5-Bromo-4-chloro-3-indolyl-beta-D-galactopyranoside, 98+%, Thermo Scientific Chemicals

Description

It is a substrate for beta-galactosidase, which cleaves the glycosidic bond to give 5-bromo-4-chloro-3-hydroxy-1H-indole, which immediately dimerises to give an intensely blue product. It is also used to detect activity of this enzyme in histochemistry and bacteriology. It is employed as a colorless, endogenous or exogenous pigment precursors that may be transformed by biological mechanisms into colored compounds. They are used in biochemical assays and in diagnosis as indicators, particularly in the form of enzyme substrates. X-Gal is the substrate of choice for blue-white selection of recombinant bacterial colonies with the lac+ genotype.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
It is a substrate for beta-galactosidase, which cleaves the glycosidic bond to give 5-bromo-4-chloro-3-hydroxy-1H-indole, which immediately dimerises to give an intensely blue product. It is also used to detect activity of this enzyme in histochemistry and bacteriology. It is employed as a colorless, endogenous or exogenous pigment precursors that may be transformed by biological mechanisms into colored compounds. They are used in biochemical assays and in diagnosis as indicators, particularly in the form of enzyme substrates. X-Gal is the substrate of choice for blue-white selection of recombinant bacterial colonies with the lac+ genotype.

Solubility
Soluble in 100 mM in DMSO.

Notes
Moisture & Light sensitive. Store away from oxidizing agents, heat, water/moisture and light. Store under inert gas. Keep the container tightly closed and place it in a cool, dry and well ventilated condition.

Specifications

Chemical Identifiers

• CAS: 7240-90-6
• Molecular Formula: C14H15BrClNO6
• Molecular Weight (g/mol): 408.629
• MDL Number: MFCD00005666
• InChI Key: OPIFSICVWOWJMJ-AEOCFKNESA-N
• Synonym: x-gal, 5-bromo-4-chloro-3-beta-d-galactopyranosyloxy indole, 5-bromo-4-chloro-3-indolyl-beta-d-galactoside, unii-v595og374w, 5-bromo-4-chloro-3-indolyl beta-galactoside, 5-bromo-4-chloroindol-3-yl-beta-d-galactopyranoside, 5-bromo-4-chloro-3-indolyl beta-d-galactoside, 5-bromo-4-chloro-3-indolyl-beta-d-galactopyranoside, 5-bromo-4-chloro-3-indolyl beta-d-galactopyranoside, indoxyl-gal
• PubChem CID: 65181
• ChEBI: CHEBI:75055
• IUPAC Name: (2S,3R,4S,5R,6R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES: C1=CC(=C(C2=C1NC=C2OC3C(C(C(C(O3)CO)O)O)O)Cl)Br

• Melting Point: ∼236°C (decomposition)
• Quantity: 50 mg
• Beilstein: 1402009
• Sensitivity: Light and moisture sensitive
• Solubility Information: Soluble in 100 mM in DMSO.
• Optical Rotation: −62° (c=1 in 50% DMF)
• Formula Weight: 408.64
• Percent Purity: ≥98%
• Chemical Name or Material: 5-Bromo-4-chloro-3-indolyl-beta-D-galactopyranoside

Safety and Handling

Hazard Category	H302+H312+H332
Precautionary Statement	P261-P264b-P270-P271-P280-P301+P312-P302+P352-P304+P340-P312-P330-P363-P501c
EINECSNumber	230-640-8
TSCA	No
Recommended Storage	Keep cold; Store under Nitrogen

SDS

RUO – Research Use Only