DL-Dopa

Base Information

• Chemical Name: DL-Dopa
• CAS No.: 63-84-3
• Deprecated CAS: 587-45-1
• Molecular Formula: C9H11NO4
• Molecular Weight: 197.191
• Hs Code.: 2922500090
• European Community (EC) Number: 200-566-0
• NSC Number: 118368,16940
• UNII: QI9C343R60
• DSSTox Substance ID: DTXSID8020549
• Nikkaji Number: J128.150J
• Wikidata: Q27121510
• NCI Thesaurus Code: C81078
• Metabolomics Workbench ID: 37331
• ChEMBL ID: CHEMBL351042
• Mol file: 63-84-3.mol

Synonyms:3 Hydroxy DL tyrosine;3,4 Dihydroxyphenylalanine;3,4-Dihydroxyphenylalanine;3-Hydroxy-DL-tyrosine;beta Hydroxytyrosine;beta-Hydroxytyrosine;Dihydroxyphenylalanine;Dihydroxyphenylalanine Hydrochloride, (2:1);Dopa

Chemical Property of DL-Dopa

Chemical Property:

• Melting Point: 270-272 °C(lit.)
• Refractive Index: 1.5270 (estimate)
• Boiling Point: 448.39 °C at 760 mmHg
• PKA: 2.24±0.20(Predicted)
• Flash Point: 224.978 °C
• PSA: 103.78000
• Density: 1.468 g/cm³
• LogP: 0.75250
• Water Solubility.: Soluble in water, 0.5M dilute hydrochloric acid and formic acid. Insoluble in ethanol, benzene, chloroform and ethyl acetate.
• XLogP3: -2.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 197.06880783
• Heavy Atom Count: 14
• Complexity: 209

Purity/Quality:

3,4-Dihydroxy-DL-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: C1=CC(=C(C=C1CC(C(=O)O)N)O)O
• Uses: 3,4-Dihydroxy-DL-phenylalanine is used as a dopamine precursor. It is also useful in organic synthesis.

Technology Process of DL-Dopa

There total 46 articles about DL-Dopa which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

(-)-2-amino-3-(3,4-dimethoxyphenyl)-propionamide hydrochloride → dopa (63-84-3,90638-38-3)

Guidance literature:

With hydrogen bromide; In hydrogenchloride; water;

Reference yield: 90.0%

N-benzoyl-β-(4-hydroxy-3-methoxyphenyl)-alaninamide (34996-80-0) → dopa (63-84-3,90638-38-3)

Guidance literature:

With hydrogen bromide; for 5h; Heating;

Reference yield: 82.0%

L-586462 (4228-66-4) → dopa (63-84-3,90638-38-3)

Guidance literature:

With [pentamethylcyclopentadienyl*Ir(N-phenyl-2-pyridinecarboxamidate)Cl]; ammonium formate; In methanol; at 37 ℃; for 6h; chemoselective reaction;

DOI:10.1016/j.tetlet.2020.152196

upstream raw materials:

N-benzoyl-4-hydroxy-3-methoxy-phenylalanine

D/L-3-hydroxy-phenylalanine

2-benzamido-3-(3,4-dihydroxyphenyl)propanoic acid

Phenylalanine

Downstream raw materials:

2-amino-3-(2,6-dibromo-3,4-dihydroxyphenyl)propanoic acid

β-(2.3.6-Tribrom-4.5-dihydroxyphenyl)alanin

6-fluoro-L-dopa

3,4-dihydroxy-6-[18F]-fluoro-phenylalanine

Refernces

• 1、 Nguyen, Dat P.,Sladek, Rudolph N.,Do, Loi H.. "Scope and limitations of reductive amination catalyzed by half-sandwich iridium complexes under mild reaction conditions". supporting information. . Retrieved 2020/07/15.
• 2、 -. "Levodopa methyl ester hydrochloride synthetic method". Paragraph 0017; 0020. . Retrieved 2017/09/01.