rac-(2R)-2-amino-3-(4-fluorophenyl)propanoic acid

• ChemBase ID: 67278
• Molecular Formular: C9H10FNO2
• Molecular Mass: 183.1796032
• Monoisotopic Mass: 183.06955679
• SMILES: C(=O)([C@@H](N)Cc1ccc(cc1)F)O
• Canonical SMILES: N[C@H](C(=O)O)Cc1ccc(cc1)F
• InChI: InChI=1S/C9H10FNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m0/s1
• InChIKey: XWHHYOYVRVGJJY-QMMMGPOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: rac-(2R)-2-amino-3-(4-fluorophenyl)propanoic acid; (2S)-2-amino-3-(4-fluorophenyl)propanoic acid
• IUPAC Traditional name: rac-(2R)-2-amino-3-(4-fluorophenyl)propanoic acid; p-fluorophenylalanine
• Synonyms: H-Phe(4-F)-OH; 4-Fluoro-L-phenylalanine; 4-FLUORO-DL-PHENYLALANINE; (S)-4-Fluorophenylalanine; 4-Fluoro-L-phenylalanine; p-Fluoro-L-phenylalanine; 4-氟-L-苯基丙氨酸

Database IDs

• CAS Number: 1132-68-9; 51-65-0
• MDL Number: MFCD00063064
• Beilstein Number: 2416148
• PubChem SID: 162033014; 24278435; 24870843
• PubChem CID: 716312

CALCULATED PROPERTIES

• Acid pKa: 1.8572544
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.0422062
• LogD (pH = 7.4): -1.0457053
• Log P: -1.0422492
• Molar Refractivity: 45.3327 cm^3
• Polarizability: 17.601952 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~255 °C (dec.); ca 240°C dec.
• Optical Rotation: [α]20/D -25±1°, c = 1% in H2O; -25 (c=1 in water)

Safety Information

• Storage Warning: IRRITANT
• RTECS: DW1765000
• German water hazard class: 3
• TSCA Listed: false; 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... TH(7054)mouse ... TH(21823)rat ... TH(25085)

Product Information

• Purity: ≥99.0% (sum of enantiomers, HPLC); 95+%; 98%; 98+%
• Grade: puriss.
• Empirical Formula (Hill Notation): C9H10FNO2

DETAILS

Sigma Aldrich - F4646

Substrates
Substrate for tyrosine hydroxylase that has been used to study the regulation of that enzyme. Substitution of p-fluorophenylalanine for phenylalanine in the culture medium inhibits mitosis and reversibly arrests HeLa cells in G2.