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C8655

Sigma-Aldrich

4-Chloro-L-phenylalanine

Synonym(s):

L-PCPA

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About This Item

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

form

powder

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)
  • to study its behavioral and electrographic effects on epileptic senegalese baboon (Papio papio)
  • as a substrate for Chromobacterium violaceum phenylalanine hydroxylase
  • to incubate sea urchin embryos for immunohistochemistry

Biochem/physiol Actions

4-Chloro-L-phenylalanine (L-PCPA) inhibits the synthesis of 5-hydroxytryptamine (5-HT). 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.
Tryptophan hydroxylase inhibitor.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

related product

Product No.
Description
Pricing

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Mechanism of metal-independent hydroxylation by Chromobacterium violaceum phenylalanine hydroxylase
Carr RT, et al.
Biochemistry, 34(22), 7525-7532 (1995)
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
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
Federico Stilo et al.
Molecules (Basel, Switzerland), 25(10) (2020-05-28)
This study applied an untargeted-targeted (UT) fingerprinting approach, based on comprehensive two-dimensional gas chromatography-time-of-flight mass spectrometry (GC×GC-TOF MS), to assess the effects of rainfall and temperature (both seasonal and elevational) on the tea metabolome. By this strategy, the same compound
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