N-Benzoyl-4-hydroxy-3-methoxy-phenylalanine

Base Information

• Chemical Name: N-Benzoyl-4-hydroxy-3-methoxy-phenylalanine
• CAS No.: 2901-78-2
• Molecular Formula: C17H17NO5
• Molecular Weight: 315.326
• Hs Code.: 2924299090
• European Community (EC) Number: 684-608-7
• DSSTox Substance ID: DTXSID70398820
• Nikkaji Number: J30.772F
• Wikidata: Q82201018
• Mol file: 2901-78-2.mol

Synonyms:N-Benzoyl-4-hydroxy-3-methoxy-phenylalanine;2901-78-2;2-benzamido-3-(4-hydroxy-3-methoxyphenyl)propanoic acid;SCHEMBL7824676;DTXSID70398820;DL-Tyrosine, N-benzoyl-3-methoxy-;AKOS015961812;AC-15009;2-Benzoylamino-3-(4-hydroxy-3-methoxyphenyl)propionic acid;2-BENZOYLAMINO-3-(4-HYDROXY-3-METHOXY-PHENYL)-PROPIONIC ACID

Chemical Property of N-Benzoyl-4-hydroxy-3-methoxy-phenylalanine

Chemical Property:

• Vapor Pressure: 8.39E-16mmHg at 25°C
• Melting Point: 157 °C
• Boiling Point: 611.4oC at 760 mmHg
• PKA: 3.05±0.10(Predicted)
• Flash Point: 323.6oC
• PSA: 95.86000
• Density: 1.308g/cm3
• LogP: 2.21740
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 315.11067264
• Heavy Atom Count: 23
• Complexity: 408

Purity/Quality:

98%Min ^*data from raw suppliers

N-Benzoyl-3-methoxytyrosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)CC(C(=O)O)NC(=O)C2=CC=CC=C2)O
• Uses: N-Benzoyl-3-methoxytyrosine is an intermediate used in the synthesis of rac 3-O-Methyl DOPA (M303805), which is an impurity of Levodopa (D533751). A useful marker that can be used to screen for the absense of Aromatic L-amino acid decarboxylase (AADC).

Technology Process of N-Benzoyl-4-hydroxy-3-methoxy-phenylalanine

There total 12 articles about N-Benzoyl-4-hydroxy-3-methoxy-phenylalanine 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: 78.0%

(Z)-α-(benzamido)-β-(4-hydroxy-3-methoxyphenyl)acrylic acid (70723-31-8) → N-benzoyl-4-hydroxy-3-methoxy-phenylalanine (2901-78-2)

Guidance literature:

With hydrogenchloride; mercury; zinc; at 120 ℃; for 4h;

DOI:10.1055/s-1992-26228

Reference yield:

4-(4-hydroxy-3-methoxybenzylidene)-2-phenyl-5(4H)-oxazolone (14326-80-8,71198-75-9,71198-76-0) → N-benzoyl-4-hydroxy-3-methoxy-phenylalanine (2901-78-2)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂, aq. NH₃ / Pd-C / ethanol

2: aq. HCl

With hydrogenchloride; ammonium hydroxide; hydrogen; palladium on activated charcoal; In ethanol;

Reference yield:

(Z)-2-Benzoylamino-3-(4-benzyloxy-3-methoxy-phenyl)-acrylic acid → N-benzoyl-4-hydroxy-3-methoxy-phenylalanine (2901-78-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In acetic acid; for 1h; Yield given;

upstream raw materials:

2-(Benzoylamino)-3-(4-hydroxy-3-methoxyphenyl)acrylsaeure

N-benzoyl-β-(4-hydroxy-3-methoxyphenyl)-alaninamide

(Z)-α-(benzamido)-β-(4-hydroxy-3-methoxyphenyl)acrylic acid

Hippuric Acid

Downstream raw materials:

dopa

Refernces

• 1、 Woodhouse, Robert N.,McDonald, Edward,Ramage, Robert,Battersby, Alan R.. "Biosynthesis. Part 29.1 Colchicine: Studies on the ring expansion step focusing on the fate of the hydrogens at C-3 of autumnaline". . p. 2995 - 3001. Retrieved 2007/10/03.
• 2、 Ali, Mohammed,Khan, Naseem H.. "A Convenient Synthesis of 3,4-Dihydroxyphenylalanine (DOPA)". . p. 868 - 869. Retrieved 2007/10/02.