5-(Hydroxymethyl)-2-furfural (CHEM017308)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:14:03 UTC
Update Date2016-11-09 01:15:34 UTC
Accession NumberCHEM017308
Identification
Common Name5-(Hydroxymethyl)-2-furfural
ClassSmall Molecule
DescriptionA member of the class of furans that is furan which is substituted at positions 2 and 5 by formyl and hydroxymethyl substituents, respectively. Virtually absent from fresh foods, it is naturally generated in sugar-containing foods during storage, and especially by drying or cooking. It is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo.
Contaminant Sources
  • FooDB Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Hydroxymethyl-5-furfuralChEBI
5-(Hydroxymethyl)-2-furaldehydeChEBI
5-(Hydroxymethyl)-2-furancarbonalChEBI
5-(Hydroxymethyl)-2-furancarboxaldehydeChEBI
5-(Hydroxymethyl)-2-furfuralChEBI
5-(Hydroxymethyl)-2-furfuraldehydeChEBI
5-(Hydroxymethyl)furan-2-aldehydeChEBI
5-(Hydroxymethyl)furfuralChEBI
5-(Hydroxymethyl)furfuroleChEBI
5-HMFChEBI
5-Hydroxymethyl-2-formylfuranChEBI
5-Hydroxymethyl-2-furaldehydeChEBI
5-Hydroxymethyl-2-furancarbaldehydeChEBI
5-Hydroxymethyl-2-furfuralChEBI
5-HydroxymethylfuraldehydeChEBI
5-Hydroxymethylfuran-2-aldehydeChEBI
5-HydroxymethylfurfuraldehydeChEBI
5-OxymethylfurfuroleChEBI
HMFChEBI
HydroxymethylfurfuralChEBI
HydroxymethylfurfuralaldehydeChEBI
HydroxymethylfurfuraldehydeChEBI
HydroxymethylfurfuroleChEBI
5-HydroxymethylfurfuralKegg
2-Formyl-5-hydroxymethylfuranHMDB
5-(Hyddroxymethyl)furfuroleHMDB
5-(Hydroxymethyl)-2-formylfuranHMDB
5-(Hydroxymethyl)-2-furfural (HMF)HMDB
5-Hydroxymethyl furaldehydeHMDB
5-Hydroxymethyl-furfuralHMDB
5-HydrxoymethylfurfuralHMDB
5-MethylolfurfuralHMDB
5-HM-2-F CPDMeSH
5-HMF CPDMeSH
Aes-103MeSH
5-Hydroxymethyl furfuralMeSH
5-(Hydroxymethyl)furancarboxaldehydePhytoBank
5-HydroxymethylfurfurolPhytoBank
HydroxymethylfuraldehydePhytoBank
Chemical FormulaC6H6O3
Average Molecular Mass126.110 g/mol
Monoisotopic Mass126.032 g/mol
CAS Registry Number67-47-0
IUPAC Name5-(hydroxymethyl)furan-2-carbaldehyde
Traditional Namehydroxymethylfurfural
SMILESOCC1=CC=C(O1)C=O
InChI IdentifierInChI=1S/C6H6O3/c7-3-5-1-2-6(4-8)9-5/h1-3,8H,4H2
InChI KeyNOEGNKMFWQHSLB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aryl-aldehydes. Aryl-aldehydes are compounds containing an aldehyde group directly attached to an aromatic ring.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAryl-aldehydes
Alternative Parents
Substituents
  • Aryl-aldehyde
  • Heteroaromatic compound
  • Furan
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility31.1 g/LALOGPS
logP-0.17ALOGPS
logP-0.1ChemAxon
logS-0.61ALOGPS
pKa (Strongest Acidic)13.65ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.44 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity31.73 m³·mol⁻¹ChemAxon
Polarizability12.03 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-3900000000-55ebf60a0b891ce8f161Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004m-9200000000-eda1f2db983cad69f22fSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-3900000000-55ebf60a0b891ce8f161Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-9700000000-eca27630e7a4c9bf8948Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-9800000000-9ae0d558930eb9fe4745Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-6b27c3d0a2ec4abec52eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-3900000000-4ef239d47c3d3992b4afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067j-9000000000-2259b6c5c081ef7725bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1900000000-80053e3f153f1ca1e6c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-7900000000-b67b3219c20de14d17a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fsl-9000000000-a86f43e2cace7a5010e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0560-9500000000-41ffb9b32a6277206985Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fsl-9000000000-17e3e9e5444bbcb9c702Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-e52f98c8816358d341c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00mk-9500000000-2fb80b87b6c1c7cf5d8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-9300000000-9c6b6541635220937bb4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-baf5bf6b59914119abaeSpectrum
MSMass Spectrum (Electron Ionization)splash10-004m-9200000000-81a66ec57fd350962398Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB12298
HMDB IDHMDB0034355
FooDB IDFDB012717
Phenol Explorer IDNot Available
KNApSAcK IDC00029547
BiGG IDNot Available
BioCyc IDCPD-11572
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkHydroxymethylfurfural
Chemspider ID207215
ChEBI ID412516
PubChem Compound ID237332
Kegg Compound IDC11101
YMDB IDNot Available
ECMDB IDM2MDB005807
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1556177
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20082406
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20420424
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21838257
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22264628
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22757699
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22957895
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23106038
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24001819
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=24054253
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=24054256
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=24399510
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=24399607
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=24408726
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=24444020
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=24518321
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=25015917
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=25333920
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=25858076
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=25922228
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=28317713
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=28395827
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=2917974
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=6391997
25. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.