Showing Compound Card for Xylitol (CDB006146)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 3 proteinsXML
Record Information
Version1.0
Created at2020-03-18 23:21:41 UTC
Updated at2020-12-07 19:06:55 UTC
CannabisDB IDCDB006146
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R,3R,4S)-Pentane-1,2,3,4,5-pentaolChEBI
XylitChEBI
XyliteChEBI
Xylo-pentitolHMDB
XylitolHMDB
D-XYLITOLChEBI
Chemical FormulaC5H12O5
Average Molecular Weight152.15
Monoisotopic Molecular Weight152.0685
IUPAC Name(2R,3r,4S)-pentane-1,2,3,4,5-pentol
Traditional Namexylitol
CAS Registry Number87-99-0
SMILES
OC[C@H](O)[C@@H](O)[C@H](O)CO
InChI Identifier
InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5+
InChI KeyHEBKCHPVOIAQTA-SCDXWVJYSA-N
Chemical Taxonomy
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point93.5 °CNot Available
Boiling Point345.39 °CWikipedia
Water Solubility642 mg/mLNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSXylitol, non-derivatized, GC-MS Spectrumsplash10-0gb9-0983000000-a3ba95772bec5304c32dSpectrum
GC-MSXylitol, non-derivatized, GC-MS Spectrumsplash10-0gba-0940000000-64e78d1e92fe9d145937Spectrum
Predicted GC-MSXylitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dl-9100000000-51c1d4635c9c103902c4Spectrum
Predicted GC-MSXylitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-9600000000-42440e0b7d380a2973602020-02-10View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-02t9-9000000000-d41bf19405e393c2be012020-02-10View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-02t9-9000000000-3d14b034f5655c90b8902020-02-10View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00dl-9000000000-2639d9ab8e6deb561f482021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-4f856d537cc8252ecc472016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-403bacad5117a30582df2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9000000000-eb879b27e7b182cfe7c02016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udu-9400000000-3db6454ab3e2315aa7442016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0btl-9200000000-b84c400427c7e44eb4dd2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-c37624fb31a8cb33b1632016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-4900000000-d02566d106f64f56452d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-9000000000-94760e1883352d4864b52021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9000000000-a22bb5556fa857db4c5c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zmr-9500000000-1887747b16d168b096092021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-83f8fb1c321a951b0e7e2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-ad178d7c96ba63131c182021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Ribose-5-phosphate isomeraseRPIA2p11.2P49247 details
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0002917
DrugBank IDDB01904
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001134
KNApSAcK IDNot Available
Chemspider ID6646
KEGG Compound IDC00379
BioCyc IDXYLITOL
BiGG IDNot Available
Wikipedia LinkXylitol
METLIN IDNot Available
PubChem Compound6912
PDB IDNot Available
ChEBI ID17151
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Haresaku S, Hanioka T, Tsutsui A, Yamamoto M, Chou T, Gunjishima Y: Long-term effect of xylitol gum use on mutans streptococci in adults. Caries Res. 2007;41(3):198-203. doi: 10.1159/000099318. [PubMed:17426399 ]
  3. Grillaud M, Bandon D, Nancy J, Delbos Y, Vaysse F: [The polyols in pediatric dentistry: advantages of xylitol]. Arch Pediatr. 2005 Jul;12(7):1180-6. doi: 10.1016/j.arcped.2005.01.032. [PubMed:15964535 ]

Enzymes

Enzyme Details
1. Ribose-5-phosphate isomerase
General function:
Involved in ribose-5-phosphate isomerase activity
Specific function:
Not Available
Gene Name:
RPIA
Uniprot ID:
P49247
Molecular weight:
33268.72