A furanic compound
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5-Hydroxymethylfurfural

Item No. 27835

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-(hydroxymethyl)-2-furancarboxaldehyde
CAS Number
67-47-0
Synonyms
  • NSC 40738
Molecular Formula
C6H6O3
Formula Weight
126.1
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 1mg/mLDMSO: 3mg/mLEthanol: 2.5mg/mLPBS (pH 7.2): 10mg/mL
λmax
223, 281 nm
SMILES
OCC1=CC=C(C=O)O1
InChi Code
InChI=1S/C6H6O3/c7-3-5-1-2-6(4-8)9-5/h1-3,8H,4H2
InChi Key
NOEGNKMFWQHSLB-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
4°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 g

    $36

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    5 g

    $103

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    10 g

    $135

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    Product Description

    5-Hydroxymethylfurfural is a furanic compound derived from the degradation of sugars.1,2,3,4 It can be derived from reducing sugars via acid-catalyzed degradation or the Maillard reaction during the heating and storage of foods.2,3 5-Hydroxymethylfurfural is an intermediate in the synthesis of a variety of compounds including 2,5-diformylfuran (DFF), 2,5-furandicarboxylic acid (FDA), 2,5-bis(hydroxymethyl)furan (5-(hydroxymethyl)furfuryl alcohol; Item No. 20658), and dimethylfuran (DMF), among others.4 5-Hydroxymethylfurfural has been found in the marine algae L. undulata and scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805), hydroxyl, alkyl, and superoxide radicals in cell-free assays (IC50s = 27.1, 22.8, 45, and 33.5 μM, respectively).5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kucherov, F.A., Romashov, L.V., Galkin, K.I., et al. Chemical transformations of biomass-derived C6-furanic platform chemicals for sustainable energy research, materials science, and synthetic building blocks. ACS Sustainable Chem. Eng. 6(7), 8064-8092 (2018).

    2. Murkovic, M., and Pichler, N. Analysis of 5-hydroxymethylfurfual in coffee, dried fruits and urine. Mol. Nutr. Food Res. 50(9), 842-846 (2006).

    3. Jöbstl, D., Husøy, T., Alexander, J., et al. Analysis of 5-hydroxymethyl-2-furoic acid (HMFA) the main metabolite of alimentary 5-hydroxymethyl-2-furfural (HMF) with HPLC and GC in urine. Food Chem. 123(3), 814-818 (2010).

    4. Rosatella, A.A., Simeonov, S.P., Frade, R.F.M., et al. 5-Hydroxymethylfurfural (HMF) as a building block platform: Biological properties, synthesis and synthetic applications. Green Chem. 13, 754-793 (2011).

    5. Li, Y.-X., Li, Y., Qian, Z.-J., et al. In vitro antioxidant activity of 5-HMF isolated from marine red alga Laurencia undulata in free-radical-mediated oxidative systems. J. Microbiol. Biotechnol. 19(11), 1319-1327 (2009).