- Indican
Chembox new
ImageFile=Indican.png
ImageSize=200px
IUPACName=(2"R",3"S",4"S",5"R",6"S")-2- (Hydroxymethyl)-6-(1"H"-indol -3-yloxy)tetrahydropyran-3,4,5-triol
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Section1= Chembox Identifiers
CASNo=1328-73-0
PubChem=441564
SMILES=C1=CC=C2C(=C1)C (=CN2)OC3C(C(C(C(O3)CO)O)O)O
Section2= Chembox Properties
Formula=C14H17NO6
MolarMass=295.29 g/mol
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Section3= Chembox Hazards
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Autoignition= Indican is a colourlessorganic compound , soluble in water, naturally occurring in "Indigofera " plants. It is a precursor ofindigo dye . [ [http://cancerweb.ncl.ac.uk/cgi-bin/omd?indican Definition: indican from Online Medical Dictionary ] ]Chemical reactions
Common and significant reactions involving indican are as follows:
*Indican is aglycoside . Itshydrolysis yields β-D-glucose andindoxyl .
*Reaction of indoxyl (indican) by a mildoxidizing agent , e.g. atmospheric oxygen, yieldsindigo dye which is blue in colour.Medical significance
"'Biosynthesis
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 peroxide does at times produce a bluish tinge.Tryptophan is first converted toindole (excreted in faeces), then to indican bybacteria in the gut. Indican, being water soluble, is thenexcreted through theurine . Following absorption from the gut,indole is converted to "3-hydroxy indole (indoxyl or indican)" in the liver, where it is again then conjugated withsulfuric acid orglucoronic acid through normalxenobiotic metabolism pathways. 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] .
Pathology
In individuals affected by the
blue diaper syndrome , the patients exhibit a defect intryptophan metabolism. and from there into thediaper where, 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
protein absorption is reduced - likeHartnup's disease , allowing for greater bacterial decomposition of theTryptophan toindole and its conversion toindican .References
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