AFCDB: Xylitol (FDB001134)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:51 UTC

Update date

2020-09-17 15:42:14 UTC

Primary ID

FDB001134

Secondary Accession Numbers

Not Available

Chemical Information

FooDB 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
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	664 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-3.1	ChemAxon
logS	0.64	ALOGPS
pKa (Strongest Acidic)	12.76	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	101.15 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	32.44 m³·mol⁻¹	ChemAxon
Polarizability	14.42 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

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

Classification

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

Sugar alcohol
Monosaccharide
Secondary alcohol
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

pentitol (CHEBI:17151 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 39.47%; H 7.95%; O 52.58%	DFC
Melting Point	Mp 93-94.5° (stable)	DFC
Boiling Point	Not Available
Experimental Water Solubility	642 mg/mL	MERCK INDEX (1996)
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	0
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Xylitol, non-derivatized, GC-MS Spectrum	splash10-0gb9-0983000000-a3ba95772bec5304c32d	Spectrum
GC-MS	Xylitol, non-derivatized, GC-MS Spectrum	splash10-0gba-0940000000-64e78d1e92fe9d145937	Spectrum
Predicted GC-MS	Xylitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03dl-9100000000-51c1d4635c9c103902c4	Spectrum
Predicted GC-MS	Xylitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-9600000000-42440e0b7d380a297360	2020-02-10	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-02t9-9000000000-d41bf19405e393c2be01	2020-02-10	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-02t9-9000000000-3d14b034f5655c90b890	2020-02-10	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00dl-9000000000-2639d9ab8e6deb561f48	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1900000000-4f856d537cc8252ecc47	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9300000000-403bacad5117a30582df	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-9000000000-eb879b27e7b182cfe7c0	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udu-9400000000-3db6454ab3e2315aa744	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0btl-9200000000-b84c400427c7e44eb4dd	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-c37624fb31a8cb33b163	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-4900000000-d02566d106f64f56452d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ox-9000000000-94760e1883352d4864b5	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9000000000-a22bb5556fa857db4c5c	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zmr-9500000000-1887747b16d168b09609	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-83f8fb1c321a951b0e7e	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-ad178d7c96ba63131c18	2021-09-23	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

17151

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB02917

CRC / DFC (Dictionary of Food Compounds) ID

EAFUS ID

Dr. Duke ID

BIGG ID

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1297141

SuperScent ID

Not Available

Wikipedia ID

Xylitol

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti cariogenic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti hemolytic	50248	Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.	DUKE
anti plaque			DUKE
bilirubinolytic			DUKE
diuretic	35498	An agent that promotes the excretion of urine through its effects on kidney function.	DUKE
flatulent			DUKE
hepatoprotective	62868	Any compound that is able to prevent damage to the liver.	DUKE
hyperuricemic			DUKE
laxative	50503	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
sweetener	50505	Substance that sweeten food, beverages, medications, etc.	DUKE
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	CHEBI

Enzymes

Name	Gene Name	UniProt ID
L-xylulose reductase	DCXR	Q7Z4W1

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
odorless	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Xylitol (FDB001134)

Structure for FDB001134 (Xylitol)