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CHEBI:38358 - (2E,4E)-hexa-2,4-dienoic acid

ChEBI IDCHEBI:38358
ChEBI Name(2E,4E)-hexa-2,4-dienoic acid
Stars
ASCII Name(2E,4E)-hexa-2,4-dienoic acid
DefinitionA sorbic acid having trans-double bonds at positions 2 and 4; a food preservative that can induce cutaneous vasodilation and stinging upon topical application to humans. It is the most thermodynamically stable of the four possible geometric isomers possible, as well as the one with the highest antimicrobial activity.
Last Modified31 October 2016
SubmitterKirill Degtyarenko
DownloadsMolfile
FormulaC6H8O2
Net Charge0
Average Mass112.128
Monoisotopic Mass112.05243
SMILESC/C=C/C=C/C(=O)O
InChIInChI=1S/C6H8O2/c1-2-3-4-5-6(7)8/h2-5H,1H3,(H,7,8)/b3-2+,5-4+
InChIKeyWSWCOQWTEOXDQX-MQQKCMAXSA-N
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
ChEBI Ontology
Outgoing Relation(s)
(2E,4E)-hexa-2,4-dienoic acid (CHEBI:38358) is a sorbic acid (CHEBI:35962)
(2E,4E)-hexa-2,4-dienoic acid (CHEBI:38358) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
(2E,4E)-hexa-2,4-dienoic acid (CHEBI:38358) is conjugate acid of (E,E)-sorbate (CHEBI:77869)
Incoming Relation(s)
trans,trans-2,4-hexadienoyl-CoA (CHEBI:85439) has functional parent (2E,4E)-hexa-2,4-dienoic acid (CHEBI:38358)
nigragillin (CHEBI:133753) has functional parent (2E,4E)-hexa-2,4-dienoic acid (CHEBI:38358)
(E,E)-sorbate (CHEBI:77869) is conjugate base of (2E,4E)-hexa-2,4-dienoic acid (CHEBI:38358)
IUPAC Name 
(2E,4E)-hexa-2,4-dienoic acid
Synonyms  Source
(E,E)-2,4-hexadienoic acidNIST Chemistry WebBook
(E,E)-sorbic acidChemIDplus
α-trans-γ-trans-sorbic acidNIST Chemistry WebBook
trans,trans-2,4-hexadienoic acidNIST Chemistry WebBook
(2E,4E)-2,4-hexadienoic acidNIST Chemistry WebBook
trans,trans-sorbic acidChemIDplus
Manual XrefsDatabases
LMFA01030100LIPID MAPS
Registry NumbersSources
Beilstein:1098547Beilstein
Gmelin:3063Gmelin
Gmelin:260824Gmelin
CAS:110-44-1NIST Chemistry WebBook
CAS:110-44-1ChemIDplus
Citations