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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:45:16 UTC

Update Date

2023-02-21 17:21:18 UTC

HMDB ID

HMDB0031759

Secondary Accession Numbers

HMDB31759

Metabolite Identification

Common Name

(E)-4-Oxo-2-hexen-1-al

Description

(E)-4-Oxo-2-hexen-1-al, also known as OHE or 4-oxo-(e)-2-hexenal, 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. Thus, (e)-4-oxo-2-hexen-1-al is considered to be a fatty aldehyde. Based on a literature review a significant number of articles have been published on (E)-4-Oxo-2-hexen-1-al.

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)-4-oxo-2-Hexenal	ChEBI
OHE	ChEBI
4-oxo-(e)-2-Hexenal	HMDB
Ethenesulfenic acid	HMDB

Chemical Formula

C₆H₈O₂

Average Molecular Weight

112.1265

Monoisotopic Molecular Weight

112.0524295

IUPAC Name

(2E)-4-oxohex-2-enal

Traditional Name

(2E)-4-oxohex-2-enal

CAS Registry Number

2492-43-5

SMILES

CCC(=O)\C=C\C=O

InChI Identifier

InChI=1S/C6H8O2/c1-2-6(8)4-3-5-7/h3-5H,2H2,1H3/b4-3+

InChI Key

GVKYFODEMNCLGS-ONEGZZNKSA-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
Alpha,beta-unsaturated ketone
Enone
Enal
Alpha,beta-unsaturated aldehyde
Acryloyl-group
Ketone
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

enone (CHEBI:76721 )
enal (CHEBI:76721 )
Fatty aldehydes (LMFA06000120 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031759)
Cytoplasm (HMDB: HMDB0031759)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031759)

Source

Endogenous

Endogenous (HMDB: HMDB0031759)

Plant

Plant (HMDB: HMDB0031759)

Exogenous

Food

Food (HMDB: HMDB0031759)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	210.13 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	20280 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.050 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	26.5 g/L	ALOGPS
logP	1.09	ALOGPS
logP	0.83	ChemAxon
logS	-0.63	ALOGPS
pKa (Strongest Basic)	-6	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	31.86 m³·mol⁻¹	ChemAxon
Polarizability	11.63 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
DeepCCS	[M+H]+	123.11	30932474
DeepCCS	[M-H]-	121.089	30932474
DeepCCS	[M-2H]-	157.201	30932474
DeepCCS	[M+Na]+	131.774	30932474
AllCCS	[M+H]+	126.9	32859911
AllCCS	[M+H-H2O]+	122.5	32859911
AllCCS	[M+NH4]+	131.0	32859911
AllCCS	[M+Na]+	132.1	32859911
AllCCS	[M-H]-	126.4	32859911
AllCCS	[M+Na-2H]-	129.5	32859911
AllCCS	[M+HCOO]-	133.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(E)-4-Oxo-2-hexen-1-al	CCC(=O)\C=C\C=O	1617.4	Standard polar	33892256
(E)-4-Oxo-2-hexen-1-al	CCC(=O)\C=C\C=O	970.0	Standard non polar	33892256
(E)-4-Oxo-2-hexen-1-al	CCC(=O)\C=C\C=O	981.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(E)-4-Oxo-2-hexen-1-al,1TMS,isomer #1	CC=C(/C=C/C=O)O[Si](C)(C)C	1243.2	Semi standard non polar	33892256
(E)-4-Oxo-2-hexen-1-al,1TMS,isomer #1	CC=C(/C=C/C=O)O[Si](C)(C)C	1164.7	Standard non polar	33892256
(E)-4-Oxo-2-hexen-1-al,1TBDMS,isomer #1	CC=C(/C=C/C=O)O[Si](C)(C)C(C)(C)C	1495.2	Semi standard non polar	33892256
(E)-4-Oxo-2-hexen-1-al,1TBDMS,isomer #1	CC=C(/C=C/C=O)O[Si](C)(C)C(C)(C)C	1400.7	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)-4-Oxo-2-hexen-1-al GC-MS (Non-derivatized) - 70eV, Positive	splash10-053r-9000000000-305b6b8dfa7a8fe1fc82	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-4-Oxo-2-hexen-1-al 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)-4-Oxo-2-hexen-1-al 10V, Positive-QTOF	splash10-03di-8900000000-1ed9ce83666a679195fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-4-Oxo-2-hexen-1-al 20V, Positive-QTOF	splash10-08fs-9300000000-b1c58f5cdf2d4bd4b4e6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-4-Oxo-2-hexen-1-al 40V, Positive-QTOF	splash10-0a4i-9000000000-0e961b2a0731e4f546cb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-4-Oxo-2-hexen-1-al 10V, Negative-QTOF	splash10-03di-2900000000-e0f627cc3bd09554f3c8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-4-Oxo-2-hexen-1-al 20V, Negative-QTOF	splash10-03di-9600000000-9c99a800e4a8a4e31d32	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-4-Oxo-2-hexen-1-al 40V, Negative-QTOF	splash10-0006-9000000000-86530c53b5d79d16deaa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-4-Oxo-2-hexen-1-al 10V, Positive-QTOF	splash10-05nr-9000000000-88ed54530d1365a83334	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-4-Oxo-2-hexen-1-al 20V, Positive-QTOF	splash10-0a4i-9000000000-248b9750c8c3779f7e76	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-4-Oxo-2-hexen-1-al 40V, Positive-QTOF	splash10-002o-9000000000-a5cbf9a785cdbdba1755	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-4-Oxo-2-hexen-1-al 10V, Negative-QTOF	splash10-03di-8900000000-7a4226b44d3eaf7a202b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-4-Oxo-2-hexen-1-al 20V, Negative-QTOF	splash10-053r-9000000000-8a646a196c00a9245150	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-4-Oxo-2-hexen-1-al 40V, Negative-QTOF	splash10-05mo-9000000000-045ffb5c65977fa92637	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹³C 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]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	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

FDB008431

KNApSAcK ID

Not Available

Chemspider ID

4895969

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6365145

PDB ID

Not Available

ChEBI ID

76721

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1444521

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (E)-4-Oxo-2-hexen-1-al (HMDB0031759)

MOL for HMDB0031759 ((E)-4-Oxo-2-hexen-1-al)

3D MOL for HMDB0031759 ((E)-4-Oxo-2-hexen-1-al)

3D SDF for HMDB0031759 ((E)-4-Oxo-2-hexen-1-al)

3D-SDF for HMDB0031759 ((E)-4-Oxo-2-hexen-1-al)

PDB for HMDB0031759 ((E)-4-Oxo-2-hexen-1-al)

3D PDB for HMDB0031759 ((E)-4-Oxo-2-hexen-1-al)

SMILES for HMDB0031759 ((E)-4-Oxo-2-hexen-1-al)

INCHI for HMDB0031759 ((E)-4-Oxo-2-hexen-1-al)

Structure for HMDB0031759 ((E)-4-Oxo-2-hexen-1-al)

3D Structure for HMDB0031759 ((E)-4-Oxo-2-hexen-1-al)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra