A precursor for advanced glycation endproducts
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3-deoxy Glucosone

Item No. 16347

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-deoxy-D-erythro-hexos-2-ulose
CAS Number
4084-27-9
Synonyms
  • 2-keto-3-Deoxyglucose
  • 3-deoxy-D-erythro-Hexosulose
Molecular Formula
C6H10O5
Formula Weight
162.1
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlEthanol: 1 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
224 nm
SMILES
OC[C@@H](O)[C@@H](O)CC(C=O)=O
InChi Code
InChI=1S/C6H10O5/c7-2-4(9)1-5(10)6(11)3-8/h2,5-6,8,10-11H,1,3H2/t5-,6+/m0/s1
InChi Key
ZGCHLOWZNKRZSN-NTSWFWBYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $69

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    5 mg

    $248

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    10 mg

    $427

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    Product Description

    3-deoxy Glucosone is a highly reactive 2-oxoaldehyde intermediate of the Maillard reaction produced during oxidative stress in response to excess sugar consumption and in association with diabetes.1,2,3 It is a precursor for the formation of advanced glycation endproducts and because it readily reacts with protein amino groups is also used for crosslinking studies.4 3-deoxy Glucosone can be used as a reference for the analysis and detection of glucose degradation products and glycating agents.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yamada, H., Miyata, S., Igaki, N., et al. Increase in 3-deoxyglucosone levels in diabetic rat plasma. Specific in vivo determination of intermediate in advanced Maillard reaction. The Journal of Biological Chemisty 269(32), 20275-20280 (1994).

    2. Kusunoki, H., Miyata, S., Ohara, T., et al. Relation between serum 3-deoxyglucosone and development of diabetic microangiopathy. Diabetes Care 26(6), 1889-1894 (2003).

    3. Niwa, T., and Tsukushi, S. 3-Deoxyglucosone and AGEs in uremic complications: Inactivation of glutathione peroxidase by 3-deoxyglucosone. Kidney Int. Suppl. 78, S37-S41 (2001).

    4. Thornalley, P.J., Langborg, A., and Minhas, H.S. Formation of glyoxal, methylglyoxal and 3-deoxyglucosone in the glycation of proteins by glucose. Biochem. J. 344(Pt 1), 109-116 (1999).