Natural Compounds

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

14-Acetoxy-13-hydroxy-5,6-trans-caryophyllen-7-one

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_837

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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): 3640, 3075, 1750, 1695, 1245, 905 [1]

MS: 292.3579 [M]+ (0.1), 261.149 [M − CH2OH]+ (3), 232 (2), 217 (1), 214 (1), 201 (2), 147 (30), 119 (21), 93 (50), 43 (100) [1]

1H NMR (400 MHz, CDCl3, TMS: 1.06 (3H, s, H-12), 1.57 (1H, dd, J = 9; 11.5, H-10β), 1.86 (1H, dd, J = 9.5; 12, H-9), 2.00 (3H, s, OAc), 2.03 (1H, dd, J = 10; 11.5, H-10α), 2.25 (1H, br ddd, J = 10; 12; 10, H-4β), 2.50 (1H, ddd, J = 9.5; 10; 9, H-1), 2.57 (1H, d, J = 15, H-8α), 2.6 (3H, m, H-3, H-4α), 2.98 (1H, dd, J = 15; 12, H-8β), 3.59 (1H, br d, J = 11, H-13b), 3.65 (1H, br d, J = 11, H-13a), 4.65 (1H, br d, J = 12, H-14b), 4.75 (1H, d, J = 12, H-14a), 4.93 (1H, br s, H-15b), 5.02 (1H, br s, H-15a), 6.54 (1H, dd, J = 5.5; 10, H-5) [1]

References

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

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