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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:42:14 UTC

Update Date

2023-02-21 17:20:19 UTC

HMDB ID

HMDB0031307

Secondary Accession Numbers

HMDB31307

Metabolite Identification

Common Name

Ethyl 3-oxohexanoate

Description

Ethyl 3-oxohexanoate, also known as ethyl butyrylacetate, belongs to the class of organic compounds known as beta-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom. Ethyl 3-oxohexanoate is a sweet, berry, and fruity tasting compound. Based on a literature review very few articles have been published on Ethyl 3-oxohexanoate.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Ethyl butyrylacetate	ChEBI
Ethyl butyrylacetic acid	Generator
Ethyl 3-oxohexanoic acid	Generator
3-keto-N-Hexanoic acid ethyl ester	HMDB
Ethyl alpha -butyrylacetate	HMDB
Ethyl alpha-butyrylacetate	HMDB
Ethyl beta-ketohexanoate	HMDB
Ethyl butyroacetate	HMDB
ETHYL-3-oxohexanoATE	HMDB
FEMA 3683	HMDB
Hexanoic acid, 3-oxo-, ethyl ester	HMDB

Chemical Formula

C₈H₁₄O₃

Average Molecular Weight

158.195

Monoisotopic Molecular Weight

158.094294314

IUPAC Name

ethyl 3-oxohexanoate

Traditional Name

ethyl 3-oxohexanoate

CAS Registry Number

3249-68-1

SMILES

CCCC(=O)CC(=O)OCC

InChI Identifier

InChI=1S/C8H14O3/c1-3-5-7(9)6-8(10)11-4-2/h3-6H2,1-2H3

InChI Key

KQWWVLVLVYYYDT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Beta-keto acids and derivatives

Direct Parent

Beta-keto acids and derivatives

Alternative Parents

Substituents

Fatty acid ester
Beta-keto acid
Fatty acyl
1,3-dicarbonyl compound
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

fatty acid ethyl ester (CHEBI:18119 )
a small molecule (ETHYL-3-OXOHEXANOATE )

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031307)
Cytoplasm (HMDB: HMDB0031307)

Source

Endogenous

Endogenous (HMDB: HMDB0031307)

Exogenous

Food

Food (HMDB: HMDB0031307)

Exogenous (HMDB: HMDB0031307)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031307)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	104.00 °C. @ 22.00 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	1.386 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.61 g/L	ALOGPS
logP	1.22	ALOGPS
logP	1.65	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	9.67	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	41.28 m³·mol⁻¹	ChemAxon
Polarizability	17.21 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	136.552	31661259
DarkChem	[M-H]-	133.454	31661259
DeepCCS	[M+H]+	135.486	30932474
DeepCCS	[M-H]-	132.885	30932474
DeepCCS	[M-2H]-	169.588	30932474
DeepCCS	[M+Na]+	144.611	30932474
AllCCS	[M+H]+	138.2	32859911
AllCCS	[M+H-H2O]+	134.3	32859911
AllCCS	[M+NH4]+	141.9	32859911
AllCCS	[M+Na]+	143.0	32859911
AllCCS	[M-H]-	138.1	32859911
AllCCS	[M+Na-2H]-	140.1	32859911
AllCCS	[M+HCOO]-	142.4	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.	5.51 minutes	32390414
Predicted by Siyang on May 30, 2022	13.2101 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.63 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1859.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	426.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	154.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	255.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	162.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	507.1 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	566.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	73.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1077.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	381.7 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	1213.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	324.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	343.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	362.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	383.1 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	34.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl 3-oxohexanoate	CCCC(=O)CC(=O)OCC	1691.9	Standard polar	33892256
Ethyl 3-oxohexanoate	CCCC(=O)CC(=O)OCC	1076.1	Standard non polar	33892256
Ethyl 3-oxohexanoate	CCCC(=O)CC(=O)OCC	1125.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ethyl 3-oxohexanoate,1TMS,isomer #1	CCCC(=CC(=O)OCC)O[Si](C)(C)C	1315.9	Semi standard non polar	33892256
Ethyl 3-oxohexanoate,1TMS,isomer #1	CCCC(=CC(=O)OCC)O[Si](C)(C)C	1289.3	Standard non polar	33892256
Ethyl 3-oxohexanoate,1TMS,isomer #2	CCC=C(CC(=O)OCC)O[Si](C)(C)C	1303.3	Semi standard non polar	33892256
Ethyl 3-oxohexanoate,1TMS,isomer #2	CCC=C(CC(=O)OCC)O[Si](C)(C)C	1322.8	Standard non polar	33892256
Ethyl 3-oxohexanoate,1TBDMS,isomer #1	CCCC(=CC(=O)OCC)O[Si](C)(C)C(C)(C)C	1530.3	Semi standard non polar	33892256
Ethyl 3-oxohexanoate,1TBDMS,isomer #1	CCCC(=CC(=O)OCC)O[Si](C)(C)C(C)(C)C	1479.8	Standard non polar	33892256
Ethyl 3-oxohexanoate,1TBDMS,isomer #2	CCC=C(CC(=O)OCC)O[Si](C)(C)C(C)(C)C	1500.9	Semi standard non polar	33892256
Ethyl 3-oxohexanoate,1TBDMS,isomer #2	CCC=C(CC(=O)OCC)O[Si](C)(C)C(C)(C)C	1524.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl 3-oxohexanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0096-9100000000-e6766bdb7a951bd05d99	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl 3-oxohexanoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl 3-oxohexanoate 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 - Ethyl 3-oxohexanoate 10V, Positive-QTOF	splash10-0a4i-2900000000-164751d38a890ab5f3f8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-oxohexanoate 20V, Positive-QTOF	splash10-01vn-9400000000-40b48fa60f02b0e6c2f5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-oxohexanoate 40V, Positive-QTOF	splash10-0006-9000000000-2e3f07c039c725d96e5e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-oxohexanoate 10V, Negative-QTOF	splash10-0bt9-4900000000-85a68c04e152bfe6051c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-oxohexanoate 20V, Negative-QTOF	splash10-000i-9300000000-ef4e1797c3297683c1b3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-oxohexanoate 40V, Negative-QTOF	splash10-052g-9000000000-3dba4b28e998bd19bc37	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-oxohexanoate 10V, Positive-QTOF	splash10-006x-9100000000-0d196847bba32addbf0c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-oxohexanoate 20V, Positive-QTOF	splash10-00kf-9000000000-583a149a49c5c0538273	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-oxohexanoate 40V, Positive-QTOF	splash10-0006-9000000000-06a898c67e0abcbc54a6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-oxohexanoate 10V, Negative-QTOF	splash10-0btj-9800000000-ad7dc1c0ee764b0dea3f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-oxohexanoate 20V, Negative-QTOF	splash10-0006-9100000000-b849d27ad5b506736da0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-oxohexanoate 40V, Negative-QTOF	splash10-00kf-9000000000-a60379ee8c5705ef1e22	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

FDB003363

KNApSAcK ID

Not Available

Chemspider ID

208322

KEGG Compound ID

C02975

BioCyc ID

ETHYL-3-OXOHEXANOATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

238498

PDB ID

Not Available

ChEBI ID

18119

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1005531

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 Ethyl 3-oxohexanoate (HMDB0031307)

MOL for HMDB0031307 (Ethyl 3-oxohexanoate)

3D MOL for HMDB0031307 (Ethyl 3-oxohexanoate)

3D SDF for HMDB0031307 (Ethyl 3-oxohexanoate)

3D-SDF for HMDB0031307 (Ethyl 3-oxohexanoate)

PDB for HMDB0031307 (Ethyl 3-oxohexanoate)

3D PDB for HMDB0031307 (Ethyl 3-oxohexanoate)

SMILES for HMDB0031307 (Ethyl 3-oxohexanoate)

INCHI for HMDB0031307 (Ethyl 3-oxohexanoate)

Structure for HMDB0031307 (Ethyl 3-oxohexanoate)

3D Structure for HMDB0031307 (Ethyl 3-oxohexanoate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra