Gyrinal
From Wikipedia, the free encyclopedia
| Gyrinal | |
|---|---|
 |
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| IUPAC name | 2E,6E,9E-3,7-dimethyl-8,11-dioxododec-2,6,9-trienal |
| Identifiers | |
| CAS number | [36518-11-3] |
| SMILES | [H]C(=O)\C=C(/C)CC\C=C(/C)C(=O)\C=C\C(C)=O |
| Properties | |
| Molecular formula | C14H18O3 |
| Molar mass | 234.29 g mol-1 |
| Melting point |
0°C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Gyrinal is an organic chemical compound - an unsaturated ketoaldehyde - with the formula C14H18O3, obtained from the whirligig beetle (the water boatman, Gyrinus natator). It is a powerful antiseptic and fish and mammal toxin, and thus used as a defensive compound. Typically the beetles contain approx. 80 microgram of the compound. The LD50 of the compound is approx. 45 mg/kg in mice.
[edit] References
Schildknecht, H. (1976). "Chemical Ecology - A Chapter of Modern Natural Products Chemistry". Angewandte Chemie International Edition in English 15 (4): 214–222. doi:.
Miller, J. R., Hendry, L. B., and Mumma, R. O. (1975). "Norsesquiterpenes as defensive toxins of whirligig beetles (Coleoptera: Gyrinidae)". Journal of Chemical Ecology 1 (1): 59–82. doi:.
