5hydroxymethylfurfural

5-Hydroxymethylfurfural (5-HMF) is an organic compound in the class of furan derivatives. Its IUPAC name is 5-hydroxymethylfuran-2-carbaldehyde, and its molecular formula is C6H6O3. It typically appears as a colorless to pale yellow solid that is sparingly soluble in water. 5-HMF is mainly formed by the acid-catalyzed dehydration of hexose sugars, such as glucose and fructose, during heating or prolonged storage, and may arise in sugar-containing foods during processing.

5-HMF occurs naturally in trace amounts in many heat-treated foods and beverages, including honey, fruit juices, coffee, dried fruit, and baked goods. It is also formed during prolonged storage of sugary solutions or during caramelization and acid hydrolysis of polysaccharides. Its formation increases with higher temperature, longer time, and greater sugar concentration, making it a common indicator of thermal processing and quality in food analysis.

In industry, 5-HMF is a platform chemical derived from renewable sugars. It can be oxidized to 2-furoic acid or converted to derivatives such as levulinic acid, furan-2,5-dicarboxylic acid, and various furanic polymers. It also serves as a building block for bio-based fuels, solvents, and specialty chemicals, and is the subject of ongoing research into sustainable materials and chemical intermediates.

Exposure to 5-HMF in typical foods is usually low. Some studies report cytotoxic or mutagenic effects only at high in vitro concentrations; in vivo relevance at dietary levels is not established. Regulatory limits exist for honey in some jurisdictions; for example, the European Union commonly cites a maximum around 40 mg/kg in honey, reflecting quality control rather than acute toxicity.

Analytical detection of 5-HMF typically uses high-performance liquid chromatography with UV detection, or LC-MS, after suitable sample preparation. Common methods include HPLC with detection near 284 nm and derivatization-free or -assisted approaches for complex matrices such as honey and juice.