Natural Compounds

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

14-Isobutyroyloxy-12-hydroxy-(Z)-caryophylla-2(15),5-dien-7-one ((Z)-12,14-Dihydroxy-7-oxo-caryophilla-2(15),5-dien-14-isobutyrate)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_842

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

Biological sources: Pulicaria paludosa Link [1]

C17H30O4: 298.2144

Mp: oil (mix. with (Z)-12,14-dihydroxy-7-oxo-caryophylla-2(15),5-dien-14-[2-methylbutyrate] (3:2)) [1]

[α]23 (λ, nm) (mix.): −119.3° (589), −134.5° (578), −143.3° (546) (c 0.1, CHCl3) [1]

UV (EtOH) (mix.) 227 (ε 2250) [1]

IR (CHCl3) (mix.): 3610, 3460, 2940, 1730, 1680, 1640, 1240, 1100, 1040, 900 [1]

EI-MS (mix.): 320 (1), 326 (1), 317 (1), 289 (2), 263 (2), 232 (4), 201 (8), 173 (8), 160 (11), 147 (50), 131 (12), 120 (21), 105 (24), 93 (64), 85 (63), 79 (38), 58 (100) [1]

1H NMR (200 MHz, CDCl3, TMS) (mix.): 1.07 (3H, s, H-13), 3.63 (1H, AB, J = 11.0, H-12a), 3.64 (1H, AB, J = 11.0, H-12b), 4.53 (1H, AB, J = 12.0, H-14a), 4.75 (1H, AB, J = 12.0, H-14b), 4.87 (1H, br s, H-15a), 4.94 (1H, br s, H-15b), 5.85 (1H, dd, J = 11.3; 5.5, H-5); OiBu: 0.94...

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References

  1. 1.
    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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