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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:31:26 UTC
Update Date2023-02-21 17:18:52 UTC
HMDB IDHMDB0029609
Secondary Accession Numbers
  • HMDB29609
Metabolite Identification
Common Name5-Methyl-2(3H)-furanone
Description5-Methyl-2(3H)-furanone, also known as beta-angelicalacton or 2-penten-4-olide, belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. 5-Methyl-2(3H)-furanone is a sweet, coumarin, and nutty tasting compound. 5-Methyl-2(3H)-furanone has been detected, but not quantified in, blackberries (Rubus) and evergreen blackberries (Rubus laciniatus). This could make 5-methyl-2(3H)-furanone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 5-Methyl-2(3H)-furanone.
Structure
Data?1676999932
Synonyms
ValueSource
2-Penten-4-olideChEBI
4-Hydroxy-2-pentenoic acid gamma-lactoneChEBI
4-Hydroxypent-2-enoic acid lactoneChEBI
5-Methyl-2(5H)-furanoneChEBI
alpha,beta-Angelica lactoneChEBI
beta-AngelicalactonChEBI
beta-AngelicalactoneChEBI
Delta(1)-Angelica lactoneChEBI
gamma-Methyl-alpha,beta-crotonolactoneChEBI
4-Hydroxy-2-pentenoate g-lactoneGenerator
4-Hydroxy-2-pentenoate gamma-lactoneGenerator
4-Hydroxy-2-pentenoate γ-lactoneGenerator
4-Hydroxy-2-pentenoic acid g-lactoneGenerator
4-Hydroxy-2-pentenoic acid γ-lactoneGenerator
4-Hydroxypent-2-enoate lactoneGenerator
a,b-Angelica lactoneGenerator
Α,β-angelica lactoneGenerator
b-AngelicalactonGenerator
Β-angelicalactonGenerator
b-AngelicalactoneGenerator
Β-angelicalactoneGenerator
Δ(1)-angelica lactoneGenerator
g-Methyl-a,b-crotonolactoneGenerator
Γ-methyl-α,β-crotonolactoneGenerator
2,3-dihydro-5-Methyl-2-furanoneHMDB
3-Pentenoic acid, 4-hydroxy-, gamma-lactoneHMDB
3-Pentenoic acid, 4-hydroxy-, laquo gammaraquo -lactoneHMDB
3-PENTENOIC ACID,4-hydroxy,lactone alpha-angelica-lactoneHMDB
4-Hydroxy-3-pentenoic acid g-lactoneHMDB
4-Hydroxy-3-pentenoic acid gamma-lactoneHMDB
4-Hydroxy-3-pentenoic acid lactoneHMDB
4-Hydroxy-3-pentenoic acid laquo gammaraquo -lactoneHMDB
4-Hydroxy-3-pentenoic acid, gamma-lactoneHMDB
4-Hydroxypent-3-enoic acid lactoneHMDB
5-Methyl-2(3H)-furanone (alpha -angelicalactone)HMDB
5-Methylfuran-2(3H)-oneHMDB
a-Angelica lactoneHMDB
alpha(alpha-Angelica lactoneHMDB
alpha(beta,gamma Or delta2)-angelica lactoneHMDB
alpha-Angelic lactoneHMDB
alpha-Angelica lactoneHMDB
alpha-AngelicalactonHMDB
alpha-AngelicalactoneHMDB
Angelic lactoneHMDB
Angelica lactoneHMDB
beta,gamma-Angelica lactoneHMDB
beta,laquo gammaraquo -Angelica lactoneHMDB
D2-Angelica lactoneHMDB
delta(2)-Angelica lactoneHMDB
FEMA 3293HMDB
gamma-Methyl-beta,gamma-crotonolactoneHMDB
laquo deltaraquo 2-Angelica lactoneHMDB
PENTEN-3-OIC ACID, 4-hydroxy-, gamma-lactoneHMDB
Penten-3-Oic acid, 4-hydroxy-, laquo gammaraquo -lactoneHMDB
b-Angelica lactoneGenerator
Β-angelica lactoneGenerator
Angelica lactone, (alpha)-isomerMeSH
Angelica lactone, (beta)-isomerMeSH
Chemical FormulaC5H6O2
Average Molecular Weight98.0999
Monoisotopic Molecular Weight98.036779436
IUPAC Name5-methyl-2,5-dihydrofuran-2-one
Traditional Nameα,β-angelica lactone
CAS Registry Number591-12-8
SMILES
CC1OC(=O)C=C1
InChI Identifier
InChI=1S/C5H6O2/c1-4-2-3-5(6)7-4/h2-4H,1H3
InChI KeyBGLUXFNVVSVEET-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydrofurans
Sub ClassFuranones
Direct ParentButenolides
Alternative Parents
Substituents
  • 2-furanone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Lactone
  • 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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point18 °CNot Available
Boiling Point208.00 to 210.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility50 mg/mL at 15 °CNot Available
LogP-0.133 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility100 g/LALOGPS
logP0.53ALOGPS
logP0.95ChemAxon
logS0.01ALOGPS
pKa (Strongest Acidic)7.6ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity25.67 m³·mol⁻¹ChemAxon
Polarizability9.44 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+119.47231661259
DarkChem[M-H]-113.6131661259
DeepCCS[M+H]+121.85230932474
DeepCCS[M-H]-119.05230932474
DeepCCS[M-2H]-155.48530932474
DeepCCS[M+Na]+130.23130932474
AllCCS[M+H]+119.832859911
AllCCS[M+H-H2O]+114.732859911
AllCCS[M+NH4]+124.532859911
AllCCS[M+Na]+125.932859911
AllCCS[M-H]-118.932859911
AllCCS[M+Na-2H]-122.032859911
AllCCS[M+HCOO]-125.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-Methyl-2(3H)-furanoneCC1OC(=O)C=C11640.2Standard polar33892256
5-Methyl-2(3H)-furanoneCC1OC(=O)C=C1845.1Standard non polar33892256
5-Methyl-2(3H)-furanoneCC1OC(=O)C=C1940.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyl-2(3H)-furanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-9000000000-d924660fd05b0a4f24ee2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyl-2(3H)-furanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2(3H)-furanone 10V, Positive-QTOFsplash10-0002-9000000000-8664120e7c9085a6c96e2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2(3H)-furanone 20V, Positive-QTOFsplash10-0002-9000000000-455a07b16bc61387238b2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2(3H)-furanone 40V, Positive-QTOFsplash10-0pb9-9000000000-51dfe2fb5733088641352016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2(3H)-furanone 10V, Negative-QTOFsplash10-0002-9000000000-7bfecdf1510b67f2f5052016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2(3H)-furanone 20V, Negative-QTOFsplash10-0f6t-9000000000-7dbf786cff83ed69720c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2(3H)-furanone 40V, Negative-QTOFsplash10-0udi-9000000000-a2e2372374e257c02f4c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2(3H)-furanone 10V, Positive-QTOFsplash10-0002-9000000000-9ab2cbf1d22ebb0d92332021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2(3H)-furanone 20V, Positive-QTOFsplash10-0w39-9000000000-ec0a82f3905d92f31ae22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2(3H)-furanone 40V, Positive-QTOFsplash10-0udi-9000000000-546d854a71bcb09203172021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2(3H)-furanone 10V, Negative-QTOFsplash10-0002-9000000000-81f2c4b9955bbe4aea222021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2(3H)-furanone 20V, Negative-QTOFsplash10-002b-9000000000-d866a621060ee919d07f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2(3H)-furanone 40V, Negative-QTOFsplash10-0udl-9000000000-4cce45b0c86e4783eecc2021-09-22Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000776
KNApSAcK IDC00052742
Chemspider ID11070
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11558
PDB IDNot Available
ChEBI ID36436
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1386791
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .