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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:19 UTC
Update Date2022-03-07 02:49:17 UTC
HMDB IDHMDB0002917
Secondary Accession Numbers
  • HMDB02917
Metabolite Identification
Common NameD-Xylitol
DescriptionXylitol is a five-carbon sugar alcohol that is obtained through the diet. It is not endogenously produced by humans. 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 can be produced industrially starting from primary matters rich in xylan which is hydrolyzed to obtain xylose. It is extracted from hemicelluloses present in the corn raids, the almond hulls or the barks of birch (or of the by-products of wood: shavings hard, paper pulp). Of all polyols, it 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 his use in confectionery, it is 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 (ear aches 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. Xylitol is found to be associated with ribose-5-phosphate isomerase deficiency, which is an inborn error of metabolism.
Structure
Data?1582752259
Synonyms
ValueSource
(2R,3R,4S)-Pentane-1,2,3,4,5-pentaolChEBI
XylitChEBI
XyliteChEBI
Xylo-pentitolHMDB
XylitolHMDB
D-XYLITOLChEBI
Chemical FormulaC5H12O5
Average Molecular Weight152.1458
Monoisotopic Molecular Weight152.068473494
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
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point93.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility642 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+135.39930932474
DeepCCS[M-H]-133.00330932474
DeepCCS[M-2H]-166.97930932474
DeepCCS[M+Na]+141.59830932474
AllCCS[M+H]+135.832859911
AllCCS[M+H-H2O]+131.932859911
AllCCS[M+NH4]+139.532859911
AllCCS[M+Na]+140.632859911
AllCCS[M-H]-126.832859911
AllCCS[M+Na-2H]-129.032859911
AllCCS[M+HCOO]-131.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
D-XylitolOC[C@H](O)[C@@H](O)[C@H](O)CO2895.7Standard polar33892256
D-XylitolOC[C@H](O)[C@@H](O)[C@H](O)CO1750.5Standard non polar33892256
D-XylitolOC[C@H](O)[C@@H](O)[C@H](O)CO1486.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
D-Xylitol,1TMS,isomer #1C[Si](C)(C)OC[C@H](O)[C@@H](O)[C@H](O)CO1545.5Semi standard non polar33892256
D-Xylitol,1TMS,isomer #2C[Si](C)(C)O[C@@H](CO)[C@@H](O)[C@H](O)CO1512.2Semi standard non polar33892256
D-Xylitol,1TMS,isomer #3C[Si](C)(C)O[C@H]([C@@H](O)CO)[C@H](O)CO1495.4Semi standard non polar33892256
D-Xylitol,1TMS,isomer #4C[Si](C)(C)O[C@H](CO)[C@H](O)[C@@H](O)CO1512.2Semi standard non polar33892256
D-Xylitol,1TMS,isomer #5C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O)CO1545.5Semi standard non polar33892256
D-Xylitol,2TMS,isomer #1C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O)[C@H](O)CO1586.6Semi standard non polar33892256
D-Xylitol,2TMS,isomer #10C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O)CO1586.6Semi standard non polar33892256
D-Xylitol,2TMS,isomer #2C[Si](C)(C)OC[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O)CO1583.3Semi standard non polar33892256
D-Xylitol,2TMS,isomer #3C[Si](C)(C)OC[C@H](O)[C@@H](O)[C@@H](CO)O[Si](C)(C)C1606.5Semi standard non polar33892256
D-Xylitol,2TMS,isomer #4C[Si](C)(C)OC[C@H](O)[C@@H](O)[C@H](O)CO[Si](C)(C)C1611.0Semi standard non polar33892256
D-Xylitol,2TMS,isomer #5C[Si](C)(C)O[C@@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O)CO1560.0Semi standard non polar33892256
D-Xylitol,2TMS,isomer #6C[Si](C)(C)O[C@@H](CO)[C@@H](O)[C@@H](CO)O[Si](C)(C)C1579.4Semi standard non polar33892256
D-Xylitol,2TMS,isomer #7C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@H](CO)O[Si](C)(C)C1606.5Semi standard non polar33892256
D-Xylitol,2TMS,isomer #8C[Si](C)(C)O[C@H](CO)[C@H](O[Si](C)(C)C)[C@@H](O)CO1560.0Semi standard non polar33892256
D-Xylitol,2TMS,isomer #9C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O)CO1583.3Semi standard non polar33892256
D-Xylitol,3TMS,isomer #1C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)CO1633.1Semi standard non polar33892256
D-Xylitol,3TMS,isomer #10C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O)CO1633.1Semi standard non polar33892256
D-Xylitol,3TMS,isomer #2C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](CO)O[Si](C)(C)C1647.8Semi standard non polar33892256
D-Xylitol,3TMS,isomer #3C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O)[C@H](O)CO[Si](C)(C)C1664.4Semi standard non polar33892256
D-Xylitol,3TMS,isomer #4C[Si](C)(C)OC[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C1643.4Semi standard non polar33892256
D-Xylitol,3TMS,isomer #5C[Si](C)(C)OC[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O)CO[Si](C)(C)C1657.8Semi standard non polar33892256
D-Xylitol,3TMS,isomer #6C[Si](C)(C)OC[C@H](O)[C@@H](O)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C1664.4Semi standard non polar33892256
D-Xylitol,3TMS,isomer #7C[Si](C)(C)O[C@@H](CO)[C@@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C1621.9Semi standard non polar33892256
D-Xylitol,3TMS,isomer #8C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@H](CO)O[Si](C)(C)C1643.4Semi standard non polar33892256
D-Xylitol,3TMS,isomer #9C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@H](CO)O[Si](C)(C)C1647.8Semi standard non polar33892256
D-Xylitol,4TMS,isomer #1C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C1661.8Semi standard non polar33892256
D-Xylitol,4TMS,isomer #2C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)CO[Si](C)(C)C1681.2Semi standard non polar33892256
D-Xylitol,4TMS,isomer #3C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C1695.2Semi standard non polar33892256
D-Xylitol,4TMS,isomer #4C[Si](C)(C)OC[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C1681.2Semi standard non polar33892256
D-Xylitol,4TMS,isomer #5C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](CO)O[Si](C)(C)C1661.8Semi standard non polar33892256
D-Xylitol,5TMS,isomer #1C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C1737.8Semi standard non polar33892256
D-Xylitol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H](O)[C@@H](O)[C@H](O)CO1798.2Semi standard non polar33892256
D-Xylitol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H](CO)[C@@H](O)[C@H](O)CO1752.5Semi standard non polar33892256
D-Xylitol,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@H]([C@@H](O)CO)[C@H](O)CO1741.0Semi standard non polar33892256
D-Xylitol,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@H](CO)[C@H](O)[C@@H](O)CO1752.5Semi standard non polar33892256
D-Xylitol,1TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O)CO1798.2Semi standard non polar33892256
D-Xylitol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)CO2023.2Semi standard non polar33892256
D-Xylitol,2TBDMS,isomer #10CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O)CO2023.2Semi standard non polar33892256
D-Xylitol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO2031.8Semi standard non polar33892256
D-Xylitol,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H](O)[C@@H](O)[C@@H](CO)O[Si](C)(C)C(C)(C)C2041.0Semi standard non polar33892256
D-Xylitol,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC[C@H](O)[C@@H](O)[C@H](O)CO[Si](C)(C)C(C)(C)C2046.5Semi standard non polar33892256
D-Xylitol,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)O[C@@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO2032.2Semi standard non polar33892256
D-Xylitol,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)O[C@@H](CO)[C@@H](O)[C@@H](CO)O[Si](C)(C)C(C)(C)C2024.2Semi standard non polar33892256
D-Xylitol,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O)[C@H](CO)O[Si](C)(C)C(C)(C)C2041.0Semi standard non polar33892256
D-Xylitol,2TBDMS,isomer #8CC(C)(C)[Si](C)(C)O[C@H](CO)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CO2032.2Semi standard non polar33892256
D-Xylitol,2TBDMS,isomer #9CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CO2031.8Semi standard non polar33892256
D-Xylitol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO2304.3Semi standard non polar33892256
D-Xylitol,3TBDMS,isomer #10CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CO2304.3Semi standard non polar33892256
D-Xylitol,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](CO)O[Si](C)(C)C(C)(C)C2313.8Semi standard non polar33892256
D-Xylitol,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)CO[Si](C)(C)C(C)(C)C2304.0Semi standard non polar33892256
D-Xylitol,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[Si](C)(C)C(C)(C)C2330.8Semi standard non polar33892256
D-Xylitol,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO[Si](C)(C)C(C)(C)C2339.9Semi standard non polar33892256
D-Xylitol,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC[C@H](O)[C@@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2304.0Semi standard non polar33892256
D-Xylitol,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)O[C@@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[Si](C)(C)C(C)(C)C2330.1Semi standard non polar33892256
D-Xylitol,3TBDMS,isomer #8CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)O[Si](C)(C)C(C)(C)C2330.8Semi standard non polar33892256
D-Xylitol,3TBDMS,isomer #9CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](CO)O[Si](C)(C)C(C)(C)C2313.8Semi standard non polar33892256
D-Xylitol,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[Si](C)(C)C(C)(C)C2542.6Semi standard non polar33892256
D-Xylitol,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO[Si](C)(C)C(C)(C)C2546.4Semi standard non polar33892256
D-Xylitol,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2537.1Semi standard non polar33892256
D-Xylitol,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2546.4Semi standard non polar33892256
D-Xylitol,4TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)O[Si](C)(C)C(C)(C)C2542.6Semi standard non polar33892256
D-Xylitol,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2763.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - D-Xylitol EI-B (Non-derivatized)splash10-0gb9-0983000000-a3ba95772bec5304c32d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Xylitol GC-EI-TOF (Non-derivatized)splash10-0gba-0940000000-64e78d1e92fe9d1459372017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Xylitol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dl-9100000000-51c1d4635c9c103902c42016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Xylitol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Xylitol Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-014i-9600000000-42440e0b7d380a2973602020-02-10HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Xylitol Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-02t9-9000000000-d41bf19405e393c2be012020-02-10HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Xylitol Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-02t9-9000000000-3d14b034f5655c90b8902020-02-10HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Xylitol 35V, Negative-QTOFsplash10-00dl-9000000000-2639d9ab8e6deb561f482021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Xylitol 10V, Positive-QTOFsplash10-0udi-1900000000-4f856d537cc8252ecc472016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Xylitol 20V, Positive-QTOFsplash10-03di-9300000000-403bacad5117a30582df2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Xylitol 40V, Positive-QTOFsplash10-03dl-9000000000-eb879b27e7b182cfe7c02016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Xylitol 10V, Negative-QTOFsplash10-0udu-9400000000-3db6454ab3e2315aa7442016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Xylitol 20V, Negative-QTOFsplash10-0btl-9200000000-b84c400427c7e44eb4dd2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Xylitol 40V, Negative-QTOFsplash10-0a4l-9000000000-c37624fb31a8cb33b1632016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Xylitol 10V, Positive-QTOFsplash10-014i-4900000000-d02566d106f64f56452d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Xylitol 20V, Positive-QTOFsplash10-01ox-9000000000-94760e1883352d4864b52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Xylitol 40V, Positive-QTOFsplash10-0007-9000000000-a22bb5556fa857db4c5c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Xylitol 10V, Negative-QTOFsplash10-0zmr-9500000000-1887747b16d168b096092021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Xylitol 20V, Negative-QTOFsplash10-0a4i-9000000000-83f8fb1c321a951b0e7e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Xylitol 40V, Negative-QTOFsplash10-0a4l-9000000000-ad178d7c96ba63131c182021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2020-02-10Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Placenta
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.677 (0.572-0.782) uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified2.5 (0.0-5.0) uMAdolescent (13-18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0 - 5.0 uMAdolescent (13-18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.3 (0.9-8.2) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified8.4 (6.0-13.8) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified3.533 +/- 2.400 umol/mmol creatinineNot SpecifiedNot SpecifiedNormal
    • Geigy Scientific ...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified3.5 +/- 2.37 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified4.9 - 7.0 umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified16.29 +/- 26.02 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.5 (0.0-5.0) uMAdolescent (13-18 years old)BothRibose-5-phosphate isomerase deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified33 - 96 uMAdolescent (13-18 years old)BothRibose-5-Phosphate Isomerase Deficiency details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Cryptosporidium infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma
details
UrineDetected and Quantified15 - 34 umol/mmol creatinineAdult (>18 years old)Not SpecifiedRibose-5-Phosphate Isomerase Deficiency details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Hepatocellular carcinoma
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Bladder cancer
details
Associated Disorders and Diseases
Disease References
Ribose-5-phosphate isomerase deficiency
  1. Huck JH, Verhoeven NM, Struys EA, Salomons GS, Jakobs C, van der Knaap MS: Ribose-5-phosphate isomerase deficiency: new inborn error in the pentose phosphate pathway associated with a slowly progressive leukoencephalopathy. Am J Hum Genet. 2004 Apr;74(4):745-51. Epub 2004 Feb 25. [PubMed:14988808 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Hepatocellular carcinoma
  1. Wu H, Xue R, Dong L, Liu T, Deng C, Zeng H, Shen X: Metabolomic profiling of human urine in hepatocellular carcinoma patients using gas chromatography/mass spectrometry. Anal Chim Acta. 2009 Aug 19;648(1):98-104. doi: 10.1016/j.aca.2009.06.033. Epub 2009 Jun 21. [PubMed:19616694 ]
Associated OMIM IDs
  • 608611 (Ribose-5-phosphate isomerase deficiency)
  • 114500 (Colorectal cancer)
  • 114550 (Hepatocellular carcinoma)
DrugBank IDDB01904
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDXYLT
MarkerDB IDMDB00000406
Good Scents IDNot Available
References
Synthesis ReferenceHasumi, Fumihiko; Teshima, Chitoku; Okura, Ichiro. Synthesis of xylitol by reduction of xylulose with the combination of hydrogenase and xylulose reductase. Chemistry Letters (1996), (8), 597-598.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Verhoeven NM, Huck JH, Roos B, Struys EA, Salomons GS, Douwes AC, van der Knaap MS, Jakobs C: Transaldolase deficiency: liver cirrhosis associated with a new inborn error in the pentose phosphate pathway. Am J Hum Genet. 2001 May;68(5):1086-92. Epub 2001 Mar 27. [PubMed:11283793 ]
  2. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  3. Shetty HU, Holloway HW, Rapoport SI: Capillary gas chromatography combined with ion trap detection for quantitative profiling of polyols in cerebrospinal fluid and plasma. Anal Biochem. 1995 Jan 1;224(1):279-85. [PubMed:7710082 ]
  4. Roe FJ: Perspectives in carbohydrate toxicology with special reference to carcinogenicity. Swed Dent J. 1984;8(3):99-111. [PubMed:6592775 ]
  5. Onkenhout W, Groener JE, Verhoeven NM, Yin C, Laan LA: L-Arabinosuria: a new defect in human pentose metabolism. Mol Genet Metab. 2002 Sep-Oct;77(1-2):80-5. [PubMed:12359133 ]
  6. Huck JH, Roos B, Jakobs C, van der Knaap MS, Verhoeven NM: Evaluation of pentitol metabolism in mammalian tissues provides new insight into disorders of human sugar metabolism. Mol Genet Metab. 2004 Jul;82(3):231-7. [PubMed:15234337 ]
  7. Funke G, Lucchini GM, Pfyffer GE, Marchiani M, von Graevenitz A: Characteristics of CDC group 1 and group 1-like coryneform bacteria isolated from clinical specimens. J Clin Microbiol. 1993 Nov;31(11):2907-12. [PubMed:8263175 ]
  8. Yeo SF, Zhang Y, Schafer D, Campbell S, Wong B: A rapid, automated enzymatic fluorometric assay for determination of D-arabinitol in serum. J Clin Microbiol. 2000 Apr;38(4):1439-43. [PubMed:10747122 ]
  9. Yamamoto T, Moriwaki Y, Takahashi S, Suda M, Higashino K: Xylitol-induced increase in the concentration of oxypurines and its mechanism. Int J Clin Pharmacol Ther. 1995 Jun;33(6):360-5. [PubMed:7582389 ]
  10. Sundaram G, Bartlett D: Preventative measures for bulimic patients with dental erosion. Eur J Prosthodont Restor Dent. 2001 Mar;9(1):25-9. [PubMed:11695131 ]
  11. Trahan L, Soderling E, Drean MF, Chevrier MC, Isokangas P: Effect of xylitol consumption on the plaque-saliva distribution of mutans streptococci and the occurrence and long-term survival of xylitol-resistant strains. J Dent Res. 1992 Nov;71(11):1785-91. [PubMed:1401440 ]
  12. Loo CY, Mitrakul K, Voss IB, Hughes CV, Ganeshkumar N: Involvement of an inducible fructose phosphotransferase operon in Streptococcus gordonii biofilm formation. J Bacteriol. 2003 Nov;185(21):6241-54. [PubMed:14563858 ]
  13. Klusmann A, Fleischer W, Waldhaus A, Siebler M, Mayatepek E: Influence of D-arabitol and ribitol on neuronal network activity. J Inherit Metab Dis. 2005;28(6):1181-3. [PubMed:16435225 ]
  14. Restaino L, Frampton EW, Lionberg WC, Becker RJ: A chromogenic plating medium for the isolation and identification of Enterobacter sakazakii from foods, food ingredients, and environmental sources. J Food Prot. 2006 Feb;69(2):315-22. [PubMed:16496571 ]
  15. Hauschildt S, Chalmers RA, Lawson AM, Schultis K, Watts RW: Metabolic investigations after xylitol infusion in human subjects. Am J Clin Nutr. 1976 Mar;29(3):258-73. [PubMed:176881 ]
  16. Wang YM, van Eys J: Nutritional significance of fructose and sugar alcohols. Annu Rev Nutr. 1981;1:437-75. [PubMed:6821187 ]
  17. Ylikahri RH, Leino T: Metabolic interactions of xylitol and ethanol in healthy males. Metabolism. 1979 Jan;28(1):25-9. [PubMed:759823 ]
  18. Sestoft L, Gammeltoft A: The effect of intravenous xylitol on the concentration of adenine nucleotides in human liver. Biochem Pharmacol. 1976 Dec 1;25(23):2619-21. [PubMed:985582 ]
  19. 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. [PubMed:17426399 ]
  20. 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. [PubMed:15964535 ]
  21. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
Gene Name:
AKR1B1
Uniprot ID:
P15121
Molecular weight:
35853.125
Reactions
D-Xylitol + NADP → D-Xylose + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NADPH-dependent reduction of several pentoses, tetroses, trioses, alpha-dicarbonyl compounds and L-xylulose. Participates in the uronate cycle of glucose metabolism. May play a role in the water absorption and cellular osmoregulation in the proximal renal tubules by producing xylitol, an osmolyte, thereby preventing osmolytic stress from occurring in the renal tubules.
Gene Name:
DCXR
Uniprot ID:
Q7Z4W1
Molecular weight:
25742.665
Reactions
D-Xylitol + NADP → L-Xylulose + NADPHdetails
D-Xylitol + NADP → L-Xylulose + NADPH + Hydrogen Iondetails
General function:
Not Available
Specific function:
Acts as all-trans-retinaldehyde reductase. Can efficiently reduce aliphatic and aromatic aldehydes, and is less active on hexoses (in vitro). May be responsible for detoxification of reactive aldehydes in the digested food before the nutrients are passed on to other organs.
Gene Name:
AKR1B10
Uniprot ID:
O60218
Molecular weight:
Not Available
Reactions
D-Xylitol + NADP → D-Xylose + NADPH + Hydrogen Iondetails