62596-63-8

Basic information

• Product Name: (S)-4-AMINO-3-PHENYLBUTANOIC ACID
• Synonyms: (S)-4-AMINO-3-PHENYLBUTANOIC ACID;(S)-4-AMINO-3-PHENYL
• CAS NO: 62596-63-8
• Molecular Formula: C10H13NO2
• Molecular Weight: 179.22
• Mol File: 62596-63-8.mol
• Article Data: 13

Chemical Properties

• Melting Point: 194-196 °C
• Boiling Point: 327.8 °C at 760 mmHg
• Flash Point: 152.1 °C
• Appearance: /
• Density: 1.161 g/cm³
• Refractive Index: 1.563
• Storage Temp.: 2-8°C
• PKA: 4.10±0.10(Predicted)
• CAS DataBase Reference: (S)-4-AMINO-3-PHENYLBUTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-AMINO-3-PHENYLBUTANOIC ACID(62596-63-8)
• EPA Substance Registry System: (S)-4-AMINO-3-PHENYLBUTANOIC ACID(62596-63-8)

Safety Data

• Hazardous Substances Data: 62596-63-8(Hazardous Substances Data)

Usage

General Description

(S)-4-Amino-3-phenylbutanoic acid, also known as L-phenylalanine, is a non-essential amino acid that is found in high-protein foods such as meat, fish, eggs, dairy, and some grains. It is an important building block of proteins and can also be converted into tyrosine, another important amino acid. L-phenylalanine is involved in the production of several important neurotransmitters, including dopamine, norepinephrine, and epinephrine, which play a role in regulating mood, energy levels, and attention. It also has potential medicinal uses, including as a pain reliever, appetite suppressant, and treatment for depression and schizophrenia. However, it is important to use L-phenylalanine supplements with caution, as excessive levels can be toxic and can cause serious health problems, particularly for individuals with the genetic disorder phenylketonuria.

InChI:InChI=1/C10H13NO2/c11-7-9(6-10(12)13)8-4-2-1-3-5-8/h1-5,9H,6-7,11H2,(H,12,13)/t9-/m1/s1

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Relevant articles and documents

Synthesis and Biological Analysis of Anti-addiction Effect and Hepatotoxicity of Tow Baclofen Analogues Complexed with β-Cyclodextrin

Aim and Objective: The excessive consumption of alcohol and the installation of dependence is, in most cases, facilitated by favorable psychological factors that trigger and maintain the behavior of consumers. Examples more frequently encountered in individuals having difficulty with alcohol are, in particular: one or more anxiety disorders, deficits in the capacities to manage stress and anxiety. The main objective of this work was to study in vivo the anti-addiction effect and hepatotoxicity of tow baclofen analogues complexed with β-Cyclodextrin (βCD) on an alcohol-dependent rat model. Materials and Methods: The synthesis of two analogues, ABF1 and ABF2, close to baclofen was reported. The structural determination of the two compounds was confirmed by NMR and IR analysis. The complexation of analogues with β-Cyclodextrin (βCD) was performed in water at room temperature (25 °C). The interactions of ABF with β-Cyclodextrin, and the stability constant (Ka) of the inclusion complex formed between them were investigated by using UV-visible spectroscopy. The biological effects of baclofen and the two analogues on alcohol dependence were studied in wistar rats. The anti-addiction effect of the analogues was tested by measuring the alcohol intake and the variation of the animal behaviour. The toxicity of the compounds was also analysed on liver injury markers. Results: The amino-3-phenylbutanoic acid (ABF1) and 3,4,5-trihydroxy-N-(methyl-2-acetate) benzamide (ABF2) were synthesized. The complexation of both analogues of baclofen (BF) with β-cyclodextrin (βCD) (ABF-βCD) was realized and confirmed by the stability constant of the inclusion complex (Ka) and Job’s method. The evaluation of anti-addiction activity in vivo showed that ABF1-βCD inhibits the consumption of alcohol at doses equivalent to those of baclofen. Both baclofen analogues have shown an anxiolytic effect. Regarding the toxicity of the two compounds, our results showed that ABF1-βCD has less toxic effect than baclofen; it reduces the activity of ALT and AST enzymes. Histologically, ABF1-βCD has no effect on the liver structure and has a protective effect against lesions alcohol-induced liver disease. Conclusion: Therefore, it can be suggested that ABF1 analogue combined with β-Cyclodextrin can be used as a treatment for alcohol dependence. Further clinical works are needed to confirm its effectiveness.

Rhodium-catalyzed asymmetric hydrogenation of β-cyanocinnamic esters with the assistance of a single hydrogen bond in a precise position

With the assistance of hydrogen bonds, the first asymmetric hydrogenation of β-cyanocinnamic esters is developed, affording chiral β-cyano esters with excellent enantioselectivities (up to 99% ee). This novel methodology provides an efficient and concise synthetic route to chiral GABA-derivatives such as (S)-Pregabalin, (R)-Phenibut, (R)-Baclofen. Interestingly, in this system, the catalyst with a single H-bond donor performs better than that with double H-bond donors, which is a novel discovery in the metalorganocatalysis area.

Chemical assembly systems: Layered control for divergent, continuous, multistep syntheses of active pharmaceutical ingredients

While continuous chemical processes have attracted both academic and industrial interest, virtually all active pharmaceutical ingredients (APIs) are still produced by using multiple distinct batch processes. To date, methods for the divergent multistep continuous production of customizable small molecules are not available. A chemical assembly system was developed, in which flow-reaction modules are linked together in an interchangeable fashion to give access to a wide breadth of chemical space. Control at three different levels - choice of starting material, reagent, or order of reaction modules - enables the synthesis of five APIs that represent three different structural classes (γ-amino acids, γ-lactams, β-amino acids), including the blockbuster drugs Lyrica and Gabapentin, in good overall yields (49-75%).