Morindone is an anthraquinone

Anthraquinone

Anthraquinone, also called anthracenedione or dioxoanthracene is an aromatic organic compound with formula . Several isomers are possible, each of which can be viewed as a quinone derivative...

 compound

Organic compound

An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 obtained from various Morinda

Morinda

Morinda is a genus of flowering plants in the madder family, Rubiaceae. The generic name is derived from the Latin words morus, meaning "mulberry," and indica, meaning "of India," referring to the shape of the fruits. -Description:...

species

Species

In biology, a species is one of the basic units of biological classification and a taxonomic rank. A species is often defined as a group of organisms capable of interbreeding and producing fertile offspring. While in many cases this definition is adequate, more precise or differing measures are...

, especially M. tinctoria

Morinda tinctoria

Morinda tinctoria, commonly known as Aal or Indian Mulberry , is a species of flowering plant in the family Rubiaceae, native to southern Asia....

, but also M. citrifolia. Its principal use is as a dye

Dye

A dye is a colored substance that has an affinity to the substrate to which it is being applied. The dye is generally applied in an aqueous solution, and requires a mordant to improve the fastness of the dye on the fiber....

, but it has also been investigated for anticancer and microbial uses.

Preparation

Morindone is obtained from the root bark of M. tinctoria or related species in two stages. In the first step, small roots of immature plants are boiled in alcohol to obtain morindin, a yellowish substance which can also be used in dyeing. Further heating brings about hydrolysis

Hydrolysis

Hydrolysis is a chemical reaction during which molecules of water are split into hydrogen cations and hydroxide anions in the process of a chemical mechanism. It is the type of reaction that is used to break down certain polymers, especially those made by condensation polymerization...

 of two glucose

Glucose

Glucose is a simple sugar and an important carbohydrate in biology. Cells use it as the primary source of energy and a metabolic intermediate...

 monomer

Monomer

A monomer is an atom or a small molecule that may bind chemically to other monomers to form a polymer; the term "monomeric protein" may also be used to describe one of the proteins making up a multiprotein complex...

s through sublimation, leaving intensely red crystals.

M. tinctoria is extensively grown in India

India

India , officially the Republic of India , is a country in South Asia. It is the seventh-largest country by geographical area, the second-most populous country with over 1.2 billion people, and the most populous democracy in the world...

 for commercial production. Moridin content in the roots peaks in two to three years and drops off considerably after that; some attempts have been made to speed up production using tissue cultures.

Use as a dye

Morindone requires a mordant

Mordant

A mordant is a substance used to set dyes on fabrics or tissue sections by forming a coordination complex with the dye which then attaches to the fabric or tissue. It may be used for dyeing fabrics, or for intensifying stains in cell or tissue preparations. The term mordant comes from the Latin...

, and the color obtained varies depending on the substance used. Aluminum mordants give a red color, while iron and chromium produce duskier shades. The traditional mordant used in Java, jirak bark (Symplocos fasciculata), is rich in aluminum salts.

Compared to modern dyestuffs, morindone is not as fast or as stable. Since it can be readily cultivated, however, interest in it remains high. Recent research has examined cell culture as a means of increasing yields.