2-amino-3-(2,4,5-trihydroxyphenyl)propanoic acid

• ChemBase ID: 134127
• Molecular Formular: C9H11NO5
• Molecular Mass: 213.18734
• Monoisotopic Mass: 213.06372246
• SMILES: c1c(c(cc(c1O)O)O)CC(C(=O)O)N
• Canonical SMILES: OC(=O)C(Cc1cc(O)c(cc1O)O)N
• InChI: InChI=1S/C9H11NO5/c10-5(9(14)15)1-4-2-7(12)8(13)3-6(4)11/h2-3,5,11-13H,1,10H2,(H,14,15)
• InChIKey: YLKRUSPZOTYMAT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-3-(2,4,5-trihydroxyphenyl)propanoic acid
• IUPAC Traditional name: 6-hydroxydopa
• Synonyms: 6-Hydroxy-DL-DOPA; (±)-2,4,5-Trihydroxyphenylalanine;; 2,5-Dihydroxy-DL-tyrosine; 6-Hydroxy-DL-DOPA; 6-Hydroxy-DOPA; 2,4,5-Trihydroxy-DL-phenylalanine; 2,4,5-三羟基-DL-苯丙氨酸; 2,5-二羟基-DL-酪氨酸; 6-羟基-DL-多巴; (±)-2,4,5-三羟基苯丙氨酸；; 6-羟基-DL-多巴; 6-羟基多巴; 2,4,5-三羟基-DL-苯丙氨酸

Database IDs

• CAS Number: 21373-30-8; 23358-64-7
• MDL Number: MFCD00004272
• Beilstein Number: 2860065
• PubChem SID: 24278464; 162228404
• PubChem CID: 107794

CALCULATED PROPERTIES

• Acid pKa: 1.3455039
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -2.0957322
• LogD (pH = 7.4): -2.1093547
• Log P: -2.095667
• Molar Refractivity: 51.059 cm^3
• Polarizability: 19.826963 Å^3
• Polar Surface Area: 124.01 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 1 M HCl: soluble50 mg/mL (Solutions should be freshly prepared and protected from exposure to light.); H2O: soluble3 mg/mL (Dissolve in oxygen-free boiled water containing 0.1% sodium metabisulfite or other antioxidant. Solutions should be freshly prepared and protected from exposure to light.)
• Apperance: off-white powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (TLC); 99%
• Empirical Formula (Hill Notation): C9H11NO5

DETAILS

Sigma Aldrich - H2380

Caution
Hygroscopic; photosensitive
Biochem/physiol Actions
Precursor of the catecholaminergic neurotoxin, 6-hydroxydopamine; converted to 6-hydroxydopamine by L-aromatic amino acid decarboxylase.