ContaminantDB: Methyl acetoacetate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-19 02:58:47 UTC

Update Date

2016-11-09 01:13:56 UTC

Accession Number

CHEM009131

Identification

Common Name

Methyl acetoacetate

Class

Small Molecule

Description

Methylacetoacetic acid has been identified in the urine of patients with an inherited deficiency of propionyl-CoA carboxylase (PMID 630060), and after isoleucine loading in the diagnosis of 2-methylacetoacetyl-CoA thiolase deficiency. (PMID 1861461) [HMDB]

Contaminant Sources

FooDB Chemicals
HPV EPA Chemicals
OECD HPV Chemicals
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Methylacetoacetate	Generator
1-Methoxybutane-1,3-dione	HMDB
3-oxo-Butanoate	HMDB
3-oxo-Butanoic acid	HMDB
3-oxo-Butanoic acid methyl ester	HMDB
3-Oxobutanoate	HMDB
3-Oxobutanoic acid	HMDB
3-Oxobutanoic acid methyl ester	HMDB
3-Oxobutyric acid methyl ester	HMDB
Acetoacetate methyl ester	HMDB
Acetoacetic acid methyl ester	HMDB
Acetoacetic methyl ester	HMDB
Methyl 3-oxobutanoate	HMDB
Methyl 3-oxobutanoic acid	HMDB
Methyl 3-oxobutyrate	HMDB
Methyl acetoacetate	HMDB
Methyl acetylacetate	HMDB
Methyl acetylacetonate	HMDB

Chemical Formula

C₅H₈O₃

Average Molecular Mass

116.115 g/mol

Monoisotopic Mass

116.047 g/mol

CAS Registry Number

105-45-3

IUPAC Name

methyl 3-oxobutanoate

Traditional Name

methyl acetoacetate

SMILES

COC(=O)CC(C)=O

InChI Identifier

InChI=1S/C5H8O3/c1-4(6)3-5(7)8-2/h3H2,1-2H3

InChI Key

WRQNANDWMGAFTP-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

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	137 g/L	ALOGPS
logP	-0.29	ALOGPS
logP	0.14	ChemAxon
logS	0.07	ALOGPS
pKa (Strongest Acidic)	10.28	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	3	ChemAxon
Refractivity	27.31 m³·mol⁻¹	ChemAxon
Polarizability	11.27 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-9801f4fde1f8c64f6baf	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-e4481e7d9e6ac8fc177b	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-f8789e71041e62cce331	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9100000000-65b70a114483f92cc1f4	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-00kr-9300000000-7a638e147c3997a85598	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-9801f4fde1f8c64f6baf	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-e4481e7d9e6ac8fc177b	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-f8789e71041e62cce331	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9100000000-65b70a114483f92cc1f4	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-00kr-9300000000-7a638e147c3997a85598	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-869c1574ff891034b665	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-000l-9100000000-be1b334229aa020fc7e8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-0006-9000000000-e512bbad2ab7f1c253a7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0006-9000000000-0627dffba19580aa6a7d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0006-9000000000-6f423389be91a0d883a2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-0006-9000000000-e4481e7d9e6ac8fc177b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive	splash10-0006-9000000000-970f150ada556d232464	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-0006-9100000000-86a6dd485ea6cf9b0632	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - CI-B (HITACHI M-80) , Positive	splash10-00kr-9300000000-0d967b807194a0d4f189	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-9300000000-e5dc637782adee6c0e04	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-9100000000-3bc03bc80fc348b48f88	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014u-9000000000-ed2c64d5d7629d00368e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-8900000000-26833f2c7b71af9eed1f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0aw9-9200000000-d2941bafc6ef6d37ea38	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a59-9000000000-765079c1255f5f8b2907	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01bc-9400000000-ac614382ccd32f161a65	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-f50f28ce0031ed1ca1af	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-7ab0f1f6abf2d008ff8e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-d66fe58106ad458e0f71	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-0c548d0b4e3b334064ce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-87bbaed151efac084591	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000310

FooDB ID

FDB021937

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

5299

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

13874867

ChEBI ID

Not Available

PubChem Compound ID

7757

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Chan, Tak-Hang; Brownbridge, Peter. Reaction of electrophiles with 1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene, a dianion equivalent of methyl acetoacetate. Journal of the Chemical Society, Chemical Communications (1979), (13), 578-9.

2. Robinson BH, Sherwood WG, Taylor J, Balfe JW, Mamer OA: Acetoacetyl CoA thiolase deficiency: a cause of severe ketoacidosis in infancy simulating salicylism. J Pediatr. 1979 Aug;95(2):228-33.

3. Aramaki S, Lehotay D, Sweetman L, Nyhan WL, Winter SC, Middleton B: Urinary excretion of 2-methylacetoacetate, 2-methyl-3-hydroxybutyrate and tiglylglycine after isoleucine loading in the diagnosis of 2-methylacetoacetyl-CoA thiolase deficiency. J Inherit Metab Dis. 1991;14(1):63-74.

4. Sweetman L, Weyler W, Nyhan WL, de Cespedes C, Loria AR, Estrada Y: Abnormal metabolites of isoleucine in a patient with propionyl-CoA carboxylase deficiency. Biomed Mass Spectrom. 1978 Mar;5(3):198-207.

Methyl acetoacetate (CHEM009131)

Structure for CHEM009131: Methyl acetoacetate