In organic chemistry, indoxyl is a nitrogenous substance with the chemical formula: C8H7NO.[1][2] Indoxyl is isomeric with oxindol and is obtained as an oily liquid.
Preparation
The Heumann indigo synthesis starts from anthranilic acid:
Indoxyl-Synthese: Anthanilic acid (1) reacts with chloroacetic acid to give phenylglycine-o-carboxylic acid. When treated in molten sodium carbonate, the 2-Indoxycarboxylic acid (3) decarboxylates to give indoxyl (4) .
In nature indoxyl is derived from indican, which is a glycoside. The hydrolysis of indican yields β-D-glucose and indoxyl.
Indigo dye is a product of the mild oxidation of indoxyl.
Indoxyl can be found in urine and is titrated with Obermayer's reagent, which is a dilute solution of ferric chloride (FeCl3) in hydrochloric acid (HCl).[3]
References
- ^ Katritzky, A. R.; Pozharskii, A. F. (2000). Handbook of Heterocyclic Chemistry (2nd ed.). Academic Press. ISBN 0080429882.
- ^ Clayden, J.; Greeves, N.; Warren, S.; Wothers, P. (2001). Organic Chemistry. Oxford, Oxfordshire: Oxford University Press. ISBN 0-19-850346-6.
- ^ Lide, David (1998). CRC - Handbook of Chemistry and Physics. CRC press LLC. pp. Section 8 page 3. ISBN 0-8493-0479-2.