114 to 116 °C (237 to 241 °F; 387 to 389 K) (1 mbar)
UV-vis (λmax)
284 nm[2]
Related compounds
Related furan-2-carbaldehydes
Furfural
Methoxymethylfurfural
Hazards
GHS labelling:
Pictograms
[3]
Signal word
Warning[3]
Hazard statements
H315, H319, H335[3]
Precautionary statements
P261, P305+P351+P338, P310[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yverify (what is YN ?)
Infobox references
Chemical compound
Hydroxymethylfurfural (HMF), also known as 5-(hydroxymethyl)furfural, is an organic compound formed by the dehydration of reducing sugars.[4][5] 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.[6] HMF is classified as a food improvement agent [7] 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.[8][9] It is also produced industrially on a modest scale[10] as a carbon-neutral feedstock for the production of fuels[11] and other chemicals.[12]
^ abc"Front Matter". Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 911. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^The Determination of HMF in Honey with an Evolution Array UV-Visible Spectrophotometer. Nicole Kreuziger Keppy and Michael W. Allen, Ph.D., Application note 51864, Thermo Fisher Scientific, Madison, WI, USA (article)
^van Putten, Robert-Jan; van der Waal, Jan C.; de Jong, Ed; Rasrendra, Carolus B.; Heeres, Hero J.; de Vries, Johannes G. (2013). "Hydroxymethylfurfural, A Versatile Platform Chemical Made from Renewable Resources". Chemical Reviews. 113 (3): 1499–1597. doi:10.1021/cr300182k. ISSN 0009-2665. PMID 23394139.
^Rosatella, Andreia A.; Simeonov, Svilen P.; Frade, Raquel F. M.; Afonso, Carlos A. M. (2011). "5-Hydroxymethylfurfural (HMF) as a building block platform: Biological properties, synthesis and synthetic applications". Green Chemistry. 13 (4): 754. doi:10.1039/c0gc00401d. ISSN 1463-9262.
^Abraham, Klaus; Gürtler, Rainer; Berg, Katharina; Heinemeyer, Gerhard; Lampen, Alfonso; Appel, Klaus E. (2011-04-04). "Toxicology and risk assessment of 5-Hydroxymethylfurfural in food". Molecular Nutrition & Food Research. 55 (5): 667–678. doi:10.1002/mnfr.201000564. ISSN 1613-4125. PMID 21462333.
^Commission Implementing Regulation (EU) No 872/2012 of 1 October 2012 adopting the list of flavouring substances provided for by Regulation (EC) No 2232/96 of the European Parliament and of the Council, introducing it in Annex I to Regulation (EC) No 1334/2008 of the European Parliament and of the Council and repealing Commission Regulation (EC) No 1565/2000 and Commission Decision 1999/217/EC Text with EEA relevance, 2012-10-02, retrieved 2018-06-25
^Kläusli, Thomas (2014). "AVA Biochem: commercialising renewable platform chemical 5-HMF". Green Processing and Synthesis. 3 (3): 235–236. doi:10.1515/gps-2014-0029. ISSN 2191-9550. S2CID 100848139.
^Huber, George W.; Iborra, Sara; Corma, Avelino (2006). "Synthesis of Transportation Fuels from Biomass: Chemistry, Catalysts, and Engineering". Chem. Rev.106 (9): 4044–98. doi:10.1021/cr068360d. PMID 16967928.MIT Technology Review
^Lewkowski, J. (2001). "Synthesis, chemistry and applications of 5-hydroxymethyl-furfural and its derivatives". Arkivoc. 1: 17–54. doi:10.3998/ark.5550190.0002.102. hdl:2027/spo.5550190.0002.102. ISSN 1424-6376.
and 20 Related for: Hydroxymethylfurfural information
Hydroxymethylfurfural (HMF), also known as 5-(hydroxymethyl)furfural, is an organic compound formed by the dehydration of reducing sugars. It is a white...
Conditions Determine the Selective Hydroconversion of Furfural and 5-Hydroxymethylfurfural". Chemical Reviews. 118 (22): 11023–11117. doi:10.1021/acs.chemrev...
in mice. Another chemical of interest found in P. indusiatus is hydroxymethylfurfural, which has attracted attention as a tyrosinase inhibitor. Tyrosinase...
results in product deterioration, as it increases the level of hydroxymethylfurfural (HMF)[citation needed] and reduces enzyme (e.g. diastase) activity...
"Industrially Applicable Strategies for Mitigating Acrylamide, Furan and 5-Hydroxymethylfurfural in Food" (PDF). Journal of Agricultural and Food Chemistry. 61 (43):...
The molecular formula C6H6O3 may refer to: Cyclohexanetriones Hydroxymethylfurfural Hydroxyquinol Isomaltol Levoglucosenone Maltol Phloroglucinol Pyrogallol...
have a bitter taste and a dark colour, due to the production of hydroxymethylfurfural and other byproducts.p. 26 This type of product is now manufactured...
produce inhibitory compounds, such as acetic acid, furfural, and 5-hydroxymethylfurfural, formic acid, and vanillin, which could have negative effects on...
formation of mutagenic compounds. Fructose readily dehydrates to give hydroxymethylfurfural ("HMF", C 6H 6O 3), which can be processed into liquid dimethylfuran...
although there may be sugar breakdown products (furfural and 5-hydroxymethylfurfural). A solution of hydrochloric acid and phloroglucinol is used for...
Swedish Musicians' Union 5-Sulfoxymethylfurfural, a metabolite of hydroxymethylfurfural Service Management Facility, a component of Solaris Simple Machines...
the dehydration of the hexoses and subsequent etherification of hydroxymethylfurfural (HMF). Already in 1936 a batch process was patented for the production...
vinyl alcohol isomers have been found in the e-cigarette vapor. Hydroxymethylfurfural and furfural have been found in the e-cigarette vapors. The amounts...
high molecular weight melanoidins and furanic compounds such as 5-hydroxymethylfurfural (HMF). Water vaporization induces the concentration of sugars, organic...
Salak; Yoshida, Hiroyuki (2006-10-16). "Dehydration of fructose to 5-hydroxymethylfurfural in sub-critical water over heterogeneous zirconium phosphate catalysts"...
with only few on the synthesis of high value-added chemicals; hydroxymethylfurfural (HMF) has been listed as one of the top 10 bio-based chemicals by...
John Grant Glucosyloxymethylfurfural, a glycosylated derivative of hydroxymethylfurfural This disambiguation page lists articles associated with the title...
technique, it produces several potent inhibitors including furfural and hydroxymethylfurfural. Ammonia Fiber Expansion (AFEX) is an example of a promising pretreatment...
lignocellulosic biomass to smaller, higher value organic compounds such as 5-hydroxymethylfurfural (HMF). These humins can be in the form of either viscous liquids...