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B4527

Sigma-Aldrich

5-Bromo-4-chloro-3-indolyl β-D-glucopyranoside

chromogenic, ≥97%, powder

Synonym(s):

X-Glc, X-glucoside

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About This Item

Empirical Formula (Hill Notation):
C14H15BrClNO6
CAS Number:
15548-60-4
Molecular Weight:
408.63
Beilstein/REAXYS Number:
1552603
EC Number:
239-603-0
MDL number:
MFCD00063690
UNSPSC Code:
12352204
PubChem Substance ID:
24891784
NACRES:
NA.83

product name

5-Bromo-4-chloro-3-indolyl β-D-glucopyranoside, ≥97%

assay

≥97%

form

powder

solubility

DMF: 50 mg/mL, clear, colorless to faintly yellow

storage temp.

−20°C

SMILES string

OC[C@H]1O[C@@H](Oc2c[nH]c3ccc(Br)c(Cl)c23)[C@H](O)[C@@H](O)[C@@H]1O

InChI

1S/C14H15BrClNO6/c15-5-1-2-6-9(10(5)16)7(3-17-6)22-14-13(21)12(20)11(19)8(4-18)23-14/h1-3,8,11-14,17-21H,4H2/t8-,11-,12+,13-,14-/m1/s1

InChI key

OPIFSICVWOWJMJ-LNNRFACYSA-N

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Substrates

A histochemical substrate for β-glucosidase.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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R Gossrau et al.
Histochemistry, 86(4), 397-404 (1987-01-01)
5-Br-4-Cl-3-Indoxyl-alpha-D-gluco(pyrano)side was found to be the most suitable synthetic substrate for the demonstration of alpha-D-glucosidases in situ. Using an azoindoxyl procedure with hexazotized pararosaniline or new fuchsine at pH 5 in freeze-dried celloidine-mounted cryostat sections acid alpha-D-glucosidase (EC 3.2.1.20) was
H Arakawa et al.
Analytical biochemistry, 199(2), 238-242 (1991-12-01)
Chemiluminescent assays of various enzymes have been developed using indoxyl derivatives as substrates. The principle of the method is as follows: an enzyme causes hydrolysis of an indoxyl derivative to an intermediate indoxyl that is readily oxidized to indigo dye
L A Shelef et al.
Letters in applied microbiology, 25(3), 202-206 (1997-11-14)
A new instrument, capable of detecting metabolic changes due to microbiological activity, is described. Optical changes in growth media are monitored in a semi-fluid zone that separates the liquid medium containing the sample. Data demonstrate that common media can be
SUBSTRATES FOR CYTOCHEMICAL DEMONSTRATION OF ENZYME ACTIVITY. I. SOME SUBSTITUTED 3-INDOLYL-BETA-D-GLYCOPYRANOSIDES.
J P HORWITZ et al.
Journal of medicinal chemistry, 7, 574-575 (1964-07-01)
W D Watkins et al.
Applied and environmental microbiology, 54(7), 1874-1875 (1988-07-01)
A new chromogenic compound, 5-bromo-4-chloro-3-indoxyl-beta-D-glucuronide, was found to be useful for the rapid, specific, differential identification of Escherichia coli in the sanitary analysis of shellfish and wastewater. Of 1,025 presumptively positive colonies (blue) and 583 presumptively negative colonies (nonblue), only

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