Description

(S)-alpha-Methyl-4-Iodophenylalanine (CAS No. 1215092-16-2) is a high-purity, non-natural amino acid derivative with the molecular formula C₁₀H₁₂INO₂. This chiral compound, also known by its IUPAC name (2S)-2-amino-3-(4-iodophenyl)-2-methylpropanoic acid, features a stereocenter at the alpha-carbon and a para-iodinated phenyl ring, making it a valuable building block for peptide modification and pharmaceutical research. With a molecular weight of 305.11 g/mol, this white to off-white crystalline powder is characterized by its high chemical stability and solubility in organic solvents such as DMSO and methanol. Ideal for medicinal chemistry applications, it serves as a key intermediate in the synthesis of bioactive peptides, enzyme inhibitors, and radiopharmaceuticals. Each batch is rigorously analyzed by HPLC, NMR, and MS to ensure ≥95% purity, meeting the stringent requirements of research and industrial applications.

Properties

• CAS Number: 1215092-16-2
• Complexity: 214
• IUPAC Name: (2S)-2-amino-3-(4-iodophenyl)-2-methyl-propanoic acid
• InChI: InChI=1S/C10H12INO2/c1-10(12,9(13)14)6-7-2-4-8(11)5-3-7/h2-5H,6,12H2,1H3,(H,13,14)/t10-/m0/s1
• InChI Key: YNCJAZPOXKKAMD-JTQLQIEISA-N
• Exact Mass: 304.99128
• Molecular Formula: C10H12INO2
• Molecular Weight: 305.11
• SMILES: C[C@](CC1=CC=C(C=C1)I)(C(=O)O)N
• Topological: 63.3
• Monoisotopic Mass: 304.99128
• Synonyms: 1215092-16-2, (S)-alpha-Methyl-4-Iodophenylalanine, alpha-Me-Phe(4-I)-OH, (S)-a-Methyl-4-iodophenylalanine, (S)-2-amino-3-(4-iodophenyl)-2-methylpropanoic acid, (2S)-2-amino-3-(4-iodophenyl)-2-methylpropanoic acid, SCHEMBL1899953, DTXSID201303942, (S)-alpha-Methyl-4-Iodophenylalaine, 4-Iodo-I+/–methyl-L-phenylalanine, AKOS030213024, E85875

Application

(S)-alpha-Methyl-4-Iodophenylalanine is widely used in peptide chemistry as a non-natural amino acid to enhance metabolic stability and modulate peptide-receptor interactions. Its para-iodo substitution makes it valuable in the development of radiolabeled compounds for PET imaging and targeted therapy. Researchers also employ this derivative in structure-activity relationship (SAR) studies to explore steric and electronic effects in drug design.

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