3-acetamido-3-phenylpropanoic acid

• ChemBase ID: 155805
• Molecular Formular: C11H13NO3
• Molecular Mass: 207.22582
• Monoisotopic Mass: 207.08954328
• SMILES: CC(=O)NC(CC(=O)O)c1ccccc1
• Canonical SMILES: OC(=O)CC(c1ccccc1)NC(=O)C
• InChI: InChI=1S/C11H13NO3/c1-8(13)12-10(7-11(14)15)9-5-3-2-4-6-9/h2-6,10H,7H2,1H3,(H,12,13)(H,14,15)
• InChIKey: HTWAFOFDKZAKQP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-acetamido-3-phenylpropanoic acid
• IUPAC Traditional name: 3-acetamido-3-phenylpropanoic acid
• Synonyms: (±)-3-(Acetylamino)-3-phenylpropionic acid; Hydrocinnamic acid; N-Acetyl-DL-β-phenylalanine; 3-Acetylamino-3-phenyl-propionic acid; 氢化肉桂酸

Database IDs

• CAS Number: 40638-98-0
• MDL Number: MFCD00181164
• Beilstein Number: 2726794
• PubChem SID: 162249943; 24881756
• PubChem CID: 3480882

CALCULATED PROPERTIES

• Acid pKa: 4.445182
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.3974275
• LogD (pH = 7.4): -2.1601446
• Log P: 0.692624
• Molar Refractivity: 54.4294 cm^3
• Polarizability: 21.27307 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 165 - 167°C
• Hydrophobicity(logP): 0.705

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥97.0% (HPLC); 95%
• Empirical Formula (Hill Notation): C11H13NO3

DETAILS

Sigma Aldrich - 59891

Biochem/physiol Actions
N-Acetyl-β-phenylalanine is a substrate for bacterial tRNA(Phe) peptidyltransferase. Hydrocinnamic acid is an aromatic lignin monomer.
N-Acetyl-DL-β-phenylalanine is a racemic mixture of N-acetylated β-phenylalanine enantiomers. N-Acetyl-DL-β-phenylalanine is a product generated from the chromogenic substrate N-acetyl-DL-phenylalanine β-napthyl ester by specific esterase(s).