Xylose

Xylose (cf. Ancient Greek: ξύλον, xylon, "wood") is a common monosaccharide, i.e. a simple sugar. Xylose is classified as aldopentose type, which means that it contains five carbon atoms and includes an aldehyde functional group, at least in its open-chain form. It is abundant in biomass, and is one of the most abundant sugars in nature. It is a white, water-soluble solid.

d-Xylose

Names

IUPAC name

d-Xylose

Systematic IUPAC name

d-xylo-Pentose

Other names

(+)-Xylose
Wood sugar

Identifiers

CAS Number

58-86-6^Y
609-06-3 (l-isomer)^Y[ESIS]
41247-05-6 (racemate)^Y[ESIS]

3D model (JSmol)

Interactive image

ChEMBL

ChEMBL502135^N

ChemSpider

119104^N

ECHA InfoCard

100.043.072

EC Number

200-400-7

PubChem CID

135191

UNII

A1TA934AKO^Y
A4JW0V2MYA (l-isomer)^Y

InChI

InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3+,4-,5?/m1/s1^N
Key: SRBFZHDQGSBBOR-IOVATXLUSA-N^N
InChI=1/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3+,4-,5?/m1/s1
Key: SRBFZHDQGSBBOR-IOVATXLUBL

SMILES

C1[C@H]([C@@H]([C@H](C(O1)O)O)O)O

Properties

Chemical formula

C
₅H
₁₀O
₅

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)

Chiral rotation ([α]_D)

+22.5° (CHCl
₃)

Magnetic susceptibility (χ)

−84.80·10⁻⁶ cm³/mol

Hazards

NFPA 704 (fire diamond)

1

0

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).

verify (what is ^YN ?)

Infobox references

Structure

The acyclic form of xylose has chemical formula HOCH
₂(CH(OH))3CHO. Cyclic hemiacetal isomers are more prevalent in solution. These cyclic isomers include the pyranoses feature six-membered C₅O rings, and the furanoses, which feature five-membered C
₄O rings (with a pendant CH
₂OH group). Each of these rings is 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.

Occurrence

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.

Xylose is also the first saccharide added to the serine or threonine in the proteoglycan type O-glycosylation, and, so, it is the first saccharide in biosynthetic pathways of most anionic polysaccharides such as heparan sulfate and chondroitin sulfate.

Xylose is also found in some species of Chrysolinina beetles, including Chrysolina coerulans. They have cardiac glycosides (including xylose) in their defensive glands.

Applications

Chemicals

The acid-catalysed degradation of hemicellulose gives furfural, a precursor to synthetic polymers and to tetrahydrofuran.

Human consumption

Xylose is not a major human nutrient and is largely excreted by the kidneys. An oxidoreductase pathway is present in eukaryotic microorganisms. Humans have enzymes called protein xylosyltransferases (XYLT1, XYLT2) which transfer xylose from UDP to a serine in the core protein of proteoglycans.

Xylose contains 2.4 calories per gram (lower than glucose or sucrose, approx. 4 calories per gram).

Animal medicine

In animal medicine, xylose is used to test for malabsorption by administration in water to the patient after fasting. If xylose is detected in blood and/or urine within the next few hours, it has been absorbed by the intestines.

High xylose intake on the order of approximately 100 g/kg of animal body weight is relatively well tolerated in pigs, and in a similar manner to results from human studies, a portion of the xylose ingested is excreted in urine unmodified.

Derivatives

Reduction of xylose by catalytic hydrogenation produces the sugar substitute xylitol.