(2S)-2-amino-3-[4-(dihydroxyboranyl)phenyl]propanoic acid

• ChemBase ID: 10023
• Molecular Formular: C9H12BNO4
• Molecular Mass: 209.00688
• Monoisotopic Mass: 209.08593827
• SMILES: O=C([C@@H](N)Cc1ccc(cc1)B(O)O)O
• Canonical SMILES: OC(=O)[C@H](Cc1ccc(cc1)B(O)O)N
• InChI: InChI=1S/C9H12BNO4/c11-8(9(12)13)5-6-1-3-7(4-2-6)10(14)15/h1-4,8,14-15H,5,11H2,(H,12,13)/t8-/m0/s1
• InChIKey: NFIVJOSXJDORSP-QMMMGPOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-[4-(dihydroxyboranyl)phenyl]propanoic acid
• IUPAC Traditional name: (2S)-2-amino-3-[4-(dihydroxyboranyl)phenyl]propanoic acid
• Synonyms: L-BPA; 4-Dihydroxyboryl-L-phenylalanine; 4-Borono-L-phenylalanine; 4-Borono-L-phenylalanine; 4-二羟基氧硼基-L-苯丙氨酸; 4-硼-L-苯丙氨酸

Database IDs

• CAS Number: 76410-58-7
• MDL Number: MFCD01075172
• Beilstein Number: 4458616
• PubChem SID: 24850368; 160973330
• PubChem CID: 150315

CALCULATED PROPERTIES

• H Donor: 4
• LogD (pH = 5.5): -2.0806193
• LogD (pH = 7.4): -2.1028657
• Log P: -2.080522
• Molar Refractivity: 49.6618 cm^3
• Polarizability: 21.12036 Å^3
• Polar Surface Area: 103.78 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true
• Acid pKa: 1.6505953
• H Acceptors: 5

PROPERTIES

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (HPLC); 97%
• Empirical Formula (Hill Notation): C9H12BNO4

DETAILS

Sigma Aldrich - 17755

Other Notes
Tyrosine analogue; employed for treatment of melanom cells by boron neutron capture therapy1
Packaging
250 mg in poly bottle