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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:58:30 UTC

Update Date

2023-02-21 17:28:16 UTC

HMDB ID

HMDB0040433

Secondary Accession Numbers

HMDB40433

Metabolite Identification

Common 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 a sweet, berry, and floral tasting compound. Ethyl levulinate has been detected, but not quantified in, blackberries (Rubus) and evergreen blackberries (Rubus laciniatus). This could make ethyl levulinate a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Ethyl levulinate.

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 levulinic acid	Generator
Ethyl 3-acetylpropionate	HMDB
Ethyl 4-ketovalerate	HMDB, MeSH
Ethyl 4-oxopentanoate	HMDB, MeSH
Ethyl 4-oxovalerate	HMDB
Ethyl acetylpropanoate	HMDB, MeSH
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

Chemical Formula

C₇H₁₂O₃

Average Molecular Weight

144.1684

Monoisotopic Molecular Weight

144.07864425

IUPAC Name

ethyl 4-oxopentanoate

Traditional Name

ethyl levulinate

CAS Registry Number

539-88-8

SMILES

CCOC(=O)CCC(C)=O

InChI Identifier

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

InChI Key

GMEONFUTDYJSNV-UHFFFAOYSA-N

Chemical Taxonomy

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

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040433)
Cytoplasm (HMDB: HMDB0040433)

Source

Exogenous

Food

Food (HMDB: HMDB0040433)

Fruit

Berry

Evergreen blackberry (FooDB: FOOD00901)
Blackberry (FooDB: FOOD00906)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040433)

Biological role

Nutrient (HMDB: HMDB0040433)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	93.00 to 94.00 °C. @ 18.00 mm Hg	The Good Scents Company Information System
Water Solubility	45660 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.400 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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	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]+	131.462	31661259
DarkChem	[M-H]-	129.264	31661259
DeepCCS	[M+H]+	132.737	30932474
DeepCCS	[M-H]-	130.208	30932474
DeepCCS	[M-2H]-	166.718	30932474
DeepCCS	[M+Na]+	141.608	30932474
AllCCS	[M+H]+	134.0	32859911
AllCCS	[M+H-H2O]+	130.0	32859911
AllCCS	[M+NH4]+	137.8	32859911
AllCCS	[M+Na]+	138.9	32859911
AllCCS	[M-H]-	133.5	32859911
AllCCS	[M+Na-2H]-	135.8	32859911
AllCCS	[M+HCOO]-	138.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl levulinate	CCOC(=O)CCC(C)=O	1771.2	Standard polar	33892256
Ethyl levulinate	CCOC(=O)CCC(C)=O	994.4	Standard non polar	33892256
Ethyl levulinate	CCOC(=O)CCC(C)=O	1081.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ethyl levulinate,1TMS,isomer #1	CCOC(=O)CC=C(C)O[Si](C)(C)C	1278.1	Semi standard non polar	33892256
Ethyl levulinate,1TMS,isomer #1	CCOC(=O)CC=C(C)O[Si](C)(C)C	1221.0	Standard non polar	33892256
Ethyl levulinate,1TMS,isomer #2	C=C(CCC(=O)OCC)O[Si](C)(C)C	1237.3	Semi standard non polar	33892256
Ethyl levulinate,1TMS,isomer #2	C=C(CCC(=O)OCC)O[Si](C)(C)C	1234.3	Standard non polar	33892256
Ethyl levulinate,1TBDMS,isomer #1	CCOC(=O)CC=C(C)O[Si](C)(C)C(C)(C)C	1482.2	Semi standard non polar	33892256
Ethyl levulinate,1TBDMS,isomer #1	CCOC(=O)CC=C(C)O[Si](C)(C)C(C)(C)C	1442.3	Standard non polar	33892256
Ethyl levulinate,1TBDMS,isomer #2	C=C(CCC(=O)OCC)O[Si](C)(C)C(C)(C)C	1434.0	Semi standard non polar	33892256
Ethyl levulinate,1TBDMS,isomer #2	C=C(CCC(=O)OCC)O[Si](C)(C)C(C)(C)C	1432.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Ethyl levulinate EI-B (Non-derivatized)	splash10-0097-9100000000-e17c4b8e6a264be46500	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethyl levulinate EI-B (Non-derivatized)	splash10-002g-9100000000-58314b79e586dde6ec61	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethyl levulinate EI-B (Non-derivatized)	splash10-0007-9300000000-a4475e8effea84591152	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethyl levulinate EI-B (Non-derivatized)	splash10-0097-9100000000-e17c4b8e6a264be46500	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethyl levulinate EI-B (Non-derivatized)	splash10-002g-9100000000-58314b79e586dde6ec61	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethyl levulinate EI-B (Non-derivatized)	splash10-0007-9300000000-a4475e8effea84591152	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl levulinate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-2e03e600798fe0d0267a	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl levulinate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl levulinate 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 levulinate 10V, Positive-QTOF	splash10-002b-3900000000-0ea35fa03edfeb06ce8b	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl levulinate 20V, Positive-QTOF	splash10-000t-9400000000-7691a84859184726e377	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl levulinate 40V, Positive-QTOF	splash10-0kal-9000000000-c7f31a62338261696c0f	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl levulinate 10V, Negative-QTOF	splash10-0007-7900000000-24e10e783fc3d79e6041	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl levulinate 20V, Negative-QTOF	splash10-0002-9300000000-899dae367a08b4ae58d5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl levulinate 40V, Negative-QTOF	splash10-0002-9000000000-ca99a895a8aa02feaf2b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl levulinate 10V, Positive-QTOF	splash10-001j-9100000000-5093b0513913a9e4ad08	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl levulinate 20V, Positive-QTOF	splash10-059w-9000000000-98ede138af8b98895ab8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl levulinate 40V, Positive-QTOF	splash10-0007-9000000000-52239daafff2a41031db	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl levulinate 10V, Negative-QTOF	splash10-0002-9000000000-ac0837bbe515e96a4ff5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl levulinate 20V, Negative-QTOF	splash10-002b-9000000000-2e348d3c5434ca1858d7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl levulinate 40V, Negative-QTOF	splash10-0a4l-9000000000-bed7ee6d306bf4a3d049	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

FDB020166

KNApSAcK ID

Not Available

Chemspider ID

13853514

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ethyl levulinate

METLIN ID

Not Available

PubChem Compound

10883

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1024311

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 levulinate (HMDB0040433)

MOL for HMDB0040433 (Ethyl levulinate)

3D MOL for HMDB0040433 (Ethyl levulinate)

3D SDF for HMDB0040433 (Ethyl levulinate)

3D-SDF for HMDB0040433 (Ethyl levulinate)

PDB for HMDB0040433 (Ethyl levulinate)

3D PDB for HMDB0040433 (Ethyl levulinate)

SMILES for HMDB0040433 (Ethyl levulinate)

INCHI for HMDB0040433 (Ethyl levulinate)

Structure for HMDB0040433 (Ethyl levulinate)

3D Structure for HMDB0040433 (Ethyl levulinate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra