ContaminantDB: 4,5-DIMETHYL-3-HYDROXY-2,5-DIHYDROFURAN-2-ONE

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

Record Information

Version

1.0

Creation Date

2016-05-19 02:02:00 UTC

Update Date

2026-04-17 16:35:08 UTC

Accession Number

CHEM005422

Identification

Common Name

4,5-DIMETHYL-3-HYDROXY-2,5-DIHYDROFURAN-2-ONE

Class

Small Molecule

Description

Description: 3-Hydroxy-4,5-dimethyl-2(5H)-furanone or sotolone is key flavoring compound found in raw cane sugar, aged sake, coffee, fenugreek, lovage and wines. Sotolon (also known as sotolone) is a lactone and an extremely powerful aroma compound, with the typical smell of fenugreek or curry at high concentrations and maple syrup, caramel, or burnt sugar at lower concentrations. In 1999 it was shown that sotolone is the cause of the odor found in patients with maple syrup urine disease (MSUD) - PMID 10234605. This compound was found in the urine of 7 MSUD patients but was undetectable in normal individuals. 3-Hydroxy-4,5-dimethyl-2(5H)-furanone belongs to the family of Butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.

Contaminant Sources

EAFUS Chemicals
FooDB Chemicals
HMDB Contaminants - Urine
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,3-Dimethyl-4-hydroxy-2,5-dihydrofuran-5-one	HMDB
2-Hydroxy-3,4-dimethyl-2-buten-1,4-olide	HMDB
2-Hydroxy-3-methyl-2-penten-4-olide	HMDB
3,4-Dimethyl-2-hydroxy-2-butan-1,4-olide	HMDB
3-Hydroxy-4,5(R)-dimethyl-2(5H)-furanone	HMDB
3-Hydroxy-4,5-dimethyl-5H-furan-2-one	HMDB
3-Hydroxy-4,5-dimethyl-furan-2(5H)-one	HMDB
3-Hydroxy-4,5-dimethylfuran-2(5H)-one	HMDB
4,5-Dimethyl-3-hydroxy-2(5H)-furanone	HMDB, MeSH
4,5-Dimethyl-3-hydroxy-2,5-dihydro-2-furanone	HMDB
4,5-Dimethyl-3-hydroxy-2,5-dihydrofuran-2-one	HMDB
Sautalone	HMDB
Sotolon	HMDB
Sotolone	HMDB, MeSH

Chemical Formula

C₆H₈O₃

Average Molecular Mass

128.126 g/mol

Monoisotopic Mass

128.047 g/mol

CAS Registry Number

28664-35-9

IUPAC Name

3-hydroxy-4,5-dimethyl-2,5-dihydrofuran-2-one

Traditional Name

sotolon

SMILES

CC1OC(=O)C(O)=C1C

InChI Identifier

InChI=1S/C6H8O3/c1-3-4(2)9-6(8)5(3)7/h4,7H,1-2H3

InChI Key

UNYNVICDCJHOPO-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Butenolides

Alternative Parents

Substituents

2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Enol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

butenolide (CHEBI:67890 )

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	218 g/L	ALOGPS
logP	-0.14	ALOGPS
logP	0.68	ChemAxon
logS	0.23	ALOGPS
pKa (Strongest Acidic)	9.28	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	31.92 m³·mol⁻¹	ChemAxon
Polarizability	12.35 Å³	ChemAxon
Number of Rings	1	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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9100000000-7fdd65bce51735b71d12	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05i0-9700000000-43cc2ff6f95044077419	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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-9300000000-4d5cfb96c51ba990b353	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zi0-9200000000-3e0b5f2cf3a4e88018fa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zfr-9000000000-ac732b4b21400d1500e7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-3900000000-26b4264da2affe2f394b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-3900000000-eb2c54bf2d77e47495b9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0api-9000000000-1a81a14f56906486c81c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-5900000000-a9b9f4b7467f05d32c85	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0aos-9100000000-15b07a7cfd09c718a188	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-8bba3e142b490d9cfb12	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-1900000000-32e912844db31429eab0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dl-9000000000-186c5ec73109434e3baa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-7185ebac9651271eeeee	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

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

HMDB0031306

FooDB ID

FDB003360

Phenol Explorer ID

Not Available

KNApSAcK ID

C00050420

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

56569

ChEBI ID

Not Available

PubChem Compound ID

62835

Kegg Compound ID

Not Available

YMDB ID

YMDB01572

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Podebrad F, Heil M, Reichert S, Mosandl A, Sewell AC, Bohles H: 4,5-dimethyl-3-hydroxy-2[5H]-furanone (sotolone)--the odour of maple syrup urine disease. J Inherit Metab Dis. 1999 Apr;22(2):107-14.

2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

4,5-DIMETHYL-3-HYDROXY-2,5-DIHYDROFURAN-2-ONE (CHEM005422)

Structure for CHEM005422: 4,5-DIMETHYL-3-HYDROXY-2,5-DIHYDROFURAN-2-ONE