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Gyrinal



Gyrinal
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

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.

     
    This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Gyrinal". A list of authors is available in Wikipedia.
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