Natural Compounds

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

12-Acetoxy-14-hydroxy-5,6-cis-caryophyllen-7-one

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_831

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

Biological sources: Pulicaria dysenterica Gaertn. [1]; P. paludosa Link [2]

C17H24O4: 292.1675

Mp: colorless gum [1]

IR (CCl4): 3620, 3080, 1745, 1680, 1240, 905 [1]

MS: 292.3579.167 [M]+ (0.5) (C17H24O4), 274 (0.5), 232 (5), 219 (10), 201 (6), 147 (41), 119 (53), 93 (100) [1]

1H NMR (400 MHz, CDCl3, TMS): 0.97 (3H, s, H-13), 1.72 (1H, m, H-4α), 1.72 (1H, m, OH), 1.72 (2H, m, H-10), 1.72 (3H, s, OAc), 2.05 (1H, m, H-4β), 2.05 (1H, m, H-9), 2.05 (2H, m, H-3), 2.17 (1H, ddd, J = 9.5; 9.5; 9.5, H-1), 2.57 (1H, dd, J = 17; 2, H-8α), 2.80 (1H, dd, J = 17; 10, H-8β), 3.95 (1H, d, J = 11, H-12b), 3.99 (1H, br d, J = 12; 1, H-14b), 4.08 (1H, d, J = 11, H-12a), 4.19 (1H, br dd, J = 12; 1, H-14a), 4.82 (1H, br s, H-15b), 4.89 (1H, br s, H-15a), 5.43 (1H, dd, J = 11.5; 5, H-5) [1]

References

  1. 1.
    F. Bohlmann, C. Zdero, Phytochemistry 20(11), 2529 (1981)CrossRefGoogle Scholar
  2. 2.
    A. San Feliciano, M. Medarde, M. Gordaliza, E. Del Olmo, J.M.M. del Corral, Phytochemistry 28(10), 2717 (1989)CrossRefGoogle Scholar

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