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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:31:16 UTC

Update Date

2023-02-21 17:18:50 UTC

HMDB ID

HMDB0029581

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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(e,e)-1,3-Pentadiene-1-carboxylic acid	ChEBI
(e,e)-2,4-Hexadienoic acid	ChEBI
(e,e)-SA	ChEBI
(e,e)-Sorbic acid	ChEBI
1,3-Pentadiene-1-carboxylic acid	ChEBI
alpha-trans-gamma-trans-Sorbic acid	ChEBI
SA	ChEBI
trans,trans-2,4-Hexadienoic acid	ChEBI
trans,trans-SA	ChEBI
trans,trans-Sorbic acid	ChEBI
(e,e)-1,3-Pentadiene-1-carboxylate	Generator
(e,e)-2,4-Hexadienoate	Generator
(e,e)-Sorbate	Generator
1,3-Pentadiene-1-carboxylate	Generator
a-trans-g-trans-Sorbate	Generator
a-trans-g-trans-Sorbic acid	Generator
alpha-trans-gamma-trans-Sorbate	Generator
Α-trans-γ-trans-sorbate	Generator
Α-trans-γ-trans-sorbic acid	Generator
trans,trans-2,4-Hexadienoate	Generator
trans,trans-Sorbate	Generator
(2E,4E)-2,4-Hexadienoate	Generator
(2E,4E)-2,4-Hexadienoic acid	ChEBI
Sorbate	Generator, HMDB
(2-Butenylidene)-acetic acid	HMDB
(2-Butenylidene)acetic acid	HMDB
(2E,4E)-Hexa-2,4-dienoic acid	HMDB
2, 4-Hexadienoic acid potassium salt	HMDB
2,4-Hexadienoic acid	HMDB
2-Propenylacrylic acid	HMDB
2E,4E-Hexadienoic acid	HMDB
Acidum sorbicum	HMDB
alpha-trans-laquo gammaraquo -trans-Sorbic acid	HMDB
Crotylidene acetic acid	HMDB
Crotylidene-acetic acid	HMDB
FEMA 3921	HMDB
Hexa-2,4-dienoic acid	HMDB
Hexadienic acid	HMDB
Hexadienoic acid	HMDB
Hexadienoic acid, (e,e)	HMDB
Hexadienoic acid1,3-pentadiene-1-carboxylic acid	HMDB
Panosorb	HMDB
Preservastat	HMDB
Sorbic acid (NF)	HMDB
Sorbic acid, potassium salt	HMDB
Sorbistat	HMDB
trans-trans-2,4-Hexadienoic acid	HMDB
Acid, sorbic	MeSH
Sorbate, sodium	MeSH
Sorbate, potassium	MeSH
Acid, propenylacrylic	MeSH
Potassium sorbate	MeSH
Sodium sorbate	MeSH
Acid, hexadienoic	MeSH
Propenylacrylic acid	MeSH

Chemical Formula

C₆H₈O₂

Average Molecular Weight

112.1265

Monoisotopic Molecular Weight

112.0524295

IUPAC Name

(2E,4E)-hexa-2,4-dienoic acid

Traditional Name

sorbic acid

CAS Registry Number

110-44-1

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 Key

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-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 Framework

Aliphatic acyclic compounds

External Descriptors

alpha,beta-unsaturated monocarboxylic acid (CHEBI:38358 )
sorbic acid (CHEBI:38358 )
Unsaturated fatty acids (LMFA01030100 )

Ontology

Physiological effect

Organoleptic effect

Odor

Bland

Disposition

Biological location

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0029581)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0029581)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0029581)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029581)

Source

Endogenous

Endogenous (HMDB: HMDB0029581)

Animal

Animal (HMDB: HMDB0029581)

Exogenous

Food

Food (HMDB: HMDB0029581)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)
Grape wine (FooDB: FOOD00612)

Synthetic

Personal care products

Personal care products (HMDB: HMDB0029581)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0029581)

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0029581)

Cellular process

Cell signaling (HMDB: HMDB0029581)

Biochemical process

Lipid transport (HMDB: HMDB0029581)

Role

Industrial application

Personal care product

Personal care product (HMDB: HMDB0029581)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0029581)

Food and nutrition

Food and nutrition (HMDB: HMDB0029581)

Biological role

Energy storage (HMDB: HMDB0029581)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	134.5 °C	Not Available
Boiling Point	232.98 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1.91 mg/mL at 30 °C	Not Available
LogP	1.33	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	17.2 g/L	ALOGPS
logP	1.77	ALOGPS
logP	1.45	ChemAxon
logS	-0.81	ALOGPS
pKa (Strongest Acidic)	5.01	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	33.28 m³·mol⁻¹	ChemAxon
Polarizability	11.8 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	127.31	31661259
DarkChem	[M-H]-	123.014	31661259
DeepCCS	[M+H]+	125.128	30932474
DeepCCS	[M-H]-	122.243	30932474
DeepCCS	[M-2H]-	158.687	30932474
DeepCCS	[M+Na]+	133.69	30932474
AllCCS	[M+H]+	125.8	32859911
AllCCS	[M+H-H2O]+	121.4	32859911
AllCCS	[M+NH4]+	129.9	32859911
AllCCS	[M+Na]+	131.1	32859911
AllCCS	[M-H]-	124.6	32859911
AllCCS	[M+Na-2H]-	127.7	32859911
AllCCS	[M+HCOO]-	131.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(2E,4E)-2,4-Hexadienoic acid	C\C=C\C=C\C(O)=O	2109.7	Standard polar	33892256
(2E,4E)-2,4-Hexadienoic acid	C\C=C\C=C\C(O)=O	1051.4	Standard non polar	33892256
(2E,4E)-2,4-Hexadienoic acid	C\C=C\C=C\C(O)=O	1091.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(2E,4E)-2,4-Hexadienoic acid,1TMS,isomer #1	C/C=C/C=C/C(=O)O[Si](C)(C)C	1183.8	Semi standard non polar	33892256
(2E,4E)-2,4-Hexadienoic acid,1TBDMS,isomer #1	C/C=C/C=C/C(=O)O[Si](C)(C)C(C)(C)C	1416.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (2E,4E)-2,4-Hexadienoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-9100000000-5613b88acb29c3469c89	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2E,4E)-2,4-Hexadienoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00xr-9200000000-957aa1f63b275675dc73	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2E,4E)-2,4-Hexadienoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-02td-9100000000-b3752b25f6984879cf22	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid , negative-QTOF	splash10-03di-2900000000-d4eb42b36810ed470695	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 40V, Positive-QTOF	splash10-0006-9000000000-90f3f65a34c78dcb95a8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 35V, Negative-QTOF	splash10-014i-9300000000-bbc83c452662b533cec8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 10V, Positive-QTOF	splash10-03xr-9600000000-f23c4245a6970fb64472	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 20V, Positive-QTOF	splash10-00kf-9000000000-1e001225ce94335a0e97	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 20V, Negative-QTOF	splash10-014i-9000000000-72552301942533b9fb16	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 10V, Negative-QTOF	splash10-014i-9200000000-fc6379b9c479651e5a33	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 10V, Positive-QTOF	splash10-03dj-9600000000-5c19197e14f2cfc99e02	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 20V, Positive-QTOF	splash10-0uxr-9100000000-e177123e55a992422e1a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 40V, Positive-QTOF	splash10-0udi-9000000000-b3dd13da1d673c99f853	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 10V, Negative-QTOF	splash10-03di-2900000000-8b6fa6fb8d8182477feb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 20V, Negative-QTOF	splash10-03xr-9800000000-7a9de47828353460dce7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 40V, Negative-QTOF	splash10-00kf-9000000000-3559005a9bdd1b4a889e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 10V, Negative-QTOF	splash10-0006-9200000000-69ae4e13265083f8056f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 20V, Negative-QTOF	splash10-004l-9000000000-4910ce8a1bf6201d8f33	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 40V, Negative-QTOF	splash10-02t9-9000000000-ebd7dafdaddabfebcfc1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 10V, Positive-QTOF	splash10-014j-9000000000-7b8c42c0ddf1f0caf73e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 20V, Positive-QTOF	splash10-014l-9000000000-f84d19a529970cfc2eb9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E,4E)-2,4-Hexadienoic acid 40V, Positive-QTOF	splash10-014r-9000000000-17f72b81834cd44b3277	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000738

KNApSAcK ID

Not Available

Chemspider ID

558605

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sorbic acid

METLIN ID

Not Available

PubChem Compound

643460

PDB ID

Not Available

ChEBI ID

38358

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1068981

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
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 ]
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 ]
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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for (2E,4E)-2,4-Hexadienoic acid (HMDB0029581)

MOL for HMDB0029581 ((2E,4E)-2,4-Hexadienoic acid)

3D MOL for HMDB0029581 ((2E,4E)-2,4-Hexadienoic acid)

3D SDF for HMDB0029581 ((2E,4E)-2,4-Hexadienoic acid)

3D-SDF for HMDB0029581 ((2E,4E)-2,4-Hexadienoic acid)

PDB for HMDB0029581 ((2E,4E)-2,4-Hexadienoic acid)

3D PDB for HMDB0029581 ((2E,4E)-2,4-Hexadienoic acid)

SMILES for HMDB0029581 ((2E,4E)-2,4-Hexadienoic acid)

INCHI for HMDB0029581 ((2E,4E)-2,4-Hexadienoic acid)

Structure for HMDB0029581 ((2E,4E)-2,4-Hexadienoic acid)

3D Structure for HMDB0029581 ((2E,4E)-2,4-Hexadienoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra