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Sigma-Aldrich

3-Deoxyglucosone

≥75% (TLC)

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Synonym(s):
3-Deoxy-D-erythro-hexosulose
Empirical Formula (Hill Notation):
C6H10O5
CAS Number:
Molecular Weight:
162.14
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.25

Quality Level

Assay

≥75% (TLC)

form

solid

color

faintly yellow to orange

storage temp.

room temp

SMILES string

OC[C@H]1OC(O)C(=O)C[C@@H]1O

InChI

1S/C6H10O5/c7-2-5-3(8)1-4(9)6(10)11-5/h3,5-8,10H,1-2H2/t3-,5+,6?/m0/s1

InChI key

UHPMJDGOAZMIID-OPAZFOKUSA-N

Application

3-Deoxyglucosone is used as a reference for the analysis and detection of glucose degradation products, glycating agents, generated by processes such as heat sterilization.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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He Li et al.
Journal of agricultural and food chemistry, 67(32), 9050-9059 (2019-07-25)
The control of 2,3-dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one (DDMP) formation in the Maillard reaction is important to improve the thermally treated food quality as a result of its intense bitterness and potential toxicity. In this work, phenolic acids, such as gallic, protocatechuic, caffeic, and
Danielle T Loughlin et al.
Wound repair and regeneration : official publication of the Wound Healing Society [and] the European Tissue Repair Society, 17(5), 739-749 (2009-09-23)
The interaction of fibroblasts with the extracellular matrix is critical for wound healing. Advanced glycation end products (AGEs) occur through nonenzymatic glycation of long-lived proteins such as collagens. One precursor to these modifications, 3-deoxyglucosone (3DG), is elevated in patients with
Alina Shapira et al.
Molecular nutrition & food research, 51(4), 473-478 (2007-03-29)
Peritoneal dialysis (PD) is commonly performed by using preprepared dialysis solutions containing glucose, which are thermally treated to achieve commercial sterilization. A series of glucose degradation products (GDPs) are being formed, which react with the tissue during the dialysis procedure
Michael Hellwig et al.
Journal of agricultural and food chemistry, 58(19), 10752-10760 (2010-09-09)
1,2-Dicarbonyl compounds are formed in food during Maillard and caramelization reactions. 3-Deoxy-D-threo-hexos-2-ulose (3-deoxygalactosone, 3-DGal) and galactosone, two 1,2-dicarbonyl compounds originating from the degradation of galactose, were synthesized and converted to the respective quinoxalines, which were characterized by NMR spectroscopy. Analytical
Caatje Y le Poole et al.
Peritoneal dialysis international : journal of the International Society for Peritoneal Dialysis, 32(1), 45-54 (2011-06-03)
Standard peritoneal dialysis (PD) solutions contain high levels of glucose and glucose degradation products (GDPs), both contributing to the formation of advanced glycation end products (AGEs). We studied the contribution to plasma GDP and AGE levels of 2 PD regimens

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