4-HYDROXY-2,5-DIMETHYL-3(2H)-FURANONE (CED0008982)

Record Information
Version1.0
Creation Date2016-05-19 02:09:32 UTC
Update Date2026-03-31 21:50:56 UTC
Accession NumberCHEM006058
Identification
Common Name4-HYDROXY-2,5-DIMETHYL-3(2H)-FURANONE
ClassSmall Molecule
Description
4-HYDROXY-2,5-DIMETHYL-3(2H)-FURANONE belongs to the furanones, a subclass of dihydrofurans within the organic compounds. This organoheterocyclic compound has the chemical formula C6H8O3 and an average molecular weight of 128.13 g/mol. In industrial applications, it is utilized as a fragrance, deodorizer, and humectant, and it also serves as a nutrient and flavouring agent. The compound is found in or released from 21 recorded sources. Within the category of food, food processing and cookware, it is associated with food contact materials and fermentation processes for beer, as well as the preparation of malt, vinegar, wine, or sparkling wine, among others. It is also present in household cleaning and consumer products, including bleaching agents, cigar cigarettes, non-electric simulated smoking devices, other smoking requisites, and pipe accessories. Additionally, it is recorded in electrical and electronic equipment such as magnets, discharge lamps, and electrically stimulated smoking devices, as well as in indoor air. Recorded exposure routes for this substance include oral, inhalation, and touch.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
2,5-Dimethyl-3-hydroxy-4-oxo-4,5-dihydrofuranChEBI
2,5-Dimethyl-4-hydroxy-2,3-dihydrofuran-3-oneChEBI
2,5-Dimethyl-4-hydroxy-3(2H)-furanoneChEBI
4-Hydroxy-2,5-dimethyl-3(2H)-furanoneChEBI
4-Hydroxy-2,5-dimethyl-furan-3(2H)-oneChEBI
Dimethylhydroxy furanoneChEBI
FuraneolChEBI
HDMFChEBI
Pineapple ketoneChEBI
Furaneol, (R)-isomerMeSH, HMDB
4-HDMFMeSH, HMDB
AlletoneMeSH, HMDB
Furaneol, (S)-isomerMeSH, HMDB
Chemical FormulaC6H8O3
Average Molecular Mass128.126 g/mol
Monoisotopic Mass128.047 g/mol
CAS Registry Number3658-77-3
IUPAC Name4-hydroxy-2,5-dimethyl-2,3-dihydrofuran-3-one
Traditional Namefuraneol
SMILESCC1OC(C)=C(O)C1=O
InChI IdentifierInChI=1S/C6H8O3/c1-3-5(7)6(8)4(2)9-3/h3,8H,1-2H3
InChI KeyINAXVXBDKKUCGI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydrofurans
Sub ClassFuranones
Direct ParentFuranones
Alternative Parents
Substituents
  • 3-furanone
  • Vinylogous ester
  • Cyclic ketone
  • Ketone
  • Oxacycle
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility446 g/LALOGPS
logP-0.33ALOGPS
logP0.21ChemAxon
logS0.54ALOGPS
pKa (Strongest Acidic)7.09ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity33.29 m³·mol⁻¹ChemAxon
Polarizability12.48 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a4i-9100000000-8c4cb8aa573b16fcfb70Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0adu-9600000000-2c6fe7e0e944a33c5cc9Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-1900000000-2a171214e5cd4706888fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-3900000000-31e666e61cc7b8411876Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-054p-9000000000-af02647aeeb779640073Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0900000000-357e93488390a2976c9dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-1900000000-602820cb95c6f5aecaaeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9100000000-4e8ccb8034b60b5362d0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-2900000000-f04fe270624eef9c155bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006x-9000000000-996faea12712159d1b18Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-9000000000-0c6cf150442af99bad61Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-7900000000-afb6007af0c955aff56bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0avl-9000000000-61679df963f1143460b0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05mp-9000000000-67eb08c0013c727e892eNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2695.0Log mg/kg[1500:4800]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
19Indoor airAir, dust & atmospheric transportNot Available
233BrushesPersonal care & cosmeticsNot Available
490Personal care & cosmeticsNot Available
494Food contact materialsFood, food processing & cookwareNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
553Treatment Of HopsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
568Tobacco Product Moisture ControlHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
663Sanitary EquipmentWastewater, sanitation & biosolidsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
ALK tyrosine kinase receptor structureClick to view 3D structureALK tyrosine kinase receptorQ9UM73HumansPredicted (SEA)4916.8
Tyrosine-protein kinase receptor UFO structureClick to view 3D structureTyrosine-protein kinase receptor UFOP30530HumansPredicted (SEA)4218.88
Induced myeloid leukemia cell differentiation protein Mcl-1 structureClick to view 3D structureInduced myeloid leukemia cell differentiation protein Mcl-1Q07820HumansPredicted (SEA)2421.19
Hepatocyte growth factor receptor structureClick to view 3D structureHepatocyte growth factor receptorP08581HumansPredicted (SEA)5554.54
Insulin-like growth factor 1 receptor structureClick to view 3D structureInsulin-like growth factor 1 receptorP08069HumansPredicted (SEA)5287.6
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)6331.01
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansPredicted (SEA)1981.73
Click to view 3D structureGag-Pol polyproteinQ7ZJM1Human immunodeficiency virus 1Predicted (SEA)747.586
Receptor-type tyrosine-protein kinase FLT3 structureClick to view 3D structureReceptor-type tyrosine-protein kinase FLT3P36888HumansPredicted (SEA)6393.45
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)4329.27
Vascular endothelial growth factor receptor 3 structureClick to view 3D structureVascular endothelial growth factor receptor 3P35916HumansPredicted (SEA)6044.52
Platelet-derived growth factor receptor alpha structureClick to view 3D structurePlatelet-derived growth factor receptor alphaP16234HumansPredicted (SEA)5680.27
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)3708.66
Serine/threonine-protein kinase pim-1 structureClick to view 3D structureSerine/threonine-protein kinase pim-1P11309HumansPredicted (SEA)6669.27
Cytochrome P450 1B1 structureClick to view 3D structureCytochrome P450 1B1Q16678HumansPredicted (SEA)1205.03
Mast/stem cell growth factor receptor Kit structureClick to view 3D structureMast/stem cell growth factor receptor KitP10721HumansPredicted (SEA)6552.26
Aurora kinase B structureClick to view 3D structureAurora kinase BQ96GD4HumansPredicted (SEA)6744.7
Aromatase structureClick to view 3D structureAromataseP11511HumansPredicted (SEA)1652.58
Click to view 3D structureM-phase inducer phosphatase 2P30306Mus musculusPredicted (SEA)43.5177
Mitogen-activated protein kinase 1 structureClick to view 3D structureMitogen-activated protein kinase 1P28482HumansPredicted (SEA)6738.55
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)4956.66
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)4530.28
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)3754.12
Carbonic anhydrase 4 structureClick to view 3D structureCarbonic anhydrase 4P22748HumansPredicted (SEA)3331.64
Dual specificity mitogen-activated protein kinase kinase 1 structureClick to view 3D structureDual specificity mitogen-activated protein kinase kinase 1Q02750HumansPredicted (SEA)6290.53
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0040594
FooDB IDFDB020380
Phenol Explorer IDNot Available
KNApSAcK IDC00052712
BiGG IDNot Available
BioCyc IDCPD-10198
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFuraneol
Chemspider ID18218
ChEBI ID76247
PubChem Compound ID19309
Kegg Compound IDNot Available
YMDB IDYMDB01694
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21702480
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21798851
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21831389
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21855074
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23589283
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23765232
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24133645
8. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.