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aldehydo-D-Xylose

HCID 644160
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
25990-60-7
표준 SMILES
O=C[C@H](O)[C@@H](O)[C@H](O)CO
InChIKey
PYMYPHUHKUWMLA-VPENINKCSA-N
분자식
C5H10O5
평균 분자량
150.13 g/mol
단동위원소 질량
150.05282342

개요

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

이름 및 식별자

우선 이름
aldehydo-D-Xylose
IUPAC
(2R,3S,4R)-2,3,4,5-tetrahydroxypentanal
영어명
DL-Xylose
분자식
C5H10O5
분자량
150.13

이름 및 동의어

aldehydo-D-xyloseD-xylo-pentose;D-xyloseRefChem:936054GlyTouCan:G01550VLG01550VLDL-Xylose25990-60-7(+)-XyloseXylose (VAN)41247-05-6CCRIS 1899HSDB 3273
이름 더 보기
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

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP
-2.3
극성 표면적
98 Ų
수소 결합 공여자 수
4
수소 결합 수용자 수
5
회전 가능 결합 수
4
무거운 원자 수
10
형식 전하
0
복잡도
104

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesCrystal structure

물리화학적 성질

녹는점
133 · 133-136 °C
끓는 점
415.5 · 415.5±38.0 °C(Predicted)
밀도
1.508 · 1.508±0.06 g/cm3(Predicted)
저장 조건
Inert atmosphere,Room Temperature
용해도
2 O: · H2O: 0.1 g/mL, 투명, 무색
산도 계수 (pKa)
12.46 · 12.46±0.20(Predicted)
물리적 상태
powder to crystal
색상
흰색에서 거의 흰색

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS ClassificationNot Classified

유해성 정보

Hazard Classes and CategoriesNot Classified

안전 데이터

wgk
3
HS 번호
2940.00.6000
safety_code
24/25
F 고인화성물질
3

화학 및 산업

약리 정보

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

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 · 1건

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 · 1건

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.

관련 반응

119건
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HRID 1432 반응식
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HRID 51256 반응식
HRID 51256반응물로uspto-grants-2004_03
HRID 81332 반응식
HRID 81332반응물로uspto-grants-2014_09
HRID 241469 반응식
HRID 241469생성물로uspto-grants-2014_02
HRID 267173 반응식
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Absorption, Distribution and Excretion · 4건

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.

응용 분야 · 1건

용도Xylose 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