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59767

Sigma-Aldrich

Chlorophenol Red-β-D-galactopyranoside

≥90% (HPLC)

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Synonym(s):
CPRG, Chlorophenol Red-β-D-galactoside
Empirical Formula (Hill Notation):
C25H22Cl2O10S
CAS Number:
99792-79-7
Molecular Weight:
585.41
MDL number:
MFCD05863726
UNSPSC Code:
12352204
PubChem Substance ID:
57651696
NACRES:
NA.83

Assay

≥90% (HPLC)

form

powder or crystals

solubility

water: 20 mg/mL, clear, orange to very deep red

storage temp.

−20°C

SMILES string

OC[C@H]1O[C@@H](Oc2ccc(cc2Cl)C(=C3/C=CC(=O)C(Cl)=C3)\c4ccccc4S(O)(=O)=O)[C@H](O)[C@@H](O)[C@H]1O

InChI

1S/C25H22Cl2O10S/c26-15-9-12(5-7-17(15)29)21(14-3-1-2-4-20(14)38(33,34)35)13-6-8-18(16(27)10-13)36-25-24(32)23(31)22(30)19(11-28)37-25/h1-10,19,22-25,28,30-32H,11H2,(H,33,34,35)/b21-12-/t19-,22+,23+,24-,25-/m1/s1

InChI key

YOUWVNCQJOMMEU-AETRGLENSA-N

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General description

Chlorophenol red-β-D-galactopyranoside (CPRG) is a long-wavelength yellow dye commonly used for colorimetric assays. It serves as a substrate for β-galactosidase (β-gal) which hydrolyzes CPRG to form chlorophenol red (purple colored). This product is quantified by measuring its absorbance at 570 nm. CPRG is used to identify fecal coliform bacteria. It is about 10 times more sensitive than other chromogenic agents such as o-nitrophenyl-β-galactoside (ONPG). CPRG also has a high rapid turnover.

Application

Chlorophenol Red-β-D-galactopyranoside has been used as a substrate for β-galactosidase (β-gal):
  • in paper-based cell-free protein expression system for target RNA detection
  • in colorimetric detection of multiple clinically relevant mutations using a lacZ output gene
  • in colorimetric assay for bacteria quantification

Other Notes

Measures the expression levels of β-galactosidase in transfected cells. The lacZ gene is a popular reporter gene in transfection reactions because its product, β-galactosidase, is a very stable enzyme.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

Certificates of Analysis (COA)

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V C Wutor et al.
Chemosphere, 68(4), 622-627 (2007-04-17)
The presence of coliforms in polluted water was determined enzymatically (in situ) by directly monitoring the activity of beta-d-galactosidase (B-GAL) through the hydrolysis of the yellow chromogenic subtrate, chlorophenol red beta-d-galactopyranoside (CPRG), which produced a red chlorophenol red (CPR) product.
Generation of antigen-specific, lacZ-inducible T-cell hybrids.
S Malarkannan et al.
Methods in molecular biology (Clifton, N.J.), 156, 265-272 (2000-11-09)
C Vega et al.
Parasitology research, 95(4), 296-298 (2005-02-01)
We have developed a new pharmacological screening assay for epimastigotes of Trypanosoma cruzi (clone CL-B5) that express the Escherichia coli LacZ gene. The assay is based on determining the activity of the cytoplasmic beta-galactosidase released into the culture on membrane
D C Eustice et al.
BioTechniques, 11(6), 739-740 (1991-12-01)
A sensitive method has been developed for the detection of E. coli beta-galactosidase in transfected HeLa cells. The chromogenic substrate, CPRG (chlorophenol red-beta-D-galactopyranoside), was compared with ONPG (o-nitrophenyl-beta-D-galactopyranoside) by kinetic analysis with purified beta-galactosidase. The Km for CPRG was 1.35
P De Boever et al.
Environmental health perspectives, 109(7), 691-697 (2001-08-04)
Here we describe a redesigned protocol of the yeast estrogen screen developed by Routledge and Sumpter. The redesigned test comprises two steps. First, a large amount of yeast with estrogenic compounds is incubated for 24 hr. Subsequently, a mixture of
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