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Gyrinal
Sign in to saveGyrinal 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.
Chemical data
- Formula
- C14H18O3
- Molecular weight
- 234.29 g/mol
- IUPAC name
- (2E,6E,9E)-3,7-dimethyl-8,11-dioxododeca-2,6,9-trienal
- SMILES
- C/C(=C\C=O)/CC/C=C(\C)/C(=O)/C=C/C(=O)C
- InChIKey
- PQXIJIXNDRFJBT-WWUHPALESA-N
- XLogP
- 1.8
- Polar surface area
- 51.2 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- fatty aldehyde
- Mass
- 234.125594
Show 3 more facts
- chemical formula
- C₁₄H₁₈O₃
- canonical SMILES
- CC(=CC=O)CCC=C(C)C(=O)C=CC(=O)C
- isomeric SMILES
- C/C(=C\C=O)/CC/C=C(\C)/C(=O)/C=C/C(=O)C
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Encyclopedic overview
1 sectionsContents
- 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==
Excerpted from Wikipedia’s “Gyrinal” article, available under the CC BY-SA 4.0 licence.