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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-09-11 17:42:13 UTC

Update Date

2023-02-21 17:20:18 UTC

HMDB ID

HMDB0031306

Secondary Accession Numbers

HMDB31306

Metabolite Identification

Common Name

3-Hydroxy-4,5-dimethyl-2(5H)-furanone

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.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

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 )

Ontology

Not Available

Exogenous (HMDB: HMDB0031306)

Food

Herb and spice

Herb

Fenugreek (FooDB: FOOD00186)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	25.00 to 29.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	93.00 to 95.00 °C. @ 2.00 mm Hg	The Good Scents Company Information System
Water Solubility	222800 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-0.296 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	125.587	30932474
DeepCCS	[M-H]-	122.248	30932474
DeepCCS	[M-2H]-	159.575	30932474
DeepCCS	[M+Na]+	134.466	30932474
AllCCS	[M+H]+	127.6	32859911
AllCCS	[M+H-H2O]+	123.0	32859911
AllCCS	[M+NH4]+	132.0	32859911
AllCCS	[M+Na]+	133.3	32859911
AllCCS	[M-H]-	123.5	32859911
AllCCS	[M+Na-2H]-	125.6	32859911
AllCCS	[M+HCOO]-	128.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxy-4,5-dimethyl-2(5H)-furanone	CC1OC(=O)C(O)=C1C	2173.0	Standard polar	33892256
3-Hydroxy-4,5-dimethyl-2(5H)-furanone	CC1OC(=O)C(O)=C1C	1029.3	Standard non polar	33892256
3-Hydroxy-4,5-dimethyl-2(5H)-furanone	CC1OC(=O)C(O)=C1C	1088.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxy-4,5-dimethyl-2(5H)-furanone,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(=O)OC1C	1211.5	Semi standard non polar	33892256
3-Hydroxy-4,5-dimethyl-2(5H)-furanone,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)OC1C	1468.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9100000000-7fdd65bce51735b71d12	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone GC-MS (1 TMS) - 70eV, Positive	splash10-05i0-9700000000-43cc2ff6f95044077419	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone 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 - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone 10V, Positive-QTOF	splash10-0udi-9300000000-4d5cfb96c51ba990b353	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone 20V, Positive-QTOF	splash10-0zi0-9200000000-3e0b5f2cf3a4e88018fa	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone 40V, Positive-QTOF	splash10-0zfr-9000000000-ac732b4b21400d1500e7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone 10V, Negative-QTOF	splash10-004i-3900000000-26b4264da2affe2f394b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone 20V, Negative-QTOF	splash10-004i-3900000000-eb2c54bf2d77e47495b9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone 40V, Negative-QTOF	splash10-0api-9000000000-1a81a14f56906486c81c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone 10V, Positive-QTOF	splash10-004i-5900000000-a9b9f4b7467f05d32c85	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone 20V, Positive-QTOF	splash10-0aos-9100000000-15b07a7cfd09c718a188	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone 40V, Positive-QTOF	splash10-0a4i-9000000000-8bba3e142b490d9cfb12	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone 10V, Negative-QTOF	splash10-004i-1900000000-32e912844db31429eab0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone 20V, Negative-QTOF	splash10-00dl-9000000000-186c5ec73109434e3baa	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4,5-dimethyl-2(5H)-furanone 40V, Negative-QTOF	splash10-052f-9000000000-7185ebac9651271eeeee	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	10234605	details
Urine	Detected and Quantified	5.99 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	24958143	details
Urine	Detected and Quantified	12.60 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	24958143	details
Urine	Detected and Quantified	5.99 - 226 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24958143	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Maple syrup urine disease	10234605	details

Associated Disorders and Diseases

Disease References

Maple syrup urine disease
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. [PubMed:10234605 ]

Associated OMIM IDs

248600 (Maple syrup urine disease)

External Links

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

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1029011

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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. [PubMed:10234605 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 3-Hydroxy-4,5-dimethyl-2(5H)-furanone (HMDB0031306)

MOL for HMDB0031306 (3-Hydroxy-4,5-dimethyl-2(5H)-furanone)

3D MOL for HMDB0031306 (3-Hydroxy-4,5-dimethyl-2(5H)-furanone)

3D SDF for HMDB0031306 (3-Hydroxy-4,5-dimethyl-2(5H)-furanone)

3D-SDF for HMDB0031306 (3-Hydroxy-4,5-dimethyl-2(5H)-furanone)

PDB for HMDB0031306 (3-Hydroxy-4,5-dimethyl-2(5H)-furanone)

3D PDB for HMDB0031306 (3-Hydroxy-4,5-dimethyl-2(5H)-furanone)

SMILES for HMDB0031306 (3-Hydroxy-4,5-dimethyl-2(5H)-furanone)

INCHI for HMDB0031306 (3-Hydroxy-4,5-dimethyl-2(5H)-furanone)

Structure for HMDB0031306 (3-Hydroxy-4,5-dimethyl-2(5H)-furanone)

3D Structure for HMDB0031306 (3-Hydroxy-4,5-dimethyl-2(5H)-furanone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra