Gyrinal

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Gyrinal
Gyrinal2.png
Names
IUPAC name
2E,6E,9E-3,7-dimethyl-8,11-dioxododec-2,6,9-trienal
Identifiers
3D model (JSmol)
ChemSpider
Properties
C14H18O3
Molar mass 234.29 g/mol
Melting point 0 °C (32 °F; 273 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.

References[edit]

  • Schildknecht, H. (1976). "Chemical Ecology - A Chapter of Modern Natural Products Chemistry". Angewandte Chemie International Edition in English. 15 (4): 214–222. doi:10.1002/anie.197602141.
  • 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:10.1007/BF00987720.CS1 maint: multiple names: authors list (link)