(2R,4S,5R)-2-[(2R)-2,3-dihydroxypropoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 169734
• Molecular Formular: C9H18O8
• Molecular Mass: 254.23442
• Monoisotopic Mass: 254.10016754
• SMILES: [C@H]1([C@@H](C([C@@H](OC1CO)OC[C@@H](CO)O)O)O)O
• Canonical SMILES: OC[C@H](CO[C@@H]1OC(CO)[C@@H]([C@@H](C1O)O)O)O
• InChI: InChI=1S/C9H18O8/c10-1-4(12)3-16-9-8(15)7(14)6(13)5(2-11)17-9/h4-15H,1-3H2/t4-,5?,6+,7+,8?,9-/m1/s1
• InChIKey: NHJUPBDCSOGIKX-QDWBFMGXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4S,5R)-2-[(2R)-2,3-dihydroxypropoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,4S,5R)-2-[(2R)-2,3-dihydroxypropoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: (2R)-2,3-Dihydroxypropyl β-D-Galactopyranoside; (R)-Glyceryl β-D-Galactopyranoside; D-Glycerol-β-D-galactopyranoside; RGG; (2R)-Glycerol-O-β-D-galactopyranoside

Database IDs

• CAS Number: 16232-91-0
• PubChem SID: 162263866
• PubChem CID: 46780447

CALCULATED PROPERTIES

• Acid pKa: 12.19484
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -3.6098497
• LogD (pH = 7.4): -3.6098566
• Log P: -3.6098497
• Molar Refractivity: 52.9294 cm^3
• Polarizability: 22.045732 Å^3
• Polar Surface Area: 139.84 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 140.5-141.5°C

DETAILS

Toronto Research Chemicals - G601500

An excellent substrate for β-galactosidase and the lactose transport system as well as the lac repressor in E. coli. RGG serves as a substrate for the third lac operon encoded enzyme, thiogalactoside transacetylase.

REFERENCES

• Takahashi, K., et al.: J. Biochem., 73, 763 (1973)
• Colombo, D., et al.: Cancer Lett., 143, 1 (1973)
• Colombo, D., et al.: Eur. J. Med. Chem., 35, 1109 (1973)
• Siaut, M., et al.: Gene, 406, 23 (1973)