(2R)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid

• ChemBase ID: 126847
• Molecular Formular: C9H11NO4
• Molecular Mass: 197.18794
• Monoisotopic Mass: 197.06880784
• SMILES: O=C(O)[C@H](N)Cc1cc(O)c(O)cc1
• Canonical SMILES: OC(=O)[C@@H](Cc1ccc(c(c1)O)O)N
• InChI: InChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m1/s1
• InChIKey: WTDRDQBEARUVNC-ZCFIWIBFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
• IUPAC Traditional name: dihydroxyphenylalanine
• Synonyms: D-DOPA; 3-(3,4-Dihydroxyphenyl)-D-alanine; D-3-Hydroxytyrosine; D-DOPA; 3,4-Dihydroxy-D-phenylalanine

Database IDs

• CAS Number: 5796-17-8
• EC Number: 227-343-0
• MDL Number: MFCD00063061
• Beilstein Number: 2417637
• PubChem SID: 24863555; 162221174
• PubChem CID: 92222
• Chemspider ID: 83260
• Wikipedia Title: D-DOPA

CALCULATED PROPERTIES

• Acid pKa: 1.650697
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.7921518
• LogD (pH = 7.4): -1.8012933
• Log P: -1.7921815
• Molar Refractivity: 49.0781 cm^3
• Polarizability: 19.161877 Å^3
• Polar Surface Area: 103.78 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 276-278 °C(lit.)
• Optical Rotation: [α]20/D +11.0±1.0°, c = 1% in 1 M HCl

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (NT)
• Grade: purum
• Empirical Formula (Hill Notation): C9H11NO4

DETAILS

Sigma Aldrich - 37840

Other Notes
False dopa reaction in (cytochemical and histochemical) studies of mammalian tyrosinase: some characteristics and precautions1