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Catalog No: A10GD-4733
Cas No: 15548-60-4
Properties: Mol Formula: C14H15BrClNO6, Mol Weight: 408.63
IUPAC Name: (2S,3R,4S,5S,6R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonym: X-glucoside, 5-Bromo-4-chloroindol-3-yl-beta-D-glucopyranoside, 5-BROMO-4-CHLORO-3-INDOLYL-beta-D-GLUCOPYRANOSIDE
5-bromo-4-chloro-3-indolyl beta-D-glucoside is an indolyl carbohydrate that is the beta-D-glucoside of 3-hydroxy-1H-indole in which the indole moiety is substituted at positions 4 and 5 by chlorine and bromine, respectively. It is used to test for the presence of an enzyme, beta-glucosidase, 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 has a role as a chromogenic compound. It is an indolyl carbohydrate, an organobromine compound, an organochlorine compound, a D-aldohexose derivative and a beta-D-glucoside. It derives from an indoxyl.
Chromogenic substrate for ?-D-glucosidase, yielding a blue precipitate and contained in a chromogenic culture media for the detection of Enterococci, Streptococci, Klebsiella species, Enterobacter species and Listeria species. It is an indolyl carbohydrate that is the beta-D-glucoside of 3-hydroxy-1H-indole, in which the indole moiety is substituted at positions 4 and 5 by chlorine and bromine, respectively. It is used to test for the presence of the enzyme, beta-glucosidase, which cleaves the glycosidic bond to give 5-bromo-4-chloro-3-hydroxy-1H-indole; this immediately dimerises to give an intensely blue product.
| CAS Number | 15548-60-4 |
| Product Name | 5-Bromo-4-chloroindol-3-yl-beta-D-glucopyranoside |
| IUPAC Name | (2S,3R,4S,5S,6R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol |
| Molecular Formula | C14H15BrClNO6 |
| Molecular Weight | 408.63 g/mol |
| InChI | 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 |
| SMILES | C1=CC(=C(C2=C1NC=C2OC3C(C(C(C(O3)CO)O)O)O)Cl)Br |
| Synonyms | 5-Br-4-Cl-3-indoxyl-alpha-D-glucoside, 5-bromo-4-chloro-3-indolyl-beta-glucoside, 5-bromo-4-chloro-3-indoxylglucoside |
| Canonical SMILES | C1=CC(=C(C2=C1NC=C2OC3C(C(C(C(O3)CO)O)O)O)Cl)Br |
| Isomeric SMILES | C1=CC(=C(C2=C1NC=C2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)Cl)Br |
CAS No: 15548-60-4 Synonyms: X-b-D-GlucosideX-Glc MDL No: MFCD00063690 Chemical Formula: C14H15BrClNO6 Molecular Weight: 408.63 |
COA:
Name: 5-Bromo-4-chloro-3-indolyl-beta-D-glucopyranoside
CAS: 15548-60-4 M.F.: C14H15BrClNO6 M.W.: 408.63
|
Items |
Standards |
Results |
|
Appearance |
White crystalline power |
Positive |
|
Solubility |
Soluble in DMF and insoluble in ether |
Positive |
|
NMR and MS |
Should comply |
Complies |
|
Identification |
IR and TLC |
Positive |
|
Alpha-Isomer |
Max. 0.5% |
0.16% |
|
TLC (15%H2SO4-C2H5OH) |
Should be one spot |
Complies |
|
Assay by HPLC |
Min. 98% |
98.6% |
References:
1. Horwitz JP, et al., J. Med. Chem. 1964, 7, 574
| Size | 1 G, 100 MG, 5 G, Other |
|---|
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