(2S)-2-amino-3-(4-methoxyphenyl)propanoic acid

• ChemBase ID: 119859
• Molecular Formular: C10H13NO3
• Molecular Mass: 195.21512
• Monoisotopic Mass: 195.08954328
• SMILES: C(=O)([C@H](Cc1ccc(cc1)OC)N)O
• Canonical SMILES: COc1ccc(cc1)C[C@@H](C(=O)O)N
• InChI: InChI=1S/C10H13NO3/c1-14-8-4-2-7(3-5-8)6-9(11)10(12)13/h2-5,9H,6,11H2,1H3,(H,12,13)/t9-/m0/s1
• InChIKey: GEYBMYRBIABFTA-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(4-methoxyphenyl)propanoic acid; rac-(2R)-2-amino-3-(4-methoxyphenyl)propanoic acid
• IUPAC Traditional name: (2S)-2-amino-3-(4-methoxyphenyl)propanoic acid; rac-(2R)-2-amino-3-(4-methoxyphenyl)propanoic acid
• Synonyms: (S)-2-amino-3-(4-methoxyphenyl)propanoic acid; 4-Methoxy-L-phenylalanine; O-Methyl-L-tyrosine; 4-METHOXY-DL-PHENYLALANINE; L-3-(p-Methoxyphenyl)alanine; L-4-Methoxyphenylalanine; L-O-Methyltyrosine; L-Tyrosine Methyl Ether; NSC 30082; O-Methyltyrosine; p-Methoxy-L-phenylalanine; β-(4-Methoxyphenyl)-L-alanine; O-Methyl-L-tyrosine; 4-甲氧基-L-苯丙氨酸; O-甲基-L-酪氨酸

Database IDs

• CAS Number: 7635-29-2; 6230-11-1
• EC Number: 228-333-9
• MDL Number: MFCD00002604
• Beilstein Number: 2212726
• PubChem SID: 162108190; 24885950; 24849727
• PubChem CID: 2723935

CALCULATED PROPERTIES

• Acid pKa: 2.0860968
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.3425161
• LogD (pH = 7.4): -1.3458074
• Log P: -1.342516
• Molar Refractivity: 51.5795 cm^3
• Polarizability: 20.416908 Å^3
• Polar Surface Area: 72.55 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~244 °C (dec.); 259-261 °C (dec.)(lit.); 259-261°C
• Optical Rotation: [α]20/D -7.0±1°, c = 1% in 5 M HCl; [α]25/D -7°, c = 0.5 in 1 M HCl

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (NT); 98%
• Impurities: ≤1% water
• Linear Formula: CH3OC6H4CH2CH(NH2)CO2H
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Sigma Aldrich - 158259

Packaging
1 g in glass bottle

Toronto Research Chemicals - M332675

A non-natural Phenylalanine (P319415) derivative.

REFERENCES

• Paradisi, F., et al.: J. Biotechnol., 128, 408 (2007)