A building block in the synthesis of carbohydrates
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2-keto D-Glucose

Item No. 20908

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
D-arabino-hexos-2-ulose
CAS Number
1854-25-7
Synonyms
  • D-Glucosone
Molecular Formula
C6H10O6
Formula Weight
178.1
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Methanol: Slightly SolubleWater: Slightly Soluble
SMILES
OC[C@@H](O)[C@@H](O)[C@H](O)C(C=O)=O
InChi Code
InChI=1S/C6H10O6/c7-1-3(9)5(11)6(12)4(10)2-8/h1,4-6,8,10-12H,2H2/t4-,5-,6-/m1/s1
InChi Key
DCNMIDLYWOTSGK-HSUXUTPPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    5 mg

    $36

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    10 mg

    $63

    Add

    25 mg

    $95

    Add

    50 mg

    $143

    Add
    Product Description

    2-keto D-Glucose has been used as a building block in the synthesis of carbohydrates.1 It is an intermediate in the conversion of D-glucose (Item No. 23733) into D-fructose that was originally isolated from a variety of fungi, algae, and shellfish.2 It has slow-onset, long-lasting antioxidant properties in an electron paramagnetic resonance (EPR) assay.3 2-keto D-Glucose has also been found as a glucose degradation product in heat-sterilized peritoneal dialysis fluids.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Huwig, A., Danneel, H.-J., and Giffhorn, F. Laboratory procedures for producing 2-keto-D-glucose, 2-keto-D-xylose and 5-keto-D-fructose from D-glucose, D-xylose and L-sorbose with immobilized pyranose oxidase of Peniophora gigantea. J. Biotechnol. 32(3), 309-315 (1994).

    2. Liu, T.E., Wolf, B., Geigert, J., et al. Convenient, laboratory procedure for producing solid D-arabino-hexos-2-ulose (D-glucosone). Carb. Res. 113(1), 151-157 (1983).

    3. Kanzler, C., Haase, P.T., and Kroh, L.W. Antioxidant capacity of 1-deoxy-D-erythro-hexo-2,3-diulose and D-arabino-hexo-2-ulose. J. Agric. Food Chem. 62(13), 2837-2844 (2014).

    4. Mittelmaier, S., Fünfrocken, M., Fenn, D., et al. Identification and quantification of the glucose degradation product glucosone in peritoneal dialysis fluids by HPLC/DAD/MSMS. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 878(11-12), 877-882 (2010).