(2R)-2-ammonio-3-(3,4-dihydroxyphenyl)propanoate

Base Information

• Chemical Name: (2R)-2-ammonio-3-(3,4-dihydroxyphenyl)propanoate
• CAS No.: 5796-17-8
• Molecular Formula: C9H11NO4
• Molecular Weight: 197.191
• Hs Code.: 2922509090
• Mol file: 5796-17-8.mol

Synonyms:(2R)-2-ammonio-3-(3,4-dihydroxyphenyl)propanoate;D-dopa zwitterion;CHEBI:149689;(2R)-2-azaniumyl-3-(3,4-dihydroxyphenyl)propanoate

Chemical Property of (2R)-2-ammonio-3-(3,4-dihydroxyphenyl)propanoate

Chemical Property:

• Appearance/Colour: white to tan powder
• Vapor Pressure: 7.97E-09mmHg at 25°C
• Melting Point: 276-278 °C (lit.)
• Refractive Index: 1.654
• Boiling Point: 448.4 °C at 760 mmHg
• PKA: 2.24±0.20(Predicted)
• Flash Point: 225 °C
• PSA: 103.78000
• Density: 1.468 g/cm³
• LogP: 0.75250
• Storage Temp.: −20°C
• Solubility.: 0.5 M HCl: soluble
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 197.06880783
• Heavy Atom Count: 14
• Complexity: 204

Purity/Quality:

98%,99%, ^*data from raw suppliers

D-DOPA| ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1CC(C(=O)[O-])[NH3+])O)O
• Isomeric SMILES: C1=CC(=C(C=C1C[C@H](C(=O)[O-])[NH3+])O)O
• Uses: A DOPA enantiomer that lacks biological activity. D-DOPA (Levodopa EP Impurity D) is a DOPA enantiomer that lacks biological activity.

Technology Process of (2R)-2-ammonio-3-(3,4-dihydroxyphenyl)propanoate

There total 23 articles about (2R)-2-ammonio-3-(3,4-dihydroxyphenyl)propanoate 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: 91.0%

(R)-2-amino-3-(3,4-dimethoxyphenyl)propanoic acid (33605-56-0) → D-Dopa (5796-17-8,90638-38-3)

Guidance literature:

With hydrogen bromide; for 12h; Reflux; Industrial scale;

Reference yield: 70.0%

(R)-1,1-dimethylethyl 2-amino-3-(3,4-methylenedioxyphenyl)propanoate (345896-50-6) → D-Dopa (5796-17-8,90638-38-3)

Guidance literature:

With hydrogenchloride; phenol; In acetic acid; at 130 - 135 ℃; for 36h;

DOI:10.1021/jo015569c

Reference yield: 62.0%

(R)-2-(N-(phenylsulfonyl)amino)-3-(3,4-dimethoxyphenyl)propionic acid (88425-44-9) → D-Dopa (5796-17-8,90638-38-3)

Guidance literature:

With hydrogen bromide; phenol; for 1h; Heating;

DOI:10.1021/ja00316a047

upstream raw materials:

tyrosine

N-acetyl-3,4-dihydroxy-D-phenylalanine

dopa

(R)-2-(N-(phenylsulfonyl)amino)-3-(3,4-dimethoxyphenyl)propionic acid

Downstream raw materials:

N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-(4-methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-3-hydroxy-D-tyrosine

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

6-fluoro-D-DOPA

(R)-3-(2-Fluoro-4,5-dimethoxy-phenyl)-2-(2,2,2-trifluoro-acetylamino)-propionic acid ethyl ester

Refernces

• 1、 Hellinghausen, Garrett,Lopez, Diego A.,Lee, Jauh T.,Wang, Yadi,Weatherly, Choyce A.,Portillo, Abiud E.,Berthod, Alain,Armstrong, Daniel W.. "Evaluation of the Edman degradation product of vancomycin bonded to core-shell particles as a new HPLC chiral stationary phase". . p. 1067 - 1078. Retrieved 2018/08/01.
• 2、 Remelli, Maurizio,Faccini, Stefania,Conato, Chiara. "Chiral ligand-exchange resolution of underivatized amino acids on a dynamically modified stationary phase for RP-HPTLC". . p. 313 - 318. Retrieved 2014/06/09.