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

HCID 107526
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Grundinformationen

CAS
19030-38-7
Standard-SMILES
O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
InChIKey
GZCGUPFRVQAUEE-SLPGGIOYSA-N
Summenformel
C6H12O6
Durchschnittliche Molmasse
180,16 g/mol
Monoisotopische Masse
180,0633881

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal
IUPAC
(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal
Englischer Name
D-GLUCOSE-UL-14C
Summenformel
C6H12O6
Molmasse
180.16

Namen und Synonyme

(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalRefChem:934733GlyTouCan:G59743JOG59743JOD-(+)-GlucoseDL-Glucosealdehydo-D-glucose58367-01-4Glucose [JAN]DTXSID4048729815-92-9Glucose, liquid
Weitere Namen anzeigen
D-GLUCOSE-UL-14CD-[U-14C]GLUCOSED-GLUCOSE, [U-14C]GLUCOSE, D-[14C(U)]-D-Glucose, labeled with carbon-14D-GLUCOSE-UL-14C 2-10 MCI PER MMOL*AQUEO US SOLUTION
Glucopur(14C)-Glucose(14C)D-Glucose(C13)D-Glucose(U-14C)GlucoseGlucose (C-13)Glucose (C-14)D-(U-14C)Glucose

Datenbank-Bezeichner

CAS
19030-38-7、28823-03-2、50-99-7、58367-01-4、8027-56-3、815-92-9
PubChem CID
107526
DTXSID
DTXSID4048729
ChEMBL

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
-2,9
Polarare Oberfläche (TPSA)
118 Ų
H-Brücken-Donoren
5
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
5
Schwere Atome
12
Formalladung
0
Komplexität
138

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesChemical shift
LogP-1.88
SolubilitySoluble

Physikochemische Eigenschaften

Flammpunkt
20 °C · 20 °C
storage temp.
2 · 2-8°C
Aggregatzustand
aqueous solution

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Gefahrenhinweise

Regulatory Information · 2 Einträge

Chemical: Liquid glucose

Liquid glucose: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Other Safety InformationIMAP assessments - Liquid glucose: Human health tier I assessment

Sicherheitsdaten

wgk
3
ridadr
UN 2910 7
risk_code
11-36/37/38
hazard_code
R,F,Xi
safety_code
16-26-36

Chemie und Industrie

Pharmakologische Informationen

Pharmacodynamics · 1 Eintrag

Blood glucose is an obligatory energy source for humans involved in various cellular activities, and it also acts as a signaling molecule for diverse glucose-sensing molecules and proteins. Glucose undergoes oxidation into carbon dioxide, water, and yields energy molecules in the process of glycolysis and subsequent citric cycle and oxidative phosphorylation. Glucose is readily converted into fat in the body which can be used as a source of energy as required. Under a similar conversion into storage of energy, glucose is stored in the liver and muscles as glycogen. Glucose stores are mobilized in a regulated manner, depending on the tissues' metabolic demands. Oral glucose tablets or injections serve to increase the supply of glucose and oral glucose administration is more effective in stimulating insulin secretion because it stimulates the incretin hormones from the gut, which promotes insulin secretion.

Mechanism of Action · 1 Eintrag

Glucose supplies most of the energy to all tissues by generating energy molecules ATP and NADH during a series of metabolism reactions called glycolysis. Glycolysis can be divided into two main phases where the preparatory phase is initiated by the phosphorylation of glucose by hexokinase to form glucose 6-phosphate. The addition of the high-energy phosphate group activates glucose for the subsequent breakdown in later steps of glycolysis and is the rate-limiting step. Products end up as substrates for following reactions, to ultimately convert C6 glucose molecule into two C3 sugar molecules. These products enter the energy-releasing phase where the total of 4ATP and 2NADH molecules are generated per one glucose molecule. The total aerobic metabolism of glucose can produce up to 36 ATP molecules. These energy-producing reactions of glucose are limited to D-glucose as L-glucose cannot be phosphorylated by hexokinase. Glucose can act as precursors to generate other biomolecules such as vitamin C. It plays a role as a signaling molecule to control glucose and energy homeostasis. Glucose can regulate gene transcription, enzyme activity, hormone secretion, and the activity of glucoregulatory neurons. The types, number, and kinetics of glucose transporters expressed depends on the tissues and fine-tunes glucose uptake, metabolism, and signal generation to preserve cellular and whole body metabolic integrity.

Biological Half-Life · 1 Eintrag

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CHEBI:42758
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The approximate half-life is 14.3 minutes following intravenous infusion. Gut glucose half-life was markedly higher in females (79 ± 2 min) than in males (65 ± 3 min, P < 0.0001) and negatively related to body height (r = -0.481; P < 0.0001).

Metabolism/Metabolites · 1 Eintrag

Glucose can undergo aerobic oxidation in conjunction with the synthesis of energy molecules. Glycolysis is the initial stage of glucose metabolism where one glucose molecule is degraded into two molecules of pyruvate via substrate-level phosphorylation. These products are transported to the mitochondria where they are further oxidized into oxygen and carbon dioxide.

Absorption, Distribution and Excretion · 4 Einträge

Polysaccharides can be broken down into smaller units by pancreatic and intestinal glycosidases or intestinal flora. Sodium-dependent glucose transporter SGLT1 and GLUT2 (SLC2A2) play predominant roles in intestinal transport of glucose into the circulation. SGLT1 is located in the apical membrane of the intestinal wall while GLUT2 is located in the basolateral membrane, but it was proposed that GLUT2 can be recruited into the apical membrane after a high luminal glucose bolus allowing bulk absorption of glucose by facilitated diffusion. Oral preparation of glucose reaches the peak concentration within 40 minutes and the intravenous infusions display 100% bioavailability.

Glucose can be renally excreted.

The mean volume of distribution after intravenous infusion is 10.6L.

The mean metabolic clearance rate of glucose (MCR) for the 10 subjects studied at the higher insulin level was 2.27 ± 0.37 ml/kg/min at euglycemia and fell to 1.51±0.21 ml/kg/ at hyperglycemia. The mean MCR for the six subjects studied at the lower insulin level was 1.91 ± 0.31 ml/kg/min at euglycemia.