Xylitol

Xylitol
Xylitol crystals
Names
Pronunciation /ˈzlɪtɒl/
IUPAC name
meso-Xylitol
Systematic IUPAC name
(2R,3r,4S)-Pentane-1,2,3,4,5-pentol
Other names
  • (2R,3r,4S)-Pentane-1,2,3,4,5-pentaol (not recommended)
  • (2R,3r,4S)-1,2,3,4,5-Pentahydroxypentane
  • Xylite
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.626
E number E967 (glazing agents, ...)
KEGG
UNII
  • InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5+ Y
    Key: HEBKCHPVOIAQTA-SCDXWVJYSA-N Y
  • OC[C@@H](O)[C@H](O)[C@@H](O)CO
Properties
C5H12O5
Molar mass 152.146 g·mol−1
Density 1.52 g/cm3
Melting point 92 to 96 °C (198 to 205 °F; 365 to 369 K)
Boiling point 345.39 °C (653.70 °F; 618.54 K) predicted value using Adapted Stein & Brown method
168 g/100 g
Hazards
NFPA 704 (fire diamond)
1
1
0
Related compounds
Related alkanes
Pentane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Xylitol is a chemical compound with the formula C
5
H
12
O
5
, or HO(CH2)(CHOH)3(CH2)OH; specifically, one particular stereoisomer with that structural formula. It is a colorless or white crystalline solid. It is classified as a polyalcohol and a sugar alcohol, specifically an alditol. Of the common sugar alcohols, only sorbitol is more soluble in water.

The name derives from Ancient Greek: ξύλον, xyl[on] 'wood', with the suffix -itol used to denote it being a sugar alcohol.

Xylitol is used as a food additive and sugar substitute. Its European Union code number is E967. Replacing sugar with xylitol in food products may promote better dental health, but evidence is lacking on whether xylitol itself prevents dental cavities. In the United States, xylitol is used as a common sugar substitute, and is considered to be safe for humans.

Xylitol can be toxic to dogs and ferrets.