Showing Compound Ethyl 3-oxobutanoate (FDB003241)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:43 UTC

Update date

2018-05-29 00:37:35 UTC

Primary ID

FDB003241

Secondary Accession Numbers

FDB003239

Chemical Information

FooDB Name

Ethyl 3-oxobutanoate

Description

The organic compound ethyl acetoacetate (EAA) is the ethyl ester of acetoacetic acid. It is mainly used as a chemical intermediate in the production of a wide variety of compounds, such as amino acids, analgesics, antibiotics, antimalarial agents, antipyrine and aminopyrine, and vitamin B1; as well as the manufacture of dyes, inks, lacquers, perfumes, plastics, and yellow paint pigments. Alone, it is used as a flavoring for food.

CAS Number

141-97-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1-Ethoxybutane-1,3-dione	ChEBI
3-Ketobutyric acid ethyl ester	ChEBI
3-Oxobutanoic acid ethyl ester	ChEBI
3-Oxobutyric acid ethyl ester	ChEBI
Acetoacetic acid ethyl ester	ChEBI
Active acetyl acetate	ChEBI
Diacetic ether	ChEBI
Ethyl 3-oxidanylidenebutanoate	ChEBI
Ethyl 3-oxobutanoate	ChEBI
Ethyl 3-oxobutyrate	ChEBI
Ethyl acetyl acetate	ChEBI
Ethyl acetylacetate	ChEBI
Ethyl acetylacetonate	ChEBI
Ethyl beta-ketobutyrate	ChEBI
3-Ketobutyrate ethyl ester	Generator
3-Oxobutanoate ethyl ester	Generator
3-Oxobutyrate ethyl ester	Generator
Acetoacetate ethyl ester	Generator
Active acetyl acetic acid	Generator
Ethyl 3-oxidanylidenebutanoic acid	Generator
Ethyl 3-oxobutanoic acid	Generator
Ethyl 3-oxobutyric acid	Generator
Ethyl acetyl acetic acid	Generator
Ethyl acetylacetic acid	Generator
Ethyl acetylacetonic acid	Generator
Ethyl b-ketobutyrate	Generator
Ethyl b-ketobutyric acid	Generator
Ethyl beta-ketobutyric acid	Generator
Ethyl β-ketobutyrate	Generator
Ethyl β-ketobutyric acid	Generator
Ethyl acetoacetic acid	Generator
EAA	HMDB
Ethyl 3-hydroxy-2-butenoate	HMDB
FEMA 2415	HMDB
Ethyl acetoacetate, 1,3-(14)C-labeled	MeSH, HMDB
Ethyl acetoacetate, 2,4-(14)C-labeled	MeSH, HMDB
Ethyl acetoacetate, 2-(14)C-labeled	MeSH, HMDB
Ethyl acetoacetate, 1,2-(14)C-labeled	MeSH, HMDB
Ethyl acetoacetate, 3-(14)C-labeled	MeSH, HMDB
Ethyl acetoacetate, 14c4-labeled	MeSH, HMDB
Ethyl acetoacetate	KEGG
3-Oxo-butyric acid ethyl ester	biospider
Butanoic acid, 3-oxo-ethyl ester	biospider

Predicted Properties

Property	Value	Source
Water Solubility	58.6 g/L	ALOGPS
logP	0.19	ALOGPS
logP	0.5	ChemAxon
logS	-0.35	ALOGPS
pKa (Strongest Acidic)	9.93	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	4	ChemAxon
Refractivity	32.06 m³·mol⁻¹	ChemAxon
Polarizability	13.2 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

Chemical Formula

C6H10O3

IUPAC name

ethyl 3-oxobutanoate

InChI Identifier

InChI=1S/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3

InChI Key

XYIBRDXRRQCHLP-UHFFFAOYSA-N

Isomeric SMILES

CCOC(=O)CC(C)=O

Average Molecular Weight

130.1418

Monoisotopic Molecular Weight

130.062994186

Classification

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

oxo carboxylic acid (CHEBI:4893 )
a small molecule (ETHYL-ACETOACETATE )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Coffea

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Food and nutrition:

Flavoring agent

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 55.37%; H 7.74%; O 36.88%	DFC
Melting Point	-45 oC
Boiling Point	Bp1 28.5°	DFC
Experimental Water Solubility	110 mg/mL at 17 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	0.25	CATZ,P & FRIEND,D (1989)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d20 1.03	DFC
Refractive Index	n20D 1.4190	DFC

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Ethyl acetoacetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-c1d7540b51e68aae277f	Spectrum
GC-MS	Ethyl acetoacetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-f40d68840be65d2cc6bd	Spectrum
GC-MS	Ethyl acetoacetate, non-derivatized, GC-MS Spectrum	splash10-000f-9000000000-aad3ec5cf145a6891816	Spectrum
GC-MS	Ethyl acetoacetate, non-derivatized, GC-MS Spectrum	splash10-000i-9200000000-d0f54fdbaded925d3619	Spectrum
GC-MS	Ethyl acetoacetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-4a1188d69a9a3efd5ef8	Spectrum
GC-MS	Ethyl acetoacetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-c1d7540b51e68aae277f	Spectrum
GC-MS	Ethyl acetoacetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-f40d68840be65d2cc6bd	Spectrum
GC-MS	Ethyl acetoacetate, non-derivatized, GC-MS Spectrum	splash10-000f-9000000000-aad3ec5cf145a6891816	Spectrum
GC-MS	Ethyl acetoacetate, non-derivatized, GC-MS Spectrum	splash10-000i-9200000000-d0f54fdbaded925d3619	Spectrum
GC-MS	Ethyl acetoacetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-4a1188d69a9a3efd5ef8	Spectrum
GC-MS	Ethyl acetoacetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-c1d7540b51e68aae277f	Spectrum
GC-MS	Ethyl acetoacetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-f40d68840be65d2cc6bd	Spectrum
GC-MS	Ethyl acetoacetate, non-derivatized, GC-MS Spectrum	splash10-000f-9000000000-aad3ec5cf145a6891816	Spectrum
GC-MS	Ethyl acetoacetate, non-derivatized, GC-MS Spectrum	splash10-000i-9200000000-d0f54fdbaded925d3619	Spectrum
GC-MS	Ethyl acetoacetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-4a1188d69a9a3efd5ef8	Spectrum
GC-MS	Ethyl acetoacetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-c1d7540b51e68aae277f	Spectrum
GC-MS	Ethyl acetoacetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-f40d68840be65d2cc6bd	Spectrum
GC-MS	Ethyl acetoacetate, non-derivatized, GC-MS Spectrum	splash10-000f-9000000000-aad3ec5cf145a6891816	Spectrum
GC-MS	Ethyl acetoacetate, non-derivatized, GC-MS Spectrum	splash10-000i-9200000000-d0f54fdbaded925d3619	Spectrum
GC-MS	Ethyl acetoacetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-4a1188d69a9a3efd5ef8	Spectrum
Predicted GC-MS	Ethyl acetoacetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004r-9100000000-39e60e7c126db56d47de	Spectrum
Predicted GC-MS	Ethyl acetoacetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-4900000000-29f09f28b24891a22618	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-029i-9300000000-af778dca9727536ec993	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9000000000-3918640dd15245bebce9	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0059-9800000000-0a07fb5054503628c784	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0569-9100000000-c332a02de02bb728d9db	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a59-9000000000-3e3615c76305bc07ac7c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000f-9100000000-a875fcd5d0d364ce51f0	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-4344d7a5332bce981fb1	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-7e90a42673f1ccc12684	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9200000000-e413c1504f20f3f3a9eb	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052f-9100000000-444b1da62777f402c237	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-78efa999cb1cca26f4ca	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB31218

CRC / DFC (Dictionary of Food Compounds) ID

CTW38-T:CTW41-P

EAFUS ID

1135

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

EAC

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1001851

SuperScent ID

Not Available

Wikipedia ID

Ethyl_acetoacetate

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
fresh	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fruity	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
green	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
apple	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fatty	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.