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Record Information
StatusDetected and Quantified
Creation Date2006-05-22 15:12:19 UTC
Update Date2020-11-09 23:17:07 UTC
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.
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
InChI Identifier
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
  • Sugar alcohol
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors

Route of exposure:


Biological location:

Physical Properties
Experimental Properties
Melting Point93.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility642 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility664 g/LALOGPS
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
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gb9-0983000000-a3ba95772bec5304c32dSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gba-0940000000-64e78d1e92fe9d145937Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dl-9100000000-51c1d4635c9c103902c4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-9600000000-42440e0b7d380a297360Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-02t9-9000000000-d41bf19405e393c2be01Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-02t9-9000000000-3d14b034f5655c90b890Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-4f856d537cc8252ecc47Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-403bacad5117a30582dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9000000000-eb879b27e7b182cfe7c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udu-9400000000-3db6454ab3e2315aa744Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0btl-9200000000-b84c400427c7e44eb4ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-c37624fb31a8cb33b163Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Placenta
  • Prostate
Normal Concentrations
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
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
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
UrineDetected and Quantified8.4 (6.0-13.8) umol/mmol creatinineAdult (>18 years old)Both
UrineDetected and Quantified3.533 +/- 2.400 umol/mmol creatinineNot SpecifiedNot SpecifiedNormal
    • Geigy Scientific ...
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
UrineDetected and Quantified3.5 +/- 2.37 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
UrineDetected and Quantified4.9 - 7.0 umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
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
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
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma
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
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Bladder cancer
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
BiGG IDNot Available
Wikipedia LinkXylitol
METLIN IDNot Available
PubChem Compound6912
PDB IDNot Available
ChEBI ID17151
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000406
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. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. Roe FJ: Perspectives in carbohydrate toxicology with special reference to carcinogenicity. Swed Dent J. 1984;8(3):99-111. [PubMed:6592775 ]
  12. Wang YM, van Eys J: Nutritional significance of fructose and sugar alcohols. Annu Rev Nutr. 1981;1:437-75. [PubMed:6821187 ]
  13. 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 ]
  14. Ylikahri RH, Leino T: Metabolic interactions of xylitol and ethanol in healthy males. Metabolism. 1979 Jan;28(1):25-9. [PubMed:759823 ]
  15. 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 ]
  16. 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 ]
  17. 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 ]
  18. 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 ]
  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 ]


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:
Uniprot ID:
Molecular weight:
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:
Uniprot ID:
Molecular weight:
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:
Uniprot ID:
Molecular weight:
Not Available
D-Xylitol + NADP → D-Xylose + NADPH + Hydrogen Iondetails