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Record Information
Version2.0
Creation Date2014-09-11 05:18:52 UTC
Update Date2014-12-24 20:26:58 UTC
Accession NumberT3D4843
Identification
Common Name(2E,4E)-2,4-Hexadienoic acid
ClassSmall Molecule
Description(2E,4E)-2,4-Hexadienoic acid is a preservative for many foodstuffs. Generally used as K salt or (less frequently) as Ca salt. (2E,4E)-2,4-Hexadienoic acid is an antimicrobial agent against a wide variety of microorganisms, especially yeasts and moulds. (2E,4E)-2,4-Hexadienoic acid is a preservative action more efficient in acidic foods. Typical usage levels 500-2000 ppm (2E,4E)-2,4-Hexadienoic acid belongs to the family of Unsaturated Fatty Acids. These are fatty acids whose chain contains at least one CC double bond.
Compound Type
  • Ester
  • Food Additive
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Organic Compound
  • Preservative
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
(2-butenylidene)-Acetic acid
(2-Butenylidene)acetic acid
(2e,4e)-2,4-Hexadienoate
(2e,4e)-2,4-Hexadienoic acid
(2E,4E)-hexa-2,4-dienoic acid
(E,E)-1,3-Pentadiene-1-carboxylic acid
(E,E)-2,4-Hexadienoic acid
(e,e)-Sorbic acid
1,3-Pentadiene-1-carboxylic acid
2, 4-Hexadienoic acid potassium salt
2,4-Hexadienoic acid
2-Propenylacrylic acid
2E,4E-Hexadienoic acid
Acidum sorbicum
alpha-trans-gamma-trans-Sorbic acid
alpha-trans-Laquo gammaRaquo -trans-sorbic acid
Crotylidene acetic acid
Crotylidene-Acetic acid
FEMA 3921
Hexa-2,4-dienoic acid
Hexadienic acid
Hexadienoic acid
Hexadienoic acid, (e,e)
Hexadienoic acid1,3-pentadiene-1-carboxylic acid
Panosorb
Preservastat
Sorbic acid
Sorbic acid (NF)
Sorbic acid, potassium salt
Sorbistat
trans,trans-2,4-Hexadienoic acid
Trans,trans-sorbic acid
trans-trans-2,4-Hexadienoic acid
Chemical FormulaC6H8O2
Average Molecular Mass112.127 g/mol
Monoisotopic Mass112.052 g/mol
CAS Registry Number110-44-1
IUPAC Name(2E,4E)-hexa-2,4-dienoic acid
Traditional Namesorbic acid
SMILES[H]\C(C)=C(\[H])/C(/[H])=C(\[H])C(O)=O
InChI IdentifierInChI=1S/C6H8O2/c1-2-3-4-5-6(7)8/h2-5H,1H3,(H,7,8)/b3-2+,5-4+
InChI KeyInChIKey=WSWCOQWTEOXDQX-MQQKCMAXSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point134.5 °C
Boiling PointNot Available
Solubility1.91 mg/mL at 30 °C
LogP1.33
Predicted Properties
PropertyValueSource
Water Solubility17.2 g/LALOGPS
logP1.77ALOGPS
logP1.45ChemAxon
logS-0.81ALOGPS
pKa (Strongest Acidic)5.01ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity33.28 m³·mol⁻¹ChemAxon
Polarizability11.8 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-9100000000-5613b88acb29c3469c89JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00xr-9200000000-957aa1f63b275675dc73JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-03di-2900000000-d4eb42b36810ed470695JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-90f3f65a34c78dcb95a8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-014i-9300000000-bbc83c452662b533cec8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03xr-9600000000-f23c4245a6970fb64472JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00kf-9000000000-1e001225ce94335a0e97JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-014i-9000000000-72552301942533b9fb16JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-014i-9200000000-fc6379b9c479651e5a33JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-9600000000-5c19197e14f2cfc99e02JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-9100000000-e177123e55a992422e1aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-b3dd13da1d673c99f853JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2900000000-8b6fa6fb8d8182477febJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-9800000000-7a9de47828353460dce7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-3559005a9bdd1b4a889eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9200000000-69ae4e13265083f8056fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9000000000-4910ce8a1bf6201d8f33JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02t9-9000000000-ebd7dafdaddabfebcfc1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-9000000000-7b8c42c0ddf1f0caf73eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014l-9000000000-f84d19a529970cfc2eb9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-9000000000-17f72b81834cd44b3277JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-02td-9100000000-b3752b25f6984879cf22JSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB29581
PubChem Compound ID643460
ChEMBL IDCHEMBL250212
ChemSpider ID558605
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI ID38358
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D4843.pdf
General References
  1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Not Available
Specific Function:
Not Available
Gene Name:
TP53
Uniprot ID:
P04637
Molecular Weight:
43652.79 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC501.029884124 uMAPR_p53Act_24h_dnApredica
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]