2-[(3-chloro-4-oxocyclohexa-2,5-dien-1-ylidene)(3-chloro-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]benzene-1-sulfonic acid

• ChemBase ID: 153715
• Molecular Formular: C25H22Cl2O10S
• Molecular Mass: 585.40718
• Monoisotopic Mass: 584.03107326
• SMILES: c1ccc(c(c1)/C(=C/1\C=CC(=O)C(=C1)Cl)/c1ccc(c(c1)Cl)O[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O)S(=O)(=O)O
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2ccc(cc2Cl)/C(=C\2/C=CC(=O)C(=C2)Cl)/c2ccccc2S(=O)(=O)O)[C@@H]([C@H]([C@H]1O)O)O
• InChI: 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)/t19-,22+,23+,24-,25-/m1/s1
• InChIKey: YOUWVNCQJOMMEU-MWJCSLLCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(3-chloro-4-oxocyclohexa-2,5-dien-1-ylidene)(3-chloro-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]benzene-1-sulfonic acid
• IUPAC Traditional name: 2-[(3-chloro-4-oxocyclohexa-2,5-dien-1-ylidene)(3-chloro-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]benzenesulfonic acid
• Synonyms: CPRG; Chlorophenol Red-β-D-galactoside; Chlorophenol Red-β-D-galactopyranoside

Database IDs

• CAS Number: 99792-79-7
• MDL Number: MFCD05863726
• PubChem SID: 162247854; 24881710
• PubChem CID: 71311721

CALCULATED PROPERTIES

• Acid pKa: -2.4320579
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -0.3145753
• LogD (pH = 7.4): -0.31458327
• Log P: -0.045059618
• Molar Refractivity: 148.4252 cm^3
• Polarizability: 54.235218 Å^3
• Polar Surface Area: 170.82 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (HPLC)
• Empirical Formula (Hill Notation): C25H22Cl2O10S

DETAILS

Sigma Aldrich - 59767

Application
Suitable as substrate for β-galactosidase.
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.1,2