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Key Documents

X3375

Sigma-Aldrich

Xylitol

≥99% (GC)

Synonym(s):

Xylite

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About This Item

Linear Formula:
HOCH2[CH(OH)]3CH2OH
CAS Number:
Molecular Weight:
152.15
Beilstein/REAXYS Number:
1720523
EC Number:
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.25

Quality Level

assay

≥99% (GC)

form

crystalline
crystals or chunks
powder

sweetness

1 × sucrose

color

colorless

mp

94-97 °C (lit.)

solubility

water: 642g/l at 25 °C (77 °F )

SMILES string

OC[C@@H](O)[C@H](O)[C@@H](O)CO

InChI

1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5+

InChI key

HEBKCHPVOIAQTA-SCDXWVJYSA-N

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General description

Xylitol is a naturally occurring five carbon sugar alcohol, equivalent to sucrose in sweetness. Xylitol finds applications in the preparation of confectionaries, chewing gum, toothpaste and mouthwashes. Xylitol is a low-energy sweetener with insulin independent metabolism, making it a promising alternative for sugar in diabetic patients. Xylitol is a natural anticaries agent used in the treatment of dental caries, as it is not utilized by cariogenic bacteria creates a starvation effect on them. Xylitol prevents otitis and upper respiratory tract infections. Commercially, microorganisms like bacteria, fungi and yeasts produce xylitol by fermentation.

Application

Xylitol has been used:
  • as a standard for high performance liquid chromatography
  • in analysing antibacterial activity on oral biofilms
  • for thermodynamic data and densities measurement

Biochem/physiol Actions

A sugar alcohol sweetener detectable by humans. Produced from hemicellulose hydrolysate fermentation.

Other Notes

To gain a comprehensive understanding of our extensive range of sugar alcohols for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synergistic effect of xylitol and ursolic acid combination on oral biofilms
Zou Y, et al.
Restorative dentistry & endodontics, 39(4), 288-295 (2014)
Molecular strategies for enhancing microbial production of xylitol
Pal S, et al.
Process Biochemistry (Oxford, United Kingdom), 51(7), 809-819 (2016)
Apparent molar volumes and apparent molar heat capacities of aqueous adonitol, dulcitol, glycerol, meso-erythritol, myo-inositol, D-sorbitol, and xylitol at temperatures from (278.15 to 368.15) K and at the pressure 0.35 MPa
Blodgett MB, et al.
The Journal of Chemical Thermodynamics, 39(4), 627-644 (2007)
Culture parameters affecting xylitol production by Debaryomyces hansenii immobilized in alginate beads
Perez-Bibbins B, et al.
Process Biochemistry (Oxford, United Kingdom), 48(3), 387-397 (2013)
Eun Joong Oh et al.
Metabolic engineering, 15, 226-234 (2012-10-30)
As Saccharomyces cerevisiae cannot utilize xylose as a carbon source, expression of XYL1 coding for xylose reductase (XR) from Scheffersomyces (Pichia) stipitis enabled production of xylitol from xylose with a high yield. However, insufficient supply of NAD(P)H for XR and

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