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C8655

Sigma-Aldrich

4-Chloro-L-phenylalanine

Synonym(s):

L-PCPA

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250 MG
$365.00
1 G
$680.00

About This Item

Linear Formula:
ClC6H4CH2CH(NH2)CO2H
CAS Number:
14173-39-8
Molecular Weight:
199.63
Beilstein/REAXYS Number:
2416150
EC Number:
238-023-5
MDL number:
MFCD00063065
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24893091
NACRES:
NA.32

$365.00

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form

powder

Quality Level

200

mp

263 °C (dec.) (lit.)

storage temp.

−20°C

SMILES string

N[C@@H](Cc1ccc(Cl)cc1)C(O)=O

InChI

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

InChI key

NIGWMJHCCYYCSF-QMMMGPOBSA-N

Gene Information

human ... TPH1(7166) , TPH2(121278)
mouse ... TPH1(21990) , TPH2(216343)
rat ... TPH1(24848) , TPH2(317675)

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Application

4-Chloro-L-phenylalanine (L-PCPA) has been used:
  • to block serotonin synthesis by inhibiting tryptophan hydroxylase (TPH)[1]
  • to study its behavioral and electrographic effects on epileptic senegalese baboon (Papio papio)[2]
  • as a substrate for Chromobacterium violaceum phenylalanine hydroxylase[3]
  • to incubate sea urchin embryos for immunohistochemistry[4]

Biochem/physiol Actions

4-Chloro-L-phenylalanine (L-PCPA) inhibits the synthesis of 5-hydroxytryptamine (5-HT).[5] 4-Chloro-DL-phenylalanine (PCPA) depletes the serotonin levels in the brain by its inhibitory effect on tryptophan hydroxylase (Tph). Studies support the protective effects of PCPA against monocrotaline-induced pulmonary vascular remodeling as well as in lung inflammation.[6]
Tryptophan hydroxylase inhibitor.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Related product

Product No.
Description
Pricing

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH0125
BCCH5598
BCCC7109
BCBW7232
BCBW2200

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Zahra Sattari Najafabadi et al.
International journal of food sciences and nutrition, 70(3), 255-266 (2018-08-31)
Intake of red and processed meat increases the risk of colorectal cancer (CRC), whereas dairy product consumption and the intake of dietary fibre are negatively associated with this risk. We investigated the effect of (i) low-protein diets with either whey
Mechanism of metal-independent hydroxylation by Chromobacterium violaceum phenylalanine hydroxylase
Carr RT, et al.
Biochemistry, 34(22), 7525-7532 (1995)
Behavioural and electrographic effects of L-5-hydroxytryptophan and D, L-parachlorophenyl-alanine on epileptic Senegalese baboon (Papio papio)
Wada JA, et al.
Electroencephalography and Clinical Neurophysiology, 33(5), 520-526 (1972)
Serotonin synthesis and metabolism-related molecules in a human prostate cancer cell line
Shinka T, et al.
Oncology Letters, 2(2), 211-215 (2011)
Mustafa Fazli et al.
Applied and environmental microbiology, 81(11), 3623-3630 (2015-03-22)
Burkholderia cenocepacia is an emerging opportunistic pathogen causing life-threatening infections in immunocompromised individuals and in patients with cystic fibrosis, which are often difficult, if not impossible, to treat. Understanding the genetic basis of virulence in this emerging pathogen is important
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