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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:31:16 UTC
Update Date2023-02-21 17:18:50 UTC
HMDB IDHMDB0029581
Secondary Accession Numbers
  • HMDB29581
Metabolite Identification
Common Name(2E,4E)-2,4-Hexadienoic acid
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 pp
Structure
Data?1676999930
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
(2E,4E)-2,4-Hexadienoic acidChEBI
SorbateGenerator, HMDB
(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
Acid, sorbicMeSH
Sorbate, sodiumMeSH
Sorbate, potassiumMeSH
Acid, propenylacrylicMeSH
Potassium sorbateMeSH
Sodium sorbateMeSH
Acid, hexadienoicMeSH
Propenylacrylic acidMeSH
Chemical FormulaC6H8O2
Average Molecular Weight112.1265
Monoisotopic Molecular Weight112.0524295
IUPAC Name(2E,4E)-hexa-2,4-dienoic acid
Traditional Namesorbic acid
CAS Registry Number110-44-1
SMILES
C\C=C\C=C\C(O)=O
InChI Identifier
InChI=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
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point134.5 °CNot Available
Boiling Point232.98 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1.91 mg/mL at 30 °CNot Available
LogP1.33Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+127.3131661259
DarkChem[M-H]-123.01431661259
DeepCCS[M+H]+125.12830932474
DeepCCS[M-H]-122.24330932474
DeepCCS[M-2H]-158.68730932474
DeepCCS[M+Na]+133.6930932474
AllCCS[M+H]+125.832859911
AllCCS[M+H-H2O]+121.432859911
AllCCS[M+NH4]+129.932859911
AllCCS[M+Na]+131.132859911
AllCCS[M-H]-124.632859911
AllCCS[M+Na-2H]-127.732859911
AllCCS[M+HCOO]-131.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(2E,4E)-2,4-Hexadienoic acidC\C=C\C=C\C(O)=O2109.7Standard polar33892256
(2E,4E)-2,4-Hexadienoic acidC\C=C\C=C\C(O)=O1051.4Standard non polar33892256
(2E,4E)-2,4-Hexadienoic acidC\C=C\C=C\C(O)=O1091.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(2E,4E)-2,4-Hexadienoic acid,1TMS,isomer #1C/C=C/C=C/C(=O)O[Si](C)(C)C1183.8Semi standard non polar33892256
(2E,4E)-2,4-Hexadienoic acid,1TBDMS,isomer #1C/C=C/C=C/C(=O)O[Si](C)(C)C(C)(C)C1416.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (2E,4E)-2,4-Hexadienoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-9100000000-5613b88acb29c3469c892016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (2E,4E)-2,4-Hexadienoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00xr-9200000000-957aa1f63b275675dc732017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (2E,4E)-2,4-Hexadienoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-02td-9100000000-b3752b25f6984879cf222014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid , negative-QTOFsplash10-03di-2900000000-d4eb42b36810ed4706952017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 40V, Positive-QTOFsplash10-0006-9000000000-90f3f65a34c78dcb95a82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 35V, Negative-QTOFsplash10-014i-9300000000-bbc83c452662b533cec82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 10V, Positive-QTOFsplash10-03xr-9600000000-f23c4245a6970fb644722021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 20V, Positive-QTOFsplash10-00kf-9000000000-1e001225ce94335a0e972021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 20V, Negative-QTOFsplash10-014i-9000000000-72552301942533b9fb162021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 10V, Negative-QTOFsplash10-014i-9200000000-fc6379b9c479651e5a332021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 10V, Positive-QTOFsplash10-03dj-9600000000-5c19197e14f2cfc99e022016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 20V, Positive-QTOFsplash10-0uxr-9100000000-e177123e55a992422e1a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 40V, Positive-QTOFsplash10-0udi-9000000000-b3dd13da1d673c99f8532016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 10V, Negative-QTOFsplash10-03di-2900000000-8b6fa6fb8d8182477feb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 20V, Negative-QTOFsplash10-03xr-9800000000-7a9de47828353460dce72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 40V, Negative-QTOFsplash10-00kf-9000000000-3559005a9bdd1b4a889e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 10V, Negative-QTOFsplash10-0006-9200000000-69ae4e13265083f8056f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 20V, Negative-QTOFsplash10-004l-9000000000-4910ce8a1bf6201d8f332021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 40V, Negative-QTOFsplash10-02t9-9000000000-ebd7dafdaddabfebcfc12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 10V, Positive-QTOFsplash10-014j-9000000000-7b8c42c0ddf1f0caf73e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 20V, Positive-QTOFsplash10-014l-9000000000-f84d19a529970cfc2eb92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 40V, Positive-QTOFsplash10-014r-9000000000-17f72b81834cd44b32772021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000738
KNApSAcK IDNot Available
Chemspider ID558605
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSorbic acid
METLIN IDNot Available
PubChem Compound643460
PDB IDNot Available
ChEBI ID38358
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1068981
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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. [PubMed:16902246 ]
  3. 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. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.