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L-xylose

D-Xylose
D-Xylopyranose
Xylofuranose
Xylose chair
Xylose linear
Names
IUPAC name
D-Xylose
Other names
(+)-Xylose
Wood sugar
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.117.085
EC Number 200-400-7
PubChem CID
UNII
Properties
C5H10O5
Molar mass 150.13 g/mol
Appearance monoclinic needles or prisms, colourless
Density 1.525 g/cm3 (20 °C)
Melting point 144 to 145 °C (291 to 293 °F; 417 to 418 K)
+22.5° (CHCl3)
-84.80·10−6 cm3/mol
Hazards
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Related compounds
Related aldopentoses
Arabinose
Ribose
Lyxose
Related compounds
Xylulose
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 an aldehyde 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 aldehyde group, it is a reducing sugar.

The acyclic form of xylose has chemical formula HOCH2(CH(OH))3CHO. The cyclic hemiacetal isomers are more prevalent in solution and are of two types: the pyranoses, which feature six-membered C5O rings, and the furanoses, which feature five-membered C4O rings (with a pendant CH2OH group). Each of these rings subject to further isomerism, depending on the relative orientation of the anomeric hydroxy group.

The dextrorotary form, D-xylose, is the one that usually occurs endogenously in living things. A levorotary form, L-xylose, can be synthesized.

Xylose is the main building block for the hemicellulose xylan, which comprises about 30% of some plants (birch for example), far less in others (spruce and pine have about 9% xylan). Xylose is otherwise pervasive, being found in the embryos of most edible plants. It was first isolated from wood by Finnish scientist, Koch, in 1881, but first became commercially viable, with a price close to sucrose, in 1930.


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