Gyrinal

Names
Preferred IUPAC name

(2E,6E,9E)-3,7-Dimethyl-8,11-dioxododeca-2,6,9-trienal

Identifiers

CAS Number

* 36518-11-3 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 4947737 N

PubChem CID

* 6443774

UNII |

* 5P42XHP9MY Y

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+ N

Key: PQXIJIXNDRFJBT-WWUHPALESA-N 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

SMILES

* O=C(\C=C\C(=O)/C(=C/CC\C(=C\C=O)C)C)C

Properties

Chemical formula

| 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).

N verify (what is YN ?)
Infobox references

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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

* 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.

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*[CID]: Compound ID