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Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (
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Added bibcode. | Use this bot. Report bugs. | Suggested by Whoop whoop pull up | Category:Aldehydes | #UCB_Category 4/94
 
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{{Orphan|date=February 2009}}
{{chembox
{{chembox
| Verifiedfields = changed
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| verifiedrevid = 355683799
| Watchedfields = changed
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| ImageFile = Gyrinal2.png
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| verifiedrevid = 424803125
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| ImageFile = Gyrinal.svg
| ImageSize = 108px
| ImageSize = 108px
| IUPACName = ''2E,6E,9E''-3,7-dimethyl-8,11-dioxododec-2,6,9-trienal
| PIN = (2''E'',6''E'',9''E'')-3,7-Dimethyl-8,11-dioxododeca-2,6,9-trienal
| OtherNames =
| OtherNames =
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 36518-11-3
| PubChem =
| CASNo = 36518-11-3
| UNII_Ref = {{fdacite|correct|FDA}}
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| SMILES = [H]C(=O)\C=C(/C)CC\C=C(/C)C(=O)\C=C\C(C)=O
| UNII = 5P42XHP9MY
| PubChem = 6443774
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4947737
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| SMILES = O=C(\C=C\C(=O)/C(=C/CC\C(=C\C=O)C)C)C
| 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+
| InChIKey = PQXIJIXNDRFJBT-WWUHPALEBW
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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+
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = PQXIJIXNDRFJBT-WWUHPALESA-N
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| C=14|H=18|O=3
| C =14|H=18|O=3
| MolarMass = 234.29 g/mol
| MolarMass = 234.29 g/mol
| Appearance =
| Appearance =
| Density =
| Density =
| MeltingPt = 0°C
| MeltingPtC = 0
| BoilingPt =
| BoilingPt =
| Solubility =
| Solubility =
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}}
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| Section3 = {{Chembox Hazards
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| MainHazards =
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| FlashPt =
| Autoignition =
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}}
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|Section3={{Chembox Hazards
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| MainHazards =
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| FlashPt =
| AutoignitionPt =
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}}
}}
}}


'''Gyrinal'''&nbsp;is an [[organic compound|organic]]&nbsp;[[chemical compound]]&nbsp; - an unsaturated ketoaldehyde - with the formula [[Carbon|C]]<sub>14</sub>[[Hydrogen|H]]<sub>18</sub>[[Oxygen|O]]<sub>3</sub>, obtained from the [[whirligig beetle]]&nbsp;(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 LD<sub>50</sub> of the compound is approx. 45 mg/kg in mice.
'''Gyrinal'''&nbsp;is an [[organic compound|organic]]&nbsp;[[chemical compound]]&nbsp; - an unsaturated ketoaldehyde - with the formula [[Carbon|C]]<sub>14</sub>[[Hydrogen|H]]<sub>18</sub>[[Oxygen|O]]<sub>3</sub>, obtained from the [[whirligig beetle]]&nbsp;(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 LD<sub>50</sub> of the compound is approx. 45&nbsp;mg/kg in mice.


==References==
==References==
{{reflist}}
{{reflist}}


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


{{cite journal
*{{cite journal
| author = Miller, J. R., Hendry, L. B., and Mumma, R. O.
| author = Miller, J. R., Hendry, L. B., and Mumma, R. O.
| title = Norsesquiterpenes as defensive toxins of whirligig beetles (Coleoptera: Gyrinidae)
| title = Norsesquiterpenes as defensive toxins of whirligig beetles (Coleoptera: Gyrinidae)
| journal = Journal of Chemical Ecology
| journal = Journal of Chemical Ecology
| volume = 1
| volume = 1
| issue = 1
| issue = 1
| pages = 59–82
| pages = 59–82
| year= 1975
| year = 1975
| doi = 10.1007/BF00987720}}
| doi = 10.1007/BF00987720| bibcode = 1975JCEco...1...59M
| s2cid = 32820323
}}


[[Category:Aldehydes]]
[[Category:Aldehydes]]
[[Category:Ketones]]
[[Category:Enones]]
[[Category:Sesquiterpenes]]
[[Category:Sesquiterpenes]]
[[Category:Alkene derivatives]]

[[fr:Gyrinal]]
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