6196-57-2

Basic information

• Product Name: 3-deoxyhexulose
• Synonyms: 3-deoxyhexulose;(4S,5R)-1,4,5,6-tetrahydroxyhexan-2-one
• CAS NO: 6196-57-2
• Molecular Formula: C6H12O5
• Molecular Weight: 164.16
• Mol File: 6196-57-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 467.6°C at 760 mmHg
• Flash Point: 250.7°C
• Appearance: /
• Density: 1.421g/cm³
• Vapor Pressure: 1.04E-10mmHg at 25°C
• Refractive Index: 1.534
• CAS DataBase Reference: 3-deoxyhexulose(CAS DataBase Reference)
• NIST Chemistry Reference: 3-deoxyhexulose(6196-57-2)
• EPA Substance Registry System: 3-deoxyhexulose(6196-57-2)

Safety Data

• Hazardous Substances Data: 6196-57-2(Hazardous Substances Data)

Usage

Description

3-Deoxyhexulose, also known as 3-deoxy-D-fructose, is a monosaccharide that serves as a metabolic fingerprint of 3-deoxyglucosone and an indicator of diabetes in plasma and urine. It plays a significant role in the diagnosis and monitoring of diabetes.

Uses

Used in Medical Applications:
3-Deoxyhexulose is used as a diagnostic marker for diabetes, helping to identify the presence of the disease in patients' plasma and urine. Its detection aids in the early diagnosis and management of diabetes, enabling timely intervention and treatment.
Used in Research:
3-Deoxyhexulose is utilized in scientific research to study the metabolic pathways and mechanisms associated with diabetes. Understanding its role in the disease can contribute to the development of new therapeutic strategies and interventions for diabetes management.

InChI:InChI=1/C6H12O5/c7-2-4(9)1-5(10)6(11)3-8/h5-8,10-11H,1-3H2/t5-,6+/m0/s1

Upstream product

• 14154-19-9 D-lyxo-3-deoxy-hexose 
• 5517-48-6 3-deoxy-D-arabino-hexose 
• 67104-35-2 3-deoxy-1,2:4,5-di-O-methylethylidene-β-D-ertythro-hex-2-ulopyranose 
• 4134-97-8 3-deoxyglucosone 
• 334999-16-5 (5S)-5-[(1R)-1,2-dihydroxyethyl]-3-benzyloxymethyl-4,5-dihydrooxazole 
• 334999-08-5 2-(3-benzyloxymethyl-4,5-dihydrooxazol-5-yl)-2-oxoethyl acetate 
• 25018-67-1 1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose 
• 50-99-7 D-glucose 
• 6706-59-8 L-Sorbitol 
• 104048-51-3 (S)-1-((S)-3-Benzyloxymethyl-4,5-dihydro-isoxazol-5-yl)-ethane-1,2-diol 
• 104048-40-0 3-Benzyloxymethyl-5-vinyl-4,5-dihydro-isoxazole 
• 104048-51-3 (R)-1-((S)-3-Benzyloxymethyl-4,5-dihydro-isoxazol-5-yl)-ethane-1,2-diol 

Downstream Products

• 1883-75-6 2,5-bis-(hydroxymethyl)furan 
• 3238-40-2 furan-2,5-dicarboxylic acid 

Relevant articles and documents

3-Deoxy-D-erythro-hexulose: a convenient synthesis and its interaction with the enzymes of fructose metabolism

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Permanganate oxidation revisited: Synthesis of 3-deoxy-2-uloses via indium-mediated chain elongation of carbohydrates

Application of the Barbier-type indium-mediated allylation method to suitable substrates offers access to carbohydrates bearing a terminal olefin moiety. The C-C bond, forming reaction generates a defined stereochemistry of the new chiral center and tolerates a wide variety of starting aldehydes thus allowing modifications in the carbohydrate backbone. Further transformations of the alkene moiety via an environmentally benign and subtle controlled protocol using potassium permanganate gives rise to the structural motif of 3-deoxy-2-uloses in good yields. The final part of the reaction sequence focuses on the deprotection of the acetyl groups essential for the success of the oxidation step. The acidic and labile 3-deoxy position of the target molecule is prone to elimination applying standard deacetylation conditions and therefore demands derivatisation of the molecule. The introduction of a thioketal moiety using microwave conditions shows promising results and subsequent standard transformations are applicable leading to the desired products.

Purification and Characterisation of NADPH-dependent 2-Oxoaldehyde Reductase from Chicken Liver

The enzymes which metabolize 2-oxoaldehyde compounds in a crude extract of chicken liver were examined using 3-deoxyglucosone (3-DG) and methylglyoxal (MG).NADH- and NADPH-dependent reductase activities were observed and the latter was more than the former. NADPH-dependent 2-oxoaldehyde reductase was purified from chicken liver by ammonium sulfate fractionation, and DEAE-cellulose, CM-cellulose, hydroxylapatite, and Sephadex G-100 column chromatographies.The molecular weight of the enzyme was estimated to be 38,000 and 32,000 by SDS-PAGE and gel filtration, respectively.The optimum pH was 6.5-7.0 and this enzyme was stable at pH 7.0-8.0.The Km for 3-DG and MG were 3.75 mM and l.52 mM, respectively.This enzyme had high activities towards 2-oxoaldehyde compounds, such as 3-DG, MG, and phenylglyoxal.This enzyme converted 3-deoxyglucosone (3-DG) to 3-deoxyfructose, and methylgloxal (MG) to acetol.