7424-00-2

Basic information

• Product Name: DL-4-Chlorophenylalanine
• Synonyms: (±)-3-(4-Chlorophenyl)-2-aminopropanoic acid;NSC-77370;DL-4-Chloro-phe-OH;DL-2-Amino-3-(4-chloro-phenyl)-propionic acid;DL-Phe(4-Cl)-OH 4-Chloro-DL-Phenylalanine;H-4-Chloro-DL-Phe-OH, (RS)-2-AMino-3-(4-chloro-phenyl)-propionic acid, Fenclonine, PCPA;4-Chloro-DL-phenylalanine, 98+%;DL-4-Chlorophenylalanine, 98+%, 98+%
• CAS NO: 7424-00-2
• Molecular Formula: C₉H₁₀ClNO₂
• Molecular Weight: 199.63
• EINECS: 231-051-9
• Mol File: 7424-00-2.mol
• Article Data: 13

Chemical Properties

• Melting Point: >240 °C (dec.)(lit.)
• Boiling Point: 339.5 °C at 760 mmHg
• Flash Point: 159.1 °C
• Appearance: White to almost white/Powder
• Density: 1.2409 (rough estimate)
• Refractive Index: 1.5790 (estimate)
• Storage Temp.: −20°C
• Solubility: Aqueous Acid (Slightly), Methanol (Slightly)
• PKA: pK1: 2.08(+1);pK2: 8.96(0) (25°C)
• Water Solubility: slightly soluble
• BRN: 2805758
• CAS DataBase Reference: DL-4-Chlorophenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: DL-4-Chlorophenylalanine(7424-00-2)
• EPA Substance Registry System: DL-4-Chlorophenylalanine(7424-00-2)

Safety Data

• Hazard Codes: T
• Statements: 25-43
• Safety Statements: 36/37-45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: AY4390010
• TSCA: Yes
• Hazardous Substances Data: 7424-00-2(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline

Uses

Different sources of media describe the Uses of 7424-00-2 differently. You can refer to the following data:
1. An irreversible tryptophan hydroxylase inhibitor.
2. 4-Chloro-DL-phenylalanine is an irreversible tryptophan hydroxylase inhibitor that depletes serotonin in the brain.
3. 4-Chloro-DL-phenylalanine has been used:as tryptophan hydroxylase 1 (TPH1) inhibitor to treat kras+ male zebrafishto induce insomnia in rat modelsused to treat embryos to examine its effect on serotoninfor the selection of Enterococcus faecalis transformants with pESentA32 plasmidto feed flies to explore serotonin effect

Biological Activity

4-Chloro-DL-phenylalanine (Fenclonine, PCPA, CP-10188) is a selective and irreversible inhibitor of tryptophan hydroxylase, a rate-limiting enzyme in the biosynthesis of serotonin (5-HYDROXYTRYPTAMINE). 4-Chloro-DL-phenylalanine acts pharmacologically to deplete endogenous levels of serotonin.

Biochem/physiol Actions

4-Chloro-DL-phenylalanine (PCPA) is an inhibitor of 5-hydroxytrytamine (5-HT) synthesis. It helps to improve the inflammation of lung tissue and remodeling pulmonary artery. PCPA can reduce the expression of tryptophan hydroxylase 1 (TPH1), matrix metalloproteinase (MMP) and pro-inflammatory factors.

Safety Profile

An experimental teratogen. When heated to decomposition it emits toxic fumes of NOx and Cl-.

in vivo

4-Chloro-DL-phenylalanine(PCPA) markedly attenuates MCT(monocrotaline)-induced pulmonary vascular remodeling and lung inflammation, inhibits the expression of Tph-1 and SERT and suppresses the expression of MMP-2/-9, TIMP-1/-2, interleukin-1β (IL-1β), tumor necrosis factor-α (TNF-α) and intercellular adhesion molecule-1 (ICAM-1). PCPA inhibits 5-HT by suppressing Tph-1, regulating SERT and the serotonin downstream signaling pathway.

InChI:InChI=1/C9H10ClNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)

Upstream product

• 21405-64-1 <(4-chlorophenyl)methyl>propanedioic acid 
• 1615-02-7 p-chlorocinnamic acid 
• 14173-39-8 p-chlorophenylalanine 
• 1353886-55-1 ethyl 3-(4-chlorophenyl)-2-(hydroxyimino)propionate 
• 39109-62-1 1,1-dichloro-3-(4-chloro-phenyl)-propene 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 84713-70-2 N-(4-chlorophenyl)methyleneglycine ethyl ester 
• 104-88-1 4-chlorobenzaldehyde 
• 140860-98-6 methyl (N-benzoyl)-4'-chlorophenylalaninate 
• 15601-44-2 (Z)-2-phenyl-4-(4-chlorobenzylidene)-5(4H)-oxazolone 
• 41888-55-5 N-benzoyl-(4'-chloro)phenylalanine 
• 84713-70-2 [(4-chloro-benzylidene)-amino]-acetic acid ethyl ester 
• 622-95-7 4-chlorobenzyl bromide 
• 52031-05-7 2-amino-3-(4-chlorophenyl)propionic acid ethyl ester hydrochloride 

Downstream Products

• 121935-79-3 2-<(4-chlorophenyl)methyl>-7-methyl-4,5-dihydro-1H-azepine-3,6-dicarbonitrile 
• 121935-80-6 2-<(4-chlorophenyl)methyl>-1,5-dicyano-4-methyl-3-azabicyclo<3.2.0>hept-3-ene-2-carboxylic acid 
• 394210-37-8 4-(4-chloro-benzyl)-2,5-dioxo-oxazolidine-3-carboxylic acid benzyl ester 
• 51301-86-1 Boc-p-chloro-L-Phe-OH 
• 14091-08-8 para-Chloro-D-phenylalanine 
• 29622-19-3 (±)-ethyl 2-amino-3-(4-chlorophenyl)propanoate 
• 14091-10-2 N-acetyl-4-chlorophenylalanine 
• 250740-51-3 Fmoc-4-chlorophenylalanine 
• 41888-55-5 N-benzoyl-(4'-chloro)phenylalanine 
• 74444-66-9 ester hexylique de la parachlorophenylalanine chlorhydrate 
• 74444-78-3 2-Amino-3-(4-chloro-phenyl)-propionic acid butyl ester; hydrochloride 

Relevant articles and documents

Bi-enzymatic Conversion of Cinnamic Acids to 2-Arylethylamines

The conversion of carboxylic acids, such as acrylic acids, to amines is a transformation that remains challenging in synthetic organic chemistry. Despite the ubiquity of similar moieties in natural metabolic pathways, biocatalytic routes seem to have been overlooked for this purpose. Herein we present the conception and optimisation of a two-enzyme system, allowing the synthesis of β-phenylethylamine derivatives from readily-available ring-substituted cinnamic acids. After characterisation of both parts of the reaction in a two-step approach, a set of conditions allowing the one-pot biotransformation was optimised. This combination of a reversible deaminating and irreversible decarboxylating enzyme, both specific for the amino acid intermediate in tandem, represents a general method by which new strategies for the conversion of carboxylic acids to amines could be designed.

PROCESS FOR THE RACEMIZATION OF ALPHA-AMINO ACIDS

According to the present invention, a method is provided wherein a basic aqueous phase containing an optically active α-amino acid is brought into contact with an organic phase containing a racemisation catalyst in the form of a copper metal complex of copper ions and an α-amino acid and salicylaldehyde, in the presence of a phase transition catalyst, thereby subjecting the optically active α-amino acid to racemisation. In the α-amino acid racemisation method according to the present invention, the reaction conditions are mild and thus there is little α-amino acid breakdown and the yield is high, the racemisation catalyst can be reused, the α-amino acid resulting from the racemisation can easily be isolated and purified, and the racemisation method can be implemented in volume such that the invention is economic.

Immunomodulatory peptides

The invention relates to peptides derivatized with a hydrophilic polymer which, in some embodiments, bind to human FcRn and inhibit binding of the Fc portion of an IgG to an FcRn, thereby modulating serum IgG levels. The disclosed compositions and methods may be used in some embodiments, for example, in treating autoimmune diseases and inflammatory disorders. The invention also relates, in further embodiments, to methods of using and methods of making the peptides of the invention.