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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Sigma-Aldrich

X1500

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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
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.
Tran N Pham et al.
Journal of the American Chemical Society, 126(40), 13100-13110 (2004-10-08)
We have developed methodology for the determination of solution structures of small molecules from residual dipolar coupling constants measured in dilute liquid crystals. The power of the new technique is demonstrated by the determination of the structure of methyl beta-d-xylopyranoside
Marìa Eugenia Hidalgo-Lara et al.
Journal of industrial microbiology & biotechnology, 32(8), 345-348 (2005-06-30)
Synthesis of extracellular xylanase in Cellulomonas flavigena is induced in the presence of xylan and sugarcane bagasse as substrates. The essential factors for efficient production of xylanase are the appropriate medium composition and an inducing substrate. The increase in xylanase
V Petrović et al.
Carbohydrate research, 302(1-2), 13-18 (1997-07-11)
Selective pivaloylations of methyl beta-D-xylopyranoside have been studied under various reaction conditions. Partially pivaloylated products were submitted to additional acetylations. The structures were established by 1H NMR spectroscopy. Representatives of acylated methyl beta-D-xylopyranosides (acyl being pivaloyl, acetyl, or a combination
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