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Revision as of 17:24, 19 April 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit Latest revision as of 23:49, 9 December 2023 edit undoRevelationDirect (talk | contribs)Autopatrolled, Extended confirmed users175,205 edits added Category:Indigo dye production using HotCat 
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{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 404712280
| Watchedfields = changed
⚫ |ImageFile=Indican.png
⚫ | verifiedrevid = 424885993
⚫ |ImageSize=200px
⚫ | ImageFile=Indican.svg
⚫ |IUPACName=(2''R'',3''S'',4''S'',5''R'',6''S'')-2- (Hydroxymethyl)-6-(1''H''-indol -3-yloxy)tetrahydropyran-3,4,5-triol
⚫ | ImageSize=200px
⚫ |OtherNames=
| IUPACName=1''H''-Indol-3-yl β-<small>D</small>-glucopyranoside
⚫ |Section1= {{Chembox Identifiers
⚫ | SystematicName=(2''R'',3''S'',4''S'',5''R'',6''S'')-2-(Hydroxymethyl)-6-oxane-3,4,5-triol
⚫ | CASNo=1328-73-0
⚫ | OtherNames=
⚫ | PubChem=441564
⚫ |Section1={{Chembox Identifiers
⚫ | SMILES=C1=CC=C2C(=C1)C (=CN2)OC3C(C(C(C(O3)CO)O)O)O
| CASNo_Ref = {{cascite|correct|CAS}}
⚫ | CASNo = 487-60-5
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = N187WK1Y1J
⚫ | PubChem=441564
⚫ | SMILES=C1=CC=C2C(=C1)C(=CN2)OC3C(C(C(C(O3)CO)O)O)O
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 390239
| InChI = 1/C14H17NO6/c16-6-10-11(17)12(18)13(19)14(21-10)20-9-5-15-8-4-2-1-3-7(8)9/h1-5,10-19H,6H2/t10-,11-,12+,13-,14-/m1/s1
| InChIKey = XVARCVCWNFACQC-RKQHYHRCBQ
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C14H17NO6/c16-6-10-11(17)12(18)13(19)14(21-10)20-9-5-15-8-4-2-1-3-7(8)9/h1-5,10-19H,6H2/t10-,11-,12+,13-,14-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = XVARCVCWNFACQC-RKQHYHRCSA-N
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| C=14 | H=17 | N=1 | O=6
| Formula=C<sub>14</sub>H<sub>17</sub>NO<sub>6</sub>
| Appearance=
| MolarMass=295.29 g/mol
| Appearance= | Density=
| MeltingPtC= 178 to 180
| Density=
| MeltingPt_notes= (decomposes)
| MeltingPt=
| BoilingPt= | BoilingPt=
| Solubility= | Solubility=
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}
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==Chemical reactions== ==Chemical reactions==
Common and significant reactions involving indican are as follows: Indican is a ]. Common and significant reactions involving indican are as follows:
*Indican is a ]. Its ] yields β-D-] and ]. *The ] of indican yields β-D-] and ].
*Reaction of indoxyl (indican) by a mild ], e.g. atmospheric oxygen, yields ] which is blue in colour. *The reaction of indoxyl (indican) with a mild ], such as atmospheric oxygen, yields blue ].


==Medical significance== ==Medical significance==

===Biosynthesis=== ===Biosynthesis===
A reaction, similar to the above mentioned is seen in the normal population,<ref></ref> who excrete small amounts of the chemical in their urine. Normal urine reacting to ] does at times produce a bluish tinge. A reaction, similar to that used to produce indigo dye, is seen in the normal population,<ref></ref> who excrete small amounts of the chemical in their urine. Normal urine reacting to ] does at times produce a bluish tinge.
Tryptophan is first converted to ] (excreted in faeces), then to indican by ] in the gut. Indican, being water soluble, is then ] through the ]. Following absorption from the gut, ] is converted to ''3-hydroxy indole (] or indican)'' in the liver, where it is again then conjugated with ] or ] through normal ] pathways. It is then transported to the kidneys for excretion.<ref></ref><ref></ref> Tryptophan is first converted to ] (which is excreted in faeces), then to indican by ] in the gut. Indican, being water-soluble, is then ] through the ]. Following absorption from the gut, ] is converted to ''3-hydroxy indole (] or indican)'' in the liver, where it is again then conjugated with ] or ] through normal ] pathways. It is then transported to the kidneys for excretion.<ref> {{webarchive|url=https://web.archive.org/web/20080807132704/http://www.vitaminlady.com/Health_Testing/BioDia107.asp |date=2008-08-07 }}</ref><ref> {{webarchive|url=https://web.archive.org/web/20080612170344/http://biocenterlab.org/tests/urine/indican.shtml |date=2008-06-12 }}</ref>


The enzyme "indoxyl esterase" has been found in humans and is involved in another pathway of chemical reactions involving indoxyl.<ref>http://www.jcb.org/cgi/reprint/39/2/286.pdf</ref> The enzyme "indoxyl esterase" has been found in humans and is involved in another pathway of chemical reactions involving indoxyl.<ref>http://www.jcb.org/cgi/reprint/39/2/286.pdf {{Bare URL PDF|date=March 2022}}</ref>


===Pathology=== ===Pathology===
In individuals affected by the ], the patients exhibit a defect in ] metabolism. and from there into the ] where, upon exposure to air, it is converted to indigo dye due to oxidation by atmospheric oxygen. Individuals affected by ] exhibit a defect in ] metabolism. Tryptophan is first converted to indole, then to indican by bacteria in the gut. Indican is then excreted into the urine and from there into the diaper where, upon exposure to air, it is oxidised by atmospheric oxygen to indigo blue dye.


Indican interferes with many commercial procedures for measuring total bilirubin<ref></ref> which can be a problem for renal failure patients where blood indican levels are raised. It can cause gastrointestinal symptoms in patients where ] absorption is reduced - like ], allowing for greater bacterial decomposition of the ] to ] and its conversion to indican. Indican interferes with many commercial procedures for measuring total bilirubin<ref></ref> which can be a problem for renal failure patients whose blood indican levels are raised. It can cause gastrointestinal symptoms in patients whose ] absorption is reduced, as in ], allowing for greater bacterial decomposition of the ] to ] and its conversion to indican.


==References== ==References==
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