Record Information
Version1.0
Creation date2010-04-08 22:04:51 UTC
Update date2020-09-17 15:42:14 UTC
Primary IDFDB001134
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameXylitol
DescriptionXylitol belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of sugars in which the carbonyl group (aldehyde or ketone of the reducing sugar) has been reduced to a primary or secondary hydroxyl group. Xylitol is an extremely weak basic (essentially neutral) compound (based on its pKa). It is a colorless or white crystalline solid that is soluble in water. Xylitol is used as a diabetic sweetener which is roughly as sweet as sucrose with 33% fewer calories. Xylitol is naturally found in many fruits (strawberries, plums, raspberries) and vegetables (e.g. cauliflower). Because of fruit and vegetable consumption the human body naturally processes 15 grams of xylitol per day. Xylitol is not endogenously produced by humans. Xylitol can be produced industrially starting from plant materials rich in xylan which is hydrolyzed to obtain xylose. It is extracted from hemicelluloses present in corn, almond hulls or tree bark (or the by-products of wood: shavings hard, paper pulp). Of all polyols, xylitol is the one that has the sweetest flavor (it borders that of saccharose). It gives a strong refreshing impression, making xylitol an ingredient of choice for the sugarless chewing gum industry. In addition to its widespread use in confectionery, xylitol is also used in the pharmaceutical industry for certain mouthwashes and toothpastes and in cosmetics (creams, soaps, etc.). Xylitol is produced starting from xylose, the isomaltose, by enzymatic transposition of the saccharose (sugar). Xylitol is not metabolized by cariogenic (cavity-causing) bacteria and gum chewing stimulates the flow of saliva; as a result, chewing xylitol gum may prevent dental caries. Chewing xylitol gum for 4 to 14 days reduces the amount of dental plaque. The reduction in the amount of plaque following xylitol gum chewing within 2 weeks may be a transient phenomenon. Chewing xylitol gum for 6 months reduced Mutans streptococci levels in saliva and plaque in adults (PMID: 17426399, 15964535). Studies have also shown xylitol chewing gum can help prevent acute otitis media (earaches and infections) as the act of chewing and swallowing assists with the disposal of earwax and clearing the middle ear, while the presence of xylitol prevents the growth of bacteria in the eustachian tubes. Xylitol is well established as a life-threatening toxin to dogs. The number of reported cases of xylitol toxicosis in dogs has significantly increased since the first reports in 2002. Dogs that have ingested foods containing xylitol (greater than 100 milligrams of xylitol consumed per kilogram of bodyweight) have presented with low blood sugar (hypoglycemia), which can be life-threatening. Altered levels of xylitol have been found to be associated with ribose-5-phosphate isomerase deficiency, which is an inborn error of metabolism.
CAS Number87-99-0
Structure
Thumb
Synonyms
SynonymSource
(2R,3R,4S)-Pentane-1,2,3,4,5-pentaolChEBI
XylitChEBI
XyliteChEBI
Xylo-pentitolHMDB
XylitolHMDB
D-XYLITOLChEBI
E967db_source
EutritHMDB
FluoretteHMDB
Kannitbiospider
Klinitdb_source
Kylitdb_source
Meso-xylitolbiospider
Newtolbiospider
Trident gumbiospider
Wood sugar alcoholbiospider
XYLbiospider
Xylisorbbiospider
Xylisorb 300biospider
Xylisorb 700biospider
Xylitab 100biospider
Xylitab 300biospider
Xylitab DCbiospider
Xylite (sugar)HMDB
Xylitol CHMDB
Xylitondb_source
Predicted Properties
PropertyValueSource
Water Solubility664 g/LALOGPS
logP-2.5ALOGPS
logP-3.1ChemAxon
logS0.64ALOGPS
pKa (Strongest Acidic)12.76ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area101.15 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity32.44 m³·mol⁻¹ChemAxon
Polarizability14.42 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H12O5
IUPAC name(2R,3r,4S)-pentane-1,2,3,4,5-pentol
InChI IdentifierInChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5+
InChI KeyHEBKCHPVOIAQTA-SCDXWVJYSA-N
Isomeric SMILESOC[C@H](O)[C@@H](O)[C@H](O)CO
Average Molecular Weight152.1458
Monoisotopic Molecular Weight152.068473494
Classification
Description belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar alcohols
Alternative Parents
Substituents
  • Sugar alcohol
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 39.47%; H 7.95%; O 52.58%DFC
Melting PointMp 93-94.5° (stable)DFC
Boiling PointNot Available
Experimental Water Solubility642 mg/mLMERCK INDEX (1996)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
Charge0
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gb9-0983000000-a3ba95772bec5304c32dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gba-0940000000-64e78d1e92fe9d145937JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dl-9100000000-51c1d4635c9c103902c4JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-9600000000-42440e0b7d380a297360JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-02t9-9000000000-d41bf19405e393c2be01JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-02t9-9000000000-3d14b034f5655c90b890JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-4f856d537cc8252ecc47JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-403bacad5117a30582dfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9000000000-eb879b27e7b182cfe7c0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udu-9400000000-3db6454ab3e2315aa744JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0btl-9200000000-b84c400427c7e44eb4ddJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-c37624fb31a8cb33b163JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID21391692
ChEMBL IDCHEMBL1865120
KEGG Compound IDC00379
Pubchem Compound ID6912
Pubchem Substance IDNot Available
ChEBI ID17151
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02917
CRC / DFC (Dictionary of Food Compounds) IDBTQ04-R:BTQ04-R
EAFUS ID3884
Dr. Duke IDXYLITOL
BIGG ID34810
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1297141
SuperScent IDNot Available
Wikipedia IDXylitol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti cariogenic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti hemolytic50248 Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.DUKE
anti plaqueDUKE
bilirubinolyticDUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
flatulentDUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
hyperuricemicDUKE
laxative50503 An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic.DUKE
sweetener50505 Substance that sweeten food, beverages, medications, etc.DUKE
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.CHEBI
Enzymes
NameGene NameUniProt ID
L-xylulose reductaseDCXRQ7Z4W1
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).