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HomeProduct name listL-xylose

L-xylose

  • CAS NO.:609-06-3
  • Empirical Formula: C5H10O5
  • Molecular Weight: 150.13
  • MDL number: MFCD00151096
  • EINECS: 210-174-1
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-22 17:01:22
L-xylose Structural

What is L-xylose?

Chemical properties

L-Xylose is a white fine crystalline powder. It is an aldopentose that has a molecular formula C5H10O5 and a molar mass of 150.13 g/mol. The structure of L-xylose is presented in Figure 1. The optical rotations of D- and L-xylose are α20D = -18.6° and α20D = +18.6°, respectively (Fischer and Ruff, 1900). L-Xylose can exist in open chain form, as a pyranose or as a furanose. The relative concentrations of different stereoisomers have not been specified for L-xylose. However, for D-xylose the distribution of different forms in water are: 36.5% α-pyranose, 6% β-pyranose and less than 1 % in open chain and furanose form (Pastinen, 2000). Most likely L-xylose acts similarly to its enantiomer, and thus pyranose rings are predominant.
structure of L-xylose
Figure 1. Structure of L-xylose A) as a Fischer projection, B) as a ball and stick model in acyclic form and C) as a ball and stick model in pyranose ring form.

The Uses of L-xylose

L-Xylose is used in the synthesis of L-Xylose derivatives as selective sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.

What are the applications of Application

L-(?)-Xylose is one of 2 isoforms of xylose

Definition

ChEBI: Aldehydo-L-xylose is a xylose of ring-opened form having L-configuration.

What are the applications of Application

l-Xylose is a suitable starting material for the production of L-ribonucleosides. L- Xylose can be converted into an L-ribose derivative via oxidation and reduction steps. This product is then glycosylated to give L-ribonucleosides: L-uridine, L-cytidine, L- adenosine and L-guanosine (Moyroud and Strazewski, 1999; Chelain et al., 1995).
L-Xylose can also be used as a starting material for the production of polyhydroxypyrrolidines and related analogues. These compounds have many biological activities. They are shown to have anti-HIV effects, inhibit tumor growth, and also act as ?- and ?-glucosidase inhibitors, which is of relevance for the development of diabetes drugs (Behr and Guillerm, 2007).

Preparation

L-Xylose can be produced from L-xylulose by isomerization. This can be achieved either enzymatically or chemically under alkaline conditions. The equilibrium of the reaction between D-xylose and D-xylulose in an aqueous solution has been determined at pH 6.8-7.4 and at 25 °C to be 85:15 in favor of D-xylose (Tewari et al., 1985).

Properties of L-xylose

Melting point: 150-152 °C(lit.)
Boiling point: 191.65°C (rough estimate)
Density  1.525
refractive index  -20 ° (C=10, H2O)
storage temp.  Keep in dark place,Sealed in dry,Room Temperature
solubility  H2O: 0.1 g/mL, clear, colorless
form  Crystalline Powder
pka 12.46±0.20(Predicted)
color  White to off-white
optical activity [α]24/D 18.7°, c = 4 in H2O
Water Solubility  within almost transparency
Sensitive  Hygroscopic
BRN  1723080
CAS DataBase Reference 609-06-3(CAS DataBase Reference)
EPA Substance Registry System L-Xylose (609-06-3)

Safety information for L-xylose

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for L-xylose

InChIKey SRBFZHDQGSBBOR-VVZXFQNISA-N

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