5-(hydroxymethyl)-2-furaldehyde
Also known as 5-Hydroxymethyl-2-furfural, 5-(Hydroxymethyl)-2-furfuraldehyde, 5-Hydroxymethyl-2-furancarbaldehyde, 5-(Hydroxymethyl)furan-2-aldehyde, 5-Hydroxymethylfurfuraldehyde, 5-Hydroxymethylfuraldehyde, 5-(Hydroxymethyl)-2-furancarboxaldehyde, Hydroxymethylfurfuraldehyde
Hydroxymethylfurfural (HMF), also known as 5-(hydroxymethyl)furfural, is an organic compound formed by the dehydration of reducing sugars. It is a white low-melting solid (although commercial samples are often yellow) which is highly soluble in both water and organic solvents. The molecule consists of a furan ring, containing both aldehyde and alcohol functional groups.
Chemical data
- Formula
- C6H6O3
- Molecular weight
- 126.11 g/mol
- IUPAC name
- 5-(hydroxymethyl)furan-2-carbaldehyde
- SMILES
- C1=C(OC(=C1)C=O)CO
- InChIKey
- NOEGNKMFWQHSLB-UHFFFAOYSA-N
- XLogP
- -0.6
- Polar surface area
- 50.4 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Article
7 sectionsContents
- Production and reactions
- Derivatives
- Occurrence in food
- Biomedical
- Quantification
- Other
- References
Hydroxymethylfurfural (HMF), also known as 5-(hydroxymethyl)furfural, is an organic compound formed by the dehydration of reducing sugars. It is a white low-melting solid (although commercial samples are often yellow) which is highly soluble in both water and organic solvents. The molecule consists of a furan ring, containing both aldehyde and alcohol functional groups.
HMF can form in sugar-containing food, particularly as a result of heating or cooking. Its formation has been the topic of significant study as HMF was regarded as being potentially carcinogenic to humans. However, so far in vivo genotoxicity was negative. No relevance for humans concerning carcinogenic and genotoxic effects can be derived. HMF is classified as a food improvement agent and is primarily being used in the food industry in form of a food additive as a biomarker as well as a flavoring agent for food products. It is also produced industrially on a modest scale as a carbon-neutral feedstock for the production of fuels and other chemicals.