5678-45-5

Basic information

• Product Name: 3-Amino-3-(4-methoxyphenyl)propionic acid
• Synonyms: DL-3-AMINO-3-(4-METHOXY-PHENYL)-PROPIONIC ACID;DL-BETA-(P-METHOXYPHENYL)ALANINE;3-AMINO-3-(P-METHOXYPHENYL)PROPIONIC ACID;3-AMINO-3-(4-METHOXYPHENYL)PROPANOIC ACID;3-AMINO-3-(4-METHOXY-PHENYL)-PROPIONIC ACID;RARECHEM AK HC T257;3-AMINO-3-(4-METHOXYPHENYL)PROPIONIC AC&;DL--(p-Methoxyphenyl)alanine
• CAS NO: 5678-45-5
• Molecular Formula: C₁₀H₁₃NO₃
• Molecular Weight: 195.22
• Product Categories: C10;Carbonyl Compounds;Carboxylic Acids;Building Blocks;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks
• Mol File: 5678-45-5.mol
• Article Data: 24

Chemical Properties

• Melting Point: 230 °C (dec.)(lit.)
• Boiling Point: 331.88°C (rough estimate)
• Appearance: /
• Density: 1.1926 (rough estimate)
• Refractive Index: 1.5150 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 3.74±0.10(Predicted)
• CAS DataBase Reference: 3-Amino-3-(4-methoxyphenyl)propionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-3-(4-methoxyphenyl)propionic acid(5678-45-5)
• EPA Substance Registry System: 3-Amino-3-(4-methoxyphenyl)propionic acid(5678-45-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 5678-45-5(Hazardous Substances Data)

Usage

Chemical Properties

white to beige crystalline powder

Upstream product

• 141-82-2 malonic acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 119208-80-9 1,3,5-tris(4-methoxyphenyl)-2,4-diazapenta-1,4-diene 
• 832-01-9 methyl p-methoxycinnamate 
• 72071-68-2 3-Hydroxyamino-3-(4-methoxy-phenyl)-propionic acid 
• 123-08-0 4-hydroxy-benzaldehyde 
• 221907-01-3 (Z)-2-(4,5-dihydro-1,3-oxazol-2-yl)-1-(4-methoxyphenyl)-1-ethen-1-amine 
• 21405-61-8 2-(4-methoxybenzylidene)malonic acid 
• 155496-02-9 tert-butyl 3-(anthracene-9-sulfonamido)-3-(4-methoxyphenyl)propanoate 
• 830-09-1 3-(4'-methoxyphenyl)propenoic acid 

Downstream Products

• 6049-54-3 3-amino-3-(4-hydroxyphenyl)propionic acid 
• 124082-17-3 3-amino-3-(4-methoxyphenyl)propionic acid methyl ester hydrochloride 
• 96363-20-1 D,L-3-<<(1,1-dimethylethoxy)carbonyl>amino>-3-(4-methoxyphenyl)propanoic acid 
• 404869-81-4 3-(4-methoxyphenyl)-3-(pyrrol-1-yl)propanoic acid 
• 167887-35-6 3-amino-3-(4-methoxyphenyl)propionic acid ethyl ester hydrochloride 
• 752960-25-1 n-propyl 3-amino-3-(4-methoxyphenyl)propionate 
• 167887-23-2 3-(4'-methoxyphenyl)-3-(3'-nitrophthalimido)propionic acid 
• 167887-14-1 3-(4'-nitrophthalimido)-3-(4'-methoxyphenyl)propionic acid 
• 180264-44-2 (+/-)-4-p-methoxy-phenyl-azetidin-2-one 
• 24393-56-4 ethyl p-methoxycinnamate 
• 945419-94-3 C₁₅H₂₅O₃NSi 
• 914099-78-8 7-{3-[2-carboxy-1-(4-methoxy-phenyl)-ethylcarbamoyl]-5-nitro-benzoylamino}-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 

Relevant articles and documents

The kinetic resolution of oxazinones by alcoholysis: access to orthogonally protected β-amino acids

The catalytic, alcoholytic kinetic resolution of oxazinones is reported. A novel, stereochemically dense cinchona alkaloid-based catalyst can facilitate the highly enantiodiscriminatory (Sup to 101) ring-opening of oxazinones equipped with electrophilic aryl units to generate orthogonally protected β-amino acids for the first time.

Base-induced Sommelet–Hauser rearrangement of N-(α-(2-oxyethyl)branched)benzylic glycine ester-derived ammonium salts via a chelated intermediate

The base-induced Sommelet–Hauser (S–H) rearrangement of N-(α-branched)benzylic glycine ester-derived ammonium salts 1 was investigated. When the α-branched substituent was a simple alkyl, such as a methyl or butyl, desired S–H rearrangement product 2 was obtained in low yield with formation of the [1,2] Stevens rearranged 4 and Hofmann eliminated products 5 and 6. However, when the α-branched substituent had a 2-oxy moiety, such as 2-acetoxyethyl or 2-benzoyloxyethyl, the yields of 2 were improved. These results could be explained by formation of chelated intermediate C that stabilizes the carbanionic ylide, and the subsequent initial dearomative [2,3] sigmatropic rearrangement would be accelerated. The existence of C was supported by mechanistic experiments. This enhancement effect is not very strong or effective; however, it will expand the synthetic usefulness of ammonium ylide rearrangements.

Synthesis, molecular docking and biological evaluation of novel phthaloyl derivatives of 3-amino-3-aryl propionic acids as inhibitors of Trypanosoma cruzi trans-sialidase

In the last two decades, trans-sialidase of Trypanosoma cruzi (TcTS) has been an important pharmacological target for developing new anti-Chagas agents. In a continuous effort to discover new potential TcTS inhibitors, 3-amino-3-arylpropionic acid derivatives (series A) and novel phthaloyl derivatives (series B, C and D) were synthesized and molecular docking, TcTS enzyme inhibition and determination of trypanocidal activity were carried out. From four series obtained, compound D-11 had the highest binding affinity value (?11.1 kcal/mol) compared to reference DANA (?7.8 kcal/mol), a natural ligand for TS enzyme. Furthermore, the 3D and 2D interactions analysis of compound D-11 showed a hydrogen bond, π-π stacking, π-anion, hydrophobic and Van der Waals forces with all important amino acid residues (Arg35, Arg245, Arg314, Tyr119, Trp312, Tyr342, Glu230 and Asp59) on the active site of TcTS. Additionally, D-11 showed the highest TcTS enzyme inhibition (86.9% ± 5) by high-performance ion exchange chromatography (HPAEC). Finally, D-11 showed better trypanocidal activity than the reference drugs nifurtimox and benznidazole with an equal % lysis (63 ± 4 and 65 ± 2 at 10 μg/mL) and LC50 value (52.70 ± 2.70 μM and 46.19 ± 2.36 μM) on NINOA and INC-5 strains, respectively. Therefore, D-11 is a small-molecule with potent TcTS inhibition and a strong trypanocidal effect that could help in the development of new anti-Chagas agents.