organic chemistry Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic matter, organic materials, i.e., matter in its various forms that contain ...

, indoxyl is a nitrogenous substance with the

chemical formula A chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, such as pare ...

: C₈H₇NO. Indoxyl is isomeric with oxindol and is obtained as an oily liquid.

Preparation

The Heumann indigo synthesis starts from anthranilic acid: : In nature indoxyl is derived from indican, which is a

glycoside In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. ...

. The

hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...

of indican yields β-D-

glucose Glucose is a sugar with the Chemical formula#Molecular formula, molecular formula , which is often abbreviated as Glc. It is overall the most abundant monosaccharide, a subcategory of carbohydrates. It is mainly made by plants and most algae d ...

and indoxyl.

Indigo dye Indigo dye is an organic compound with a distinctive indigo, blue color. Indigo is a natural dye obtained from the leaves of some plants of the Indigofera#Uses, ''Indigofera'' genus, in particular ''Indigofera tinctoria''. Dye-bearing ''Indigofer ...

is a product of the mild

oxidation Redox ( , , reduction–oxidation or oxidation–reduction) is a type of chemical reaction in which the oxidation states of the reactants change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is ...

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 Hydrochloric acid, also known as muriatic acid or spirits of salt, is an aqueous solution of hydrogen chloride (HCl). It is a colorless solution with a distinctive pungency, pungent smell. It is classified as a acid strength, strong acid. It is ...

(HCl).

References

Indoles Enols {{heterocyclic-stub