Structure via PubChem · Public domain (PubChem)
indican
Sign in to saveAlso known as indoxyl-β-glucoside
Indican is a colourless organic compound, soluble in water, naturally occurring in Indigofera plants. It is a precursor of indigo dye.
Chemical data
- Formula
- C14H17NO6
- Molecular weight
- 295.29 g/mol
- IUPAC name
- (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(1H-indol-3-yloxy)oxane-3,4,5-triol
- SMILES
- C1=CC=C2C(=C1)C(=CN2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
- InChIKey
- XVARCVCWNFACQC-RKQHYHRCSA-N
- XLogP
- -0.1
- Polar surface area
- 115 Ų
- H-bond donors
- 5
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Research
1,422 papers- Chemoenzymatic indican for light-driven denim dyeing.Nature communications · 2024
- Normal and pathologic concentrations of uremic toxins.Journal of the American Society of Nephrology : JASN · 2012
- Indican excretion in the elderly.Postgraduate medical journal · 1983
- Transporter-mediated interaction of indican and methotrexate in rats.Journal of food and drug analysis · 2018
- Tissue-specific and intracellular localization of indican synthase from Polygonum tinctorium.Plant physiology and biochemistry : PPB · 2018
via PubMed
Wikidata facts
- Mass
- 295.105587
Show 3 more facts
- chemical formula
- C₁₄H₁₇NO₆
- canonical SMILES
- C1=CC=C2C(=C1)C(=CN2)OC3C(C(C(C(O3)CO)O)O)O
- isomeric SMILES
- C1=CC=C2C(=C1)C(=CN2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
via Wikidata · CC0
~2 min read
Article
5 sectionsContents
- Chemical reactions
- Medical significance
- Biosynthesis
- Pathology
- References
Indican is a colourless organic compound, soluble in water, naturally occurring in Indigofera plants. It is a precursor of indigo dye.
==Chemical reactions== Indican is a glycoside. Its most significant reaction is hydrolysis of to yields β-D-glucose and indoxyl. Beta-glucosidase, a common enzyme, catalyzes this process. Because the hydrolysis is slow in the absence of the enzyme, indican can be viewed as a protected version of indoxyl. Once formed, the indoxyl is oxidized by atmospheric oxygen to give blue indigo dye. Since synthetic indigo is produced on a massive scale by chemical routes, i.e. 50,000 tons/y (2011), the prospect of a biological pathway is of practical interest.