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M5878

Sigma-Aldrich

Methyl β-D-xylopyranoside

≥99% (GC)

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About This Item

Empirical Formula (Hill Notation):
C6H12O5
CAS Number:
612-05-5
Molecular Weight:
164.16
EC Number:
210-289-7
MDL number:
MFCD00047532
UNSPSC Code:
12352201
PubChem Substance ID:
24897051
NACRES:
NA.25

biological source

synthetic (organic)

assay

≥99% (GC)

form

powder

optical activity

[α]20/D -66.5 to -64.5, c = 10% (w/v) in water

technique(s)

gas chromatography (GC): suitable

color

white to off-white

mp

155-158 °C (lit.)

solubility

water: 100 mg/mL, clear to hazy, colorless to light yellow

storage temp.

room temp

SMILES string

CO[C@@H]1OC[C@@H](O)[C@H](O)[C@H]1O

InChI

1S/C6H12O5/c1-10-6-5(9)4(8)3(7)2-11-6/h3-9H,2H2,1H3/t3-,4+,5-,6-/m1/s1

InChI key

ZBDGHWFPLXXWRD-JGWLITMVSA-N

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Application

Methyl β-D-xylopyranoside has been used in a study to assess tetraisopropyldisiloxane-1,3-diyl as a versatile protecting group for pentopyranosides. It has also been used in a study that investigated transacetylations to carbohydrates catalyzed by acetylxylan esterase in the presence of an organic solvent.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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D-(+)-Xylose ≥99% (GC)

Sigma-Aldrich

X1500

D-(+)-Xylose

Peter Biely et al.
Biochimica et biophysica acta, 1622(2), 82-88 (2003-07-26)
Streptomyces lividans acetylxylan esterase removes the 2- or 3-O-acetyl groups from methyl 2,4-di-O-acetyl- and 3,4-di-O-acetyl beta-D-xylopyranoside. When the free hydroxyl group was replaced with a hydrogen or fluorine, the rate of deacetylation was markedly reduced, but regioselectivity was not affected.
The partial methylation of methyl beta-D-xylopyranoside with methyl sulfate.
O WINTERSTEINER et al.
Journal of the American Chemical Society, 71(3), 939-942 (1949-03-01)
R Morosoli et al.
Archives of biochemistry and biophysics, 265(1), 183-189 (1988-08-15)
The yeast Cryptococcus albidus secretes a glycosylated xylanase (48 kDa) in the culture medium in response to beta-methylxyloside as inducer. Addition of tunicamycin to the medium results in the formation of a modified xylanase (40 kDa) which is depleted in
Richard Johnsson
Carbohydrate research, 353, 92-95 (2012-04-27)
The protecting group tetraisopropyldisiloxane-1,3-yl has been investigated for simultaneous protection of two hydroxyls on pentopyranosides. Methyl α-D-xylopyranoside is protected in excellent regioselectivity and high yield to form the 2,3-protected xylopyranoside whereas methyl β-D-xylopyranoside gives the 3,4-protected product also with excellent
Mária Mastihubová et al.
Carbohydrate research, 339(12), 2101-2110 (2004-07-29)
Four modified substrates for acetylxylan esterases, 2-deoxy, 3-deoxy, 2-deoxy-2-fluoro, and 3-deoxy-3-fluoro derivatives of di-O-acetylated methyl beta-D-xylopyranoside were synthesized via 2,3-anhydropentopyranoside precursors. Methyl 2,3-anhydro-4-O-benzyl-beta-D-ribopyranoside was transformed into methyl 2,3-anhydro-4-O-benzyl-beta-D-lyxopyranoside in three steps. The epoxide ring opening of 2,3-anhydropentopyranosides was accomplished either
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