Hydroxymethylfurfural

Hydroxymethylfurfural (HMF), also known as 5-hydroxymethylfurfural, is an organic compound derived from dehydration of certain sugars. This yellow low-melting solid is highly water-soluble. The molecule consists of a furan ring, containing both aldehyde and alcohol functional groups.

Chemistry

HMF forms upon heating of hexoses in the presence of acid. This reaction occurs via the Maillard reaction, a form of non-enzymatic browning. The process starts with the dehydration of the hexose to an enol. The enol then tautomerizes to give a dicarbonyl compound, which cyclizes. The process is accelerated in an acidic environment.

Occurrence

HMF has been identified in a wide variety of heated processed foods, including milk, fruit juices, spirits, and honey. It is also formed during the caramelization of sugars and during the browning of bread. The presence of HMF in honey is used as a marker for excess heating during honey processing.

Health effects

While HMF is not directly harmful, it is a precursor to compounds that are. HMF can be converted in the body to 5-sulfoxymethylfurfural, which is potentially toxic and mutagenic. The potential health effects of HMF have been the subject of ongoing research.

See also

• Furan
• Maillard reaction
• 5-sulfoxymethylfurfural

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  Synthesis of Hydroxymethylfurfural
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  Dictyophora indusiata mushroom