Livestock Metabolome Database: Showing metabocard for D-Xylitol (LMDB00410)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:49:13 UTC

Update Date

2016-09-23 18:45:23 UTC

Lmdb

LMDB00410

Secondary Accession Numbers

None

Metabolite Identification

Common Name

D-Xylitol

Description

Xylitol is a five-carbon sugar alcohol that is obtained through the diet. It is not endogenously produced by animals. 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 animal 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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Eutrit	HMDB
Fluorette	HMDB
Klinit	HMDB
Kylit	HMDB
Meso-xylitol	HMDB
Wood sugar alcohol	HMDB
Xylisorb	HMDB
Xylisorb 300	HMDB
Xylisorb 700	HMDB
Xylit	HMDB
Xylitab 100	HMDB
Xylitab 300	HMDB
Xylitab DC	HMDB
Xylite	HMDB
Xylite (sugar)	HMDB
Xylitol C	HMDB
Xyliton	HMDB
Xylo-pentitol	HMDB
Xylitol	HMDB

Chemical Formula

C₅H₁₂O₅

Average Molecular Weight

152.1458

Monoisotopic Molecular Weight

152.068473494

IUPAC Name

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

Traditional Name

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

CAS Registry Number

87-99-0

SMILES

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

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-NGQZWQHPSA-N

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

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	14.48 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (5 TMS)	splash10-0gb9-0962000000-d64d55ac02d5d037d679	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0gb9-0962000000-d64d55ac02d5d037d679	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0gba-0941000000-0d418fcb2879fa30315e	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0gba-0941000000-1842afabd092c907a920	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dl-9100000000-738016d8bd07caed9ccc	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-0a4i-6033900000-a5ac27dc62580d112ccd	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-9600000000-42440e0b7d380a297360	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-02t9-9000000000-d41bf19405e393c2be01	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-02t9-9000000000-3d14b034f5655c90b890	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-f1fdaf270fa4019f06f0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-ef4e8d5500172a225da2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0kg9-9300000000-5f1e0026beb6d5912fdc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0a4i-9000000000-16f8d89acf9c1e54f756	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0abc-9000000000-697f2395fe4e49e15a91	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0ab9-9000000000-efbaa28b4a07b54d5506	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0pi9-9300000000-76b6c343711a853fd155	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-066r-9000000000-70d02dc79a15c64e5531	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-066u-9000000000-25d3b7bd0b03258cc782	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0zmr-9500000000-09f08078748af68f5df3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-56a59a12a9043a7a1ccd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1900000000-4f856d537cc8252ecc47	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9300000000-403bacad5117a30582df	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-9000000000-eb879b27e7b182cfe7c0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udu-9400000000-3db6454ab3e2315aa744	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0btl-9200000000-b84c400427c7e44eb4dd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-c37624fb31a8cb33b163	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-4900000000-d02566d106f64f56452d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ox-9000000000-94760e1883352d4864b5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9000000000-a22bb5556fa857db4c5c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zmr-9500000000-1887747b16d168b09609	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-83f8fb1c321a951b0e7e	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Feces
Plasma
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Feces	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	24070026	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	23255817	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	22761248	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0242149

FooDB ID

FDB030801

Phenol Explorer ID

Not Available

KNApSAcK ID

C00052270

BiGG ID

34810

BioCyc ID

CPD-496

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]

Showing metabocard for D-Xylitol (LMDB00410)

Structure for LMDB00410 (D-Xylitol)