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5-Hydroxymethyl-2-furancarboxaldehyde (FDB012717)

Record Information
Version1.0
Creation date2010-04-08 22:10:19 UTC
Update date2019-11-26 03:07:26 UTC
Primary IDFDB012717
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name5-Hydroxymethyl-2-furancarboxaldehyde
Description5-Hydroxymethyl-2-furancarboxaldehyde, also known as HMF or 5-(hydroxymethyl)-2-furfural, 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. 5-Hydroxymethyl-2-furancarboxaldehyde exists in all living organisms, ranging from bacteria to humans. 5-Hydroxymethyl-2-furancarboxaldehyde is a caramel, cardboard, and fatty tasting compound. 5-Hydroxymethyl-2-furancarboxaldehyde is found, on average, in the highest concentration within grape wine and beer. 5-Hydroxymethyl-2-furancarboxaldehyde has also been detected, but not quantified in, garden onions (Allium cepa) and garden tomatoes (Solanum lycopersicum). This could make 5-hydroxymethyl-2-furancarboxaldehyde a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 5-Hydroxymethyl-2-furancarboxaldehyde.
CAS Number67-47-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H6O3
IUPAC name5-(hydroxymethyl)furan-2-carbaldehyde
InChI IdentifierInChI=1S/C6H6O3/c7-3-5-1-2-6(4-8)9-5/h1-3,8H,4H2
InChI KeyNOEGNKMFWQHSLB-UHFFFAOYSA-N
Isomeric SMILESOCC1=CC=C(O1)C=O
Average Molecular Weight126.11
Monoisotopic Molecular Weight126.031694058
Classification
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 57.14%; H 4.80%; O 38.06%DFC
Melting PointMp 35-35.5° (31.5°)DFC
Boiling PointBp0.02 110°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive Indexn18D 1.5627DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-004m-9200000000-81a66ec57fd3509623982015-03-01View Spectrum
GC-MS5-Hydroxymethyl-2-furancarboxaldehyde, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-000i-3900000000-55ebf60a0b891ce8f161Spectrum
GC-MS5-Hydroxymethyl-2-furancarboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-004m-9200000000-eda1f2db983cad69f22fSpectrum
GC-MS5-Hydroxymethyl-2-furancarboxaldehyde, non-derivatized, GC-MS Spectrumsplash10-000i-3900000000-55ebf60a0b891ce8f161Spectrum
Predicted GC-MS5-Hydroxymethyl-2-furancarboxaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-056r-9700000000-eca27630e7a4c9bf8948Spectrum
Predicted GC-MS5-Hydroxymethyl-2-furancarboxaldehyde, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fr-9800000000-9ae0d558930eb9fe4745Spectrum
Predicted GC-MS5-Hydroxymethyl-2-furancarboxaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5-Hydroxymethyl-2-furancarboxaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-6b27c3d0a2ec4abec52e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-3900000000-4ef239d47c3d3992b4af2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067j-9000000000-2259b6c5c081ef7725bd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1900000000-80053e3f153f1ca1e6c52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-7900000000-b67b3219c20de14d17a32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fsl-9000000000-a86f43e2cace7a5010e12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0560-9500000000-41ffb9b32a62772069852021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fsl-9000000000-17e3e9e5444bbcb9c7022021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-e52f98c8816358d341c62021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00mk-9500000000-2fb80b87b6c1c7cf5d8f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-9300000000-9c6b6541635220937bb42021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-baf5bf6b59914119abae2021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 50.18 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
ChemSpider ID207215
ChEMBL IDCHEMBL185885
KEGG Compound IDC11101
Pubchem Compound ID237332
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34355
CRC / DFC (Dictionary of Food Compounds) IDHKB60-L:HKB60-L
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00029547
HET IDFUX
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID67-47-0
GoodScent IDrw1040211
SuperScent IDNot Available
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
cardboard
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
fatty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
musty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
waxy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
caramel
  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— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.