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

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2014-10-11 02:27:50 UTC

Update Date

2023-02-21 17:30:37 UTC

HMDB ID

HMDB0061945

Secondary Accession Numbers

HMDB61945

Metabolite Identification

Common Name

2-Ethyl-2-hexenal

Description

2-Ethyl-2-hexenal, also known as 2-ethylhex-2-en-1-al, 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. 2-Ethyl-2-hexenal is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Ethylhex-2-en-1-al	HMDB

Chemical Formula

C₈H₁₄O

Average Molecular Weight

126.1962

Monoisotopic Molecular Weight

126.10446507

IUPAC Name

(2E)-2-ethylhex-2-enal

Traditional Name

2-ethyl-2-hexenal

CAS Registry Number

Not Available

SMILES

CCC\C=C(/CC)C=O

InChI Identifier

InChI=1S/C8H14O/c1-3-5-6-8(4-2)7-9/h6-7H,3-5H2,1-2H3/b8-6+

InChI Key

PYLMCYQHBRSDND-SOFGYWHQSA-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

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 24421258)

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	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	1.3 g/L	ALOGPS
logP	2.67	ALOGPS
logP	2.49	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Basic)	-4.2	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	4	ChemAxon
Refractivity	40.2 m³·mol⁻¹	ChemAxon
Polarizability	15.26 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]+	130.14	31661259
DarkChem	[M-H]-	127.023	31661259
DeepCCS	[M+H]+	130.856	30932474
DeepCCS	[M-H]-	128.243	30932474
DeepCCS	[M-2H]-	164.894	30932474
DeepCCS	[M+Na]+	139.66	30932474
AllCCS	[M+H]+	132.0	32859911
AllCCS	[M+H-H2O]+	127.8	32859911
AllCCS	[M+NH4]+	136.0	32859911
AllCCS	[M+Na]+	137.1	32859911
AllCCS	[M-H]-	133.1	32859911
AllCCS	[M+Na-2H]-	135.8	32859911
AllCCS	[M+HCOO]-	138.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Ethyl-2-hexenal	CCC\C=C(/CC)C=O	1299.6	Standard polar	33892256
2-Ethyl-2-hexenal	CCC\C=C(/CC)C=O	980.7	Standard non polar	33892256
2-Ethyl-2-hexenal	CCC\C=C(/CC)C=O	988.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2-Ethyl-2-hexenal EI-B (Non-derivatized)	splash10-056u-9000000000-a2b1bf5f5659fd1dc002	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Ethyl-2-hexenal EI-B (Non-derivatized)	splash10-056u-9000000000-a2b1bf5f5659fd1dc002	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Ethyl-2-hexenal GC-MS (Non-derivatized) - 70eV, Positive	splash10-004j-9100000000-52d1d077559b1998606f	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Ethyl-2-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 - 2-Ethyl-2-hexenal 10V, Positive-QTOF	splash10-004i-3900000000-a9739b264cd2c9331616	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-2-hexenal 20V, Positive-QTOF	splash10-0a6r-9300000000-aac5d6663329fe9f023a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-2-hexenal 40V, Positive-QTOF	splash10-0k96-9000000000-86509cacc75af3c099eb	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-2-hexenal 10V, Negative-QTOF	splash10-004i-0900000000-e44c3458552bece77143	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-2-hexenal 20V, Negative-QTOF	splash10-004i-2900000000-ed7f56ceb4b83f2028a2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-2-hexenal 40V, Negative-QTOF	splash10-0kvp-9100000000-1306fe8cc9c13d14e1ba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-2-hexenal 10V, Negative-QTOF	splash10-004i-0900000000-cd4682adb484c6183f8b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-2-hexenal 20V, Negative-QTOF	splash10-05r1-9400000000-72061449e91463509672	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-2-hexenal 40V, Negative-QTOF	splash10-014i-9000000000-3aa722693554d0155d1e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-2-hexenal 10V, Positive-QTOF	splash10-0a4i-9000000000-231f9d79185c6dc8de4f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-2-hexenal 20V, Positive-QTOF	splash10-0a4i-9000000000-f7906aa76f9c37b3e3f4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-2-hexenal 40V, Positive-QTOF	splash10-0aor-9000000000-7b76b3a07452bd1163e0	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

Not Available

Biospecimen Locations

Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5354264

PDB ID

Not Available

ChEBI ID

88838

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

Carrapiso AI, Ventanas J, Garcia C: Characterization of the most odor-active compounds of Iberian ham headspace. J Agric Food Chem. 2002 Mar 27;50(7):1996-2000. [PubMed:11902946 ]
Carrapiso AI, Jurado A, Timon ML, Garcia C: Odor-active compounds of Iberian hams with different aroma characteristics. J Agric Food Chem. 2002 Oct 23;50(22):6453-8. [PubMed:12381133 ]
Buttery RG, Takeoka GR: Some unusual minor volatile components of tomato. J Agric Food Chem. 2004 Oct 6;52(20):6264-6. [PubMed:15453697 ]
Moreira JA, Millar JG: Short and simple syntheses of 4-oxo-(E)-2-hexenal and homologs: pheromone components and defensive compounds of Hemiptera. J Chem Ecol. 2005 Apr;31(4):965-8. [PubMed:16124263 ]
POWELL SG, NIELSEN AT: Condensation of butanal with 4-heptanone and 3-hexanone and attempted condensation of 2-ethyl-2-hexenal with 4-heptanone. J Am Chem Soc. 1948 Nov;70(11):3627-30. [PubMed:18102909 ]
Azhu Valappil Z, Fan X, Zhang HQ, Rouseff RL: Impact of thermal and nonthermal processing technologies on unfermented apple cider aroma volatiles. J Agric Food Chem. 2009 Feb 11;57(3):924-9. doi: 10.1021/jf803142d. [PubMed:19154152 ]
Steinhaus M, Sinuco D, Polster J, Osorio C, Schieberle P: Characterization of the key aroma compounds in pink guava (Psidium guajava L.) by means of aroma re-engineering experiments and omission tests. J Agric Food Chem. 2009 Apr 8;57(7):2882-8. doi: 10.1021/jf803728n. [PubMed:19254022 ]
Helmut Gebauer, Hans Mehlin, '2-ethyl-2-prenyl-3-hexenol its preparation and use as a fragrant.' U.S. Patent US4647406, issued April, 1983. [Link]
Gunther Kessen, Boy Cornils, Wilhelm Gick, Ernst Wiebus, Joseph Hibbel, Hanswilhelm Bach, Wolfgang Zgorzelski, 'Process for the production of 2-ethyl-hexanol.' U.S. Patent US4684750, issued October, 1979. [Link]
Blaise J. Arena, Jennifer S. Holmgren, '2-ethyl-2-hexenal by aldol condensation of butyraldehyde in a continuous process.' U.S. Patent US5144089, issued April, 1966. [Link]

Showing metabocard for 2-Ethyl-2-hexenal (HMDB0061945)

MOL for HMDB0061945 (2-Ethyl-2-hexenal)

3D MOL for HMDB0061945 (2-Ethyl-2-hexenal)

3D SDF for HMDB0061945 (2-Ethyl-2-hexenal)

3D-SDF for HMDB0061945 (2-Ethyl-2-hexenal)

PDB for HMDB0061945 (2-Ethyl-2-hexenal)

3D PDB for HMDB0061945 (2-Ethyl-2-hexenal)

SMILES for HMDB0061945 (2-Ethyl-2-hexenal)

INCHI for HMDB0061945 (2-Ethyl-2-hexenal)

Structure for HMDB0061945 (2-Ethyl-2-hexenal)

3D Structure for HMDB0061945 (2-Ethyl-2-hexenal)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra