Record Information
Creation date2010-04-08 22:04:51 UTC
Update date2018-05-28 22:37:38 UTC
Primary IDFDB001134
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameXylitol
DescriptionOccurs in a variety of plants, berries and fruits including plums, raspberries, cauliflower and endive; sweetening agent used in sugar free sweets and chewing gum Possessing approximately 40% less food energy, xylitol is a low-calorie alternative to table sugar. Absorbed more slowly than sugar, it does not contribute to high blood sugar levels or the resulting hyperglycemia caused by insufficient insulin response.; Xylitol (from Greek ????? - xyl[on], "wood" + suffix -itol, used to denote sugar alcohols) is an organic compound with the formula (CHOH)3(CH2OH)2. This achiral species is one of four isomers of 1,2,3,4,5-pentapentanol. This sugar alcohol is used as a naturally occurring sugar substitute found in the fibres of many fruits and vegetables, including various berries, corn husks, oats, and mushrooms. It can be extracted from corn fibre, birch, raspberries, plums, and corn. Xylitol is roughly as sweet as sucrose with only two-thirds the food energy. As with most sugar alcohols, consumption can result in bloating, diarrhea, and flatulence, although generally rather less so than other sugar alcohols like sorbitol.; Xylitol is a "tooth friendly" non-fermentable sugar alcohol. A systematic review study on the efficacy of xylitol has indicated dental heath benefits in caries prevention, showing superior performance to other polyols (poly-alcohols). Early studies from Finland in the 1970s found that a group chewing sucrose gum had 2.92 decayed, missing, or filled (dmf) teeth compared to 1.04 in the group chewing xylitol gums. In another study, researchers had mothers chew xylitol gum 3 months after delivery until their children were 2 years old. The researchers found that children in the xylitol group had "a 70% reduction in cavities (dmf)." Recent research confirms a plaque-reducing effect and suggests that the compound, having some chemical properties similar to sucrose, attracts and then "starves" harmful micro-organisms, allowing the mouth to remineralise damaged teeth with less interruption. (However, this same effect also interferes with yeast micro-organisms and others, so xylitol is inappropriate for making yeast-based bread, for instance.); Xylitol is a five-carbon sugar alcohol. Xylitol is in a natural state in many fruits (strawberries, plums, raspberries) and vegetables (cauliflower.). The human body naturally processes 15gram xylitol per day during digestion. It can be produced industrially starting from primary matters rich in xylan which is hydrolized 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, while remaining not cariogene; as a result, chewing xylitol gum may prevent dental caries. Chewing xylitol gum for 4 to 14 days reduces the amount of 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); these three qualities make xylitol an ingredient of choice for the industry of chewing gums without sugar. In addition to his use in confectionery, one finds it in pharmaceutical industry, certain baths of mouth and toothpastes, in cosmetic (creams, soaps.). Xylitol is produced starting from xylose, the isomaltose, by enzymatic transposition of the saccharose (sugar). Xylitol is not metabolized by cariogenic bacteria and gum chewing stimulates the flow of saliva.
CAS Number87-99-0
Wood sugar alcoholHMDB
Xylisorb 300HMDB
Xylisorb 700HMDB
Xylitab 100HMDB
Xylitab 300HMDB
Xylitab DCHMDB
Xylite (sugar)HMDB
Xylitol CHMDB
Trident gumbiospider
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
Polarizability14.4 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H12O5
IUPAC name(2R,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+
Isomeric SMILESOC[C@H](O)[C@@H](O)[C@H](O)CO
Average Molecular Weight152.1458
Monoisotopic Molecular Weight152.068473494
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 DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
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
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-0gb9-0962000000-d64d55ac02d5d037d679View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gb9-0962000000-d64d55ac02d5d037d679View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gba-0941000000-0d418fcb2879fa30315eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gba-0941000000-1842afabd092c907a920View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dl-9100000000-738016d8bd07caed9cccView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-0a4i-6033900000-a5ac27dc62580d112ccdView 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, Positivesplash10-0udi-1900000000-4f856d537cc8252ecc47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-403bacad5117a30582dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9000000000-eb879b27e7b182cfe7c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udu-9400000000-3db6454ab3e2315aa744View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0btl-9200000000-b84c400427c7e44eb4ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-c37624fb31a8cb33b163View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID21391692
KEGG Compound IDC00379
Pubchem Compound ID6912
Pubchem Substance IDNot Available
ChEBI ID17151
Phenol-Explorer IDNot Available
DrugBank IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBTQ04-R:BTQ04-R
BIGG ID34810
KNApSAcK IDNot Available
HET 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
Biological Effects and Interactions
Health Effects / Bioactivities
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
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
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
NameGene NameUniProt ID
L-xylulose reductaseDCXRQ7Z4W1
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <> Accessed 15.10.23.
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).