(3E)-4-[4-(benzyloxy)-3-methoxyphenyl]-3-(ethoxycarbonyl)but-3-enoic acid

• ChemBase ID: 161818
• Molecular Formular: C21H22O6
• Molecular Mass: 370.39578
• Monoisotopic Mass: 370.14163842
• SMILES: c1(c(ccc(c1)/C=C(\CC(=O)O)/C(=O)OCC)OCc1ccccc1)OC
• Canonical SMILES: CCOC(=O)/C(=C/c1ccc(c(c1)OC)OCc1ccccc1)/CC(=O)O
• InChI: InChI=1S/C21H22O6/c1-3-26-21(24)17(13-20(22)23)11-16-9-10-18(19(12-16)25-2)27-14-15-7-5-4-6-8-15/h4-12H,3,13-14H2,1-2H3,(H,22,23)/b17-11+
• InChIKey: KEXQZIIRCUEJNR-GZTJUZNOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3E)-4-[4-(benzyloxy)-3-methoxyphenyl]-3-(ethoxycarbonyl)but-3-enoic acid
• IUPAC Traditional name: (3E)-4-[4-(benzyloxy)-3-methoxyphenyl]-3-(ethoxycarbonyl)but-3-enoic acid
• Synonyms: [[3-Methoxy-4-(phenylmethoxy)phenyl]methylene]butanedioic Acid Ethyl Ester; [[4-Benzyloxy-3-methoxyphenyl]methylene]butanedioic Acid Ethyl Ester

Database IDs

• PubChem SID: 162255953
• PubChem CID: 71313897

CALCULATED PROPERTIES

• Acid pKa: 3.7528694
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.0534039
• LogD (pH = 7.4): 0.51773524
• Log P: 3.8011296
• Molar Refractivity: 100.7401 cm^3
• Polarizability: 38.963367 Å^3
• Polar Surface Area: 82.06 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Yellow Oil

DETAILS

Toronto Research Chemicals - B286595

Intermediate in the preparation of a lignan (phenylpropanoid) with significant estrogenic activity.