Identification
- Generic Name
- Xylose
- DrugBank Accession Number
- DB09419
- Background
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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Xylose (DB09419)
- Weight
- Average: 150.1299
Monoisotopic: 150.05282343 - Chemical Formula
- C5H10O5
- Synonyms
- (+)-Xylose
- aldehydo-D-xylose
- D-Xylose
- Wood sugar
- Xylose
- External IDs
- FEMA NO. 3606
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.
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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. 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 1, 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.
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- 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.
- Adverse Effects
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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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
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Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Xylo-pfan Powder, for solution 25 g / bottle Oral Pharmacia 1995-12-31 1997-08-28 Canada 
Xylo-tol Pwr 25gm/pck Powder 25 g / pck Oral Endovations Inc. 1988-12-31 1997-07-15 Canada
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- Alcohol / Aldehyde / Aliphatic acyclic compound / Alpha-hydroxyaldehyde / Beta-hydroxy aldehyde / Carbonyl group / Hydrocarbon derivative / Organic oxide / Pentose monosaccharide / Polyol
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- D-xylose (CHEBI:15936)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- A1TA934AKO
- CAS number
- 58-86-6
- 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
References
- General References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Craig RM, Atkinson AJ Jr: D-xylose testing: a review. Gastroenterology. 1988 Jul;95(1):223-31. [Article]
- Nancy B. Cummings, S. Klahr (2012). Chronic Renal Disease: Causes, Complications, and Treatment. Springer Science & Business Media. [ISBN:1468448269]
- Sugar Alcohols (Polyols) and Polydextrose Used as Sweeteners in Foods - Food Safety - Health Canada [Link]
- U.S. Food & Drug Administration: High-Intensity Sweeteners [Link]
- MedlinePlus: D-xylose absorption [Link]
- External Links
- Human Metabolome Database
- HMDB0060254
- PubChem Compound
- 644160
- PubChem Substance
- 347827849
- ChemSpider
- 559198
- 11378
- ChEBI
- 15936
- ChEMBL
- CHEMBL1236821
- ZINC
- ZINC000018168715
- PDBe Ligand
- XLS
- Wikipedia
- Xylose
- PDB Entries
- 1xic / 2brp / 2qw5 / 3mxg / 3xis / 4d5v / 4xis / 5nh7 / 5nh8 / 5nh9 … show 9 more
- MSDS
- Download (47 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Powder, for solution Oral 25 g / bottle Powder Oral 25 g / pck - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 380.0 mg/mL ALOGPS logP -2.3 ALOGPS logP -2.9 Chemaxon logS 0.4 ALOGPS pKa (Strongest Acidic) 12.34 Chemaxon pKa (Strongest Basic) -3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 97.99 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 31.38 m3·mol-1 Chemaxon Polarizability 13.45 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Drug created at November 30, 2015 19:10 / Updated at February 03, 2022 06:26