AFCDB: 4-Oxopentanoic acid (FDB003296)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:44 UTC

Update date

2019-11-26 02:58:51 UTC

Primary ID

FDB003296

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

4-Oxopentanoic acid

Description

Levulinic acid, also known as laevulinsaeure or levulate, 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. Levulinic acid exists in all living organisms, ranging from bacteria to humans. Levulinic acid is a sweet, acetoin, and acidic tasting compound. Levulinic acid has been detected, but not quantified in, several different foods, such as breakfast cereal, brassicas, fruits, green vegetables, and alcoholic beverages. This could make levulinic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Levulinic acid.

CAS Number

123-76-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	139 g/L	ALOGPS
logP	-0.14	ALOGPS
logP	-0.069	ChemAxon
logS	0.08	ALOGPS
pKa (Strongest Acidic)	4.32	ChemAxon
pKa (Strongest Basic)	-7.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	27.09 m³·mol⁻¹	ChemAxon
Polarizability	11.23 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

C5H8O3

IUPAC name

4-oxopentanoic acid

InChI Identifier

InChI=1S/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8)

InChI Key

JOOXCMJARBKPKM-UHFFFAOYSA-N

Isomeric SMILES

CC(=O)CCC(O)=O

Average Molecular Weight

116.1152

Monoisotopic Molecular Weight

116.047344122

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
Short-chain keto acid
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

oxopentanoic acid (CHEBI:45630 )
straight-chain saturated fatty acid (CHEBI:45630 )
Oxo fatty acids (LMFA01060006 )

Ontology

Ingestion

Source:

Biological:

Plant:

Poaceae

Biological location:

Cell and elements:

Cell:

Nerve cell

Subcellular:

Cytoplasm

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 51.72%; H 6.94%; O 41.34%	DFC
Melting Point	Mp 33.5°	DFC
Boiling Point	Bp14 143-147°	DFC
Experimental Water Solubility	Not Available
Experimental logP	-0.49	HANSCH,C ET AL. (1995)
Experimental pKa	pKa 4.62	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	4-Oxopentanoic acid, 1 MEOX; 1 TMS, GC-MS Spectrum	splash10-0ug0-6900000000-1e5d9b8d9a359287a6b0	Spectrum
GC-MS	4-Oxopentanoic acid, 1 MEOX; 1 TMS, GC-MS Spectrum	splash10-0ug0-6900000000-ffad5af79457e68cca02	Spectrum
GC-MS	4-Oxopentanoic acid, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-dd0d17209893b2b71d10	Spectrum
GC-MS	4-Oxopentanoic acid, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-0b0447e3daa65b1cd932	Spectrum
GC-MS	4-Oxopentanoic acid, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-e0d39a4a978220036faa	Spectrum
GC-MS	4-Oxopentanoic acid, non-derivatized, GC-MS Spectrum	splash10-0ug0-6900000000-1e5d9b8d9a359287a6b0	Spectrum
GC-MS	4-Oxopentanoic acid, non-derivatized, GC-MS Spectrum	splash10-0ug0-6900000000-ffad5af79457e68cca02	Spectrum
Predicted GC-MS	4-Oxopentanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9000000000-beecc1bba7b8b0ca4201	Spectrum
Predicted GC-MS	4-Oxopentanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00fr-9500000000-8c1e2090296fa71bf0d0	Spectrum
Predicted GC-MS	4-Oxopentanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Oxopentanoic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Oxopentanoic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Oxopentanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Oxopentanoic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Oxopentanoic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00xr-9400000000-923a1fccce36ba18d088	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-01vo-9300000000-2c09d37e792efac90655	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0303-9800000000-d158f0c32e82eca0ef90	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0006-9000000000-dd0d17209893b2b71d10	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-006x-9000000000-adbd744553b432e3c700	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9000000000-469fd98086c8d9ad1830	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9200000000-e73b5a48710de1cc7a5d	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kb-9400000000-1043277f0ad49a5664a3	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006t-9100000000-0a0fca12836c8c8ba113	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zfr-9000000000-247961be84518f0ebcda	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-3900000000-b8133a0e2c97f98cef46	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01b9-9600000000-e133b145c780f2c290d3	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052e-9000000000-6ff5c46cdc591b725694	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00xs-9300000000-eb059cdb2e36fd93dd56	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0007-9000000000-1e533a2764dd57c91302	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-c7b0e35a1f31ca5d7853	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00ea-9000000000-8e96196fb7b3bcd96a40	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-a8096e58fd006cbfe211	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-83517d34c408e5f9d048	2021-09-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

11091

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

11579

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

DB02239

HMDB ID

HMDB00720

CRC / DFC (Dictionary of Food Compounds) ID

CVR73-P:CVR73-P

EAFUS ID

2019

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

SHF

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1016791

SuperScent ID

Not Available

Wikipedia ID

Levulinic acid

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.
caramel	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
acidic	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
acetoin	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
buttery	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

4-Oxopentanoic acid (FDB003296)

Structure for FDB003296 (4-Oxopentanoic acid)