(2S)-3-(4-hydroxyphenyl)-2-(methylamino)propanoic acid

• ChemBase ID: 154616
• Molecular Formular: C10H13NO3
• Molecular Mass: 195.21512
• Monoisotopic Mass: 195.08954328
• SMILES: CN[C@@H](Cc1ccc(cc1)O)C(=O)O
• Canonical SMILES: CN[C@H](C(=O)O)Cc1ccc(cc1)O
• InChI: InChI=1S/C10H13NO3/c1-11-9(10(13)14)6-7-2-4-8(12)5-3-7/h2-5,9,11-12H,6H2,1H3,(H,13,14)/t9-/m0/s1
• InChIKey: AXDLCFOOGCNDST-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-3-(4-hydroxyphenyl)-2-(methylamino)propanoic acid
• IUPAC Traditional name: L-tyrosine, N-methyl-
• Synonyms: (S)-3-(4-Hydroxyphenyl)-2-(methylamino)propionic acid; N-Me-Tyr-OH; Surinamine; N-Methyl-L-tyrosine

Database IDs

• CAS Number: 537-49-5
• EC Number: 208-670-8
• MDL Number: MFCD00238322
• Beilstein Number: 2646795
• PubChem SID: 162248754
• PubChem CID: 68309

CALCULATED PROPERTIES

• Acid pKa: 1.6689992
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.2649099
• LogD (pH = 7.4): -1.26855
• Log P: -1.2649757
• Molar Refractivity: 51.8718 cm^3
• Polarizability: 20.346928 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]/D +16.0±1.0°, c = 1 in 1 M HCl

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36-38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319
• GHS Precautionary statements: P305 + P351 + P338

Product Information

• Purity: ≥98% (HPLC)
• Compostion: carbon, 60.7-62.3%; nitrogen, 6.9-7.5%
• Empirical Formula (Hill Notation): C10H13NO3

DETAILS

Sigma Aldrich - 04632

Biochem/physiol Actions
N-Methyl amino acids play an important role in investigations on prevention or therapy of Alzheimer′s disease2, neurofibrillary tangles or amyloid plaque are physiological characteristics of this disease and ?-amyloid(40) fibrillogenesis and disassembly of ?-amyloid(40) fibrils is inhibited by short ?-amyloid congeners containing N-methyl amino acids at alternate residue.
Application
N-Methyl-L-tyrosine was used in experiments as a control group to show that methylation of the imino group in N-p-phenylpropionyl-L-tyrosine eliminates its inhibitory effect on the firing of the giant neurone of the giant African snail. 1