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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:17:12 UTC

Update Date

2023-02-21 17:23:24 UTC

HMDB ID

HMDB0033549

Secondary Accession Numbers

HMDB33549

Metabolite Identification

Common Name

(E)-4-Hexenal

Description

(E)-4-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 (E)-4-Hexenal is a green and vegetable tasting compound. Based on a literature review a significant number of articles have been published on (E)-4-Hexenal.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
6-Carbomethyoxyuracil	HMDB
6-Methylcarboxyuracil	HMDB
Methyl 1,2,3,6-tetrahydro-2,6-dioxopyrimidine-4-carboxylate	HMDB
Methyl 2,6-dihydroxy-4-pyrimidinecarboxylate	HMDB
Methyl 2,6-dioxo-1,2,3,6-tetrahydro-4-pyrimidinecarboxylate	HMDB
Methyl orotate	HMDB
Methylorotate	HMDB
Orotic acid methyl ester	HMDB
Orotic acid, methyl ester	HMDB

Chemical Formula

C₆H₁₀O

Average Molecular Weight

98.143

Monoisotopic Molecular Weight

98.073164942

IUPAC Name

(4Z)-hex-4-enal

Traditional Name

(4Z)-hex-4-enal

CAS Registry Number

25166-87-4

SMILES

C\C=C/CCC=O

InChI Identifier

InChI=1S/C6H10O/c1-2-3-4-5-6-7/h2-3,6H,4-5H2,1H3/b3-2-

InChI Key

DPCMFIRORYQTCL-IHWYPQMZSA-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-hydrogen aldehyde
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0033549)
Cytoplasm (HMDB: HMDB0033549)

Source

Exogenous

Exogenous (HMDB: HMDB0033549)

Food

Food (HMDB: HMDB0033549)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033549)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	125.00 to 129.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	5261 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.471 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.44 g/L	ALOGPS
logP	1.64	ALOGPS
logP	1.29	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	15.74	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	31.26 m³·mol⁻¹	ChemAxon
Polarizability	11.5 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]+	122.504	31661259
DarkChem	[M-H]-	115.631	31661259
DeepCCS	[M+H]+	127.539	30932474
DeepCCS	[M-H]-	125.54	30932474
DeepCCS	[M-2H]-	161.157	30932474
DeepCCS	[M+Na]+	135.802	30932474
AllCCS	[M+H]+	124.2	32859911
AllCCS	[M+H-H2O]+	119.8	32859911
AllCCS	[M+NH4]+	128.4	32859911
AllCCS	[M+Na]+	129.6	32859911
AllCCS	[M-H]-	127.7	32859911
AllCCS	[M+Na-2H]-	131.5	32859911
AllCCS	[M+HCOO]-	135.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.11 minutes	32390414
Predicted by Siyang on May 30, 2022	11.7003 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.53 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1624.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	375.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	152.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	272.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	129.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	393.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	418.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	92.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1009.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	363.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	897.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	342.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	319.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	478.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	410.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	61.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(E)-4-Hexenal	C\C=C/CCC=O	1137.6	Standard polar	33892256
(E)-4-Hexenal	C\C=C/CCC=O	782.3	Standard non polar	33892256
(E)-4-Hexenal	C\C=C/CCC=O	806.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(E)-4-Hexenal,1TMS,isomer #1	C/C=C\CC=CO[Si](C)(C)C	1025.6	Semi standard non polar	33892256
(E)-4-Hexenal,1TMS,isomer #1	C/C=C\CC=CO[Si](C)(C)C	972.8	Standard non polar	33892256
(E)-4-Hexenal,1TBDMS,isomer #1	C/C=C\CC=CO[Si](C)(C)C(C)(C)C	1248.0	Semi standard non polar	33892256
(E)-4-Hexenal,1TBDMS,isomer #1	C/C=C\CC=CO[Si](C)(C)C(C)(C)C	1207.8	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-Hexenal GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9000000000-d8372136799f80092ef0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-4-Hexenal 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-Hexenal 10V, Positive-QTOF	splash10-0002-9000000000-88dfa01c760d56a75e5a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-4-Hexenal 20V, Positive-QTOF	splash10-000t-9000000000-dd2236266dd0dd179ea1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-4-Hexenal 40V, Positive-QTOF	splash10-052o-9000000000-2b15989e64c8e7b86ecd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-4-Hexenal 10V, Negative-QTOF	splash10-0002-9000000000-ba9b57c82eeed12b2387	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-4-Hexenal 20V, Negative-QTOF	splash10-0002-9000000000-ff3643add53b1fe7eb6f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-4-Hexenal 40V, Negative-QTOF	splash10-0006-9000000000-47cda3e1e4f8a91b3be9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-4-Hexenal 10V, Positive-QTOF	splash10-00lu-9000000000-ae06a23f24f715936417	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-4-Hexenal 20V, Positive-QTOF	splash10-0apr-9000000000-a85cfec2213b0a24f610	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-4-Hexenal 40V, Positive-QTOF	splash10-004i-9000000000-de5ea880fd11b5b68bb3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-4-Hexenal 10V, Negative-QTOF	splash10-0002-9000000000-21c5ae8d52f2e0f4cd33	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-4-Hexenal 20V, Negative-QTOF	splash10-004i-9000000000-55dae204912117a01093	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-4-Hexenal 40V, Negative-QTOF	splash10-0006-9000000000-e44e5165989f513b11f6	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

FDB011613

KNApSAcK ID

Not Available

Chemspider ID

9269689

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11094547

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1135351

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-Hexenal (HMDB0033549)

MOL for HMDB0033549 ((E)-4-Hexenal)

3D MOL for HMDB0033549 ((E)-4-Hexenal)

3D SDF for HMDB0033549 ((E)-4-Hexenal)

3D-SDF for HMDB0033549 ((E)-4-Hexenal)

PDB for HMDB0033549 ((E)-4-Hexenal)

3D PDB for HMDB0033549 ((E)-4-Hexenal)

SMILES for HMDB0033549 ((E)-4-Hexenal)

INCHI for HMDB0033549 ((E)-4-Hexenal)

Structure for HMDB0033549 ((E)-4-Hexenal)

3D Structure for HMDB0033549 ((E)-4-Hexenal)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra