Natural Compounds

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

13,14-Diacetoxycaryophyllen-7-one

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_847

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

Biological sources: Pulicaria dysenterica Gaertn. [1]

C19H26O5: 334.1780

Mp: colorless gum [1]

[α]24 (λ, nm): −135.8° (589), −141.9° (578), −163.0° (546) (c 1.22, CHCl3) [1]

IR (CCl4): 3080, 1750, 1697, 1245, 900 [1]

MS: 334.178 [M]+ (0.2) (C19H26O5), 274 (2), 261 (8), 232 (10), 214 (19), 201 (17), 147 (90), 119 (75), 93 (82), 43 (100) [1]

CI-MS: 335 [M + 1]+ (100), 275 (15), 215 (15), 187 (4) [1]

1H NMR (400 MHz, CDCl3, TMS: 1.12 (3H, s, H-12), 1.58 (1H, dd, J = 9; 11.5, H-10β), 1.86 (1H, dd, J = 9.5; 12, H-9), 1.99 (3H, s, OAc), 2.02 (1H, dd, J = 10; 11.5, H-10α), 2.10 (3H, s, OAc), 2.26 (1H, br ddd, J = 10; 12; 10, H-4β), 2.45 (1H, ddd, J = 9.5; 10; 9, H-1), 2.54 (1H, d, J = 15, H-8α), 2.57 (2H, m, H-3), 2.65 (1H, dd, J = 12; 5.5, H-4α), 2.97 (1H, dd, J = 15; 12, H-8β), 4.07 (1H, d, J = 11, H-13b), 4.11 (1H, d, J =...

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References

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

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