ethyl 4-{[(2R,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino}benzoate

• ChemBase ID: 161251
• Molecular Formular: C15H21NO7
• Molecular Mass: 327.32974
• Monoisotopic Mass: 327.13180202
• SMILES: c1(ccc(cc1)C(=O)OCC)N[C@@H]1OC([C@H]([C@@H](C1O)O)O)CO
• Canonical SMILES: CCOC(=O)c1ccc(cc1)N[C@@H]1OC(CO)[C@H]([C@@H](C1O)O)O
• InChI: InChI=1S/C15H21NO7/c1-2-22-15(21)8-3-5-9(6-4-8)16-14-13(20)12(19)11(18)10(7-17)23-14/h3-6,10-14,16-20H,2,7H2,1H3/t10?,11-,12+,13?,14-/m1/s1
• InChIKey: FREAPVFREJJKCA-OONHEIRLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 4-{[(2R,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino}benzoate
• IUPAC Traditional name: ethyl 4-{[(2R,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino}benzoate
• Synonyms: Benzocaine N-glucoside; N-Glucoanesthesin; 4-(β-D-glucopyranosylamino)benzoic Acid Ethyl Ester; p-(β-D-glucopyranosylamino)benzoic Acid Ethyl Ester; Benzocaine N-β-D-Glucoside

Database IDs

• CAS Number: 28315-50-6
• PubChem SID: 162255386
• PubChem CID: 71313694

CALCULATED PROPERTIES

• Acid pKa: 11.268377
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -0.607654
• LogD (pH = 7.4): -0.60770935
• Log P: -0.60765326
• Molar Refractivity: 80.6878 cm^3
• Polarizability: 31.3728 Å^3
• Polar Surface Area: 128.48 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B202985

The N-Glucoside of Benzocaine (B202970) with anesthetic activity. A potential sun-screening agent.

REFERENCES

• Rybczynska, B. et al.: Parfum. Kosm., 48, 125 (1967)
• Nikolin, A. et al.: Glas. Hemi. Tehnol. Bosne Herceg., 16, 93 (1967)