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  • 15548-60-4, 5-溴-4-氯-3-吲哚基-beta-D-吡喃葡糖苷,X-b-D-Glucoside, CAS:15548-60-4
15548-60-4, 5-溴-4-氯-3-吲哚基-beta-D-吡喃葡糖苷,X-b-D-Glucoside, CAS:15548-60-4

15548-60-4, 5-溴-4-氯-3-吲哚基-beta-D-吡喃葡糖苷,X-b-D-Glucoside, CAS:15548-60-4

X-b-D-Glucoside
X-Glc
, 5-Bromo-4-chloro-3-indolyl-beta-D-glucopyranoside,
CAS:15548-60-4
C14H15BrClNO6 / 408.63
MFCD00063690

5-溴-4-氯-3-吲哚基-beta-D-吡喃葡糖苷,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 β-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 Number15548-60-4
Product Name5-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 FormulaC14H15BrClNO6
Molecular Weight408.63 g/mol
InChIInChI=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 KeyOPIFSICVWOWJMJ-LNNRFACYSA-N
SMILESC1=CC(=C(C2=C1NC=C2OC3C(C(C(C(O3)CO)O)O)O)Cl)Br
Synonyms5-Br-4-Cl-3-indoxyl-alpha-D-glucoside, 5-bromo-4-chloro-3-indolyl-beta-glucoside, 5-bromo-4-chloro-3-indoxylglucoside
Canonical SMILESC1=CC(=C(C2=C1NC=C2OC3C(C(C(C(O3)CO)O)O)O)Cl)Br
Isomeric SMILESC1=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

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