Indican

Structural formula
General
Surname	Indican
other names	3-indoxyl-β- D -glucopyranoside; Indoxyl-β- D -glucoside; 3- (β- D -glucosido) indole; Plant indican;
Molecular formula	C 14 H 17 NO 6
Brief description	colorless solid
External identifiers / databases
EC number	610-433-2
ECHA InfoCard	100.126.244
PubChem	441564
Wikidata	Q418392
properties
Molar mass	295.29 g mol −1
Physical state	firmly
Melting point	57–58 ° C (trihydrate); 178–180 ° C (decomposition);
solubility	soluble in water; soluble in ethanol and acetone;
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

The name Indikan (also: Indican ) designates two similar derivatives of indole .

Occurrence

Plant indican is a glycoside of indoxyl and occurs naturally in some plants known as indigo plants, for example Isatis tinctoria ( woad ) or Indigofera tinctoria .

Woad ( Isatis tinctoria )
Indigofera tinctoria

properties

The indican is a colorless, water-soluble compound that is split by enzymes into ((glucose)) and yellow ((indoxyl)). Oxidation turns indoxyl into the blue dye indigo .

Urinary indican

Urinary indican (also: uroxanthine ) is the potassium salt of indoxylsulfuric acid. The confusion with the plant Indian is based on an early form of medical diagnosis, the so-called urine examination , in which the color of the urine was used for diagnostic purposes. Attention was paid to the sometimes green to blue coloration of the urine, which is now called in extreme cases purple urine bag syndrome (PUBS) and occurs especially in older catheterized women. This is also due to the dye indigo, but it does not come from the plant indican. The German biochemist Felix Hoppe-Seyler discovered the difference between plant indican and urinary indican in 1863 .

literature

WN Arnold: King George III's urine and indigo blue. In: The Lancet , 347, 1996, pp. 1811-1813. PMID 8667928 .

Individual evidence

↑ ^a ^b ^c ^d data sheet Indoxyl β-D-glucoside, ≥97% from Sigma-Aldrich , accessed on February 7, 2019 ( PDF ).
↑ ^a ^b ^c ^d Entry on Indican. In: Römpp Online . Georg Thieme Verlag, accessed on February 7, 2019.
↑ EFJ Hoppe-Seyler: About Indican as a constant urine component. In: Virchows Arch. 27, 1863, pp. 388-393.

[Sigma-1] ta sheet Indoxyl β-D-glucoside, ≥97% from Sigma-Aldrich , accessed on February 7, 2019 ( PDF ).

[Römpp-2] Entry on Indican. In: Römpp Online . Georg Thieme Verlag, accessed on February 7, 2019.

[3] EFJ Hoppe-Seyler: About Indican as a constant urine component. In: Virchows Arch. 27, 1863, pp. 388-393.