Gyrinal

Chembox new
ImageFile = Gyrinal2.png ImageSize = 108px
IUPACName = "2E,6E,9E"-3,7-dimethyl-8,11-dioxododec-2,6,9-trienal
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Section1 = Chembox Identifiers
CASNo = 36518-11-3
PubChem =
SMILES = [H] C(=O)C=C(/C)CCC=C(/C)C(=O)C=CC(C)=O
Section2 = Chembox Properties
C=14|H=18|O=3
MolarMass = 234.29 g/mol
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MeltingPt = 0°C
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Section3 = Chembox Hazards
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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.

References

cite journal
author = Schildknecht, H.
title = Chemical Ecology - A Chapter of Modern Natural Products Chemistry
journal = Angewandte Chemie International Edition in English
volume = 15 (4)
pages = 214–222
year= 1976
doi = 10.1002/anie.197602141

cite journal
author = Miller, J. R., Hendry, L. B., and Mumma, R. O.
title = Norsesquiterpenes as defensive toxins of whirligig beetles (Coleoptera: Gyrinidae)
journal = Journal of Chemical Ecology
volume = 1
issue = 1
pages = 59–82
year= 1975
doi = 10.1007/BF00987720