Gyrinal

Gyrinal
IUPAC name 2E,6E,9E-3,7-dimethyl-8,11-dioxododec-2,6,9-trienal
Identifiers
CAS number	36518-11-3 Y
PubChem	6443774
ChemSpider	4947737
Jmol-3D images	Image 1
SMILES O=C(\C=C\C(=O)/C(=C/CC\C(=C\C=O)C)C)C
InChI InChI=1S/C14H18O3/c1-11(9-10-15)5-4-6-12(2)14(17)8-7-13(3)16/h6-10H,4-5H2,1-3H3/b8-7+,11-9+,12-6+ Key: PQXIJIXNDRFJBT-WWUHPALESA-N InChI=1/C14H18O3/c1-11(9-10-15)5-4-6-12(2)14(17)8-7-13(3)16/h6-10H,4-5H2,1-3H3/b8-7+,11-9+,12-6+ Key: PQXIJIXNDRFJBT-WWUHPALEBW
Properties
Molecular formula	C14H18O3
Molar mass	234.29 g mol−1
Melting point	0 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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

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