2901-78-2

Usage

Uses

Used in Pharmaceutical Synthesis:
N-BENZOYL-4-HYDROXY-3-METHOXY-PHENYLALANINE is used as an intermediate in the synthesis of rac 3-O-Methyl DOPA (M303805), which is an impurity of Levodopa (D533751). This application is essential for the development of medications used in the treatment of Parkinson's disease and other related conditions.
Used in Diagnostic Applications:
N-BENZOYL-4-HYDROXY-3-METHOXY-PHENYLALANINE is used as a marker for screening the absence of Aromatic L-amino acid decarboxylase (AADC). This enzyme is involved in the conversion of Levodopa to dopamine, and its deficiency can lead to various neurological disorders. The use of N-Benzoyl-3-methoxytyrosine as a marker aids in the early detection and diagnosis of these conditions, enabling timely intervention and treatment.

InChI:InChI=1/C17H17NO5/c1-23-15-10-11(7-8-14(15)19)9-13(17(21)22)18-16(20)12-5-3-2-4-6-12/h2-8,10,13,19H,9H2,1H3,(H,18,20)(H,21,22)

Upstream product

• 34996-80-0 N-benzoyl-β-(4-hydroxy-3-methoxyphenyl)-alaninamide 
• 121-33-5 vanillin 
• 14326-80-8 4-(4-hydroxy-3-methoxybenzylidene)-2-phenyl-5(4H)-oxazolone 
• 495-69-2 Hippuric Acid 
• 70723-31-8 (Z)-α-(benzamido)-β-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 875325-99-8 2-(Benzoylamino)-3-(4-hydroxy-3-methoxyphenyl)acrylsaeure 
• 18692-68-7 m-methoxy-p-acetoxy-α-benzoylaminocinnamic acid azlactone 
• 71413-82-6 (Z)-2-methoxy-4-((5-oxo-2-phenyloxazol-4(5H)-ylidene)methyl)phenyl acetate 

Downstream Products

• 63-84-3 dopa 

Relevant academic research and scientific papers

Biosynthesis. Part 29.1 Colchicine: Studies on the ring expansion step focusing on the fate of the hydrogens at C-3 of autumnaline

The dienone ring of the intermediate 2 undergoes expansion to form the tropolone nucleus as N-formyldemecolcine 3 and colchicine 4 are biosynthesised. The additional carbon atom needed to form the 7-membered ring is provided by C-12 of the dienone 2 whils

A modified synthesis of (±)-β-aryllactic acids

The synthesis of racemic forms of the reportedly active principle of Danshen, namely (±)-β-(3,4-dihydroxyphenyl)lactic acid [(±)3-(3,4-dihydroxyphenyl)-2-hydroxypropanoic acid] and its seven racemic derivatives is reported.

A Convenient Synthesis of 3,4-Dihydroxyphenylalanine (DOPA)

A modified method for the synthesis of 3,4-dihydroxyphenylalanine (IV) is described.It involves catalytic (Raney Ni or 10percent Pd-C) hydrogenation of 4-(4'-acetoxy-3'-methoxybenzal)-2-phenyl-5-oxazolone (I) followed by hydrolysis of the reduced product N-Benzoyl-β-(4-hydroxy-3-methoxyphenyl)alaninamide (II) to give N-benzoyl-β-(4-hydroxy-3-methoxyphenyl)alanine (III) or IV in high yields under different conditions.