L-m-Tyrosine

Base Information

• Chemical Name: L-m-Tyrosine
• CAS No.: 587-33-7
• Deprecated CAS: 29562-33-2
• Molecular Formula: C₉H₁₁NO₃
• Molecular Weight: 181.191
• Hs Code.: 2922500090
• UNII: D5YF57V4QW
• DSSTox Substance ID: DTXSID60871778
• Nikkaji Number: J6.741E
• Wikidata: Q27096325
• NCI Thesaurus Code: C61817
• Metabolomics Workbench ID: 49745
• ChEMBL ID: CHEMBL1232501
• Mol file: 587-33-7.mol

Synonyms:3-hydroxyphenylalanine;3-tyrosine;3-tyrosine, (D)-isomer;3-tyrosine, (DL)-isomer;3-tyrosine, (L)-isomer;3-tyrosine, 14C-labeled, (DL)-isomer;m-tyrosine;meta-tyrosine

Chemical Property of L-m-Tyrosine

Chemical Property:

• Vapor Pressure: 1.09E-06mmHg at 25°C
• Melting Point: 260-270°C
• Boiling Point: 387.2°Cat760mmHg
• PKA: 2.20±0.10(Predicted)
• Flash Point: 188°C
• PSA: 83.55000
• Density: 1.333g/cm³
• LogP: 1.04690
• Storage Temp.: Store at RT.
• Solubility.: Soluble in dimethyl sulfoxide, dilute acid.
• 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:

99% ^*data from raw suppliers

L-m-Tyrosine ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

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
• Uses: An unnatural amino acid, that has demonstrated potential in treating Parkinsons disease, Alzheimers disease, and arthritis. It is an unnatural amino acid ; shown application in the treatment of Parkinson disease, Alzheimer disease, artritis It is an unnatural amino acid ; shown application in the treatment of Parkinson’s disease, Alzheimer’s disease, artritis.

Technology Process of L-m-Tyrosine

There total 25 articles about L-m-Tyrosine 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: 69.0%

(S)-2-acetylamino-3-(3-hydroxyphenyl)propionic acid (64325-07-1) → m-tyrosine (587-33-7,775-06-4,2180-37-2,32140-49-1,29562-33-2)

Guidance literature:

(S)-2-acetylamino-3-(3-hydroxyphenyl)propionic acid; With hydrogenchloride; In methanol; water; at 100 ℃; for 2h;

With sodium hydroxide; In methanol; water; at 20 ℃; pH=6;

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

methyl (2S)-2-amino-3-(3-hydroxyphenyl)propanoate hydrochloride

(S)-3-(3-Hydroxy-phenyl)-2-(2,2,2-trichloro-ethoxycarbonylamino)-propionic acid

Fmoc-3-hydroxy-L-Phe

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.