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D-Xylose

PubChem CID
135191
Structure
D-Xylose_small.png
D-Xylose_3D_Structure.png
Molecular Formula
Synonyms
  • D-xylose
  • xylose
  • D-xylopyranose
  • XYLOPYRANOSE
  • D-Xyl
Molecular Weight
150.13 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-06-24
  • Modify:
    2025-01-18
Description
D-xylopyranose is d-Xylose in its pyranose form.
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 [DB11195]. 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.
D-Xylose is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
D-Xylose.png

1.2 3D Conformer

2 Biologic Description

1 of 2
SVG Image
SVG Image
IUPAC Condensed
Xyl
LINUCS
[][D-Xylp]{}
IUPAC
D-xylo-pentopyranose
2 of 2
Permethylated Mass
Monosaccharide Composition
Xxx1

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

(3R,4S,5R)-oxane-2,3,4,5-tetrol
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

3.1.2 InChI

InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3+,4-,5?/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.3 InChIKey

SRBFZHDQGSBBOR-IOVATXLUSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.4 SMILES

C1[C@H]([C@@H]([C@H](C(O1)O)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C5H10O5
Computed by PubChem 2.2 (PubChem release 2021.10.14)

3.3 Other Identifiers

3.3.1 CAS

25990-60-7
58-86-6
50855-32-8
7261-26-9

3.3.2 Deprecated CAS

133-56-2, 141492-19-5

3.3.3 European Community (EC) Number

3.3.4 ChEBI ID

3.3.5 ChEMBL ID

3.3.6 DrugBank ID

3.3.7 FEMA Number

3.3.8 HMDB ID

3.3.9 KEGG ID

3.3.10 Metabolomics Workbench ID

3.3.11 NCI Thesaurus Code

3.3.12 Nikkaji Number

3.3.13 Wikidata

3.3.14 Wikipedia

3.4 Synonyms

3.4.1 MeSH Entry Terms

  • D Xylose
  • D-Xylose
  • Xylose

3.4.2 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
150.13 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-2.5
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
150.05282342 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
150.05282342 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
90.2 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
10
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
117
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
3
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

4.2 Experimental Properties

4.2.1 Physical Description

Solid; [Merck Index] White crystalline powder; Hygroscopic; [Alfa Aesar MSDS]
Solid

4.2.2 Color / Form

Monoclinic needles or prisms
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1724
White crystalline powder
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 1236

4.2.3 Taste

Very sweet
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1724

4.2.4 Melting Point

153-154 °C
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1724
90.5 °C

4.2.5 Solubility

1 g dissolves in 0.8 ml water; sol in pyridine & hot alc
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1724
555.0 mg/mL

4.2.6 Density

1.525 @ 20 °C/4 °C
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1724

4.2.7 Stability / Shelf Life

STABLE @ ROOM TEMP
Bergmeyer, H.W. (ed.). Methods of Enzymatic Analysis. 2nd English ed. New York City: Academic Press, 1974., p. 556

4.2.8 Optical Rotation

Specific optical rotation: +92 deg & +18.6 deg (16 hr, 10%) @ 20 °C/D
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1724

4.2.9 Decomposition

When heated to decomposition it emits acrid smoke and irritating vapors.
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 3409

4.2.10 Dissociation Constants

pKa = 12.14 @ 18 °C
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1724

4.2.11 Collision Cross Section

134.9 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
134.6 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
125.93 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Ross et al. JASMS 2022; 33; 1061-1072. DOI:10.1021/jasms.2c00111
132.07 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]
135 Ų [M+Na]+
S50 | CCSCOMPEND | The Unified Collision Cross Section (CCS) Compendium | DOI:10.5281/zenodo.2658162

4.2.12 Other Experimental Properties

Shows mutarotation; reduces warm Fehling's soln
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1724

4.3 Chemical Classes

Biological Agents -> Monosaccharides and Derivatives

4.3.1 Drugs

4.3.1.1 Human Drugs
Human drug -> Discontinued; Active ingredient (XYLOSE)
Human drug -> Discontinued

4.3.2 Cosmetics

Cosmetic ingredients (Xylose) -> CIR (Cosmetic Ingredient Review)
Humectant
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

4.3.3 Food Additives

FLAVORING AGENT OR ADJUVANT, NUTRITIVE SWEETENER -> FDA Substance added to food

5 Spectral Information

5.1 1D NMR Spectra

1D NMR Spectra
NMR: 7074 (Sadtler Research Laboratories Spectral Collection)

5.1.1 1H NMR Spectra

1 of 3
View All
Spectra ID
Instrument Type
Varian
Frequency
500 MHz
Solvent
Water
pH
7.00
Shifts [ppm]:Intensity
3.40:51.74, 3.63:26.10, 3.52:31.99, 3.51:23.83, 3.93:37.33, 3.44:51.76, 3.68:46.93, 3.33:57.32, 3.61:32.37, 3.91:41.18, 3.90:43.32, 3.21:60.14, 3.50:23.95, 3.59:37.27, 4.56:38.54, 3.60:40.19, 3.29:47.62, 3.68:46.18, 3.64:24.13, 3.31:68.01, 3.53:31.65, 3.67:80.27, 3.62:50.18, 5.18:33.18, 4.57:36.18, 3.62:39.36, 3.22:69.39, 3.31:67.66, 3.23:63.56, 3.61:30.14, 3.67:60.56, 5.19:32.91, 3.63:41.08, 3.60:37.91, 3.92:40.79, 3.20:52.93, 3.42:100.00, 3.65:39.90
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Instrument Name
Varian A-60
Source of Sample
Pfanstiehl Chemical Company, Waukegan, Illinois
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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5.1.2 13C NMR Spectra

1 of 3
View All
Spectra ID
Instrument Type
Bruker
Frequency
125 MHz
Solvent
Water
pH
7.00
Shifts [ppm]:Intensity
67.87:31.01, 0.00:5.70, 99.37:37.53, 72.16:20.66, 76.86:35.97, 78.63:35.79, 63.66:15.47, 74.26:19.21, 94.98:21.16, 75.63:19.48, 72.00:36.01
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Source of Sample
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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5.2 2D NMR Spectra

5.2.1 1H-1H NMR Spectra

2D NMR Spectra Type
1H-1H TOCSY
Spectra ID
Shifts [ppm] (F2:F1)
3.92:3.62, 3.67:3.67, 4.57:4.58, 4.56:3.65, 3.66:3.60, 3.91:3.34, 3.22:3.59, 5.18:3.49, 3.91:3.58, 3.31:4.56, 4.56:3.63, 3.91:3.21, 3.32:3.40, 4.57:4.55, 3.22:3.19, 3.31:3.94, 3.61:3.40, 3.61:3.31, 3.51:3.52, 4.57:3.90, 3.61:3.28, 3.91:4.56, 3.31:3.28, 3.92:3.31, 4.57:3.58, 3.91:3.44, 3.42:3.44, 3.75:3.75, 4.57:3.94, 3.42:4.55, 3.61:3.60, 3.67:3.69, 3.42:3.28, 4.56:3.24, 3.51:3.65, 4.57:3.42, 4.57:3.34, 3.31:3.58, 3.31:3.19, 3.42:3.42, 3.21:3.40, 3.31:3.89, 3.91:3.94, 3.61:3.91, 3.92:3.42, 4.78:4.78, 4.56:3.61, 3.42:4.58, 3.31:3.31, 3.91:3.90, 3.42:3.58, 3.51:3.58, 3.91:4.57, 3.22:4.55, 3.67:3.63, 3.92:3.20, 3.31:3.21, 4.57:3.28, 3.31:4.57, 3.92:3.28, 3.42:3.21, 3.79:3.79, 4.56:3.31, 5.18:3.67, 3.87:3.87, 5.18:5.18, 3.91:3.23, 3.68:3.56, 4.56:3.44, 5.18:3.65, 5.18:3.58, 3.22:3.21, 3.42:3.24, 3.60:4.55, 3.92:3.92, 3.52:5.18, 3.21:3.42, 3.41:3.39, 3.31:3.34, 3.21:4.58, 3.61:3.20, 3.22:3.64, 3.61:3.34, 3.22:3.24, 3.67:3.58, 3.64:3.62, 3.31:3.63, 3.21:3.44, 3.42:3.90, 3.42:3.19, 3.92:3.64, 3.61:3.21, 3.61:3.44, 5.18:3.52, 4.57:3.19, 3.31:3.23, 3.61:3.93, 4.56:3.60, 4.57:3.21, 3.31:3.42, 3.61:3.42, 3.51:3.50, 5.18:3.60, 3.42:3.65, 3.42:3.61, 3.91:3.40, 5.18:3.63, 4.57:3.39, 3.61:3.23, 3.68:3.50, 3.31:3.60, 3.31:3.44, 3.61:3.90, 3.67:3.52, 3.67:5.18, 3.51:3.61, 3.60:4.58, 3.31:3.65
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5.2.2 1H-13C NMR Spectra

2D NMR Spectra Type
1H-13C HSQC
Spectra ID
Instrument Type
Bruker
Frequency
400 MHz
Solvent
Water
pH
7.00
Shifts [ppm] (F2:F1):Intensity
3.58:72.15:0.37, 3.94:67.91:0.41, 3.42:78.67:0.67, 3.69:63.65:0.57, 3.65:75.55:0.32, 3.50:74.24:0.27, 3.60:72.07:0.53, 4.55:99.44:0.97, 3.52:74.28:0.33, 5.18:94.98:0.74, 3.68:72.12:0.20, 3.63:75.67:0.23, 3.62:72.15:0.46, 4.58:99.43:1.00, 3.21:76.91:0.73, 3.67:63.64:0.69, 3.89:67.88:0.38, 3.31:67.87:0.62
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5.3 Mass Spectrometry

5.3.1 GC-MS

1 of 4
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Spectra ID
Instrument Type
GC-EI-TOF
Ionization Mode
positive
Top 5 Peaks

103.0 100

217.0 41.04

147.0 35.54

307.0 14.31

133.0 12.41

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Notes
instrument=Leco Pegasus IV
2 of 4
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MS Category
Experimental
MS Type
GC-MS
Instrument
Leco Pegasus IV
Instrument Type
GC-EI-TOF
Ionization Mode
positive
Top 5 Peaks

103.0 100

217.0 40.54

147.0 34.13

89.0 16.42

307.0 12.91

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5.3.2 MS-MS

1 of 6
View All
Spectra ID
Instrument Type
Quattro_QQQ
Ionization Mode
Positive
Top 5 Peaks

101.0 100

133.0 61.14

119.0 58.90

151.0 55.32

89.0 54.07

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Notes
delivery=Flow_Injectionanalyzer=Triple_Quad
2 of 6
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Spectra ID
Instrument Type
Quattro_QQQ
Ionization Mode
Positive
Top 5 Peaks

101.0 100

87.0 77.10

119.0 49.98

89.0 43.79

86.0 36.79

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Notes
delivery=Flow_Injectionanalyzer=Triple_Quad

5.3.3 LC-MS

1 of 3
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MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
149.0455474
Instrument
Thermo Q Exactive HF
Instrument Type
LC-ESI-QFT
Ionization Mode
negative
Collision Energy
HCD (NCE 20-30-40%)
Top 5 Peaks

59.01371 100

71.01381 70

89.02454 34.10

82.92976 8.20

62.02185 6.80

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MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
149.0455474
Instrument
Agilent qTOF 6545
Instrument Type
LC-ESI-QTOF
Ionization Mode
negative
Collision Energy
40 eV
Top 5 Peaks

54.59081 100

57.00738 46

56.99959 37.70

112.69733 20.40

144.73866 12.10

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5.3.4 Other MS

1 of 2
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
149.045
Instrument
qTof
Ionization Mode
negative
Top 5 Peaks

59.016319 20

59.029339 10

59.020660 10

59.282330 10

79.963760 10

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2 of 2
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+Na]+
Precursor m/z
173.042
Instrument
Orbitrap
Ionization Mode
positive
Top 5 Peaks

173.042328 100

159.013382 76.92

130.981949 16.31

144.997681 13.69

116.966293 11.48

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5.4 UV Spectra

UV: 6-55 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
Weast, R.C. and M.J. Astle. CRC Handbook of Data on Organic Compounds. Volumes I and II. Boca Raton, FL: CRC Press Inc. 1985., p. V2 444

5.5 IR Spectra

IR Spectra
IR: 15302 (Sadtler Research Laboratories IR Grating Collection)

5.5.1 FTIR Spectra

1 of 2
Instrument Name
Bruker IFS 85
Technique
KBr-Pellet
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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2 of 2
Technique
Mull
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Aldrich
Catalog Number
X1075
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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5.5.2 ATR-IR Spectra

Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II) ground
Source of Spectrum
Forensic Spectral Research
Source of Sample
Spectrum Chemical Manufacturing Corp.
Catalog Number
XY110
Lot Number
VU0042
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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5.6 Raman Spectra

1 of 2
Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Spectrum Chemical Manufacturing Corp.
Catalog Number
XY110
Lot Number
VU0042
Copyright
Copyright © 2015-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Catalog Number
X1075
Copyright
Copyright © 2017-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2017-2024 John Wiley & Sons, Inc. All Rights Reserved.
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5.7 Other Spectra

SADTLER REFERENCE NUMBER: 1068 (IR, PRISM)
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-546

7 Chemical Vendors

8 Drug and Medication Information

8.1 Drug 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. 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. 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.

8.2 FDA Approved Drugs

8.3 FDA Orange Book

8.4 Clinical Trials

8.4.1 ClinicalTrials.gov

8.5 Therapeutic Uses

XYLOSE BLOOD LEVEL MEASUREMENTS...TO DETERMINE WHETHER ABNORMALLY LOW URINARY XYLOSE EXCRETION IS DUE TO IMPAIRED ABSORPTION OR RENAL INSUFFICIENCY. BLOOD XYLOSE LEVELS /DETERMINED/ 2 HR AFTER INGESTION OF 25 G DOSE.
American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1976
/DIFFERENTIATE/ STEATORRHEA CAUSED BY PANCREATIC INSUFFICIENCY FROM THAT CAUSED BY MALABSORPTION /5 G DISSOLVED IN 150 ML WATER OR 25 G DISSOLVED IN 250 ML WATER, FOLLOWED BY 250 ML WATER, ORAL. URINE POOLED DURING NEXT 5 HR & QUANTITY OF XYLOSE DETERMINED/.
American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1976
EVALUATE INTESTINAL ABSORPTION...DIAGNOSIS OF MALABSORPTIVE STATES DUE TO DISEASES INVOLVING INTESTINAL MUCOSA /5 G DISSOLVED IN 150 ML WATER OR 25 G DISSOLVED IN 250 ML WATER, FOLLOWED BY 250 ML WATER, ORAL. URINE POOLED DURING NEXT 5 HR & QUANTITY OF XYLOSE DETERMINED/.
American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1976
DIAGNOSIS OF MALABSORPTIVE STATES DUE TO...SURGICAL RESECTION. /ASSESS/ DEG OF IMPAIRED ABSORPTION OR EXTENT OF RESPONSE TO THERAPY /5 G DISSOLVED IN 250 ML WATER & ADMIN ORALLY. ADDITIONAL FLUIDS PERMITTED. URINE COLLECTED IN 2 CONSECUTIVE PERIODS OF 2 & 3 HR. XYLOSE CONTENT DETERMINED/.
American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1976
FOR INFANTS, YOUNG CHILDREN OR ELDERLY INCONTINENT PATIENTS...XYLOSE BLOOD LEVELS MAY BE USED TO EVALUATE INTESTINAL ABSORPTION /500 MG/KG BODY WT (OR MAX OF 25 G) AS 5-10% AQ SOLN, ORAL. XYLOSE LEVELS ARE DETERMINED IN BLOOD SAMPLES TAKEN 30 MIN, 1 HR, & 2 HR AFTER XYLOSE ADMIN/.
American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1976

8.6 Drug Warnings

URINARY EXCRETION OF XYLOSE IN PATIENTS OLDER THAN 60 YR OF AGE IS USUALLY LOW...XYLOSE TEST SHOULD BE USED IN PREGNANT WOMEN OR WOMEN WHO MAY BECOME PREGNANT ONLY WHEN POTENTIAL BENEFITS OUTWEIGH POSSIBLE HAZARDS.
American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1976
CONDITIONS WHICH CAN PRODUCE "FALSE-POS" TEST VALUES INCLUDE VOMITING, GASTRIC STASIS, THYROID DYSFUNCTION & SEVERE DIARRHEA FOLLOWING INGESTION OF TEST DOSE. PATIENTS WITH THYROTOXICOSIS HAVE SHOWN INCREASED URINARY EXCRETION OF XYLOSE.
American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1976
USE OF XYLOSE TEST REQUIRES CLOSE ATTENTION TO TECHNICAL DETAILS...IN PATIENTS WITH IMPAIRED RENAL FUNCTION, DEHYDRATION, INADEQUATE CIRCULATING BLOOD VOL, EDEMA OR MASSIVE ASCITES, URINARY EXCRETION OF D-XYLOSE WILL BE LOWER THAN NORMAL & THUS PRODUCE "FALSE-POS" TEST VALUES.
American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1976

8.7 Biomarker Information

9 Food Additives and Ingredients

9.1 FDA Substances Added to Food

Substance
Used for (Technical Effect)
FLAVORING AGENT OR ADJUVANT, NUTRITIVE SWEETENER
FEMA Number
3606
GRAS Number
12

9.2 Associated Foods

10 Pharmacology and Biochemistry

10.1 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. 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, having a 100% relative sweetness versus normal sucrose, it also has a low impact on blood sugar and insulin secretion and a minimal caloric value of 2.4 calories/gm. 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. Various studies cite this effect for allowing xylitol products like chewing gum to be effective at reducing dental caries. 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.

10.2 Absorption, Distribution and Excretion

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). The maximum concentration observed in the subjects was 0.53 mg/L with 71 minutes being the time to reach the maximum concentration. The absolute bioavailability recorded was 69%.
Route of Elimination
In patients with normal kidney function, renal excretion accounts for approximately half (50%) of their total D-xylose elimination. Any non-renal D-xylose elimination is presumed to be hepatic clearance.
Volume of Distribution
The volume of distribution observed for d-xylose in normal healthy subjects is 0.22 L/kg.
Clearance
The renal clearance rate observed in healthy individuals is 89 ml/min. The accompanying plasma and non-renal clearances are 180 and 91 ml/min, respectively.
XYLOSE HAS BEEN SHOWN TO GET INTO AQ HUMOR /OF RATS/ FROM GENERAL CIRCULATION & THEREFORE TO HAVE ACCESS TO LENS.
Grant, W. M. Toxicology of the Eye. 2nd ed. Springfield, Illinois: Charles C. Thomas, 1974., p. 1090
/ABSORBED/ FROM GI TRACT...5-G DOSES...ABSORBED MORE RAPIDLY & COMPLETELY THAN ARE 25-G DOSES...AT LEAST 60%...ABSORBED IN PROXIMAL PART OF SMALL INTESTINE... NOT DEPENDENT UPON PRESENCE OF BILE OR PANCREATIC JUICE.../PEAK BLOOD LEVELS/ 1 TO 2 HR...TO 0 AFTER...5 HR /HUMAN, ORAL 5 OR 25 G/.
American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1976
PLASMA HALF-LIFE...ABOUT 1 HR /IV ADMIN/...ABOUT 60%...METABOLIZED TO CARBON DIOXIDE & WATER, D-THREITOL, &...UNIDENTIFIED METABOLITES...EXCRETED IN URINE...ABOUT 25% OF 25 G /DOSE/ & ABOUT 35% OF 5 G /DOSE/ EXCRETED UNCHANGED IN URINE WITHIN 5 HR /HUMAN, ORAL/.
American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1976
URINARY EXCRETION /MAINLY BY/ GLOMERULAR FILTRATION...SOME TUBULAR RESORPTION MAY OCCUR /HUMAN, ORAL/.
American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1976
For more Absorption, Distribution and Excretion (Complete) data for (D)-XYLOSE (8 total), please visit the HSDB record page.

10.3 Metabolism / Metabolites

The most common and traditional metabolism pathway for xylose is the oxidoreductase pathway (or xylose reductase-xylitol dehydrogenase, XR-XDH pathway). In this pathway, xylose is first reduced to xylitol using the xylitol dehydrogenase (XDH) enzyme with NADH or NADPH. The resultant xylitol is subsequently oxidized to D-xylulose by the xylitol dehydrogenase (XDH) enzyme while utilizing the cofactor NAD. 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.
...RAT-LIVER MICROSOMES CATALYZE THE TRANSFER OF...XYLOSE TO BILIRUBIN, FROM...UDP-XYLOSE...
The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 385
ABOUT 60% OF ABSORBED XYLOSE IS METABOLIZED TO CARBON DIOXIDE & WATER, D-THREITOL, & OTHER UNIDENTIFIED METABOLITES /HUMAN, ORAL/.
American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1976
AFTER IP INJECTION OF (14)C-LABELED D-XYLOSE INTO GUINEA PIGS, 10.8 OF RADIOACTIVITY WAS RECOVERED AS EXPIRED CARBON DIOXIDE IN 4 HR & 41.3 AS URINARY (14)CARBON IN 5 HR. APPROX 60 OF URINARY RADIOACTIVITY WAS D-XYLOSE.
WESER E, LASTER L; BIOCHEM MED 2 (1): 53-69 (1968)
(14)C-LABELED D-XYLONIC ACID WAS OXIDIZED TO LABELED CARBON DIOXIDE BY INTACT ANIMALS & IN VITRO BY KIDNEY & LIVER. OXIDATION OF D-XYLOSE BY GUINEA PIG PROBABLY INVOLVES ITS INITIAL CONVERSION TO D-XYLONIC ACID & SUBSEQUENT DECARBOXYLATION.
WESER E, LASTER L; BIOCHEM MED 2 (1): 53-69 (1968)
IN VITRO KIDNEY & LIVER COULD OXIDIZE D-XYLOSE TO CARBON DIOXIDE. LIVER EXTRACT COULD CATALYZE CONVERSION TO D-XYLONIC ACID WITH PYRIDINE NUCLEOTIDE AS COFACTOR. THIS ENZYME ACTIVITY WAS DIFFERENT FROM HEPATIC GLUCOSE DEHYDROGENASE.
WESER E, LASTER L; BIOCHEM MED 2 (1): 53-69 (1968)

10.4 Biological Half-Life

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

10.5 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. 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. In particular, xylulose-5-phosphate can be used to directly generate glycerinaldehyde-3-phosphate in the pathway. 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.

10.6 Human Metabolite Information

10.6.1 Tissue Locations

  • Erythrocyte
  • Intestine

10.6.2 Cellular Locations

  • Cytoplasm
  • Extracellular
  • Lysosome

10.7 Biochemical Reactions

11 Use and Manufacturing

11.1 Uses

Cosmetic Ingredient Review Link
CIR ingredient: Xylose
Sources/Uses
Found in many plant materials, especially wood, straw, and hulls; Used in tanning, dyeing, diabetic foods, and medical diagnosis (intestinal function); [Merck Index] Used as a flavoring agent and nutritive sweetener; [FDA]
Merck Index - O'Neil MJ, Heckelman PE, Dobbelaar PH, Roman KJ (eds). The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 15th Ed. Cambridge, UK: The Royal Society of Chemistry, 2013.
Industrial Processes with risk of exposure
Leather Tanning and Processing [Category: Industry]
In tanning, dyeing, & as diabetic food
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1724
Nonnutritive sweetner
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 1236
MEDICATION

11.1.1 Use Classification

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients
Cosmetics -> Humectant
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

11.1.2 Household Products

Household & Commercial/Institutional Products

Information on 5 consumer products that contain Xylose in the following categories is provided:

• Personal Care

11.2 Methods of Manufacturing

Isolation from corn cobs by boiling with 8% sulfuric acid. Peanut shells & cottonseed hulls also are practical sources of xylose.
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1724

11.3 Formulations / Preparations

Grades: Reagent, Technical
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 1236

11.4 General Manufacturing Information

EPA TSCA Commercial Activity Status
D-Xylose: ACTIVE
Upon heating with water in closed tube to 140 °C or by boiling with dil H2SO4 furfurol is formed. Hydrazones of D-xylose are more sol than those of L-arabinose & used to separate the 2 sugars.
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1724

12 Identification

12.1 Analytic Laboratory Methods

AOAC 950.57. Arabinose, Galactose, and Xylose and other sugars in sugars and sirups.
Association of Official Analytical Chemists. Official Methods of Analysis. 15th ed. and Supplements. Washington, DC: Association of Analytical Chemists, 1990, p. 1019

12.2 Clinical Laboratory Methods

D-XYLULOSE & D-XYLOSE DETERMINATION WITH D-XYLOSE ISOMERASE BY SPECTROPHOTOMETRY OR COLORIMETRY. DP BURMA & BL HORECKER, J BIOL CHEM 231, 1053 (1958).
Bergmeyer, H.W. (ed.). Methods of Enzymatic Analysis. 2nd English ed. New York City: Academic Press, 1974., p. 1371
METHOD OF ESTIMATING XYLOSE DETECTING COLOR @ 410 NM.
KHATTAB F, HAROUN I; J PHARM BELG 33 (4): 261-3 (1978)

13 Safety and Hazards

13.1 Hazards Identification

13.1.1 GHS Classification

1 of 2
View All
Note
This chemical does not meet GHS hazard criteria for 100% (294 of 294) of all reports. Pictograms displayed are for < 0.1% (0 of 294) of reports that indicate hazard statements.
GHS Hazard Statements

Not Classified

Reported as not meeting GHS hazard criteria by 294 of 294 companies. For more detailed information, please visit ECHA C&L website.

ECHA C&L Notifications Summary

Aggregated GHS information provided per 294 reports by companies from 2 notifications to the ECHA C&L Inventory.

Reported as not meeting GHS hazard criteria per 294 of 294 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 0 notifications provided by 0 of 294 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

13.1.2 Hazard Classes and Categories

Not Classified

Skin Irrit. 2 (100%)

Eye Irrit. 2A (100%)

STOT SE 3 (100%)

13.1.3 Hazards Summary

May cause irritation; [Alfa Aesar MSDS]

13.2 Accidental Release Measures

13.2.1 Disposal Methods

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

13.3 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: D-Xylose
The Australian Inventory of Industrial Chemicals
Chemical: Xylose
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Xylose: Does not have an individual approval but may be used under an appropriate group standard
New Zealand EPA Inventory of Chemical Status
D-Xylose: Does not have an individual approval but may be used under an appropriate group standard

13.4 Other Safety Information

Chemical Assessment

IMAP assessments - Xylose: Environment tier I assessment

IMAP assessments - Xylose: Human health tier I assessment

Chemical Assessment

IMAP assessments - D-Xylose: Human health tier I assessment

IMAP assessments - D-Xylose: Environment tier I assessment

14 Toxicity

14.1 Toxicological Information

14.1.1 Carcinogen Classification

Carcinogen Classification
No indication of carcinogenicity to humans (not listed by IARC).

14.1.2 Interactions

D-XYLOSE RELIEVED INHIBITION BY PUROMYCIN & CYCLOHEXIMIDE OF INCORPORATION OF ACETATE INTO CHONDROITIN SULFATE IN WHOLE TIBIAS & FEMURS OF EMBRYONIC CHICKEN CARTILAGE.
ROBINSON HC ET AL, BIOCHEM J; VOL 148, ISS 1, 1975, 25-34
ADDN OF GUAR TO ORAL DOSAGE OF D-XYLOSE SLOWED DOWN GI ABSORPTION OF D-XYLOSE IN VOLUNTEERS. TOTAL AMT ABSORBED & PLASMA T/2 OF D-XYLOSE WERE NOT AFFECTED.
ABELE R ET AL; PHARM ACTA HELV 53 (9-10): 253-60 (1978)
CONCOMITANT ADMIN OF INDOMETHACIN, NEOMYCIN, PHENFORMIN, COLCHICINE, OR LARGE DOSES OF AMINOSALICYLIC ACID WITH D-XYLOSE INHIBITS INTESTINAL ABSORPTION OF D-XYLOSE /REDUCING/ QUANTITIES OF SUGAR BEING EXCRETED...ASPIRIN /REDUCES URINARY EXCRETION OF D-XYLOSE/ APPARENTLY BY ALTERING RENAL FUNCTION.
American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1976

14.1.3 Human Toxicity Excerpts

LOW INCIDENCE OF SIDE EFFECTS. NAUSEA, INTESTINAL BLOATING, BORBORYGMI, CRAMPING, ABDOMINAL DISCOMFORT, & DIARRHEA OCCUR FREQUENTLY FOLLOWING 25-G ORAL DOSE...RARELY OCCUR FOLLOWING 5-G ORAL DOSE, EXCEPT IN VERY SMALL INFANTS /ADVERSE EFFECT, ORAL/
American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1976
XYLOSE WAS NONCARIOGENIC AFTER 1 WK AS COMPARED TO SUCROSE CONTROL.
KOULOURIDES T ET AL; CARIES RES 10 (6): 427-41 (1976)
NON-TOXIC
Hawley, G.G. The Condensed Chemical Dictionary. 9th ed. New York: Van Nostrand Reinhold Co., 1977., p. 932

14.1.4 Non-Human Toxicity Excerpts

IT HAS BEEN SHOWN TO PRODUCE CATARACTS IN WEANLING RATS, BUT OLDER RATS ARE RESISTANT TO THIS EFFECT...CONSISTS OF OPACIFICATION OF LENS WHICH IS TRANSIENT, IN CONTRAST TO PERMANENT OPACITY PRODUCED BY GALACTOSE. ... INFLUENCE OF AGE OF RATS APPEARS TO BE DUE TO DIFFERENCES IN METABOLISM &...IN CONCN OF XYLOSE...IN BLOOD.
Grant, W.M. Toxicology of the Eye. 3rd ed. Springfield, IL: Charles C. Thomas Publisher, 1986., p. 985

14.1.5 Non-Human Toxicity Values

LD50 Mouse oral 23 g/kg
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 3409
LD50 Mouse iv 11,300 mg/kg
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 3409

14.1.6 Protein Binding

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

14.2 Ecological Information

14.2.1 Environmental Fate / Exposure Summary

D-Xylose's production and use as a non-nutritive sweetener and as a tanning or dyeing agent may result in its release to the environment through various waste streams. D-Xylose is found naturally in plant materials, especially wood (maple, cherry), in straw and hulls. It is not found in the free state, but occurs as xylan, a polysaccharide built from xylose units and occurring in association with cellulose. If released to air, an estimated vapor pressure of 9.6X10-7 mm Hg at 25 °C indicates D-xylose will exist in both the vapor and particulate phases. Vapor-phase D-xylose will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 5 hours. Particulate-phase D-xylose will be removed from the atmosphere by wet and dry deposition. If released to soil, D-xylose is expected to have very high mobility based upon an estimated Koc of 2. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 1.2X10-9 atm-cu m/mole. This compound is a simple monosaccharide and should be readily biodegradable in the environment. If released into water, D-xylose is not expected to adsorb to suspended solids and sediment in the water column based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 1 suggests bioconcentration in aquatic organisms is low. Occupational exposure to D-xylose may occur through inhalation of dust particles and dermal contact with this compound at workplaces where D-xylose is produced or used. (SRC)

14.2.2 Natural Pollution Sources

D-Xylose is found naturally in plant materials, especially wood (maple, cherry) in straw and hulls(1). It is not found in the free state, but occurs as xylan, a polysaccharide built from xylose units and occurring in association with cellulose(1).
(1) Budvari S; Merck Index, 12th ed, Whitehouse Station, NJ Merck & Co. p. 1724 (1996)

14.2.3 Artificial Pollution Sources

D-Xylose's production and use as a non-nutritive sweetener(1) and as a tanning or dyeing agent(2) may result in its release to the environment through various waste streams(SRC).
(1) Lewis RJ; Hawley's Condensed Chemical Dictionary. 12th ed. NY,NY: Van Nostrand Reinhold Co., p. 1236 (1993)
(2) Budvari S; Merck Index, 12th ed, Whitehouse Station, NJ Merck & Co. p. 1724 (1996)

14.2.4 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2(SRC), determined from an estimated log Kow of -1.98(2,SRC) and a regression-derived equation(3), indicates that D-xylose is expected to have very high mobility in soil(SRC). Volatilization of D-xylose from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(4). D-Xylose is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.4X10-7 mm Hg(SRC), determined from a fragment constant method(5). D-Xylose is a simple monosaccharide and should be readily biodegradable in the environment(SRC).
(1) Swann RL et al; Res Rev 85: 23 (1983)
(2) Meylan WM, Howard PH; J Pharm Sci 84: 83-92 (1995)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington,DC: Amer Chem Soc pp. 4-9 (1990)
(4) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(5) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE (eds), Boca Raton,FL: CRC Press (1985)
(6) Engelbrecht RS, McKinney RE; Sew Indust Wastes 29: 1350-62 (1957)
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2(SRC), determined from an estimated log Kow of -1.98(2,SRC) and a regression-derived equation(3), indicates that D-xylose is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.2X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 1(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). D-Xylose was biodegraded 63 percent in a 15-day river die away test(6).
(1) Swann RL et al; Res Rev 85: 23 (1983)
(2) Meylan WM, Howard PH; J Pharm Sci 84: 83-92 (1995)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington,DC: Amer Chem Soc pp. 4-9, 5-4, 5-10, 15-1 to 15-29 (1990)
(4) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(5) Franke C et al; Chemosphere 29: 1501-14 (1994)
(6) Lawrance WA, Fukui HN; Sew Indust Wastes 28: 1484-94 (1956)
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), D-xylose, which has an estimated vapor pressure of 9.6X10-7 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase D-xylose is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 5 hours(SRC) from its estimated rate constant of 7.4X10-11 cu cm/molecule-sec at 25 °C(SRC), determined from a fragment constant estimation method(3). Particulate-phase D-xylose may be removed from the air by wet and dry deposition(SRC).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE (eds), Boca Raton,FL: CRC Press (1985)
(3) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)

14.2.5 Environmental Biodegradation

D-Xylose is a simple monosaccharide and should be readily biodegradable in the environment(SRC). D-Xylose was biodegraded 63 percent in a 15-day river die away test(1). D-Xylose has been shown to biodegrade to acetic acid in the presence of acetogenic bacteria(2).
(1) Lawrance WA, Fukui HN; Sew Indust Wastes 28: 1484-94 (1956)
(2) Wagner FS; Kirk-Othmer's Encycl Chem Technol 4th ed. Kroschwitz JI ed. NY,NY: John Wiley & Sons 1: 133 (1991)

14.2.6 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of D-xylose with photochemically-produced hydroxyl radicals has been estimated as 7.4X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). D-Xylose is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2) nor to directly photolyze due to the lack of absorption in the environmental UV spectrum.
(1) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington,DC: Amer Chem Soc pp. 7-4, 7-5 (1990)

14.2.7 Environmental Bioconcentration

An estimated BCF of 1 was calculated for D-xylose(SRC), using an estimated log Kow of -1.98(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
(1) Meylan WM, Howard PH; J Pharm Sci 84: 83-92 (1995)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington,DC: Amer Chem Soc pp. 5-4, 5-10 (1990)
(3) Franke C et al; Chemosphere 29: 1501-14 (1994)

14.2.8 Soil Adsorption / Mobility

The Koc of D-xylose is estimated as approximately 2(SRC), using an estimated log Kow of -1.98(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that D-xylose is expected to have very high mobility in soil(SRC).
(1) Meylan WM, Howard PH; J Pharm Sci 84: 83-92 (1995)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington,DC: Amer Chem Soc pp. 4-9 (1990)
(3) Swann RL et al; Res Rev 85: 23 (1983)

14.2.9 Volatilization from Water / Soil

The Henry's Law constant for D-xylose is estimated as 1.2X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that D-xylose is expected to be essentially nonvolatile from water surfaces(2). D-Xylose's Henry's Law constant(1) indicates that volatilization from moist soil surfaces is not expected(SRC). D-Xylose is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 9.6X10-7 mm Hg(SRC), determined from a fragment constant method(3).
(1) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington,DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)
(3) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE (eds), Boca Raton,FL: CRC Press (1985)

14.2.10 Environmental Water Concentrations

SURFACE WATER: D-Xylose was detected in the Tama River, Japan at concns of 14.1-20.7 ug/l(1).
(1) Ochiai M et al; Mar Chem 25: 265-78 (1985)

14.2.11 Probable Routes of Human Exposure

NIOSH (NOES Survey 1981-1983) has statistically estimated that 11,636 workers (10,399 of these are female) are potentially exposed to D-xylose in the US(1). Occupational exposure to D-xylose may occur through inhalation of dust particles and dermal contact with this compound at workplaces where D-xylose is produced or used(SRC).
(1) NIOSH; National Occupational Exposure Survey (NOES) (1983)

15 Associated Disorders and Diseases

Disease
Small intestinal malabsorption
References
PubMed: 11418788
Disease
Kidney disease
References
Disease
Small bowel bacterial overgrowth syndrome
References
PubMed: 11418788
Disease
Colorectal cancer
References

PubMed: 7482520, 19006102, 23940645, 24424155, 20156336, 19678709, 22148915, 25105552, 21773981, 25037050, 27015276, 27107423, 27275383, 28587349

Silke Matysik, Caroline Ivanne Le Roy, Gerhard Liebisch, Sandrine Paule Claus. Metabolomics of fecal samples: A practical consideration. Trends in Food Science & Technology. Vol. 57, Part B, Nov. 2016, p.244-255: http://www.sciencedirect.com/science/article/pii/S0924224416301984

Disease
Lung Cancer
References
Disease
Eosinophilic esophagitis
References
Mordechai, Hien, and David S. Wishart

16 Literature

16.1 Consolidated References

16.2 NLM Curated PubMed Citations

16.3 Springer Nature References

16.4 Thieme References

16.5 Nature Journal References

16.6 Chemical Co-Occurrences in Literature

16.7 Chemical-Gene Co-Occurrences in Literature

16.8 Chemical-Disease Co-Occurrences in Literature

17 Patents

17.1 Depositor-Supplied Patent Identifiers

17.2 WIPO PATENTSCOPE

17.3 Chemical Co-Occurrences in Patents

17.4 Chemical-Disease Co-Occurrences in Patents

17.5 Chemical-Gene Co-Occurrences in Patents

18 Interactions and Pathways

18.1 Chemical-Target Interactions

18.2 Pathways

19 Biological Test Results

19.1 BioAssay Results

20 Taxonomy

WormJam Metabolites Local CSV for MetFrag | DOI:10.5281/zenodo.3403364
WormJam: A consensus C. elegans Metabolic Reconstruction and Metabolomics Community and Workshop Series, Worm, 6:2, e1373939, DOI:10.1080/21624054.2017.1373939
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
A metabolome atlas of the aging mouse brain. Nat Commun. 2021 Oct 15;12(1):6021. DOI:10.1038/s41467-021-26310-y. PMID:34654818; PMCID:PMC8519999.
The Metabolome Atlas of the Aging Mouse Brain: https://mouse.atlas.metabolomics.us

21 Classification

21.1 MeSH Tree

21.2 NCI Thesaurus Tree

21.3 ChEBI Ontology

21.4 KEGG: Metabolite

21.5 ChemIDplus

21.6 ChEMBL Target Tree

21.7 UN GHS Classification

21.8 NORMAN Suspect List Exchange Classification

21.9 CCSBase Classification

21.10 Consumer Product Information Database Classification

21.11 EPA TSCA and CDR Classification

21.12 LOTUS Tree

21.13 EPA Substance Registry Services Tree

21.14 Glycan Naming and Subsumption Ontology (GNOme)

21.15 MolGenie Organic Chemistry Ontology

22 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAS Common Chemistry
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  3. ChemIDplus
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  4. DrugBank
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  6. European Chemicals Agency (ECHA)
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    https://echa.europa.eu/web/guest/legal-notice
  7. Hazardous Substances Data Bank (HSDB)
  8. Human Metabolome Database (HMDB)
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  9. New Zealand Environmental Protection Authority (EPA)
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  10. CCSbase
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    https://ccsbase.net/
  11. NORMAN Suspect List Exchange
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    https://creativecommons.org/licenses/by/4.0/
    D-(+)-Xylose
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  12. ChEBI
  13. E. coli Metabolome Database (ECMDB)
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    https://ecmdb.ca/citations
  14. LOTUS - the natural products occurrence database
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    https://lotus.nprod.net/
  15. Toxin and Toxin Target Database (T3DB)
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  16. ChEMBL
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  17. ClinicalTrials.gov
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  18. Comparative Toxicogenomics Database (CTD)
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  19. Consumer Product Information Database (CPID)
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    https://www.whatsinproducts.com/contents/view/1/6
    Consumer Products Category Classification
    https://www.whatsinproducts.com/
  20. Cosmetic Ingredient Review (CIR)
  21. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
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    https://haz-map.com/About
  22. Drugs@FDA
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  23. ECI Group, LCSB, University of Luxembourg
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    https://creativecommons.org/licenses/by/4.0/
    aldehydo-D-xylose
  24. Natural Product Activity and Species Source (NPASS)
  25. West Coast Metabolomics Center-UC Davis
    Xylose
  26. FDA Orange Book
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  27. FDA Substances Added to Food
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  28. Flavor and Extract Manufacturers Association (FEMA)
  29. FooDB
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    https://foodb.ca/about
  30. GlyGen
  31. SpectraBase
  32. MassBank of North America (MoNA)
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    https://mona.fiehnlab.ucdavis.edu/documentation/license
  33. Japan Chemical Substance Dictionary (Nikkaji)
  34. KEGG
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    https://www.kegg.jp/kegg/legal.html
  35. MarkerDB
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  36. Metabolomics Workbench
  37. Nature Chemical Biology
  38. Nature Chemistry
  39. NCI Thesaurus (NCIt)
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  40. Rhea - Annotated Reactions Database
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  43. Thieme Chemistry
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    https://www.nlm.nih.gov/copyright.html
  48. GHS Classification (UNECE)
  49. EPA Substance Registry Services
  50. Glycan Naming and Subsumption Ontology (GNOme)
    GNOme
  51. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  52. PATENTSCOPE (WIPO)
  53. NCBI
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