Description

(S)-2-Amino-2-methyl-3-(4-(trifluoromethoxy)phenyl)propanoic acid (CAS No. 1269926-90-0) is a high-purity, non-natural amino acid derivative designed for advanced research applications. With the molecular formula C₁₁H₁₂F₃NO₃, this compound features a chiral center at the alpha-carbon and a trifluoromethoxy-substituted phenyl group, offering unique steric and electronic properties. Its IUPAC name, (2S)-2-amino-2-methyl-3-[4-(trifluoromethoxy)phenyl]propanoic acid, reflects its precise stereochemistry. This product is ideal for peptide modification, medicinal chemistry, and biochemical studies, where its methylated backbone and fluorine-rich aromatic moiety can enhance metabolic stability and binding affinity. Supplied as a white to off-white crystalline powder with ≥95% purity (HPLC), it is rigorously characterized by ¹H/¹³C NMR, LC-MS, and chiral HPLC to ensure batch consistency. Store desiccated at -20°C for long-term stability.

Properties

• CAS Number: 1269926-90-0
• Complexity: 300
• IUPAC Name: (2S)-2-amino-2-methyl-3-[4-(trifluoromethoxy)phenyl]propanoic acid
• InChI: InChI=1S/C11H12F3NO3/c1-10(15,9(16)17)6-7-2-4-8(5-3-7)18-11(12,13)14/h2-5H,6,15H2,1H3,(H,16,17)/t10-/m0/s1
• InChI Key: AYWWOOCNIXIIJO-JTQLQIEISA-N
• Exact Mass: 263.07692773
• Molecular Formula: C11H12F3NO3
• Molecular Weight: 263.21
• SMILES: C[C@](CC1=CC=C(C=C1)OC(F)(F)F)(C(=O)O)N
• Topological: 72.6
• Monoisotopic Mass: 263.07692773
• Synonyms: 1269926-90-0, (S)-2-Amino-2-methyl-3-(4-(trifluoromethoxy)phenyl)propanoic acid, L-Tyrosine, alpha-methyl-O-(trifluoromethyl)-, (2S)-2-AMINO-2-METHYL-3-[4-(TRIFLUOROMETHOXY)PHENYL]PROPANOIC ACID, (S)-alpha-Methyl 4-Trifluoromethoxyphenylalaine;alpha-Me-Phe(4-OCF3)-OH, |A-Me-Phe(4-OCF3)-OH, AKOS025290692, CS-W020181, CS-13280, DS-019190, F12112, (S)–Methyl 4-Trifluoromethoxyphenylalaine;-Me-Phe(4-OCF3)-OH, (S)-2-Amino-2-methyl-3-(4-(trifluoromethoxy)phenyl)propanoicacid

Application

This chiral amino acid derivative serves as a critical building block in peptidomimetic drug discovery, particularly for targeting GPCRs and enzymes where fluorine substitution modulates bioavailability. The trifluoromethoxy group enhances lipophilicity for improved blood-brain barrier penetration in CNS drug candidates. Researchers utilize it to introduce conformational constraints in peptide backbones or as a probe for ¹⁹F NMR studies. Its structural features make it valuable for developing protease-resistant analogs in therapeutic peptide design.

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