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Record Information
Version1.0
Created at2021-12-17 23:36:50 UTC
Updated at2021-12-17 23:45:25 UTC
NP-MRD IDNP0044216
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-hydroxy-2-furancarboxaldhyde
Description5-Hydroxymethyl-2-furancarboxaldehyde, also known as 5-(hydroxymethyl)-2-furfural or HMF, 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 is an extremely weak basic (essentially neutral) compound (based on its pKa). 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. Outside of the human body, 5-Hydroxymethyl-2-furancarboxaldehyde has been detected, but not quantified in, garden onions and garden tomato. This could make 5-hydroxymethyl-2-furancarboxaldehyde a potential biomarker for the consumption of these foods. It was first documented in 1992 (PMID: 1556177). Aes-103 has been used in trials studying the treatment and prevention of Hypoxia, Anemia, Sickle Cell, and Sickle Cell Disease (PMID: 20082406) (PMID: 20420424) (PMID: 21838257) (PMID: 33978488).
Structure
Thumb
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 Mass126.1100 Da
Monoisotopic Mass126.03169 Da
IUPAC Name5-(hydroxymethyl)furan-2-carbaldehyde
Traditional Namehydroxymethylfurfural
CAS Registry NumberNot Available
SMILES
OCC1=CC=C(O1)C=O
InChI Identifier
InChI=1S/C6H6O3/c7-3-5-1-2-6(4-8)9-5/h1-3,8H,4H2
InChI KeyNOEGNKMFWQHSLB-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2021-12-17View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, experimental)Ahselim2021-12-17View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50.18 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0034355
DrugBank IDDB12298
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012717
KNApSAcK IDC00029547
Chemspider ID207215
KEGG Compound IDC11101
BioCyc IDCPD-11572
BiGG IDNot Available
Wikipedia LinkHydroxymethylfurfural
METLIN IDNot Available
PubChem Compound237332
PDB IDFUX
ChEBI ID412516
Good Scents IDNot Available
References
General References
  1. Miyata S, Monnier V: Immunohistochemical detection of advanced glycosylation end products in diabetic tissues using monoclonal antibody to pyrraline. J Clin Invest. 1992 Apr;89(4):1102-12. doi: 10.1172/JCI115690. [PubMed:1556177 ]
  2. Tong X, Li Y: Efficient and selective dehydration of fructose to 5-hydroxymethylfurfural catalyzed by Bronsted-acidic ionic liquids. ChemSusChem. 2010 Mar 22;3(3):350-5. doi: 10.1002/cssc.200900224. [PubMed:20082406 ]
  3. Mesias-Garcia M, Guerra-Hernandez E, Garcia-Villanova B: Determination of furan precursors and some thermal damage markers in baby foods: ascorbic acid, dehydroascorbic acid, hydroxymethylfurfural and furfural. J Agric Food Chem. 2010 May 26;58(10):6027-32. doi: 10.1021/jf100649z. [PubMed:20420424 ]
  4. Nikolov PY, Yaylayan VA: Thermal decomposition of 5-(hydroxymethyl)-2-furaldehyde (HMF) and its further transformations in the presence of glycine. J Agric Food Chem. 2011 Sep 28;59(18):10104-13. doi: 10.1021/jf202470u. Epub 2011 Aug 25. [PubMed:21838257 ]
  5. Boning D, Kuebler WM, Bloch W: The oxygen dissociation curve of blood in COVID-19. Am J Physiol Lung Cell Mol Physiol. 2021 Aug 1;321(2):L349-L357. doi: 10.1152/ajplung.00079.2021. Epub 2021 May 12. [PubMed:33978488 ]