Record Information
Version1.0
Creation date2010-04-08 22:04:42 UTC
Update date2019-11-26 02:55:23 UTC
Primary IDFDB000776
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name5-Methyl-2(3H)-furanone
Description5-Methyl-2(3H)-furanone, also known as alpha-angelic lactone or β-angelicalacton, 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 an extremely weak basic (essentially neutral) compound (based on its pKa). 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, evergreen blackberries. This could make 5-methyl-2(3H)-furanone a potential biomarker for the consumption of these foods.
CAS Number591-12-8
Structure
Thumb
Synonyms
SynonymSource
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
α-angelic lactonebiospider
α-angelica lactonebiospider
α(α-angelica lactonebiospider
β,«gamma»-angelica lactonebiospider
«delta»2-Angelica lactonebiospider
2(3H)-Furanone, 5-methyl-biospider
3-Pentenoic acid, 4-hydroxy-, «gamma»-lactonebiospider
3-PENTENOIC ACID,4-HYDROXY,LACTONE ALPHA-ANGELICA-LACTONEbiospider
4-Hydroxy-3-pentenoic acid «gamma»-lactonebiospider
4-hydroxy-3-pentenoic acid gamma-lactonebiospider
4-hydroxy-3-pentenoic acid lactonebiospider
5-Methyl-2(3H)-furanone (α-angelicalactone)biospider
Alpha-angelica lactonebiospider
Alpha-angelicalactonbiospider
Alpha-angelicalactonebiospider
alpha(beta,gamma or delta2)-Angelica lactonebiospider
Beta,gamma-angelica lactonebiospider
Delta(2)-angelica lactonebiospider
delta(sup 2)-Angelica lactonebiospider
Gamma-methyl-beta,gamma-crotonolactonebiospider
Penten-3-oic acid, 4-hydroxy-, «gamma»-lactonebiospider
PENTEN-3-OIC ACID, 4-HYDROXY-, GAMMA-LACTONEbiospider
Predicted 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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H6O2
IUPAC name5-methyl-2,5-dihydrofuran-2-one
InChI IdentifierInChI=1S/C5H6O2/c1-4-2-3-5(6)7-4/h2-4H,1H3
InChI KeyBGLUXFNVVSVEET-UHFFFAOYSA-N
Isomeric SMILESCC1OC(=O)C=C1
Average Molecular Weight98.0999
Monoisotopic Molecular Weight98.036779436
Classification
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
Disposition

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 61.22%; H 6.16%; O 32.62%DFC
Melting PointMp 18°DFC
Boiling PointBp12 53°DFC
Experimental Water Solubility50 mg/mL at 15 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-9000000000-d924660fd05b0a4f24eeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-8664120e7c9085a6c96eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-455a07b16bc61387238bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-9000000000-51dfe2fb573308864135JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-7bfecdf1510b67f2f505JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6t-9000000000-7dbf786cff83ed69720cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-9000000000-a2e2372374e257c02f4cJSpectraViewer
ChemSpider ID11070
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID11558
Pubchem Substance IDNot Available
ChEBI ID36433
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB29609
CRC / DFC (Dictionary of Food Compounds) IDBHB48-E:BHB48-E
EAFUS ID1776
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1029001
SuperScent ID11559
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
oily
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
solvent
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
nutty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
tonka
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
coumarin
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
tobacco
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference