Xylitol

First approved in 1978

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 Search

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

Description
Sources: http://www.webmd.com/vitamins-supplements/ingredientmono-996-xylitol.aspx?activeingredientid=996
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
cell adhesion 5 Target ID: GO:0007155 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9630410	Inhibitor 8297
fructose metabolic process 1 Target ID: GO:0006000 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1658712	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Dental caries 44 Sources: https://www.drugs.com/npp/xylitol.html	Preventing	Approved 8429	Unknown Approved Use Xylitol inhibits the cariogenicity, adhesivity, and acidogenic potential of plaque.
Acute otitis media 28 Sources: https://www.ncbi.nlm.nih.gov/pubmedhealth/PMH0016412/	Primary	Approved 8429	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%.
Osteoporosis 97 Sources: https://www.drugs.com/npp/xylitol.html	Primary	Preclinical	Unknown Approved Use Unknown
Diabetes mellitus 91 Sources: https://www.drugs.com/npp/xylitol.html	Palliative	Approved 8429	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

PubMed

Title	Date	PubMed
URI and antibiotics.	2001 Apr	11300995
Phenotypic characterization of Microsporum canis isolated from cats and dogs.	2001 Dec	11820261
Evaluation of nonglucose carbohydrates in parenteral nutrition for diabetic patients.	2001 Dec	11781679
Characterization of two operons that encode components of fructose-specific enzyme II of the sugar:phosphotransferase system of Streptococcus mutans.	2001 Dec 18	11750824
Xylitol production by recombinant Saccharomyces cerevisiae expressing the Pichia stipitis and Candida shehatae XYL1 genes.	2001 Jan	11234962
An evaluation of a commercial chewing gum in combination with normal toothbrushing for reducing dental plaque and gingivitis.	2001 Jul	11913304
Does chewing explain the caries-preventive results with xylitol?	2001 Jul	11597017
Gas phase RNA and DNA ions 2. Conformational dependence of the gas-phase H/D exchange of nucleotide-5'-monophosphates.	2001 Jul	11444599
Template-directed C-H insertion: synthesis of the dioxabicyclo[3.2.1]octane core of the zaragozic acids.	2001 Jul 26	11463291
An in vitro study of the pH-lowering potential of salivary lactobacilli associated with dental caries.	2001 Jun	11412333
Phylogenetic diversity of Klebsiella pneumoniae and Klebsiella oxytoca clinical isolates revealed by randomly amplified polymorphic DNA, gyrA and parC genes sequencing and automated ribotyping.	2001 May	11411715
The effect of chlorhexidine acetate/xylitol chewing gum on the plaque and gingival indices of elderly occupants in residential homes.	2001 Nov	11686821
Cloning and expression of a fungal L-arabinitol 4-dehydrogenase gene.	2001 Nov 2	11514550
Influence of temperature and pH on xylitol production from xylose by Debaryomyces hansenii.	2001 Oct 5	11536125
Quantification of bacterial polysaccharides by the purpald assay: measurement of periodate-generated formaldehyde from glycol in the repeating unit.	2001 Sep 1	11520034
Activity of xylose reductase from Candida mogii grown in media containing different concentrations of rice straw hydrolysate.	2001 Spring	11963901
Model compound studies: influence of aeration and hemicellulosic sugars on xylitol production by Candida tropicalis.	2001 Spring	11963871
Influence of pH on the xylose reductase activity of Candida guilliermondii during fed-batch xylitol bioproduction.	2002	12111747
Furfural, 5-hydroxymethyl furfural, and acetoin act as external electron acceptors during anaerobic fermentation of xylose in recombinant Saccharomyces cerevisiae.	2002 Apr 20	11870608
Population analysis of a binary bacterial culture by multi-parametric flow cytometry.	2002 Aug 7	12067522
The structure of apo and holo forms of xylose reductase, a dimeric aldo-keto reductase from Candida tenuis.	2002 Jul 16	12102621
Metabolic behavior of immobilized Candida guilliermondii cells during batch xylitol production from sugarcane bagasse acid hydrolyzate.	2002 Jul 20	12115432
Sugar alcohols enhance calcium transport from rat small and large intestine epithelium in vitro.	2002 Jun	12064809
Metal trifluoromethanesulfonate-catalyzed regioselective borane-reductive ring opening of benzylidene acetals: a concise synthesis of 1,4-dideoxy-1,4-imino-L-xylitol.	2002 Mar 7	11869143
Influence of oxygen availability on cell growth and xylitol production by Candida guilliermondii.	2002 Spring	12018271
Xylose reductase and xylitol dehydrogenase activities of Candida guilliermondii as a function of different treatments of sugarcane bagasse hemicellulosic hydrolysate employing experimental design.	2002 Spring	12018268
Characterization of heterologous and native enzyme activity profiles in metabolically engineered Zymomonas mobilis strains during batch fermentation of glucose and xylose mixtures.	2002 Spring	12018261

Patents

Sample Use Guides

In Vivo Use Guide

As a sugar substitute or a medicine to prevent middle ear infection, xylitol is administered orally. Xylitol could also administered as a chewing gum or intravenously as a nutrition for patients with glucose intolerance.

Route of Administration: Other

In Vitro Use Guide

A 5% concentration of xylitol inhibited the growth of Streptococcus pneumoniae . The xylitol-induced inhibition of S. pneumoniae is mediated through a fructose phosphotransferase system. Inhibition of growth was measured by optical density determination at wavelength of 650 nm.

Name

Type

Language

Xylitol

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

EUTRIT

Brand 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

XYLITOL [INCI]

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