Indican

Indican

Chembox new
ImageFile=Indican.pngImageSize=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
Appearance=
Density=
MeltingPt=
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Section3= Chembox Hazards
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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 ] ]

Chemical reactions

Common and significant reactions involving indican are as follows:
*Indican is a glycoside. Its hydrolysis yields β-D-glucose and indoxyl.
*Reaction of indoxyl (indican) by a mild oxidizing agent, e.g. atmospheric oxygen, yields indigo 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 to indole (excreted in faeces), then to indican by bacteria in the gut. Indican, being water soluble, is then excreted through the urine. Following absorption from the gut, indole is converted to "3-hydroxy indole (indoxyl or indican)" in the liver, where it is again then conjugated with sulfuric acid or glucoronic acid through normal xenobiotic 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 in tryptophan metabolism. and from there into the diaper 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 - like Hartnup's disease, allowing for greater bacterial decomposition of the Tryptophan to indole and its conversion to indican.

References


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Look at other dictionaries:

  • indican — [ ɛ̃dikɑ̃ ] n. m. • 1873; du lat. indicum « indigo » ♦ Chim. Indican végétal : glucoside extrait des feuilles de l indigotier, utilisé comme colorant. ⇒ indigo. Biochim. Indican métabolique, urinaire, apparaissant dans l urine en cas d… …   Encyclopédie Universelle

  • indican — INDICÁN s.n. Substanţă organică ce se găseşte în indigo (3). – Din fr. indican. Trimis de valeriu, 13.09.2007. Sursa: DEX 98  indicán s. n. Trimis de siveco, 10.08.2004. Sursa: Dicţionar ortografic  INDICÁN s.n. Substanţă care există în indigo …   Dicționar Român

  • Indican — Général Nom IUPAC (2R,3S,4S,5R,6S) 2 (Hhydroxyméthyl) 6 (1H indol 3 yloxy)tétrahydropyran 3,4,5 triol No CAS …   Wikipédia en Français

  • indican — glucósido del D 3 hidroxindol, un compuesto presente en las plantas que contienen el índigo, un colorante azul.También es el producto de transformación del triptófano en indol por acción de las bacterias intestinales. El indol producido es… …   Diccionario médico

  • Indican — In di*can, n. [See {Indigo}.] [1913 Webster] 1. (Chem.) A glucoside ({C14H17NO6}) obtained from woad (indigo plant, {Isatis Tinctoria}) and other plants (see {indigo}), as a yellow or light brown sirup. When purified it is obtained as spear… …   The Collaborative International Dictionary of English

  • Indican — C26H31NO17, ein in allen Indigo liefernden Pflanzen enthaltenes Glykosid; s. Farbstoffe, pflanzliche, Bd. 3, S. 638 …   Lexikon der gesamten Technik

  • indican — [in′di kan΄] n. [< L indicum, INDIGO + AN] 1. a glucoside, C14H17NO6, found in a natural state in the indigo plant: it is converted by water and oxygen into indigo 2. an indigo forming substance, C8H6NOSO2OH, the potassium salt of which is… …   English World dictionary

  • Indican — Strukturformel von Indikan aus Pflanzen Der Name Indikan (auch: Indican) bezeichnet zwei ähnliche, aber nicht identische, Verbindungen, deren Gemeinsamkeit ist, dass sie beide als Derivate des Indols angesehen werden können. Inhaltsverzeichnis 1… …   Deutsch Wikipedia

  • Indican — In|di|can [lat. Indicum (griech. Indikón) = das Indische (Blau); ↑ an (4)], das; s: 1) sog. metabolisches Indican; S: Indikan; Syn.: 1H Indol 3 ylsulfat: als Kaliumsalz (Harnindican) ein natürliches Tryptophanabbauprodukt im Blut u. Harn; 2) sog …   Universal-Lexikon

  • indican — 1. Indoxyl β d glucoside from Indigofera species and Polygonium tinctorium; a source of indigo. SYN: plant i.. 2. 3 Indoxylsulfuric acid, a substance found (as its salts) in sweat and in variable amounts in urine; indicative, when in quantity, of …   Medical dictionary

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