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
SMILES
OC[C@H](O)[C@H](O)[C@H](O)CO
InChI
InChIKey=HEBKCHPVOIAQTA-ZXFHETKHSA-N
InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5-
| 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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/8992241 | https://www.ncbi.nlm.nih.gov/pubmed/26693956http://www.webmd.com/vitamins-supplements/ingredientmono-996-xylitol.aspx?activeingredientid=996Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmedhealth/PMH0016412/
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8992241 | https://www.ncbi.nlm.nih.gov/pubmed/26693956http://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
Sources: Journal - Chemical Society, London, Volume 64, Part 1http://onlinelibrary.wiley.com/doi/10.1002/cber.189102401100/full
Curator's Comment: # Merck
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: GO:0007155 |
|||
Target ID: GO:0006000 |
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Target ID: ribitol dehydrogenase from Providencia alcalifaciens RIMD 1656011 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | Unknown Approved UseXylitol inhibits the cariogenicity, adhesivity, and acidogenic potential of plaque. |
|||
| Primary | Unknown Approved UseXylitol, 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 | Unknown Approved UseUnknown |
|||
| Palliative | Unknown Approved UseXylitol 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
| Dose | Population | Adverse 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: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Other AEs: Diarrhea... Other AEs: Diarrhea (50%) Sources: |
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: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
Other AEs: Oxalosis... |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| 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: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
Sample Use Guides
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
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Mon Mar 31 23:32:49 GMT 2025
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| Record UNII |
353ZQ9TVDA
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| Record Status |
Validated (UNII)
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FDA ORPHAN DRUG |
666518
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47884-2
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m1427
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KL-112
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25899
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