5-Hydroxymethyl-2-furfuraldehyde

With acid degradation, the first step appears to involve the formation of 1,2-enols from the aldose or ketose (7), followed by a series of dehydration reactions resulting in the formation of 5-hydroxymethyl-2-furfuraldehyde. If the initial sugar is a pentose, the final product is 2-furfuraldehyde. 

Janicki CA, Almond HR Jr. 1974. Reaction of haloperidol with 5-(hydroxymethyl)-2-furfuraldehyde an impurity in anhydrous lactose. J. Pharm. Sci. 63 4143. 

Tu D, Xue S, Meng C, Espinosa-Mansilla A, Mimoz de la Pena A, Salinas Lopez F. Simultaneous determination of 2-furfuraldehyde and 5-(hydroxymethyl)-2-furfuraldehyde by derivative spectrophotometry. J Agric Food Chem 1992 40 1022-10255. 

Heat treatment of sugar solutions containing acids and proteins results in nonenzymatic browning. The presence of 5-(hydroxymethyl)-2-furfuraldehyde (HMF) was shown to be a good indicator of Maillard reactions [158]. Decolorization of the solution can be done with activated carbon, charcoal as filtration coadjuvant and polyvinylpyrrolidone [132,160,161],... 

Methods of monitoring aldehydes in food and pharmaceutical samples have also been reported. A semiautomatic method by a stopped-flow flow injection analysis technique was successful in identifying the presence of furfural and 5-hydroxymethyl-2-furfuraldehyde in several commercial pharmaceutical preparations and food samples [398], The analysis is based on the reaction of the aldehydes with 2-thiobarbituric acid, with determination of the derivatives. 

Finally, levels of furfural and 5-hydroxymethyl-2-furfuraldehyde have also been monitored in processed fruit juices by a high performance liquid chromatography method using a reversed-phase macroreticular column and phosphate buffer as eluent [399], These aldehydes are degradation products of L-ascorbic acid. The detection limit of this method was reported as 0.05 mg r which was insufficiently sensitive to detect the presence of furfural. 

To provide better understanding of the reactions taking place when sugars are heated at 250°C in the presence or absence of H2SO4, the aqueous phase chemistry of glycerol, 2-propanol, 1,4-butanediol, tetrahydrofuran, glyceraldehyde, pyruvaldehyde, and dihydroxyacetone under these conditions has been examined. In a related study, focussed on the formation of 5-hydroxymethyl-2-furfuraldehyde from D-fructose or sucrose in aqueous... 

Davidson AG, Dawodu TO. DUference spectrophotometric assay of 5-hydroxymethyl-furfuraldehyde in hydrolyzed pharmaceutical syrups. I. Sodium borohydride reagent. J Pharm Biomed Anal 1987 5 213-222. 

The major soluble components of acid hydrolysates are sugars, such as xylose, glucose, and cellobiose furfurals, such as furfuraldehyde and hydroxymethyl furfural and organic acids, such as levulinic acid, formic acid, and acetic acid (13). When natural sources of cellulose are acid-hydrolized, numerous products can result, largely because of the hemicellulose materials. These make it difficult to produce a relatively pure sugar product and limit the utility of the acid hydrolysis process. 

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