Hydroxymethylfurfural

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.

Hydroxymethylfurfural
Names
Preferred IUPAC name
5-(Hydroxymethyl)furan-2-carbaldehyde
Other names
5-(Hydroxymethyl)-2-furaldehyde
5-(Hydroxymethyl)furfural
Identifiers
3D model (JSmol)
110889
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.595
EC Number
  • 200-654-9
278693
KEGG
PubChem CID
UNII
  • InChI=1S/C6H6O3/c7-3-5-1-2-6(4-8)9-5/h1-3,8H,4H2 Y
    Key: NOEGNKMFWQHSLB-UHFFFAOYSA-N Y
  • InChI=1/C6H6O3/c7-3-5-1-2-6(4-8)9-5/h1-3,8H,4H2
    Key: NOEGNKMFWQHSLB-UHFFFAOYAB
SMILES
  • c1cc(oc1CO)C=O
Properties
C6H6O3
Molar mass 126.111 g·mol−1
Appearance Low melting white solid
Odor Buttery, caramel
Density 1.29 g/cm3
Melting point 30 to 34 °C (86 to 93 °F; 303 to 307 K)
Boiling point 114 to 116 °C (237 to 241 °F; 387 to 389 K) (1 mbar)
UV-vis (λmax) 284 nm
Related compounds
Related furan-2-carbaldehydes
 Furfural

Methoxymethylfurfural

Hazards
GHS labelling:
Warning
H315, H319, H335
P261, P305+P351+P338, P310
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

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.

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