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Sigma-Aldrich

Chlorophenol Red-β-D-galactopyranoside

β-galactosidase, ≥90% (HPLC), powder or crystals

Synonym(s):

CPRG, Chlorophenol Red-β-D-galactoside

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About This Item

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

product name

Chlorophenol Red-β-D-galactopyranoside, ≥90% (HPLC)

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.

Storage Class Code

11 - Combustible Solids

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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J H Felgner et al.
The Journal of biological chemistry, 269(4), 2550-2561 (1994-01-28)
The application of cationic liposome reagents has advanced DNA and mRNA transfection research in vitro, and data are accumulating which show their utility for in vivo gene transfer. However, chemical structure-activity data leading to a better mechanistic understanding of their
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)
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
Monpichar Srisa-Art et al.
Analytical chemistry, 90(1), 1035-1043 (2017-12-07)
Salmonella causes over a million foodborne illnesses per year in the United States resulting in more hospitalizations and deaths than any other foodborne bacterial pathogen. To help prevent outbreaks, a rapid, portable, sensitive, and reliable method for onsite detection of
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