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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:41:29 UTC

Update Date

2023-02-21 17:19:58 UTC

HMDB ID

HMDB0031180

Secondary Accession Numbers

HMDB31180

Metabolite Identification

Common Name

(E,E)-2,4-Hexadienedial

Description

(E,E)-2,4-Hexadienedial, also known as (e,e)-muconaldehyde or hexa-2,4-dienedial, belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Based on a literature review very few articles have been published on (E,E)-2,4-Hexadienedial.

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)-Muconaldehyde	HMDB
2,4-Hexadienedial	HMDB
Hexa-2,4-dienedial	HMDB
Muconaldehyde	HMDB
Mucondialdehyde	HMDB
Muconic aldehyde	HMDB
Muconic dialdehyde	HMDB
trans,trans-Muconaldehyde	HMDB

Chemical Formula

C₆H₆O₂

Average Molecular Weight

110.1106

Monoisotopic Molecular Weight

110.036779436

IUPAC Name

(2Z,4E)-hexa-2,4-dienedial

Traditional Name

(2Z,4E)-hexa-2,4-dienedial

CAS Registry Number

18409-46-6

SMILES

O=C\C=C\C=C/C=O

InChI Identifier

InChI=1S/C6H6O2/c7-5-3-1-2-4-6-8/h1-6H/b3-1-,4-2+

InChI Key

NDCAAPXLWRAESY-HSFFGMMNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Medium-chain aldehydes

Alternative Parents

Substituents

Medium-chain aldehyde
Enal
Alpha,beta-unsaturated aldehyde
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031180)
Cytoplasm (HMDB: HMDB0031180)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031180)

Source

Endogenous

Endogenous (HMDB: HMDB0031180)

Plant

Poaceae (HMDB: HMDB0031180)

Exogenous

Food

Food (HMDB: HMDB0031180)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	120.5 - 121 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	8.32 g/L	ALOGPS
logP	1.32	ALOGPS
logP	0.17	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	33.07 m³·mol⁻¹	ChemAxon
Polarizability	10.96 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]+	126.791	31661259
DarkChem	[M-H]-	120.574	31661259
DeepCCS	[M+H]+	124.948	30932474
DeepCCS	[M-H]-	122.96	30932474
DeepCCS	[M-2H]-	158.662	30932474
DeepCCS	[M+Na]+	133.296	30932474
AllCCS	[M+H]+	125.1	32859911
AllCCS	[M+H-H2O]+	120.8	32859911
AllCCS	[M+NH4]+	129.2	32859911
AllCCS	[M+Na]+	130.3	32859911
AllCCS	[M-H]-	124.7	32859911
AllCCS	[M+Na-2H]-	127.7	32859911
AllCCS	[M+HCOO]-	131.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(E,E)-2,4-Hexadienedial	O=C\C=C\C=C/C=O	1975.1	Standard polar	33892256
(E,E)-2,4-Hexadienedial	O=C\C=C\C=C/C=O	1048.8	Standard non polar	33892256
(E,E)-2,4-Hexadienedial	O=C\C=C\C=C/C=O	1155.7	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 - (E,E)-2,4-Hexadienedial GC-MS (Non-derivatized) - 70eV, Positive	splash10-03e9-9500000000-a02f320ad7186601dbe4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E,E)-2,4-Hexadienedial GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E,E)-2,4-Hexadienedial GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-2,4-Hexadienedial 10V, Positive-QTOF	splash10-03di-4900000000-bc0dd58197a179a6e1fa	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-2,4-Hexadienedial 20V, Positive-QTOF	splash10-03di-9700000000-a6767b8127546cb0d5ec	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-2,4-Hexadienedial 40V, Positive-QTOF	splash10-0ldi-9000000000-11ea80c8000377efd5ca	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-2,4-Hexadienedial 10V, Negative-QTOF	splash10-0a4i-0900000000-e9d27d5940f1287154fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-2,4-Hexadienedial 20V, Negative-QTOF	splash10-0a4i-3900000000-caf8c89449d5fd8e6275	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-2,4-Hexadienedial 40V, Negative-QTOF	splash10-0006-9100000000-38688207395fd159bacb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-2,4-Hexadienedial 10V, Positive-QTOF	splash10-0159-9000000000-798691e72d5526c8334a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-2,4-Hexadienedial 20V, Positive-QTOF	splash10-016u-9000000000-fd4656cb2adf183660a9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-2,4-Hexadienedial 40V, Positive-QTOF	splash10-014i-9000000000-e23f434ac8b62cca7761	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-2,4-Hexadienedial 10V, Negative-QTOF	splash10-0a59-5900000000-38bfdc0998243a815e64	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-2,4-Hexadienedial 20V, Negative-QTOF	splash10-0fef-9000000000-2bab49d1e96f51dfb727	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-2,4-Hexadienedial 40V, Negative-QTOF	splash10-0j4i-9000000000-c5b64b272cd69752a8b3	2021-09-24	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+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB003199

KNApSAcK ID

Not Available

Chemspider ID

9587244

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11412357

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Henderson AP, Bleasdale C, Delaney K, Lindstrom AB, Rappaport SM, Waidyanatha S, Watson WP, Golding BT: Evidence for the formation of Michael adducts from reactions of (E,E)-muconaldehyde with glutathione and other thiols. Bioorg Chem. 2005 Oct;33(5):363-73. Epub 2005 Jul 11. [PubMed:16005934 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (E,E)-2,4-Hexadienedial (HMDB0031180)

MOL for HMDB0031180 ((E,E)-2,4-Hexadienedial)

3D MOL for HMDB0031180 ((E,E)-2,4-Hexadienedial)

3D SDF for HMDB0031180 ((E,E)-2,4-Hexadienedial)

3D-SDF for HMDB0031180 ((E,E)-2,4-Hexadienedial)

PDB for HMDB0031180 ((E,E)-2,4-Hexadienedial)

3D PDB for HMDB0031180 ((E,E)-2,4-Hexadienedial)

SMILES for HMDB0031180 ((E,E)-2,4-Hexadienedial)

INCHI for HMDB0031180 ((E,E)-2,4-Hexadienedial)

Structure for HMDB0031180 ((E,E)-2,4-Hexadienedial)

3D Structure for HMDB0031180 ((E,E)-2,4-Hexadienedial)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra