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Xylose

aldehydo-D-Xylose

HCID 644160
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Grundinformationen

CAS
25990-60-7
Standard-SMILES
O=C[C@H](O)[C@@H](O)[C@H](O)CO
InChIKey
PYMYPHUHKUWMLA-VPENINKCSA-N
Summenformel
C5H10O5
Durchschnittliche Molmasse
150,13 g/mol
Monoisotopische Masse
150,05282342

Überblick

Aldehydo-D-xylose is a D-xylose. It has a role as a Saccharomyces cerevisiae metabolite and a human metabolite.

Namen und Bezeichner

Bevorzugter Name
aldehydo-D-Xylose
IUPAC
(2R,3S,4R)-2,3,4,5-tetrahydroxypentanal
Lokaler Name
Xylose
Englischer Name
DL-Xylose
Summenformel
C5H10O5
Molmasse
150.13

Namen und Synonyme

aldehydo-D-xyloseD-xylo-pentose;D-xyloseRefChem:936054GlyTouCan:G01550VLG01550VLDL-Xylose25990-60-7(+)-XyloseXylose (VAN)41247-05-6CCRIS 1899HSDB 3273
Weitere Namen anzeigen
XYLOSEDL-XYL(±)-XylosXYLOSE, DL-Xylose (9CI)DL-XYLOSE USP/EP/BPDL-Xylose, 10 mM in DMSO(2S,3R,4S,5R)-oxane-2,3,4,5-tetrolrel-(2R,3S,4R)-2,3,4,5-Tetrahydroxypentanal
MFCD00198055MFCD00151475C5H10O525702-75-4XLS(+-)-XyloseXylose CRSD-(+)-Xylose;(+)-Xylose;Wood sugar

Datenbank-Bezeichner

CAS
25990-60-7、41247-05-6、58-86-6
PubChem CID
644160
ChEMBL
CHEMBL1236821
ChEBI
CHEBI:15936
UNII
A1TA934AKO

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-2,3
Polarare Oberfläche (TPSA)
98 Ų
H-Brücken-Donoren
4
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
4
Schwere Atome
10
Formalladung
0
Komplexität
104

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesCrystal structure

Physikochemische Eigenschaften

Schmelzpunkt
133 · 133-136 °C
Siedepunkt
415.5 · 415.5±38.0 °C(Predicted)
Dichte
1.508 · 1.508±0.06 g/cm3(Predicted)
storage temp.
Inert atmosphere,Room Temperature
Löslichkeit
2 O: · H2O: 0.1 g/mL, clear, colorless
pka
12.46 · 12.46±0.20(Predicted)
Aggregatzustand
powder to crystal
Farbe
White to Almost white
CAS Datenbank
25990 · 25990-60-7(CAS DataBase Reference)

Sicherheit und Regulatorisches

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

GHS-Klassifizierung

GHS ClassificationNot Classified

Gefahrenhinweise

Hazard Classes and CategoriesNot Classified

Sicherheitsdaten

F
3
wgk
3
hs_code
2940.00.6000
safety_code
24/25

Chemie und Industrie

Pharmakologische Informationen

Protein BindingReadily accessible data regarding the protein binding of xylose within the context of the human body is not available.
Pharmacodynamics · 1 Eintrag

Xylose is often used as a parent sugar alcohol from which the commonly used food additive sweetener, xylitol, can be derived via the hydrogenation of xylose. Xylitol possesses many characteristics that make it a healthy and effective alternative to regular sugar. For example, although it looks and tastes exactly like ordinary sugar, having a 100% relative sweetness versus normal sucrose, it also has a low impact on blood sugar and insulin secretion and a minimal caloric value of 2.4 calories/gm. Furthermore, xylitol is non-fermentable and thus cannot be transformed to acids by oral bacteria, allowing it to restore a proper alkaline/acid balance in the mouth. Various studies cite this effect for allowing xylitol products like chewing gum to be effective at reducing dental caries. Altogether, these characteristics make xylose and its xylitol metabolite an effective alternative sweetener for healthy food choices for individuals who may be diabetic or for individuals simply wanting to make healthy dietary choices for their bodies.

Mechanism of Action · 1 Eintrag

Xylose is metabolized into various chemical intermediates that can play critical functions in the biological homeostasis of the human body. Via the oxido-reductase metabolism pathway of xylose in eukaryotic organisms, xylose is ultimately catabolized into (D)-xylulose-5-phosphate, which functions as an intermediate in the pentose phosphate pathway. Within the pentose phosphate pathway, NADPH, pentose 5-carbon sugars, and ribose 5-phosphate are generated as materials and precursors for the synthesis of nucleotides. In particular, xylulose-5-phosphate can be used to directly generate glycerinaldehyde-3-phosphate in the pathway. Other studies have also demonstrated that xylulose-5-phosphate may also play a role in gene expression, perhaps by promoting ChREBP transcription factor in the well-fed state.

Biological Half-LifeThe elimination half-life observed in healthy individuals is 75 minutes.
Metabolism/Metabolites · 1 Eintrag

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EC Number
255-277-2、608-587-0
Nikkaji
J2.806A

The most common and traditional metabolism pathway for xylose is the oxidoreductase pathway (or xylose reductase-xylitol dehydrogenase, XR-XDH pathway). In this pathway, xylose is first reduced to xylitol using the xylitol dehydrogenase (XDH) enzyme with NADH or NADPH. The resultant xylitol is subsequently oxidized to D-xylulose by the xylitol dehydrogenase (XDH) enzyme while utilizing the cofactor NAD. Finally, the D-xylulose is phosphorylated by an ATP utilizing kinase (xylulose kinase enzyme) to generate D-xylulose-5-phosphate, which serves as an intermediate in the pentose phosphate pathway for nucleotide synthesis.

Absorption, Distribution and Excretion · 4 Einträge

When 12 normal healthy subjects were given an intravenous D-xylose dosing of 10 grams and then an oral dose of 25 grams a week later, the observed absorption percentage was about 69.4% (p < 0.002) and the observed absorption rate was approximately 1.03/hr (p< 0.05). The maximum concentration observed in the subjects was 0.53 mg/L with 71 minutes being the time to reach the maximum concentration. The absolute bioavailability recorded was 69%.

In patients with normal kidney function, renal excretion accounts for approximately half (50%) of their total D-xylose elimination. Any non-renal D-xylose elimination is presumed to be hepatic clearance.

The volume of distribution observed for d-xylose in normal healthy subjects is 0.22 L/kg.

The renal clearance rate observed in healthy individuals is 89 ml/min. The accompanying plasma and non-renal clearances are 180 and 91 ml/min, respectively.

Anwendungen · 1 Eintrag

VerwendenXylose is a sugar first isolated from wood. Xylose is classified as a monosaccharide of the aldopentose type, which means that it contains five carbon atoms and includes an aldehyde functional group. It is the precursor to hemicellulose, one of the main c