Xylose

Title: Xylose
CAS Registry Number: 58-86-6
CAS Name: D-Xylose
Additional Names: wood sugar
Trademarks: Xylomed (Bio-Medical); Xylo-Pfan (Savage)
Molecular Formula: C5H10O5
Molecular Weight: 150.13
Percent Composition: C 40.00%, H 6.71%, O 53.29%
Literature References: Widely distributed in plant materials, especially in wood (maple, cherry), in straw, in hulls. Not found in free state, but in form of xylan, a polysaccharide built from D-xylose units and occurring in association with cellulose. Xylose occurs also as part of glycosides. Isoln from corn cobs by boiling with 8% H2SO4: Monroe, J. Am. Chem. Soc. 41, 1002 (1919). Peanut shells and cottonseed hulls also are practical sources of xylose: Ling, Nanji, J. Chem. Soc. 1923, 620. Configuration: Hudson, Yanovsky, J. Am. Chem. Soc. 39, 1029 (1917); Haworth, Nature 116, 430 (1925). Review on history, constitution and prepn: Harding, Sugar 24, 14 (1922).
Properties: Monoclinic needles or prisms. Very sweet taste. mp 144-145° (Wheeler, Tollens, Ann. 254, 309); mp 153-154° (Hébert, Compt. Rend. 110, 970). d420 1.525. Shows mutarotation. [a]D20 +92° ® +18.6° (16 hrs c = 10). One gram dissolves in 0.8 ml water. Sol in pyridine, hot alcohol. pKa (18°): 12.14. Reduces warm Fehling's soln. Upon heating with water in closed tube to 140° or by boiling with dil H2SO4, furfurol is formed.
Melting point: mp 144-145° (Wheeler, Tollens, Ann. 254, 309); mp 153-154° (Hébert, Compt. Rend. 110, 970)
pKa: pKa (18°): 12.14
Optical Rotation: [a]D20 +92° ® +18.6° (16 hrs c = 10)
Density: d420 1.525
Use: In tanning, dyeing, and as a diabetic food.
Therap-Cat: Diagnostic aid (intestinal function).
Keywords: Diagnostic Aid.
Xylulose Xylyl Bromide Xylyl Chloride Yam, Mexican Yellow AB

D-Xylose
D-Xylopyranose Xylofuranose
Xylose chair
Xylose linear
Identifiers
CAS number 58-86-6 YesY, 609-06-3 (L-isomer) YesY[ESIS], 41247-05-6 (racemate) YesY[ESIS]
PubChem 135191
ChemSpider 119104 N
UNII A1TA934AKO YesY
EC-number 200-400-7
ChEMBL CHEMBL502135 N
Jmol-3D images Image 1
Properties[1][2]
Molecular formula C5H10O5
Molar mass 150.13 g/mol
Appearance monoclinic needles or prisms, colourless
Density 1.525 g/cm3 (20 °C)
Melting point 144–145 °C
Chiral rotation [α]D +22.5° (CHCl3)
Hazards
NFPA 704
NFPA 704.svg
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1
0
Related compounds
Related aldopentoses Arabinose
Ribose
Lyxose
Related compounds Xylulose
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Xylose (cf. Greek ξύλον, xylon, "wood") is a sugar first isolated from wood, and named for it. Xylose is classified as a monosaccharide of the aldopentose type, which means that it contains five carbon atoms and includes a formyl functional group. It is derived from hemicellulose, one of the main constituents of biomass. Like most sugars, it can adopt several structures depending on conditions. With its free carbonyl group, it is a reducing sugar.