Gyrinal

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

Schildknecht, H. (1976). "Chemical Ecology - A Chapter of Modern Natural Products Chemistry". Angewandte Chemie International Edition in English. 15 (4): 214–222.

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.CS1 maint: Multiple names: authors list (link) Template:WikiDoc Sources