Showing Compound Ethyl levulinate (FDB020166)

Record Information

Version

1.0

Creation date

2010-04-08 22:14:51 UTC

Update date

2019-11-27 17:39:11 UTC

Primary ID

FDB020166

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Ethyl levulinate

Description

Ethyl levulinate belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. Ethyl levulinate is an extremely weak basic (essentially neutral) compound (based on its pKa). Ethyl levulinate is a sweet, berry, and floral tasting compound. Ethyl levulinate has been detected, but not quantified in, evergreen blackberries. This could make ethyl levulinate a potential biomarker for the consumption of these foods.

CAS Number

539-88-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Ethyl levulinic acid	Generator
Ethyl acetylpropanoate	MeSH
Ethyl 4-oxopentanoate	MeSH
Ethyl 4-ketovalerate	MeSH
Ethyl 3-acetylpropionate	HMDB
Ethyl 4-oxovalerate	HMDB
Ethyl ketovalerate	HMDB
Ethyl laevulinate	HMDB
Ethyl levulate	HMDB
FEMA 2442	HMDB
Levulinic acid, ethyl ester	HMDB
Pentanoic acid, 4-oxo-, ethyl ester	HMDB
Ethyl 4-oxopentanoic acid	Generator
Ethyl levulinate	MeSH
1,1-Dimethoxy-heptane	HMDB
Aldehyde C-7 dimethyl acetal	HMDB
Enanthal dimethyl acetal	HMDB
FEMA 2541	HMDB
Heptaldehyde dimethyl acetal	HMDB
Heptanal dimethyl acetal	HMDB
Heptanal, dimethyl acetal	HMDB
N-Heptanal dimethyl acetal	HMDB
Oenanthal dimethyl acetal	HMDB
Hexyl benzoic acid	Generator
1-Hexyl benzoate	HMDB
2-Ethylhexyl-4-hydroxybenzoate	HMDB
Benzoic acid N-hexyl ester	HMDB
Benzoic acid, hexyl ester	HMDB
FEMA 3691	HMDB
Hexylbenzoate	HMDB
Hexylester kyseliny benzoove	HMDB
N-Hexyl benzoate	HMDB
N-Hexylbenzoate	HMDB

Predicted Properties

Property	Value	Source
Water Solubility	22.7 g/L	ALOGPS
logP	0.38	ALOGPS
logP	0.43	ChemAxon
logS	-0.8	ALOGPS
pKa (Strongest Acidic)	17.54	ChemAxon
pKa (Strongest Basic)	-6.8	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	5	ChemAxon
Refractivity	36.61 m³·mol⁻¹	ChemAxon
Polarizability	15.4 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C7H12O3

IUPAC name

ethyl 4-oxopentanoate

InChI Identifier

InChI=1S/C7H12O3/c1-3-10-7(9)5-4-6(2)8/h3-5H2,1-2H3

InChI Key

GMEONFUTDYJSNV-UHFFFAOYSA-N

Isomeric SMILES

CCOC(=O)CCC(C)=O

Average Molecular Weight

144.1684

Monoisotopic Molecular Weight

144.07864425

Classification

Description

belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Gamma-keto acids and derivatives

Direct Parent

Gamma-keto acids and derivatives

Alternative Parents

Substituents

Gamma-keto acid
Fatty acid ester
Fatty acyl
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

Not Available

Ontology

Disposition

Source:

Food

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Food and nutrition:

Flavoring agent

Biological role:

Nutrient

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 58.32%; H 8.39%; O 33.29%	DFC
Melting Point	< 25 oC
Boiling Point	Bp0.1 38°	DFC
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d20 1.01	DFC
Refractive Index	n20D 1.4220	DFC

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0097-9100000000-e17c4b8e6a264be46500	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-002g-9100000000-58314b79e586dde6ec61	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0007-9300000000-a4475e8effea84591152	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0097-9100000000-e17c4b8e6a264be46500	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-002g-9100000000-58314b79e586dde6ec61	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0007-9300000000-a4475e8effea84591152	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-2e03e600798fe0d0267a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-3900000000-0ea35fa03edfeb06ce8b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000t-9400000000-7691a84859184726e377	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0kal-9000000000-c7f31a62338261696c0f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0007-7900000000-24e10e783fc3d79e6041	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9300000000-899dae367a08b4ae58d5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9000000000-ca99a895a8aa02feaf2b	View in MoNA

External Links

ChemSpider ID

13853514

ChEMBL ID

CHEMBL3182933

KEGG Compound ID

Not Available

Pubchem Compound ID

10883

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB40433

CRC / DFC (Dictionary of Food Compounds) ID

CVR73-P:MLM52-X

EAFUS ID

1243

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1024311

SuperScent ID

Not Available

Wikipedia ID

Not Available

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
sweet	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.
floral	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
berry	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.
pineapple	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
rhubarb	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Ethyl levulinate (FDB020166)

Structure for FDB020166 (Ethyl levulinate)