Record Information |
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Version | 1.0 |
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Created at | 2021-12-17 23:36:50 UTC |
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Updated at | 2021-12-17 23:45:25 UTC |
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NP-MRD ID | NP0044216 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 5-hydroxy-2-furancarboxaldhyde |
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Description | 5-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). |
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Structure | InChI=1S/C6H6O3/c7-3-5-1-2-6(4-8)9-5/h1-3,8H,4H2 |
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Synonyms | Value | Source |
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2-Hydroxymethyl-5-furfural | ChEBI | 5-(Hydroxymethyl)-2-furaldehyde | ChEBI | 5-(Hydroxymethyl)-2-furancarbonal | ChEBI | 5-(Hydroxymethyl)-2-furancarboxaldehyde | ChEBI | 5-(Hydroxymethyl)-2-furfural | ChEBI | 5-(Hydroxymethyl)-2-furfuraldehyde | ChEBI | 5-(Hydroxymethyl)furan-2-aldehyde | ChEBI | 5-(Hydroxymethyl)furfural | ChEBI | 5-(Hydroxymethyl)furfurole | ChEBI | 5-HMF | ChEBI | 5-Hydroxymethyl-2-formylfuran | ChEBI | 5-Hydroxymethyl-2-furaldehyde | ChEBI | 5-Hydroxymethyl-2-furancarbaldehyde | ChEBI | 5-Hydroxymethyl-2-furfural | ChEBI | 5-Hydroxymethylfuraldehyde | ChEBI | 5-Hydroxymethylfuran-2-aldehyde | ChEBI | 5-Hydroxymethylfurfuraldehyde | ChEBI | 5-Oxymethylfurfurole | ChEBI | HMF | ChEBI | Hydroxymethylfurfural | ChEBI | Hydroxymethylfurfuralaldehyde | ChEBI | Hydroxymethylfurfuraldehyde | ChEBI | Hydroxymethylfurfurole | ChEBI | 5-Hydroxymethylfurfural | Kegg | 2-Formyl-5-hydroxymethylfuran | HMDB | 5-(Hyddroxymethyl)furfurole | HMDB | 5-(Hydroxymethyl)-2-formylfuran | HMDB | 5-(Hydroxymethyl)-2-furfural (HMF) | HMDB | 5-Hydroxymethyl furaldehyde | HMDB | 5-Hydroxymethyl-furfural | HMDB | 5-Hydrxoymethylfurfural | HMDB | 5-Methylolfurfural | HMDB | 5-HM-2-F CPD | MeSH | 5-HMF CPD | MeSH | Aes-103 | MeSH | 5-Hydroxymethyl furfural | MeSH | 5-(Hydroxymethyl)furancarboxaldehyde | PhytoBank | 5-Hydroxymethylfurfurol | PhytoBank | Hydroxymethylfuraldehyde | PhytoBank |
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Chemical Formula | C6H6O3 |
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Average Mass | 126.1100 Da |
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Monoisotopic Mass | 126.03169 Da |
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IUPAC Name | 5-(hydroxymethyl)furan-2-carbaldehyde |
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Traditional Name | hydroxymethylfurfural |
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CAS Registry Number | Not Available |
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SMILES | OCC1=CC=C(O1)C=O |
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InChI Identifier | InChI=1S/C6H6O3/c7-3-5-1-2-6(4-8)9-5/h1-3,8H,4H2 |
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InChI Key | NOEGNKMFWQHSLB-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, simulated) | Ahselim | | | 2021-12-17 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, experimental) | Ahselim | | | 2021-12-17 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50.18 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | Not Available |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbonyl compounds |
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Direct Parent | Aryl-aldehydes |
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Alternative Parents | |
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Substituents | - Aryl-aldehyde
- Heteroaromatic compound
- Furan
- Oxacycle
- Organoheterocyclic compound
- Organic oxide
- Hydrocarbon derivative
- Aromatic alcohol
- Primary alcohol
- Alcohol
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
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