67770

Methyl α-D-mannopyranoside

≥99.0%, suitable for microbiology, enables differentiation between species of Listeria

• Synonym(s): Methyl alpha-D-mannoside, Methyl-alpha-D-mannopyranoside, α-Methyl D-mannoside
• Empirical Formula (Hill Notation): C₇H₁₄O₆
• CAS Number: 617-04-9
• Molecular Weight: 194.18
• Beilstein: 81566
• EC Number: 210-502-3
• MDL number: MFCD00063262
• UNSPSC Code: 41106212
• PubChem Substance ID: 329760486
• NACRES: NA.85

Properties

• Quality Level: 200
• Assay: ≥99.0% (sum of enantiomers, HPLC); ≥99.0%
• form: powder
• optical activity: [α]20/D 77.0 to 82.0°, c = 10% in H₂O
• mol wt: 194.18 g/mol
• mp: 187-195 °C; 193-196 °C (lit.)
• solubility: H₂O: 0.1 g/mL, clear, colorless
• application(s): microbiology
• SMILES string: CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O
• InChI: 1S/C7H14O6/c1-12-7-6(11)5(10)4(9)3(2-8)13-7/h3-11H,2H2,1H3/t3-,4-,5+,6+,7+/m1/s1
• InChI key: HOVAGTYPODGVJG-VEIUFWFVSA-N

Description

General description

Methyl α-D-mannopyranoside is a compound that belongs to the class of organic compounds known as o-glycosyl compounds. It is used for the differentiation of Listeria species, Listeria monocytogenes, Listeria innocua, and Listeria welshimeri can ferment the sugar, producing acid which can be identified using an appropriate pH indicator. It has been used to synthesize a series of tri- and tetrahydroxylated seven-membered imino sugars in a study that worked towards a stable Noeuromycin (glycosyl cation mimic that strongly inhibits glycosidases) analog with a D-manno configuration. It has also been used in a study to investigate the primary mannose-binding site of Pradimicin A. (antifungal agent)

Application

Methyl α-D-mannopyranoside can be used to identify different species of Listeria based on their ability to ferment the sugar.

Other Notes

Unwanted binding of avidin to endogenous lectins

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): 404.1 °F
• Flash Point(C): 206.74 °C
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves