(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Base Information

• Chemical Name: (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal
• CAS No.: 50-99-7
• Deprecated CAS: 162222-91-5,165659-51-8,50933-92-1,8012-24-6,80206-31-1,8030-23-7,111688-73-4,111688-73-4,165659-51-8,2280-44-6,8012-24-6,80206-31-1,8030-23-7
• Molecular Formula: C6H12O6
• Molecular Weight: 180.158
• Hs Code.: 17023051
• UNII: 5SL0G7R0OK
• DSSTox Substance ID: DTXSID7022910,DTXSID4048729
• Nikkaji Number: J4.109B
• Wikidata: Q21036645
• Metabolomics Workbench ID: 52322
• ChEMBL ID: CHEMBL448805
• Mol file: 50-99-7.mol

Synonyms:Anhydrous Dextrose;D Glucose;D-Glucose;Dextrose;Dextrose, Anhydrous;Glucose;Glucose Monohydrate;Glucose, (alpha-D)-Isomer;Glucose, (beta-D)-Isomer;Glucose, (DL)-Isomer;Glucose, (L)-Isomer;L Glucose;L-Glucose;Monohydrate, Glucose

Chemical Property of (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 2.59E-13mmHg at 25°C
• Melting Point: 150-152 °C(lit.)
• Refractive Index: 53 ° (C=10, H2O)
• Boiling Point: 527.112 °C at 760 mmHg
• PKA: pKa 12.43(H2O,t = 18,)(Approximate)
• Flash Point: 286.664 °C
• PSA: 118.22000
• Density: 1.581 g/cm³
• LogP: -3.37880
• Storage Temp.: 2-8°C
• Solubility.: H2O: 1 M at 20 °C, clear, colorless
• Water Solubility.: Soluble
• XLogP3: -2.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 180.06338810
• Heavy Atom Count: 12
• Complexity: 138

Purity/Quality:

99% min ^*data from raw suppliers

Hexose ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-63-62-46-36/38-21
• Safety Statements: 26-36/37-24/25-53-25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C(C(C(C(C=O)O)O)O)O)O
• Isomeric SMILES: C([C@H]([C@H]([C@@H]([C@H](C=O)O)O)O)O)O
• Recent EU Clinical Trials: Acute gastroenteritis in paediatrics :
• General Description: D(+)-Glucose can be selectively detected in aqueous solutions through a fluorescence turn-on mechanism involving its enzymatic oxidation by glucose oxidase (GOx) to produce hydrogen peroxide (H2O2), which then reacts with a modified tetraphenylethylene (TPE)-based probe. This reaction triggers aggregation-induced emission (AIE), resulting in a measurable fluorescence signal, demonstrating high sensitivity and specificity for D-glucose with a detection limit as low as 3.0 μM. The method is highly selective, showing minimal interference from other sugars or reactive oxygen species.

Technology Process of (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

There total 3919 articles about (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 38.3%

4-nitrophenyl-β-D-glucoside (2492-87-7) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + D-glucose (50-99-7)

Guidance literature:

4-nitrophenyl-β-D-glucoside; With C₁₅H₂₇ClCuN₃O₆⁽¹⁺⁾*ClO₄^(1-); dihydrogen peroxide; triethylamine; In water; at 60 ℃; for 2h; Inert atmosphere;

In water; Reagent/catalyst; Catalytic behavior; Kinetics; Inert atmosphere;

DOI:10.1016/j.jcat.2019.03.019

Reference yield:

hydrogenchloride (7647-01-0,15364-23-5) + methanol (67-56-1) + Sucrose (57-50-1) → D-glucose (50-99-7) + methyl β-D-fructofuranoside (13403-14-0,15219-93-9,16975-88-5,51295-55-7,51295-56-8,52443-09-1,60504-77-0,60504-79-2,63526-47-6,69460-17-9,92283-23-3) + methyl α-D-fructofuranoside (13403-14-0,15219-93-9,16975-88-5,51295-55-7,51295-56-8,52443-09-1,60504-77-0,60504-79-2,63526-47-6,69460-17-9,92283-23-3)

Guidance literature:

at 20 ℃;

DOI:10.1021/ja01324a041

Reference yield:

methanol (67-56-1) + Sucrose (57-50-1) → D-glucose (50-99-7) + methyl β-D-fructofuranoside (13403-14-0,15219-93-9,16975-88-5,51295-55-7,51295-56-8,52443-09-1,60504-77-0,60504-79-2,63526-47-6,69460-17-9,92283-23-3) + methyl α-D-fructofuranoside (13403-14-0,15219-93-9,16975-88-5,51295-55-7,51295-56-8,52443-09-1,60504-77-0,60504-79-2,63526-47-6,69460-17-9,92283-23-3)

Guidance literature:

at 140 ℃;

upstream raw materials:

D-Fructose

glucose

methyl-alpha-D-glucopyranoside

D-Glucono-1,5-lactone

Downstream raw materials:

(-)-2-hydroxyparaconic acid methylester

1-(β-D-glucopyranosyl)-piperidine

1-deoxy-1-morpholino-D-fructose

D-Fructose

Refernces

A highly selective fluorescence turn-on detection of hydrogen peroxide and d-glucose based on the aggregation/deaggregation of a modified tetraphenylethylene

10.1016/j.tetlet.2014.01.056

The research presents a study on a selective fluorescence turn-on detection method for hydrogen peroxide (H2O2) and D-glucose, utilizing a tetraphenylethylene (TPE)-based molecule, compound 1. The detection mechanism relies on the aggregation-induced emission (AIE) behavior of the TPE unit and the reaction of H2O2 with the arylboronic ester group in compound 1. Upon reaction with H2O2, compound 1 transforms into compound 2, which is less soluble in water, leading to aggregation and a consequent fluorescence turn-on due to AIE properties. The study also demonstrates the application of compound 1 for the selective detection of D-glucose in aqueous solutions, leveraging the enzymatic oxidation of D-glucose by glucose oxidase (GOx) to produce H2O2, which then reacts with compound 1. The experiments involved the synthesis of compound 1, its characterization using 1H NMR, 13C NMR, and mass spectra, and fluorescence spectroscopy to monitor the reaction with H2O2 and the detection of D-glucose. The results showed high selectivity and sensitivity for H2O2 detection, with a low detection limit of 180 nM, and successful D-glucose detection down to a concentration of 3.0 μM. The selectivity was confirmed by testing the fluorescence response of compound 1 to other reactive oxygen species and sugars, with significant enhancement observed only in the presence of H2O2 and D-glucose.

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