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Record Information
Creation Date2006-05-22 15:12:19 UTC
Update Date2016-02-11 01:05:52 UTC
Secondary Accession NumbersNone
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.
Wood sugar alcoholHMDB
Xylisorb 300HMDB
Xylisorb 700HMDB
Xylitab 100HMDB
Xylitab 300HMDB
Xylitab DCHMDB
Xylite (sugar)HMDB
Xylitol CHMDB
Chemical FormulaC5H12O5
Average Molecular Weight152.1458
Monoisotopic Molecular Weight152.068473494
IUPAC Name(2R,4S)-pentane-1,2,3,4,5-pentol
Traditional Name(2R,4S)-pentane-1,2,3,4,5-pentol
CAS Registry Number87-99-0
InChI Identifier
Chemical Taxonomy
DescriptionThis compound 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 ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassSugar alcohols
Direct ParentSugar alcohols
Alternative Parents
  • Sugar alcohol
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
StatusDetected and Quantified
  • Plant
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
Experimental Properties
Melting Point93.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility642 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility664.0 mg/mLALOGPS
pKa (Strongest Acidic)12.76ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area101.15 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity32.44 m3·mol-1ChemAxon
Polarizability14.4 Å3ChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-0gb9-0962000000-d64d55ac02d5d037d679View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-9600000000-42440e0b7d380a297360View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-02t9-9000000000-d41bf19405e393c2be01View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-02t9-9000000000-3d14b034f5655c90b890View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Prostate
PathwaysNot Available
Normal Concentrations
BloodDetected and Quantified0.677 (0.572-0.782) uMAdult (>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 ApplicableInfant (0-1 year old)Both
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal 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 but not QuantifiedNot ApplicableAdult (>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 ApplicableAdult (>18 years old)Male
UrineDetected and Quantified16.29 +/- 26.02 umol/mmol creatinineInfant (0-1 year 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 ApplicableNot SpecifiedNot Specified
Cryptosporidium infection
UrineDetected and Quantified15 - 34 umol/mmol creatinineAdult (>18 years old)Not SpecifiedRibose-5-Phosphate Isomerase Deficiency details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Hepatocellular carcinoma
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. [14988808 ]
Associated OMIM IDs
  • 608611 (Ribose-5-phosphate isomerase deficiency)
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001134
KNApSAcK IDNot Available
Chemspider ID21391692
KEGG Compound IDC00379
BioCyc IDCPD-496
BiGG ID34810
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02917
Metagene LinkHMDB02917
METLIN IDNot Available
PubChem Compound6912
PDB IDNot Available
ChEBI ID1305691
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. [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. [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. [7710082 ]
  4. Roe FJ: Perspectives in carbohydrate toxicology with special reference to carcinogenicity. Swed Dent J. 1984;8(3):99-111. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [176881 ]
  16. Wang YM, van Eys J: Nutritional significance of fructose and sugar alcohols. Annu Rev Nutr. 1981;1:437-75. [6821187 ]
  17. Ylikahri RH, Leino T: Metabolic interactions of xylitol and ethanol in healthy males. Metabolism. 1979 Jan;28(1):25-9. [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. [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. [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. [15964535 ]


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-Threo-2-pentulose + NADPHdetails
D-Xylitol + NADP → L-Threo-2-pentulose + 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