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Details

Stereochemistry ACHIRAL
Molecular Formula C5H12O5
Molecular Weight 152.1458
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Xylitol

SMILES

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

InChI

InChIKey=HEBKCHPVOIAQTA-SCDXWVJYSA-N
InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5+

HIDE SMILES / InChI
Molecular Formula C5H12O5
Molecular Weight 152.1458
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmedhealth/PMH0016412/

Xylitol is a naturally occurring alcohol found in most plant material, including many fruits and vegetables. Xylitol is widely used as a sugar substitute and in "sugar-free" chewing gums, mints, and other candies. As a medicine, xylitol is used to prevent middle ear infections (otitis media) in young children, and as a sugar substitute for people with diabetes. Xylitol is added to some chewing gums and other oral care products to prevent tooth decay and dry mouth.

CNS Activity

Originator

Universitat Wurzburg
2
Sources: Journal - Chemical Society, London, Volume 64, Part 1http://onlinelibrary.wiley.com/doi/10.1002/cber.189102401100/full
Curator's Comment: # Merck

Approval Year

1978
88
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Inhibitor
8504
ribitol dehydrogenase from Providencia alcalifaciens RIMD 1656011
2
Target ID: ribitol dehydrogenase from Providencia alcalifaciens RIMD 1656011
Substrate
661
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Approved
8583
Unknown

Approved Use

Xylitol inhibits the cariogenicity, adhesivity, and acidogenic potential of plaque.
Primary
Approved
8583
Unknown

Approved Use

Xylitol, administered in chewing gum, lozenges or syrup, can reduce the occurrence of AOM among healthy children with no acute upper respiratory infection from 30% to 22%.
Primary
Preclinical
Unknown

Approved Use

Unknown
Palliative
Approved
8583
Unknown

Approved Use

Xylitol is a low-calorie sweetening alternative and is absorbed more slowly than sugar. It contains 40% fewer calories and does not cause increased blood sugar levels, because it is metabolized independently of insulin
Doses

Doses

DosePopulationAdverse events​
430 g 3 times / day multiple, oral
Highest studied dose
Dose: 430 g, 3 times / day
Route: oral
Route: multiple
Dose: 430 g, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/795261/
https://pubmed.ncbi.nlm.nih.gov/21994147/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/795261/
https://pubmed.ncbi.nlm.nih.gov/21994147/
Other AEs: Diarrhea...
Other AEs:
Diarrhea (50%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/795261/
https://pubmed.ncbi.nlm.nih.gov/21994147/
500 g 1 times / day multiple, intravenous
Overdose
Dose: 500 g, 1 times / day
Route: intravenous
Route: multiple
Dose: 500 g, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/32357847/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/32357847/
Other AEs: Oxalosis...
Other AEs:
Oxalosis
Sources:
https://pubmed.ncbi.nlm.nih.gov/32357847/
AEs

AEs

AESignificanceDosePopulation
Diarrhea 50%
430 g 3 times / day multiple, oral
Highest studied dose
Dose: 430 g, 3 times / day
Route: oral
Route: multiple
Dose: 430 g, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/795261/
https://pubmed.ncbi.nlm.nih.gov/21994147/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/795261/
https://pubmed.ncbi.nlm.nih.gov/21994147/
Oxalosis
500 g 1 times / day multiple, intravenous
Overdose
Dose: 500 g, 1 times / day
Route: intravenous
Route: multiple
Dose: 500 g, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/32357847/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/32357847/
PubMed

PubMed

TitleDatePubMed
Population analysis of a binary bacterial culture by multi-parametric flow cytometry.
2002-08-07
Metabolic behavior of immobilized Candida guilliermondii cells during batch xylitol production from sugarcane bagasse acid hydrolyzate.
2002-07-20
The structure of apo and holo forms of xylose reductase, a dimeric aldo-keto reductase from Candida tenuis.
2002-07-16
Optimization of fed-batch fermentation for xylitol production by Candida tropicalis.
2002-07
Inactivation of the Streptococcus mutans fxpC gene confers resistance to xylitol, a caries-preventive natural carbohydrate sweetener.
2002-06
Sugar alcohols enhance calcium transport from rat small and large intestine epithelium in vitro.
2002-06
The missing link in the fungal L-arabinose catabolic pathway, identification of the L-xylulose reductase gene.
2002-05-21
Molecular characterization of mammalian dicarbonyl/L-xylulose reductase and its localization in kidney.
2002-05-17
Preventive practice of Mongolian dental students.
2002-05
Furfural, 5-hydroxymethyl furfural, and acetoin act as external electron acceptors during anaerobic fermentation of xylose in recombinant Saccharomyces cerevisiae.
2002-04-20
Effect of a triclosan-containing toothpaste supplemented with 10% xylitol on mutans streptococci in saliva and dental plaque. A 6-month clinical study.
2002-04-19
Improvement in xylitol production from sugarcane bagasse hydrolysate achieved by the use of a repeated-batch immobilized cell system.
2002-04-05
Effect of starting xylose concentration on the microaerobic metabolism of Debaryomyces hansenii: the use of carbon material balances.
2002-04
How xylitol-containing products affect cariogenic bacteria.
2002-04
Cariogenic traits in xylitol-resistant and xylitol-sensitive mutans streptococci.
2002-04
Metal trifluoromethanesulfonate-catalyzed regioselective borane-reductive ring opening of benzylidene acetals: a concise synthesis of 1,4-dideoxy-1,4-imino-L-xylitol.
2002-03-07
From strong to fragile glass formers: secondary relaxation in polyalcohols.
2002-03-04
Controlled transient changes reveal differences in metabolite production in two Candida yeasts.
2002-03
HPLC and LC-MS studies of the transesterification reaction of methylparaben with twelve 3- to 6-carbon sugar alcohols and propylene glycol and the isomerization of the reaction products by acyl migration.
2002-03
Comparison of ribitol and glycerol teichoic acid genes in Bacillus subtilis W23 and 168: identical function, similar divergent organization, but different regulation.
2002-03
Transplacental carbohydrate and sugar alcohol concentrations and their uptakes in ovine pregnancy.
2002-03
Structural analysis of an Escherichia coli endonuclease VIII covalent reaction intermediate.
2002-02-15
New structures of the O-specific polysaccharides of bacteria of the genus Proteus. 1. Phosphate-containing polysaccharides.
2002-02
Xylitol administered only during respiratory infections failed to prevent acute otitis media.
2002-02
Xylitol concentrations in the saliva of children after chewing xylitol gum or consuming a xylitol mixture.
2002-01
Cold adaptation of xylose isomerase from Thermus thermophilus through random PCR mutagenesis. Gene cloning and protein characterization.
2002-01
Improved bone biomechanical properties in xylitol-fed aged rats.
2002-01
Influence of pH on the xylose reductase activity of Candida guilliermondii during fed-batch xylitol bioproduction.
2002
Xylose reductase activity of Candida guilliermondii during xylitol production by fed-batch fermentation: selection of process variables.
2002
Utilization of xylitol dehydrogenase in a combined microbial/enzymatic process for production of xylitol from D-glucose.
2002
Use of immobilized Candida yeast cells for xylitol production from sugarcane bagasse hydrolysate: cell immobilization conditions.
2002
Influence of oxygen availability on cell growth and xylitol production by Candida guilliermondii.
2002
Xylose reductase and xylitol dehydrogenase activities of Candida guilliermondii as a function of different treatments of sugarcane bagasse hemicellulosic hydrolysate employing experimental design.
2002
Characterization of heterologous and native enzyme activity profiles in metabolically engineered Zymomonas mobilis strains during batch fermentation of glucose and xylose mixtures.
2002
Oxygen uptake rate in production of xylitol by Candida guilliermondii with different aeration rates and initial xylose concentrations.
2002
Characterization of two operons that encode components of fructose-specific enzyme II of the sugar:phosphotransferase system of Streptococcus mutans.
2001-12-18
Substrate specificity and kinetic mechanism of Escherichia coli ribulokinase.
2001-12-15
Design, synthesis, and evaluation of 9-D-ribityl-1,3,7-trihydro-2,6,8-purinetrione, a potent inhibitor of riboflavin synthase and lumazine synthase.
2001-12-14
Phenotypic characterization of Microsporum canis isolated from cats and dogs.
2001-12
Evaluation of nonglucose carbohydrates in parenteral nutrition for diabetic patients.
2001-12
Metabolic study of the adaptation of the yeast Candida guilliermondii to sugarcane bagasse hydrolysate.
2001-12
[Renal oxalosis with renal failure after infusion of xylitol].
2001-11-30
Increased bone volume and bone mineral content in xylitol-fed aged rats.
2001-11-27
An evaluation of a commercial chewing gum in combination with normal toothbrushing for reducing dental plaque and gingivitis.
2001-07
Phenotypic characterization of Trichophyton rubrum isolates from two geographic locations in Brazil.
2001
Extraction by reversed micelles of the intracellular enzyme xylose reductase.
2001
Activity of xylose reductase from Candida mogii grown in media containing different concentrations of rice straw hydrolysate.
2001
Preliminary kinetic characterization of xylose reductase and xylitol dehydrogenase extracted from Candida guilliermondii FTI 20037 cultivated in sugarcane bagasse hydrolysate for xylitol production.
2001
Model compound studies: influence of aeration and hemicellulosic sugars on xylitol production by Candida tropicalis.
2001
Application of Saccharomyces cerevisiae and Pichia stipitis karyoductants to the production of ethanol from xylose.
2001
Patents

Patents

04144027
3
05158789
5
05162517
2
06124443
5
06303353
2
06419941
2
06538133
2
06911565
4
07507579
2
07629156
2
07745177
2
07960152
3
08440451
2

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Ribitol kinase was assayed by measuring the residual ribitol after incubation by the colorimetric method, after the removal of proteins and phosphorylated compounds from the incubation mixture. The standard assay mixture contained ATP, 20 umol; ribitol, 25 umol; ennzyme solution containing 200-500 ug of protein.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:21:31 GMT 2025
Edited
by admin
on Mon Mar 31 18:21:31 GMT 2025
Record UNII
VCQ006KQ1E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EUTRIT
Preferred Name English
Xylitol
EP   FCC   II   INCI   MART.   MI   USP-RS   VANDF   WHO-DD  
INCI  
Official Name English
XYLITOL [MI]
Common Name English
XYLITOL [EP MONOGRAPH]
Common Name English
XYLITOL [MART.]
Common Name English
INS NO.967
Code English
XYLITOL [USP-RS]
Common Name English
Xylitol [WHO-DD]
Common Name English
KLINIT
Brand Name English
XYLITOL, D-
Common Name English
TORCH
Brand Name English
XYLITE
Common Name English
E-967
Code English
XYLO-PENTITOL
Common Name English
D-XYLITOL
Systematic Name English
KANNIT
Brand Name English
XYLITOL [EP IMPURITY]
Common Name English
XYLITOL [JAN]
Common Name English
C-XYLIDEX CR 16055
Common Name English
XYLITAB 300
Common Name English
XYLITOL [II]
Common Name English
NSC-25283
Code English
XYLITE (SUGAR)
Common Name English
XYLITOL CM 90
Common Name English
XYLITON
Brand Name English
KYLIT
Brand Name English
XYLITOL [FCC]
Common Name English
FLUORETTE
Common Name English
XYLITOL [VANDF]
Common Name English
XYLO-PENTANE-1,2,3,4,5-PENTOL
Common Name English
INS-967
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 780220
Created by admin on Mon Mar 31 18:21:31 GMT 2025 , Edited by admin on Mon Mar 31 18:21:31 GMT 2025
JECFA EVALUATION INS-967
Created by admin on Mon Mar 31 18:21:31 GMT 2025 , Edited by admin on Mon Mar 31 18:21:31 GMT 2025
EPA PESTICIDE CODE 60187
Created by admin on Mon Mar 31 18:21:31 GMT 2025 , Edited by admin on Mon Mar 31 18:21:31 GMT 2025
DSLD 2243 (Number of products:166)
Created by admin on Mon Mar 31 18:21:31 GMT 2025 , Edited by admin on Mon Mar 31 18:21:31 GMT 2025
CFR 21 CFR 172.395
Created by admin on Mon Mar 31 18:21:31 GMT 2025 , Edited by admin on Mon Mar 31 18:21:31 GMT 2025
NCI_THESAURUS C283
Created by admin on Mon Mar 31 18:21:31 GMT 2025 , Edited by admin on Mon Mar 31 18:21:31 GMT 2025
CODEX ALIMENTARIUS (GSFA) INS-967
Created by admin on Mon Mar 31 18:21:31 GMT 2025 , Edited by admin on Mon Mar 31 18:21:31 GMT 2025
Code System Code Type Description
SMS_ID
100000076749
Created by admin on Mon Mar 31 18:21:31 GMT 2025 , Edited by admin on Mon Mar 31 18:21:31 GMT 2025
PRIMARY
RXCUI
11377
Created by admin on Mon Mar 31 18:21:31 GMT 2025 , Edited by admin on Mon Mar 31 18:21:31 GMT 2025
PRIMARY RxNorm
DRUG CENTRAL
4604
Created by admin on Mon Mar 31 18:21:31 GMT 2025 , Edited by admin on Mon Mar 31 18:21:31 GMT 2025
PRIMARY
EVMPD
SUB15737MIG
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PRIMARY
DRUG BANK
DB11195
Created by admin on Mon Mar 31 18:21:31 GMT 2025 , Edited by admin on Mon Mar 31 18:21:31 GMT 2025
PRIMARY
NCI_THESAURUS
C76517
Created by admin on Mon Mar 31 18:21:31 GMT 2025 , Edited by admin on Mon Mar 31 18:21:31 GMT 2025
PRIMARY
MERCK INDEX
m11553
Created by admin on Mon Mar 31 18:21:31 GMT 2025 , Edited by admin on Mon Mar 31 18:21:31 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID7042514
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PRIMARY
CAS
87-99-0
Created by admin on Mon Mar 31 18:21:31 GMT 2025 , Edited by admin on Mon Mar 31 18:21:31 GMT 2025
PRIMARY
WIKIPEDIA
XYLITOL
Created by admin on Mon Mar 31 18:21:31 GMT 2025 , Edited by admin on Mon Mar 31 18:21:31 GMT 2025
PRIMARY
ChEMBL
CHEMBL96783
Created by admin on Mon Mar 31 18:21:31 GMT 2025 , Edited by admin on Mon Mar 31 18:21:31 GMT 2025
PRIMARY
FDA UNII
VCQ006KQ1E
Created by admin on Mon Mar 31 18:21:31 GMT 2025 , Edited by admin on Mon Mar 31 18:21:31 GMT 2025
PRIMARY
NSC
25283
Created by admin on Mon Mar 31 18:21:31 GMT 2025 , Edited by admin on Mon Mar 31 18:21:31 GMT 2025
PRIMARY
ECHA (EC/EINECS)
201-788-0
Created by admin on Mon Mar 31 18:21:31 GMT 2025 , Edited by admin on Mon Mar 31 18:21:31 GMT 2025
PRIMARY
DAILYMED
VCQ006KQ1E
Created by admin on Mon Mar 31 18:21:31 GMT 2025 , Edited by admin on Mon Mar 31 18:21:31 GMT 2025
PRIMARY
HSDB
7967
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PRIMARY
MESH
D014993
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PRIMARY
RS_ITEM_NUM
1720600
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PRIMARY
CHEBI
17151
Created by admin on Mon Mar 31 18:21:31 GMT 2025 , Edited by admin on Mon Mar 31 18:21:31 GMT 2025
PRIMARY
Related Record Type Details
Structure of Xylitol
ACTIVE MOIETY
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