X-Glc

X-b-D-Glucoside,5-Bromo-4-chloro-3-indolyl b-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. : C 14 H 15 BrClNO 6 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%H 2 SO 4 -C 2 H 5 OH) Should be one spot Complies Assay by HPLC Min. 98% 98.6% References: 1. Horwitz JP, et al., J. Med. Chem. 1964, 7, 574