Xylose

Identification

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Name
Xylose
Accession Number
DB09419
Type
Small Molecule
Groups
Approved
Description

Xylose is a monosaccharide of the aldopentose type consisted of five carbon atoms and an aldehyde functional group. Xylose is a sugar isolated from wood. D-Xylose is a sugar widely used as a diabetic sweetener in food and beverage. Xylose has also been used as a diagnostic agent to observe malabsorption. Reduction of xylose by catalytic hydrogenation produces the common food additive sweetener substitute xylitol Xylitol.

The dextrorotary form of xylose, D-xylose, refers usually to the endogenously occurring form of the sugar in living things. The levorotary form, L-xylose, can refer to the form that is synthesized. Nevertheless, xylose by itself may not necessarily serve many purposes immediately - but its metabolism results in a variety of substrates that can serve important nutritional and biological purposes.

Structure
Thumb
Synonyms
  • (+)-Xylose
  • aldehydo-D-xylose
  • D-Xylose
  • Wood sugar
External IDs
FEMA NO. 3606
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Xylo-pfanPowder, for solution25 gOralPharmacia1995-12-311997-08-28Canada
Xylo-tol Pwr 25gm/pckPowder25 gOralEndovations Inc.1988-12-311997-07-15Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories
UNII
A1TA934AKO
CAS number
58-86-6
Weight
Average: 150.1299
Monoisotopic: 150.05282343
Chemical Formula
C5H10O5
InChI Key
PYMYPHUHKUWMLA-VPENINKCSA-N
InChI
InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4+,5+/m0/s1
IUPAC Name
(2R,3S,4R)-2,3,4,5-tetrahydroxypentanal
SMILES
OC[C@@H](O)[C@H](O)[C@@H](O)C=O

Pharmacology

Indication

The predominant everyday nutritional usage of xylose is as a parent sugar alcohol from which another sugar alcohol - xylitol- can be derived from and used as an extremely common food additive or sweetener to be used in place of regular sugars as a lower calorie alternative 7,8,1.

Alternatively, xylose was also involved in a procedure known as a D-xylose absorption test that used to be employed to evaluate how well an individual was capable of absorbing a simple sugar like D-xylose from the intestines 9. By measuring the amount of D-xylose in urine and blood samples after an individual ingested a certain amount of the simple sugar dissolved in some water, the test sought to determine if nutrients were being properly absorbed in the patient's gastrointestinal tract 9.

Pharmacodynamics

Xylose is often used as a parent sugar alcohol from which the commonly used food additive sweetener, xylitol, can be derived via the hydrogenation of xylose 1. Xylitol possesses many characteristics that make it a healthy and effective alternative to regular sugar. For example, although it looks and tastes exactly like ordinary sugar [A32662], having a 100% relative sweetness versus normal sucrose 7, it also has a low impact on blood sugar and insulin secretion and a minimal caloric value of 2.4 calories/gm 7,1. Furthermore, xylitol is non-fermentable and thus cannot be transformed to acids by oral bacteria, allowing it to restore a proper alkaline/acid balance in the mouth 1. Various studies cite this effect for allowing xylitol products like chewing gum to be effective at reducing dental caries 1. Altogether, these characteristics make xylose and its xylitol metabolite an effective alternative sweetener for healthy food choices for individuals who may be diabetic or for individuals simply wanting to make healthy dietary choices for their bodies.

Mechanism of action

Xylose is metabolized into various chemical intermediates that can play critical functions in the biological homeostasis of the human body. Via the oxido-reductase metabolism pathway of xylose in eukaryotic organisms, xylose is ultimately catabolized into (D)-xylulose-5-phosphate, which functions as an intermediate in the pentose phosphate pathway 2. Within the pentose phosphate pathway, NADPH, pentose 5-carbon sugars, and ribose 5-phosphate are generated as materials and precursors for the synthesis of nucleotides 2. In particular, xylulose-5-phosphate can be used to directly generate glycerinaldehyde-3-phosphate in the pathway 2. Other studies have also demonstrated that xylulose-5-phosphate may also play a role in gene expression, perhaps by promoting ChREBP transcription factor in the well-fed state 3.

Absorption

When 12 normal healthy subjects were given an intravenous D-xylose dosing of 10 grams and then an oral dose of 25 grams a week later, the observed absorption percentage was about 69.4% (p < 0.002) and the observed absorption rate was approximately 1.03/hr (p< 0.05) 4.

The maximum concentration observed in the subjects was 0.53 mg/L with 71 minutes being the time to reach the maximum concentration 6. The absolute bioavailability recorded was 69% 6.

Volume of distribution

The volume of distribution observed for d-xylose in normal healthy subjects is 0.22 L/kg 6.

Protein binding

Readily accessible data regarding the protein binding of xylose within the context of the human body is not available.

Metabolism

The most common and traditional metabolism pathway for xylose is the oxidoreductase pathway (or xylose reductase-xylitol dehydrogenase, XR-XDH pathway) 2. In this pathway, xylose is first reduced to xylitol using the xylitol dehydrogenase (XDH) enzyme with NADH or NADPH 2. The resultant xylitol is subsequently oxidized to D-xylulose by the xylitol dehydrogenase (XDH) enzyme while utilizing the cofactor NAD 2. Finally, the D-xylulose is phosphorylated by an ATP utilizing kinase (xylulose kinase enzyme) to generate D-xylulose-5-phosphate, which serves as an intermediate in the pentose phosphate pathway for nucleotide synthesis 2.

Route of elimination

In patients with normal kidney function, renal excretion accounts for approximately half (50%) of their total D-xylose elimination 5. Any non-renal D-xylose elimination is presumed to be hepatic clearance 5.

Half life

The elimination half-life observed in healthy individuals is 75 minutes 6.

Clearance

The renal clearance rate observed in healthy individuals is 89 ml/min 6. The accompanying plasma and non-renal clearances are 180 and 91 ml/min, respectively 6.

Toxicity

Although many national health agencies like the FDA and Health Canada have concluded that the addition or use of food additive sweeteners like xylose is safe and effective for their intended purposes of use in food, it is also known that eating too much of these substances can also ultimately cause gastrointestinal discomfort and laxative effects 7. These effects are largely the result of excessive amounts of ingested sugar alcohols being poorly taken up from the gastrointestinal tract 7. Regardless, the extent to which these kinds of effects occur depends on variances between individuals and it is also possible for individuals to develop a tolerance via frequent consumption of such sweetener containing products 7. In doing so, such individuals can increase consumption of these agents without experiencing adverse effects 7.

The acute oral toxicity (LD50) for the mouse animal model has been recorded as 23000 mg/kg MSDS.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Chattopadhyay S, Raychaudhuri U, Chakraborty R: Artificial sweeteners - a review. J Food Sci Technol. 2014 Apr;51(4):611-21. doi: 10.1007/s13197-011-0571-1. Epub 2011 Oct 21. [PubMed:24741154]
  2. Lee SM, Jellison T, Alper HS: Directed evolution of xylose isomerase for improved xylose catabolism and fermentation in the yeast Saccharomyces cerevisiae. Appl Environ Microbiol. 2012 Aug;78(16):5708-16. doi: 10.1128/AEM.01419-12. Epub 2012 Jun 8. [PubMed:22685138]
  3. Iizuka K, Horikawa Y: ChREBP: a glucose-activated transcription factor involved in the development of metabolic syndrome. Endocr J. 2008 Aug;55(4):617-24. Epub 2008 May 19. [PubMed:18490833]
  4. Craig RM, Murphy P, Gibson TP, Quintanilla A, Chao GC, Cochrane C, Patterson A, Atkinson AJ Jr: Kinetic analysis of D-xylose absorption in normal subjects and in patients with chronic renal failure. J Lab Clin Med. 1983 Mar;101(3):496-506. [PubMed:6827177]
  5. Craig RM, Atkinson AJ Jr: D-xylose testing: a review. Gastroenterology. 1988 Jul;95(1):223-31. [PubMed:3286361]
  6. Nancy B. Cummings, S. Klahr (2012). Chronic Renal Disease: Causes, Complications, and Treatment. Springer Science & Business Media. [ISBN:1468448269]
  7. Sugar Alcohols (Polyols) and Polydextrose Used as Sweeteners in Foods - Food Safety - Health Canada [Link]
  8. U.S. Food & Drug Administration: High-Intensity Sweeteners [Link]
  9. MedlinePlus: D-xylose absorption [Link]
External Links
Human Metabolome Database
HMDB0060254
PubChem Compound
644160
PubChem Substance
347827849
ChemSpider
559198
ChEBI
15936
HET
XLS
Wikipedia
Xylose
PDB Entries
1xic / 2brp / 2qw5 / 3mxg / 3xis / 4d5v / 4xis / 5nh7 / 5nh8 / 5nh9
show 7 more
MSDS
Download (47 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Powder, for solutionOral25 g
PowderOral25 g
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility380.0 mg/mLALOGPS
logP-2.3ALOGPS
logP-2.9ChemAxon
logS0.4ALOGPS
pKa (Strongest Acidic)12.34ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.38 m3·mol-1ChemAxon
Polarizability13.45 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udi-0920000000-53943f97f7f99da85d3b
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0uxr-0920000000-c093331f073f56253951
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0fl0-2900000000-c3d264491ad74c68ca6b
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0ff0-3900000000-c0dfd07fbd8ccb830c4a
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000b-0900000000-9c4c41394d62ca78b71c
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000b-0900000000-7134e3fb5f4a8332a873
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0006-0900000000-8985ea1909d749550911
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0006-0900000000-aaf3f704297d8e339c0e

Taxonomy

Description
This compound belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Pentoses
Alternative Parents
Beta-hydroxy aldehydes / Alpha-hydroxyaldehydes / Secondary alcohols / Polyols / Short-chain aldehydes / Primary alcohols / Organic oxides / Hydrocarbon derivatives
Substituents
Pentose monosaccharide / Beta-hydroxy aldehyde / Alpha-hydroxyaldehyde / Secondary alcohol / Polyol / Organic oxide / Hydrocarbon derivative / Short-chain aldehyde / Primary alcohol / Carbonyl group
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
D-xylose (CHEBI:15936)

Drug created on November 30, 2015 12:10 / Updated on August 02, 2019 08:43