1.0 2010-04-08 22:04:51 UTC 2020-09-17 15:42:14 UTC FDB001134 Xylitol Xylitol 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. E967 Eutrit Fluorette Kannit Klinit Kylit Meso-xylitol Newtol Trident gum Wood sugar alcohol XYL Xylisorb Xylisorb 300 Xylisorb 700 Xylit Xylitab 100 Xylitab 300 Xylitab DC Xylite Xylite (sugar) Xylitol C Xyliton Xylo-pentitol C5H12O5 152.1458 152.068473494 (2R,3r,4S)-pentane-1,2,3,4,5-pentol xylitol 87-99-0 OC[C@H](O)[C@@H](O)[C@H](O)CO InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5+ HEBKCHPVOIAQTA-SCDXWVJYSA-N 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. Sugar alcohols Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic acyclic compounds Hydrocarbon derivatives Monosaccharides Polyols Primary alcohols Secondary alcohols Alcohol Aliphatic acyclic compound Hydrocarbon derivative Monosaccharide Polyol Primary alcohol Secondary alcohol Sugar alcohol pentitol Solid logp -2.53 ALOGPS logs 0.64 ALOGPS solubility 6.64e+02 g/l ALOGPS melting_point Mp 93-94.5° (stable) logp -3.1 ChemAxon pka_strongest_acidic 12.76 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R,3r,4S)-pentane-1,2,3,4,5-pentol ChemAxon average_mass 152.1458 ChemAxon mono_mass 152.068473494 ChemAxon smiles OC[C@H](O)[C@@H](O)[C@H](O)CO ChemAxon formula C5H12O5 ChemAxon inchi InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5+ ChemAxon inchikey HEBKCHPVOIAQTA-SCDXWVJYSA-N ChemAxon polar_surface_area 101.15 ChemAxon refractivity 32.44 ChemAxon polarizability 14.42 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 3446 Specdb::CMs 30155 Specdb::CMs 30715 Specdb::CMs 156959 Specdb::NmrOneD 5250 Specdb::NmrOneD 129038 Specdb::NmrOneD 129039 Specdb::NmrOneD 129040 Specdb::NmrOneD 129041 Specdb::NmrOneD 129042 Specdb::NmrOneD 129043 Specdb::NmrOneD 129044 Specdb::NmrOneD 129045 Specdb::NmrOneD 129046 Specdb::NmrOneD 129047 Specdb::NmrOneD 129048 Specdb::NmrOneD 129049 Specdb::NmrOneD 129050 Specdb::NmrOneD 129051 Specdb::NmrOneD 129052 Specdb::NmrOneD 129053 Specdb::NmrOneD 129054 Specdb::NmrOneD 129055 Specdb::NmrOneD 129056 Specdb::NmrOneD 129057 Specdb::NmrTwoD 2067 Specdb::MsMs 53661 Specdb::MsMs 53662 Specdb::MsMs 53663 Specdb::MsMs 176460 Specdb::MsMs 176461 Specdb::MsMs 176462 Specdb::MsMs 1448556 Specdb::MsMs 1448557 Specdb::MsMs 1448558 Specdb::MsMs 2243838 Specdb::MsMs 2320133 Specdb::MsMs 2320134 Specdb::MsMs 2320135 Specdb::MsMs 2618513 Specdb::MsMs 2618514 Specdb::MsMs 2618515 HMDB02917 17151 #<Reference:0x000055ce323a1cd0> #<Reference:0x000055ce323a1b18> #<Reference:0x000055ce323a1938> #<Reference:0x000055ce323a1780> #<Reference:0x000055ce323a15c8> #<Reference:0x000055ce323a11b8> #<Reference:0x000055ce323a1000> #<Reference:0x000055ce323a0e48> #<Reference:0x000055ce323a0c90> #<Reference:0x000055ce323a0a88> #<Reference:0x000055ce323a08d0> #<Reference:0x000055ce323a0560> #<Reference:0x000055ce323a0330> #<Reference:0x000055ce323a0178> #<Reference:0x000055ce323a0b28> #<Reference:0x000055ce3239fe58> #<Reference:0x000055ce3239fca0> #<Reference:0x000055ce3239fae8> #<Reference:0x000055ce3239f750> #<Reference:0x000055ce3239f570> Brassicas Unknown generic 3705 Carrot Type 1 specific Daucus carota ssp. sativus 79200 Fruits Unknown generic Garden onion Type 1 specific Allium cepa 4679 Green vegetables Unknown generic Papaya Type 1 specific Carica papaya 3649 Red raspberry Type 1 specific Rubus idaeus 32247 Spinach Type 1 specific Spinacia oleracea 3562 Wild carrot Type 1 specific Daucus carota 4039 odorless L-xylulose reductase Q7Z4W1 DCXR Allergenic 43 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy. Anti cariogenic 165 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-hemolytic 319 Drug that acts on blood and blood-forming organs and those that affect the hemostatic system. Anti-plaque 531 Bilirubinolytic 731 Diuretic 883 An agent that promotes the excretion of urine through its effects on kidney function. Flatulent 935 Hepatoprotective 981 Any compound that is able to prevent damage to the liver. Hyperuricemic 1011 Laxative 1065 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. Sweetener 1341 Substance that sweeten food, beverages, medications, etc.