IUPACName=(2"R",3"S",4"S",5"R",6"S")-2- (Hydroxymethyl)-6-(1"H"-indol -3-yloxy)tetrahydropyran-3,4,5-triol
Section1= Chembox Identifiers
Section2= Chembox Properties
Section3= Chembox Hazards
Autoignition= Indican is a colourless
organic compound, soluble in water, naturally occurring in " Indigofera" plants. It is a precursor of indigo dye. [ [http://cancerweb.ncl.ac.uk/cgi-bin/omd?indican Definition: indican from Online Medical Dictionary ] ]
Common and significant reactions involving indican are as follows:
*Indican is a
glycoside. Its hydrolysisyields β-D- glucoseand indoxyl.
*Reaction of indoxyl (indican) by a mild
oxidizing agent, e.g. atmospheric oxygen, yields indigo dyewhich is blue in colour.
A reaction, similar to the above mentioned is seen in the normal population [ [http://www.ajcn.org/cgi/content/abstract/19/2/113 Urinary Excretion of Indoxyl Sulfate (Indican) by Human Subjects Ingesting a Semisynthetic Diet Containing Variable Quantities of l-Tryptophan - BRYAN 19 (2): 113 - American J... ] ] , who excrete small amounts of the chemical in their urine. Normal urine reacting to
hydrogen peroxidedoes at times produce a bluish tinge.Tryptophan is first converted to indole(excreted in faeces), then to indican by bacteriain the gut. Indican, being water soluble, is then excretedthrough the urine. Following absorption from the gut, indoleis converted to "3-hydroxy indole ( indoxylor indican)" in the liver, where it is again then conjugated with sulfuric acidor glucoronic acidthrough normal xenobiotic metabolismpathways. It is then transported to the kidneys for excretion. [ [http://www.vitaminlady.com/Health_Testing/BioDia107.asp Urine Indican Test ] ] [ [http://biocenterlab.org/tests/urine/indican.shtml Bio Center Lab tests Urine Metabolism - Indican ] ]
The enzyme "indoxyl esterase" has been found in humans and is involved in another pathway of chemical reactions involving indoxyl [http://www.jcb.org/cgi/reprint/39/2/286.pdf] .
In individuals affected by the
blue diaper syndrome, the patients exhibit a defect in tryptophanmetabolism. and from there into the diaperwhere, upon exposure to air, it is converted to indigo dye due to oxidation by atmospheric oxygen.
Indican interferes with many commercial procedures for measuring total bilirubin [ [http://www.clinchem.org/cgi/content/abstract/31/1/92 Indican interference with six commercial procedures for measuring total bilirubin - Poon and Hinberg 31 (1): 92 - Clinical Chemistry ] ] which can be a problem for renal failure patients where blood indican levels are raised. It can cause gastrointestinal symptoms in patients where
proteinabsorption is reduced - like Hartnup's disease, allowing for greater bacterial decomposition of the Tryptophanto indoleand its conversion to indican.
Wikimedia Foundation. 2010.