FComEx: Xylitol (PC000724)

Record Information

Version

1.0

Creation date

2015-10-09 22:32:14 UTC

Update date

2017-01-19 02:36:34 UTC

FoodComEx ID

PC000724

FoodDB Record

FDB001134

Chemical Information

Name

Xylitol

Description

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.

CAS Number

87-99-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
E967	db_source
Eutrit	HMDB
Fluorette	HMDB
Kannit	biospider
Klinit	db_source
Kylit	db_source
Meso-xylitol	biospider
Newtol	biospider
Trident gum	biospider
Wood sugar alcohol	biospider
XYL	biospider
Xylisorb	biospider
Xylisorb 300	biospider
Xylisorb 700	biospider
Xylit	biospider
Xylitab 100	biospider
Xylitab 300	biospider
Xylitab DC	biospider
Xylite	db_source
Xylite (sugar)	HMDB
Xylitol C	HMDB
Xyliton	db_source
Xylo-pentitol	biospider

Chemical Formula

C5H12O5

IUPAC name

(2R,3r,4S)-pentane-1,2,3,4,5-pentol

InChI Identifier

InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5+

InChI Key

HEBKCHPVOIAQTA-SCDXWVJYSA-N

Isomeric SMILES

OC[C@H](O)[C@@H](O)[C@H](O)CO

Average Molecular Weight

152.1458

Monoisotopic Molecular Weight

152.068473494

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Sugar alcohols

Alternative Parents

Substituents