(2S,4S,5R)-2-(4-chloro-2-cyclopentylphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 164157
• Molecular Formular: C17H23ClO6
• Molecular Mass: 358.81392
• Monoisotopic Mass: 358.11831614
• SMILES: [C@H]1([C@@H](C([C@@H](OC1CO)Oc1ccc(cc1C1CCCC1)Cl)O)O)O
• Canonical SMILES: OCC1O[C@@H](Oc2ccc(cc2C2CCCC2)Cl)C([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C17H23ClO6/c18-10-5-6-12(11(7-10)9-3-1-2-4-9)23-17-16(22)15(21)14(20)13(8-19)24-17/h5-7,9,13-17,19-22H,1-4,8H2/t13?,14-,15-,16?,17+/m0/s1
• InChIKey: OIPLGSGCPWWFRT-LAYQYYCJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5R)-2-(4-chloro-2-cyclopentylphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2S,4S,5R)-2-(4-chloro-2-cyclopentylphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: 4-Chloro-2-cyclopentylphenyl-β-D-galactopyranoside

Database IDs

• CAS Number: 24718-43-2
• PubChem SID: 162258292
• PubChem CID: 46783457

CALCULATED PROPERTIES

• Acid pKa: 12.200129
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 1.6760776
• LogD (pH = 7.4): 1.6760708
• Log P: 1.6760776
• Molar Refractivity: 86.5787 cm^3
• Polarizability: 34.88015 Å^3
• Polar Surface Area: 99.38 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ether; Ethyl Acetate; Methanol
• Apperance: Off-White to Greenish Yellow Solid
• Melting Point: 75-78°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C365125

Used for selective enrichment of Shigella in the presence of E. coli.

REFERENCES

• Park, C.E. et al.: Can. J. Micro., 22 (5)
• 654-657 (1976)