(2R)-2-amino-3-(3-hydroxyphenyl)propanoic acid

Base Information

• Chemical Name: (2R)-2-amino-3-(3-hydroxyphenyl)propanoic acid
• CAS No.: 32140-49-1
• Molecular Formula: C9H11NO3
• Molecular Weight: 181.191
• Hs Code.: 2922509090
• European Community (EC) Number: 608-709-2
• DSSTox Substance ID: DTXSID601019808
• Nikkaji Number: J35.770G
• Mol file: 32140-49-1.mol

Synonyms:D-m-Tyrosine;32140-49-1;3-Hydroxy-D-phenylalanine;(2R)-2-amino-3-(3-hydroxyphenyl)propanoic acid;(R)-2-AMINO-3-(3-HYDROXYPHENYL)PROPANOIC ACID;D-Phenylalanine, 3-hydroxy-;(2R)-2-azaniumyl-3-(3-hydroxyphenyl)propanoate;MFCD03788083;H-D-PHE(3-OH)-OH;SCHEMBL4356402;DTXSID601019808;AKOS016842414;AM83355;AS-38542;CS-0060412;EN300-98885;Z995228562

Chemical Property of (2R)-2-amino-3-(3-hydroxyphenyl)propanoic acid

Chemical Property:

• Vapor Pressure: 1.09E-06mmHg at 25°C
• Refractive Index: 1.614
• Boiling Point: 387.238 °C at 760 mmHg
• PKA: 2.20±0.10(Predicted)
• Flash Point: 187.995 °C
• PSA: 83.55000
• Density: 1.333 g/cm³
• LogP: 1.04690
• Storage Temp.: Store at RT.
• XLogP3: -2.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 181.07389321
• Heavy Atom Count: 13
• Complexity: 184

Purity/Quality:

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

D-m-Tyrosine 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)O)CC(C(=O)O)N
• Isomeric SMILES: C1=CC(=CC(=C1)O)C[C@H](C(=O)O)N

Technology Process of (2R)-2-amino-3-(3-hydroxyphenyl)propanoic acid

There total 33 articles about (2R)-2-amino-3-(3-hydroxyphenyl)propanoic acid 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: 99.0%

(3S,5S,6R)-3-(3-Benzyloxy-benzyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester → m-tyrosine (587-33-7,775-06-4,2180-37-2,32140-49-1,29562-33-2)

Guidance literature:

With hydrogen; palladium dichloride; In tetrahydrofuran; ethanol; for 18h; under 2585.7 Torr;

DOI:10.1021/jo9706584

Reference yield: 85.0%

D/L-3-hydroxy-phenylalanine (775-06-4,29562-33-2) → m-tyrosine (587-33-7,775-06-4,2180-37-2,32140-49-1,29562-33-2) + m-hydroxy-D-phenylalanine (32140-49-1,29562-33-2)

Guidance literature:

With α-chymotrypsin;

DOI:10.1002/recl.19841030402

Reference yield: 85.0%

D/L-3-hydroxy-phenylalanine (775-06-4,29562-33-2) → m-tyrosine (587-33-7,775-06-4,2180-37-2,32140-49-1,29562-33-2) + m-hydroxy-D-phenylalanine (32140-49-1,29562-33-2)

Guidance literature:

With α-chymotrypsin;

DOI:10.1002/recl.19841030402

upstream raw materials:

L-phenylalanine

D/L-3-hydroxy-phenylalanine

3-benzyloxybenzyl bromide

(3-(benzyloxy)phenyl)methanol

Downstream raw materials:

(S)-2-((tert-butoxycarbonyl)amino)-3-(3-hydroxyphenyl)propanoic acid

Boc-L-m-Tyr-Gly-Gly-L-Phe-L-Leu-OEt

D/L-3-hydroxy-phenylalanine

Boc-D-m-tyrosine

Refernces

• 1、 Lovelock, Sarah L.,Lloyd, Richard C.,Turner, Nicholas J.. "Phenylalanine ammonia lyase catalyzed synthesis of amino acids by an MIO-cofactor independent pathway". supporting information. p. 4652 - 4656. Retrieved 2014/05/20.
• 2、 -. "FLUORINE RADIOLABELLING PROCESS". Page/Page column 100. . Retrieved 2012/02/01.