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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:05:16 UTC

Update Date

2023-02-21 17:24:37 UTC

HMDB ID

HMDB0035143

Secondary Accession Numbers

HMDB35143

Metabolite Identification

Common Name

Dihydro-3-methyl-2(3H)-furanone

Description

Dihydro-3-methyl-2(3H)-furanone belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Dihydro-3-methyl-2(3H)-furanone has been detected, but not quantified in, fruits. This could make dihydro-3-methyl-2(3H)-furanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Dihydro-3-methyl-2(3H)-furanone.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Gama-valerolactone	ChEMBL, HMDB
2-Methyl-4-butanolide	HMDB
2-Methyl-laquo gammaraquo -butyrolactone	HMDB
2-Methylbutanolide	HMDB
3-methyldihydro-2(3H)-Furanone	HMDB
3-Methyldihydrofuran-2(3H)-one	HMDB
4,5-dihydro-3-Methyl-2(3H)-furanone	HMDB
4-Hydroxy-2-methylbutanoic acid lactone	HMDB
4-Hydroxy-2-methylbutyric acid lactone	HMDB
a-Methyl-g-butyrolactone	HMDB
alpha -Methyl-alpha -methylbutyrolactone	HMDB
alpha -Methyl-laquo gammaraquo -butyrolactone	HMDB
alpha -Methylbutyrolactone	HMDB
alpha-Methyl-gamma-butyrolactone	HMDB
2-Methyl-g-butyrolactone	Generator
2-Methyl-γ-butyrolactone	Generator

Chemical Formula

C₅H₈O₂

Average Molecular Weight

100.1158

Monoisotopic Molecular Weight

100.0524295

IUPAC Name

3-methyloxolan-2-one

Traditional Name

3-methylbutyrolactone

CAS Registry Number

1679-47-6

SMILES

CC1CCOC1=O

InChI Identifier

InChI=1S/C5H8O2/c1-4-2-3-7-5(4)6/h4H,2-3H2,1H3

InChI Key

QGLBZNZGBLRJGS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0035143)
Cytoplasm (HMDB: HMDB0035143)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035143)

Source

Exogenous

Food

Food (HMDB: HMDB0035143)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0035143)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0035143)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	93810 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	93.1 g/L	ALOGPS
logP	0.36	ALOGPS
logP	0.69	ChemAxon
logS	-0.03	ALOGPS
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	24.88 m³·mol⁻¹	ChemAxon
Polarizability	10.09 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	118.531	31661259
DarkChem	[M-H]-	112.708	31661259
DeepCCS	[M+H]+	131.798	30932474
DeepCCS	[M-H]-	129.039	30932474
DeepCCS	[M-2H]-	165.424	30932474
DeepCCS	[M+Na]+	140.119	30932474
AllCCS	[M+H]+	119.6	32859911
AllCCS	[M+H-H2O]+	114.6	32859911
AllCCS	[M+NH4]+	124.3	32859911
AllCCS	[M+Na]+	125.6	32859911
AllCCS	[M-H]-	120.0	32859911
AllCCS	[M+Na-2H]-	123.1	32859911
AllCCS	[M+HCOO]-	126.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydro-3-methyl-2(3H)-furanone	CC1CCOC1=O	1615.2	Standard polar	33892256
Dihydro-3-methyl-2(3H)-furanone	CC1CCOC1=O	869.6	Standard non polar	33892256
Dihydro-3-methyl-2(3H)-furanone	CC1CCOC1=O	991.4	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 - Dihydro-3-methyl-2(3H)-furanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6u-9000000000-32d95893e5488b32993e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydro-3-methyl-2(3H)-furanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydro-3-methyl-2(3H)-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 - Dihydro-3-methyl-2(3H)-furanone 10V, Positive-QTOF	splash10-0udi-2900000000-3bcae927eb729bd70633	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-3-methyl-2(3H)-furanone 20V, Positive-QTOF	splash10-0udi-9500000000-72a8338f74e5142898d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-3-methyl-2(3H)-furanone 40V, Positive-QTOF	splash10-052f-9000000000-e606ab76e69e12b46811	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-3-methyl-2(3H)-furanone 10V, Negative-QTOF	splash10-0002-9000000000-f0ca563ddce844af1673	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-3-methyl-2(3H)-furanone 20V, Negative-QTOF	splash10-052b-9000000000-972ee7517750c720bf9a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-3-methyl-2(3H)-furanone 40V, Negative-QTOF	splash10-0f79-9000000000-398ece2159773c30ab63	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-3-methyl-2(3H)-furanone 10V, Negative-QTOF	splash10-0002-9000000000-5289cc75fe7aae11de79	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-3-methyl-2(3H)-furanone 20V, Negative-QTOF	splash10-00ke-9000000000-6b40b7e40a3ffa346c5a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-3-methyl-2(3H)-furanone 40V, Negative-QTOF	splash10-0pb9-9000000000-299197d97fd1fa3fefcc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-3-methyl-2(3H)-furanone 10V, Positive-QTOF	splash10-0zfs-9300000000-cc373a0562e93fd5acb8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-3-methyl-2(3H)-furanone 20V, Positive-QTOF	splash10-0a4i-9100000000-eb6ab83378ad72421939	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-3-methyl-2(3H)-furanone 40V, Positive-QTOF	splash10-0a4l-9000000000-c0112492dcbc56be6eba	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

FDB013779

KNApSAcK ID

C00054041

Chemspider ID

88786

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

98323

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1218421

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 Dihydro-3-methyl-2(3H)-furanone (HMDB0035143)

MOL for HMDB0035143 (Dihydro-3-methyl-2(3H)-furanone)

3D MOL for HMDB0035143 (Dihydro-3-methyl-2(3H)-furanone)

3D SDF for HMDB0035143 (Dihydro-3-methyl-2(3H)-furanone)

3D-SDF for HMDB0035143 (Dihydro-3-methyl-2(3H)-furanone)

PDB for HMDB0035143 (Dihydro-3-methyl-2(3H)-furanone)

3D PDB for HMDB0035143 (Dihydro-3-methyl-2(3H)-furanone)

SMILES for HMDB0035143 (Dihydro-3-methyl-2(3H)-furanone)

INCHI for HMDB0035143 (Dihydro-3-methyl-2(3H)-furanone)

Structure for HMDB0035143 (Dihydro-3-methyl-2(3H)-furanone)

3D Structure for HMDB0035143 (Dihydro-3-methyl-2(3H)-furanone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra