Xylitol

Xylitol[1]
Xylitol crystals
Names
Pronunciation /ˈzaɪlɪtɒl/
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
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.626
E number E967 (glazing agents, ...)
KEGG
PubChem CID
UNII
InChI
  • 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
SMILES
  • OC[C@@H](O)[C@H](O)[C@@H](O)CO
Properties
Chemical formula
 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[2]
Solubility in water
 168 g/100 g[3]
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
5H
12O
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.[4] Replacing sugar with xylitol in food products may promote better dental health, but evidence is lacking on whether xylitol itself prevents dental cavities.[5][6] In the United States, xylitol is used as a common sugar substitute, and is considered to be safe for humans.[7]

Xylitol can be toxic to dogs and ferrets.[8]

  1. ^ Safety data sheet for xylitol Archived 3 March 2016 at the Wayback Machine from Fisher Scientific. Retrieved 2014-11-02.
  2. ^ "Xylitol". Chemspider.com. Chemical Structure. Retrieved 13 May 2015.
  3. ^ Cite error: The named reference Ullmann was invoked but never defined (see the help page).
  4. ^ "Food legislation". polyols-eu.org. European Association of Polyol Producers. 22 March 2017. Retrieved 7 February 2019.
  5. ^ Riley, P.; Moore, D.; Ahmed, F.; Sharif, M.O.; Worthington, H.V. (26 March 2015). "Xylitol-containing products for preventing dental caries in children and adults". The Cochrane Database of Systematic Reviews. 2015 (3): CD010743. doi:10.1002/14651858.CD010743.pub2. PMC 9345289. PMID 25809586.
  6. ^ Riley, P.; Moore, D.; Ahmed, F.; Sharif, M. O.; Worthington, H. V. (2015). "Can xylitol – used in products like sweets, candy, chewing gum, and toothpaste – help prevent tooth decay in children and adults?". The Cochrane Database of Systematic Reviews. Lay summary. 2015 (3): CD010743. doi:10.1002/14651858.CD010743.pub2. PMC 9345289. PMID 25809586.
  7. ^ "Aspartame and Other Sweeteners in Food". US Food and Drug Administration. 14 July 2023. Archived from the original on 1 June 2023. Retrieved 12 September 2024.
  8. ^ "Paws off xylitol; It's dangerous for dogs". US Food and Drug Administration. 7 July 2021. Retrieved 9 September 2021.
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