 (4), 232 (10), 147 (30), 119 (31), 93 (80), 43 (100) [1]

1H NMR (400 MHz, CDCl3, TMS): 1.12 (3H, s, H-12), 1.58 (1H, dd, J = 9; 11.5, H-10β), 1.88 (1H, dd, J = 12.5; 12, H-9), 2.03 (1H, dd, J = 10; 11.5, H-10α), 2.10 (3H, s, OAc), 2.27 (1H, br ddd, J = 10; 12; 10, H-4β), 2.27 (1H, br d, J = 9, OH), 2.45 (1H, ddd, J = 12.5; 10; 9, H-1), 2.53 (1H, d, J = 15, H-8α), 2.57 (2H, m, H-3), 2.67 (1H, dd, J = 12; 4, H-4α), 2.96 (1H, dd, J = 15; 12, H-8β), 4.08 (2H, ABq, J = 11, H-13), 4.10 (1H, dd, J = 12; 2.5, H-14b), 4.25 (1H, dd, J = 12; 9, H-14a), 4.99 (1H, br s, H-15b), 5.06 (1H, br s, H-15a), 6.37 (1H, dd, J = 4; 10, H-5) [1]

References

  1. 1.
    F. Bohlmann, C. Zdero, Phytochemistry 20(11), 2529 (1981)CrossRefGoogle Scholar

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