(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 :
• Description: D(+)-glucose ,a short form of dextrorotatory glucose, is a stereoisomer of glucose molecule, which is biologically active and whose bottom chiral carbon has its hydroxyl group (OH) located spatially to the right. Its molecule can exist in an open-chain (acyclic) and ring (cyclic) form and has two isomers α- and β-. It is the main source of energy in the form of ATP for living organisms. It is naturally occurring and is found in fruits and other parts of plants in its free state. In animals, it arises from the breakdown of glycogen in a process known as glycogenolysis. D-(+)-Glucose has been used as a standard for the estimation of total sugar in hydrolyzed starch by phenol-sulfuric acid method. It has also been used in the preparation of the liquid media for culturing some yeast cells. In addition, it is used therapeutically in fluid and nutrient replacement, such as glucose syrup and glucose powder. It can be obtained by enzymatic cleavage of starch, so there are multiple sources like sugar cane, sugar beet, corn (corn syrup), potatoes and wheat. Today, large-scale starch hydrolysis is used to produce glucose. D-(+)-Glucose is a monosaccharide that occurs in nature and is used by organisms as an energy source. D-(+)-Glucose is the more common enantiomer of L-(–)-glucose (Item No. 20829). Anhydrous Dextrose is the anhydrous form of D-glucose, a natural monosaccharide and carbohydrate. Dextrose serves to replenish lost nutrients and electrolytes. The agent provides metabolic energy and is the primary ingredient in oral rehydration salts (ORS) and is used in intravenous (IV) fluids to provide nutrients to patients under intensive care who are unable to receive them by the oral route. Solutions containing dextrose restore blood glucose levels and provide calories and may aid in minimizing liver glycogen depletion and exerts a protein-sparing action. Dextrose anhydrous also plays a role in the production of proteins and in lipid metabolism. Watery odorless colorless liquid. Denser than water and soluble in water. Hence sinks in and mixes with water. (USCG, 1999) Aldehydo-D-glucose is the open chain form of D-glucose. It is a D-glucose and an aldehydo-glucose. It is an enantiomer of an aldehydo-L-glucose. D(+)-Glucose?is one of the most important biological compounds found in nature. It is a main product in photosynthesis and is oxidized in cellular respiration. D(+)-Glucose?polymerizes to form several important classes of biomolecules including cellulose, starch, and glycogen. It also combines with other compounds to produce common sugars such as sucrose and lactose. The form of D(+)-Glucose?displayed above is D-D(+)-Glucose. The “D” designation indicates the configuration of the molecule. The “D” configuration specifies that the hydroxyl group on the number 5 carbon is on the right side of the molecule. The mirror image of D-D(+)-Glucose?produces another form of D(+)-Glucose?called L-D(+)-Glucose.D(+)-Glucose?is the most common form of a large class of molecules called carbohydrates. Carbohydrates are the predominant type of organic compounds found in organisms and include sugar, starches, and fats. Carbohydrates, as the name implies, derive their name from D(+)-Glucose,C6H12O6, which was considered a hydrate of carbon with the general formula of Cn(H2O)n, where n is a positive integer. Although the idea of water bonded to carbon to form a hydrate of carbon was wrong, the term carbohydrate persisted. Carbohydrates consist of carbon, hydrogen, and oxygen atoms, with the carbon atoms generally forming long unbranched chains. Carbohydrates are also known as saccharides derived from the Latin word for sugar, saccharon.
• Uses: Glucose is the primary fuel for biological respiration. During digestion, complex sugarsand starches are broken down into glucose (as well as fructose and galactose) in the small intestine.Glucose then moves into the bloodstream and is transported to the liver where glucoseis metabolized through a series of biochemical reactions, collectively referred to as glycolysis.Glycolysis, the breakdown of glucose, occurs in most organisms. In glycolysis, the final productis pyruvate. The fate of pyruvate depends on the type of organism and cellular conditions.In animals, pyruvate is oxidized under aerobic conditions producing carbon dioxide. Underanaerobic conditions in animals, lactate is produced. This occurs in the muscle of humansand other animals. During strenuous conditions the accumulation of lactate causes musclefatigue and soreness. Certain microorganisms, such as yeast, under anaerobic conditions convertpyruvate to carbonic dioxide and ethanol. This is the basis of the production of alcohol.Glycolysis also results in the production of various intermediates used in the synthesis of otherbiomolecules. Depending on the organism, glycolysis takes various forms, with numerousproducts and intermediates possible. glucose has moisture-binding properties and provides the skin with a soothing effect. It is a sugar that is generally obtained by the hydrolysis of starch. Glucose is a corn sweetener that is commercially made from starch by the action of heat and acids or enzymes, resulting in the complete hydrolysis of the cornstarch. There are two types of refined commercially available: hydrate, which contains 9% by weight water of crystallization and is the most often used, and anhydrous glucose, which contains less than 0.5% water. is a reducing sugar and produces a high-temperature browning effect in baked goods. It is used in ice cream, bakery products, and confections. It is also termed corn sugar. Dextrose(D-glucose), a simple sugar (monosaccharide), is an important carbohydrate in biology Labelled D-Glucose is a simple sugar that is present in plants. A monosaccharide that may exist in open chain or cyclic conformation if in solution. It plays a vital role in photosynthesis and fuels the energy required for cellular respiration. D-Glucose is used in various metabolic processes including enzymic synthesis of cyclohexyl-α and β-D-glucosides. Can also be used as a diagnostic tool in detection of type 2 diabetes mellitus and potentially Huntington's disease through analysis of blood-glucose in type 1 diabetes mellitus. A primary source of energy for living organisms D(+)-Glucose anhydrous for biochemistry Reag. Ph Eur. CAS 50-99-7, molar mass 180.16?g/mol.

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:

1-(β-D-glucopyranosyl)-piperidine

D-glucoheptonic acid

D-glycero-D-ido-heptonic acid

N-(1-deoxy-D-fructos-1-yl)-L-alanine

Refernces

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