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3-Chloro-L-phenylalanine

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

3-chloro-L-phenylalanine is a non-proteinogenic L-alpha-amino acid that is L-phenylalanine in which one of the meta-hydrogens of the phenyl group has been replaced by a chlorine. It is a chloroamino acid, a L-phenylalanine derivative, a non-proteinogenic L-alpha-amino acid and a member of monochlorobenzenes.

Category

L-Amino Acids

Catalog number

BAT-007829

CAS number

80126-51-8

Molecular Formula

C9H10ClNO2

Molecular Weight

199.63

Specification
Reference Reading

IUPAC Name

(2S)-2-amino-3-(3-chlorophenyl)propanoic acid

Synonyms

L-Phe(3-Cl)-OH; m-Chloro-L-phenylalanine; (S)-2-Amino-3-(3-chlorophenyl)propionic acid; L-3-Chlorophenylalanine; H-Phe(3-Cl)-OH; (2S)-2-amino-3-(3-chlorophenyl)propanoic acid; 3-Chlorophenylalanine; 3-Chloro-L-phenylalanine hydrochloride; L-PHE(3-CL)-OH; D-3-Chlorophenylalanine; L-M-CHLOROPHENYLALANINE

Appearance

Light yellow to white powder

Purity

≥ 98%

Density

1.336±0.06 g/cm3 (Predicted)

Melting Point

215-216 °C

Boiling Point

339.5±32.0 °C (Predicted)

Storage

Store at 2-8 °C

InChI

InChI=1S/C9H10ClNO2/c10-7-3-1-2-6(4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m0/s1

InChI Key

JJDJLFDGCUYZMN-QMMMGPOBSA-N

Canonical SMILES

C1=CC(=CC(=C1)Cl)CC(C(=O)O)N

1.4-Chloro-DL-phenylalanine protects against monocrotaline‑induced pulmonary vascular remodeling and lung inflammation.

Bai Y1, Wang HM1, Liu M1, Wang Y1, Lian GC1, Zhang XH1, Kang J2, Wang HL1. Int J Mol Med. 2014 Feb;33(2):373-82. doi: 10.3892/ijmm.2013.1591. Epub 2013 Dec 16.

The present study was performed to investigate the effects of 4-chloro-DL-phenylalanine (PCPA), a tryptophan hydroxylase (Tph) inhibitor (TphI), on pulmonary vascular remodeling and lung inflammation in monocrotaline (MCT)-induced pulmonary arterial hypertension (PAH) in rats. Animal models of PAH were established using Sprague-Dawley (SD) rats by a single intraperitoneal injection of MCT (60 mg/kg). PCPA (50 or 100 mg/kg/day) was administered to the rats with PAH. On day 22, hemodynamic measurements and morphological observations of the lung tissues were performed. The levels of Tph-1 and serotonin transporter (SERT) in the lungs were analyzed by immunohistochemistry and western blot analysis. The expression of matrix metalloproteinase (MMP)-2 and MMP-9, tissue inhibitor of metalloproteinase (TIMP)-1 and TIMP-2 and inflammatory cytokines were assayed by western blot analysis. The activity of MMP-2 and MMP-9 was evaluated by gelatin zymography (GZ).