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Record Information
Version1.0
Creation Date2014-09-11 05:18:52 UTC
Update Date2016-10-28 10:03:18 UTC
Accession NumberCHEM003799
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.
Contaminant Sources
  • Cosmetic Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ester
  • Food Additive
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Organic Compound
  • Preservative
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
(e,e)-1,3-Pentadiene-1-carboxylic acidChEBI
(e,e)-2,4-Hexadienoic acidChEBI
(e,e)-SAChEBI
(e,e)-Sorbic acidChEBI
1,3-Pentadiene-1-carboxylic acidChEBI
alpha-trans-gamma-trans-Sorbic acidChEBI
SAChEBI
trans,trans-2,4-Hexadienoic acidChEBI
trans,trans-SAChEBI
trans,trans-Sorbic acidChEBI
(e,e)-1,3-Pentadiene-1-carboxylateGenerator
(e,e)-2,4-HexadienoateGenerator
(e,e)-SorbateGenerator
1,3-Pentadiene-1-carboxylateGenerator
a-trans-g-trans-SorbateGenerator
a-trans-g-trans-Sorbic acidGenerator
alpha-trans-gamma-trans-SorbateGenerator
Α-trans-γ-trans-sorbateGenerator
Α-trans-γ-trans-sorbic acidGenerator
trans,trans-2,4-HexadienoateGenerator
trans,trans-SorbateGenerator
(2E,4E)-2,4-HexadienoateGenerator
SorbateHMDB
(2-Butenylidene)-acetic acidHMDB
(2-Butenylidene)acetic acidHMDB
(2E,4E)-Hexa-2,4-dienoic acidHMDB
2, 4-Hexadienoic acid potassium saltHMDB
2,4-Hexadienoic acidHMDB
2-Propenylacrylic acidHMDB
2E,4E-Hexadienoic acidHMDB
Acidum sorbicumHMDB
alpha-trans-Laquo gammaraquo -trans-sorbic acidHMDB
Crotylidene acetic acidHMDB
Crotylidene-acetic acidHMDB
FEMA 3921HMDB
Hexa-2,4-dienoic acidHMDB
Hexadienic acidHMDB
Hexadienoic acidHMDB
Hexadienoic acid, (e,e)HMDB
Hexadienoic acid1,3-pentadiene-1-carboxylic acidHMDB
PanosorbHMDB
PreservastatHMDB
Sorbic acid (NF)HMDB
Sorbic acid, potassium saltHMDB
SorbistatHMDB
trans-trans-2,4-Hexadienoic acidHMDB
(2E,4E)-2,4-Hexadienoic acidChEBI
Acid, sorbicMeSH
Sorbate, sodiumMeSH
Sorbate, potassiumMeSH
Acid, propenylacrylicMeSH
Potassium sorbateMeSH
Sodium sorbateMeSH
Acid, hexadienoicMeSH
Propenylacrylic acidMeSH
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
SMILESC\C=C\C=C\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 KeyWSWCOQWTEOXDQX-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
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 Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-014i-9100000000-5613b88acb29c3469c89View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS)splash10-00xr-9200000000-957aa1f63b275675dc73View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-03di-2900000000-d4eb42b36810ed470695View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-9600000000-5c19197e14f2cfc99e02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-9100000000-e177123e55a992422e1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-b3dd13da1d673c99f853View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2900000000-8b6fa6fb8d8182477febView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-9800000000-7a9de47828353460dce7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-3559005a9bdd1b4a889eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-02td-9100000000-b3752b25f6984879cf22View in MoNA
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
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0029581
FooDB IDFDB000738
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSorbic acid
Chemspider ID558605
ChEBI ID38358
PubChem Compound ID643460
Kegg Compound IDNot Available
YMDB IDYMDB01784
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11206806
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=7979442
3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
4. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
5. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
7. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
8. The lipid handbook with CD-ROM