ChemFOnt: Showing chemical card for 3-Hydroxy-4,5-dimethyl-2-furanone (CFc000334692)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:26:45 UTC

Chemfont ID

CFc000334692

Molecule Identification

Common Name

3-Hydroxy-4,5-dimethyl-2-furanone

Definition

Sotolon, also known as 3-hydroxy-4,5-dimethyl-furan-2(5h)-one or 4,5-dimethyl-3-hydroxy-2(5h)-furanone, is a member of the class of compounds known as butenolides. Butenolides are dihydrofurans with a carbonyl group at the C2 carbon atom. Sotolon is soluble (in water) and a very weakly acidic compound (based on its pKa). Sotolon is a strong, extremely sweet, and burnt tasting compound found in alcoholic beverages, coffee and coffee products, fenugreek, and herbs and spices, which makes sotolon a potential biomarker for the consumption of these food products. Sotolon can be found primarily in urine. Sotolon exists in all eukaryotes, ranging from yeast to humans.

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 Weight

128.1259

Monoisotopic Molecular Weight

128.047344122

IUPAC Name

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

Traditional Name

sotolon

CAS Registry Number

28664-35-9

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 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0031306)

Food

Herb and spice

Herb

Fenugreek (FooDB: FOOD00186)

Process

Not Available

Role

Not Available

Physical Properties

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0031306

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003360

KNApSAcK ID

C00050420

Chemspider ID

56569

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

62835

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3-Hydroxy-4,5-dimethyl-2-furanone (CFc000334692)

MOL for CFc000334692 (3-Hydroxy-4,5-dimethyl-2-furanone)

3D MOL for CFc000334692 (3-Hydroxy-4,5-dimethyl-2-furanone)

3D SDF for CFc000334692 (3-Hydroxy-4,5-dimethyl-2-furanone)

3D-SDF for CFc000334692 (3-Hydroxy-4,5-dimethyl-2-furanone)

PDB for CFc000334692 (3-Hydroxy-4,5-dimethyl-2-furanone)

3D PDB for CFc000334692 (3-Hydroxy-4,5-dimethyl-2-furanone)

SMILES for CFc000334692 (3-Hydroxy-4,5-dimethyl-2-furanone)

INCHI for CFc000334692 (3-Hydroxy-4,5-dimethyl-2-furanone)

Structure for CFc000334692 (3-Hydroxy-4,5-dimethyl-2-furanone)

3D Structure for CFc000334692 (3-Hydroxy-4,5-dimethyl-2-furanone)