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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:46:45 UTC

Update Date

2023-02-21 17:24:25 UTC

HMDB ID

HMDB0034851

Secondary Accession Numbers

HMDB34851

Metabolite Identification

Common Name

Ethyl 2,4-dioxohexanoate

Description

Ethyl 2,4-dioxohexanoate belongs to the class of organic compounds known as 3-acylpyruvic acids. 3-Acylpyruvic acids are compounds containing a pyruvic acid substituted at the 3-position by an acyl group. Based on a literature review very few articles have been published on Ethyl 2,4-dioxohexanoate.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.826  -1.897   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.496  -1.897   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.160  -2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.162  -2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.827  -2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.494  -1.897   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.161  -1.897   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.495  -2.667   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.494  -0.357   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      10.161  -0.357   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      11.495  -4.207   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      12.828  -1.897   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    6                                                       
CONECT    4    2   12                                                       
CONECT    5    6    7                                                       
CONECT    6    3    5    9                                                  
CONECT    7    5    8   10                                                  
CONECT    8    7   11   12                                                  
CONECT    9    6                                                            
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12    4    8                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Ethyl 2,4-dioxohexanoic acid	Generator
2,4-Dioxohexanoic acid, ethyl ester	HMDB
Ethyl 2,4-diketocaproate	HMDB
Ethyl beta-propionylpyruvate	HMDB
FEMA 3278	HMDB
Hexanoic acid, 2,4-dioxo-, ethyl ester	HMDB

Chemical Formula

C₈H₁₂O₄

Average Molecular Weight

172.1785

Monoisotopic Molecular Weight

172.073558872

IUPAC Name

ethyl 2,4-dioxohexanoate

Traditional Name

ethyl 2,4-dioxohexanoate

CAS Registry Number

13246-52-1

SMILES

CCOC(=O)C(=O)CC(=O)CC

InChI Identifier

InChI=1S/C8H12O4/c1-3-6(9)5-7(10)8(11)12-4-2/h3-5H2,1-2H3

InChI Key

JGFBKJBAYISHAG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-acylpyruvic acids. 3-Acylpyruvic acids are compounds containing a pyruvic acid substituted at the 3-position by an acyl group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Gamma-keto acids and derivatives

Direct Parent

3-Acylpyruvic acids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034851)
Cytoplasm (HMDB: HMDB0034851)

Source

Exogenous

Food

Food (HMDB: HMDB0034851)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034851)

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0034851)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	100.00 to 105.00 °C. @ 6.00 mm Hg	The Good Scents Company Information System
Water Solubility	466200 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.399 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.96 g/L	ALOGPS
logP	1.08	ALOGPS
logP	1.72	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	8.4	ChemAxon
pKa (Strongest Basic)	-7.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	60.44 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	42.03 m³·mol⁻¹	ChemAxon
Polarizability	17.28 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
DeepCCS	[M+H]+	139.671	30932474
DeepCCS	[M-H]-	135.844	30932474
DeepCCS	[M-2H]-	173.277	30932474
DeepCCS	[M+Na]+	148.816	30932474
AllCCS	[M+H]+	140.0	32859911
AllCCS	[M+H-H2O]+	136.1	32859911
AllCCS	[M+NH4]+	143.6	32859911
AllCCS	[M+Na]+	144.7	32859911
AllCCS	[M-H]-	138.7	32859911
AllCCS	[M+Na-2H]-	140.3	32859911
AllCCS	[M+HCOO]-	142.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl 2,4-dioxohexanoate	CCOC(=O)C(=O)CC(=O)CC	1800.9	Standard polar	33892256
Ethyl 2,4-dioxohexanoate	CCOC(=O)C(=O)CC(=O)CC	1027.9	Standard non polar	33892256
Ethyl 2,4-dioxohexanoate	CCOC(=O)C(=O)CC(=O)CC	1190.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ethyl 2,4-dioxohexanoate,1TMS,isomer #1	CCOC(=O)C(=CC(=O)CC)O[Si](C)(C)C	1453.8	Semi standard non polar	33892256
Ethyl 2,4-dioxohexanoate,1TMS,isomer #1	CCOC(=O)C(=CC(=O)CC)O[Si](C)(C)C	1361.7	Standard non polar	33892256
Ethyl 2,4-dioxohexanoate,1TMS,isomer #2	CC=C(CC(=O)C(=O)OCC)O[Si](C)(C)C	1449.9	Semi standard non polar	33892256
Ethyl 2,4-dioxohexanoate,1TMS,isomer #2	CC=C(CC(=O)C(=O)OCC)O[Si](C)(C)C	1383.4	Standard non polar	33892256
Ethyl 2,4-dioxohexanoate,1TMS,isomer #3	CCOC(=O)C(=O)C=C(CC)O[Si](C)(C)C	1424.0	Semi standard non polar	33892256
Ethyl 2,4-dioxohexanoate,1TMS,isomer #3	CCOC(=O)C(=O)C=C(CC)O[Si](C)(C)C	1357.5	Standard non polar	33892256
Ethyl 2,4-dioxohexanoate,2TMS,isomer #1	CC=C(C=C(O[Si](C)(C)C)C(=O)OCC)O[Si](C)(C)C	1599.3	Semi standard non polar	33892256
Ethyl 2,4-dioxohexanoate,2TMS,isomer #1	CC=C(C=C(O[Si](C)(C)C)C(=O)OCC)O[Si](C)(C)C	1523.9	Standard non polar	33892256
Ethyl 2,4-dioxohexanoate,1TBDMS,isomer #1	CCOC(=O)C(=CC(=O)CC)O[Si](C)(C)C(C)(C)C	1676.0	Semi standard non polar	33892256
Ethyl 2,4-dioxohexanoate,1TBDMS,isomer #1	CCOC(=O)C(=CC(=O)CC)O[Si](C)(C)C(C)(C)C	1556.1	Standard non polar	33892256
Ethyl 2,4-dioxohexanoate,1TBDMS,isomer #2	CC=C(CC(=O)C(=O)OCC)O[Si](C)(C)C(C)(C)C	1657.6	Semi standard non polar	33892256
Ethyl 2,4-dioxohexanoate,1TBDMS,isomer #2	CC=C(CC(=O)C(=O)OCC)O[Si](C)(C)C(C)(C)C	1588.6	Standard non polar	33892256
Ethyl 2,4-dioxohexanoate,1TBDMS,isomer #3	CCOC(=O)C(=O)C=C(CC)O[Si](C)(C)C(C)(C)C	1646.6	Semi standard non polar	33892256
Ethyl 2,4-dioxohexanoate,1TBDMS,isomer #3	CCOC(=O)C(=O)C=C(CC)O[Si](C)(C)C(C)(C)C	1557.4	Standard non polar	33892256
Ethyl 2,4-dioxohexanoate,2TBDMS,isomer #1	CC=C(C=C(O[Si](C)(C)C(C)(C)C)C(=O)OCC)O[Si](C)(C)C(C)(C)C	2029.7	Semi standard non polar	33892256
Ethyl 2,4-dioxohexanoate,2TBDMS,isomer #1	CC=C(C=C(O[Si](C)(C)C(C)(C)C)C(=O)OCC)O[Si](C)(C)C(C)(C)C	1919.8	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 2,4-dioxohexanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-052b-9100000000-62a15c5f171777aabc58	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl 2,4-dioxohexanoate 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 2,4-dioxohexanoate 10V, Positive-QTOF	splash10-05fr-2900000000-3fac1a38b8708ca4e4cc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2,4-dioxohexanoate 20V, Positive-QTOF	splash10-0a4i-9400000000-56e3b631c1f602cf0ec6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2,4-dioxohexanoate 40V, Positive-QTOF	splash10-0a4i-9000000000-f1b1780882ef9975d68a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2,4-dioxohexanoate 10V, Negative-QTOF	splash10-00dj-5900000000-b0dd4d9393acb735b1b6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2,4-dioxohexanoate 20V, Negative-QTOF	splash10-002b-9600000000-e577483476092343e35e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2,4-dioxohexanoate 40V, Negative-QTOF	splash10-0005-9000000000-287977056fcfc12d6675	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2,4-dioxohexanoate 10V, Negative-QTOF	splash10-0fk9-2900000000-47b08cf37ca6c9df042b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2,4-dioxohexanoate 20V, Negative-QTOF	splash10-0avm-9000000000-39b921887bc4641b2c9d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2,4-dioxohexanoate 40V, Negative-QTOF	splash10-006y-9000000000-74b282055cdfc81f795b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2,4-dioxohexanoate 10V, Positive-QTOF	splash10-05i1-9800000000-5bdf1b1fa0a0769b3ea7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2,4-dioxohexanoate 20V, Positive-QTOF	splash10-05gi-9100000000-33624be4cbbce44e77c7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2,4-dioxohexanoate 40V, Positive-QTOF	splash10-0a4m-9000000000-cc1f5626e1722108b5d5	2021-09-25	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

FDB013417

KNApSAcK ID

Not Available

Chemspider ID

55499

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61590

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1022571

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 2,4-dioxohexanoate (HMDB0034851)

MOL for HMDB0034851 (Ethyl 2,4-dioxohexanoate)

3D MOL for HMDB0034851 (Ethyl 2,4-dioxohexanoate)

3D SDF for HMDB0034851 (Ethyl 2,4-dioxohexanoate)

3D-SDF for HMDB0034851 (Ethyl 2,4-dioxohexanoate)

PDB for HMDB0034851 (Ethyl 2,4-dioxohexanoate)

3D PDB for HMDB0034851 (Ethyl 2,4-dioxohexanoate)

SMILES for HMDB0034851 (Ethyl 2,4-dioxohexanoate)

INCHI for HMDB0034851 (Ethyl 2,4-dioxohexanoate)

Structure for HMDB0034851 (Ethyl 2,4-dioxohexanoate)

3D Structure for HMDB0034851 (Ethyl 2,4-dioxohexanoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra