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DL-キシロース

aldehydo-D-Xylose

HCID 644160
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
25990-60-7
標準SMILES
O=C[C@H](O)[C@@H](O)[C@H](O)CO
InChIKey
PYMYPHUHKUWMLA-VPENINKCSA-N
分子式
C5H10O5
平均分子量
150.13 g/mol
単同位体質量
150.05282342

概要

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

名称と識別子

優先名称
aldehydo-D-Xylose
IUPAC
(2R,3S,4R)-2,3,4,5-tetrahydroxypentanal
現地名
DL-キシロース
英語名
DL-Xylose
分子式
C5H10O5
分子量
150.13

名称と別名

aldehydo-D-xyloseD-xylo-pentose;D-xyloseRefChem:936054GlyTouCan:G01550VLG01550VLDL-Xylose25990-60-7(+)-XyloseXylose (VAN)41247-05-6CCRIS 1899HSDB 3273
名称をさらに表示
DL-キシロース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

データベース識別子

CAS
25990-60-7、41247-05-6、58-86-6
PubChem CID
644160
ChEMBL
CHEMBL1236821
ChEBI
CHEBI:15936
UNII
A1TA934AKO
EC Number
255-277-2、608-587-0
Nikkaji
J2.806A

物性

構造計算による物性

XLogP
-2.3
極性表面積
98 Ų
水素結合供与体数
4
水素結合受容体数
5
回転可能結合数
4
重原子数
10
形式電荷
0
複雑度
104

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesCrystal structure

物理化学的性質

融点
133 · 133-136 °C
沸点
415.5 · 415.5±38.0 °C(Predicted)
比重(密度)
1.508 · 1.508±0.06 g/cm3(Predicted)
貯蔵温度
Inert atmosphere,Room Temperature
溶解性
2 O: · H2O: 0.1 g/mL 無色透明
酸解離定数(Pka)
12.46 · 12.46±0.20(Predicted)
外見
powder to crystal
色
White to Almost white
CAS データベース
25990 · 25990-60-7(CAS DataBase Reference)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS ClassificationNot Classified

危険有害性情報

Hazard Classes and CategoriesNot Classified

安全データ

F
3
wgk
3
hs_code
2940.00.6000
化審法
(9)-318 届出不要化学物質
safety_code
24/25

化学と産業

薬理情報

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

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 件

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 件

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.

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化合物ノート

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Absorption, Distribution and Excretion · 4 件

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.

応用分野 · 1 件

使用Xylose 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