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

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

Uses

Used in Pharmaceutical Research:
DL-4-Chlorophenylalanine is used as a tryptophan hydroxylase 1 (TPH1) inhibitor for various research applications, including the study of serotonin's role in biological processes and the development of potential therapeutic agents targeting the serotonin pathway.
Used in Neurobiological Research:
DL-4-Chlorophenylalanine is used to induce insomnia in rat models, providing insights into the mechanisms underlying sleep regulation and the potential for developing treatments for sleep disorders.
Used in Developmental Biology:
DL-4-Chlorophenylalanine is used to treat embryos in order to examine its effects on serotonin levels and related developmental processes, contributing to a better understanding of serotonin's role in embryonic development.
Used in Microbiology:
DL-4-Chlorophenylalanine is used for the selection of Enterococcus faecalis transformants with pESentA32 plasmid, aiding in the study of gene expression and antibiotic resistance in bacteria.
Used in Entomology:
DL-4-Chlorophenylalanine is used to feed flies in order to explore the effects of serotonin on insect behavior and physiology, furthering the understanding of neurotransmitter function in insects.

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

• 41888-55-5 N-benzoyl-(4'-chloro)phenylalanine 
• 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 
• 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 
• 14437-20-8 2-chloro-3-(4-chloro-phenyl)-propionic acid 

Downstream Products

• 99950-57-9 N,N'Bis--acetamidin 
• 52031-05-7 2-amino-3-(4-chlorophenyl)propionic acid ethyl ester hydrochloride 
• 123760-73-6 3-(4-Chloro-phenyl)-2-(4-phenoxy-benzylamino)-propionic acid 
• 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 
• 123760-74-7 2-[(Biphenyl-4-ylmethyl)-amino]-3-(4-chloro-phenyl)-propionic acid 
• 127888-10-2 (S)-(N-benzyloxycarbonyl)-p-chlorophenylalanine 
• 746672-89-9 2-allyloxycarbonylamino-3-(4-chlorophenyl)-propanoic acid 
• 14091-08-8 para-Chloro-D-phenylalanine 
• 103-82-2 phenylacetic acid 
• 482281-07-2 N-phenylacetyl-4-chloro-L-phenylalanine 
• 74444-78-3 2-Amino-3-(4-chloro-phenyl)-propionic acid butyl ester; hydrochloride 
• 68090-87-9 N-trifluoroacetyl-p-chloro-DL-phenylalanine 
• 123760-82-7 3-(4-Chloro-phenyl)-2-((E)-3-phenyl-allylamino)-propionic acid 

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.

Organocatalytic Enantioselective Addition of α-Aminoalkyl Radicals to Isoquinolines

With a dual organocatalytic system involving a chiral phosphoric acid and a dicyanopyrazine-derived chromophore (DPZ) photosensitizer and under the irradiation with visible light, an enantioselective Minisci-type addition of α-amino acid-derived redox-active esters (RAEs) to isoquinolines has been developed. A variety of prochiral α-aminoalkyl radicals generated from RAEs were successfully introduced on isoquinolines, providing a range of valuable α-isoquinoline-substituted chiral secondary amines in high yields with good to excellent enantioselectivities.

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.

Phenylalanine ammonia lyase catalyzed synthesis of amino acids by an MIO-cofactor independent pathway

Phenylalanine ammonia lyases (PALs) belong to a family of 4-methylideneimidazole-5-one (MIO) cofactor dependent enzymes which are responsible for the conversion of L-phenylalanine into trans-cinnamic acid in eukaryotic and prokaryotic organisms. Under conditions of high ammonia concentration, this deamination reaction is reversible and hence there is considerable interest in the development of PALs as biocatalysts for the enantioselective synthesis of non-natural amino acids. Herein the discovery of a previously unobserved competing MIO-independent reaction pathway, which proceeds in a non-stereoselective manner and results in the generation of both L- and D-phenylalanine derivatives, is described. The mechanism of the MIO-independent pathway is explored through isotopic-labeling studies and mutagenesis of key active-site residues. The results obtained are consistent with amino acid deamination occurring by a stepwise E1cB elimination mechanism. All manner of things: A competing MIO-independent (MIO=4-methylideneimidazole-5-one) reaction pathway has been identified for phenylalanine ammonia lyases (PALs), which proceeds in a non-stereoselective manner, resulting in the generation of D-phenylalanine derivatives. The mechanism of D-amino acid formation is explored through isotopic-labeling studies and mutagenesis of key active-site residues.

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.

Enhanced reduction of C-N multiple bonds using sodium borohydride and an amorphous nickel catalyst

Amorphous nickel powder (Ni0) was utilised as a catalyst under mild, aqueous, basic conditions for enhancing the sodium borohydride-mediated reduction of C-N multiple bonds such as oximes, imines, hydrazones and nitriles to produce the corresponding amines in good to excellent yields.

Convenient method for reduction of C-N double bonds in oximes, imines, and hydrazones using sodium Borohydride-Raney ni system

(Chemical Equation Presented) A practical method has been developed for reduction of C-N double bond in oximes, imines, and hydrazones with sodium borohydride catalyzed by Raney Ni. The reactions were carried out in basic aqueous solution, and the desired products were obtained in moderate yields after a simple procedure. This method can be applied to synthesize simpler aliphatic or aromatic amines and its analogs. Copyright Taylor & Francis Group, LLC.

Solid phase reduction of oxazolones using BER-Ni2B-A simple synthesis of N-benzoylphenylalanines

Borohydride exchange resin (BER)-Ni2B is successfully used as a reagent for the solid phase reduction of the C-4 exocyclic double bond of oxazolones to give the N-benzoylphenylalanines and hence the corresponding amino acids.

N1 modified glycopeptides

Described herein are N′-acylated derivatives of desleucylA82846B. The compounds are useful as antibacterial agents.