Morindone

Morindone is an anthraquinone compound obtained from various Morinda species, especially M. tinctoria, but also M. citrifolia. Its principal use is as a dye, but it has also been investigated for anticancer and microbial uses.

Morindone
Skeletal formula of morindone
Ball-and-stick model of morindone
Names
Preferred IUPAC name
1,2,5-Trihydroxy-6-methylanthracene-9,10-dione
Other names
Morindone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.107.333
UNII
  • InChI=1S/C15H10O5/c1-6-2-3-7-10(12(6)17)13(18)8-4-5-9(16)15(20)11(8)14(7)19/h2-5,16-17,20H,1H3 checkY
    Key: BATFHSIVMJJJAF-UHFFFAOYSA-N checkY
  • InChI=1/C15H10O5/c1-6-2-3-7-10(12(6)17)13(18)8-4-5-9(16)15(20)11(8)14(7)19/h2-5,16-17,20H,1H3
    Key: BATFHSIVMJJJAF-UHFFFAOYAG
  • O=C2c1c(ccc(c1O)C)C(=O)c3c2ccc(O)c3O
Properties
C15H10O5
Molar mass 270.2369 g/mol
Appearance red needle-like crystals
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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 of two glucose monomers through sublimation, leaving intensely red crystals.

M. tinctoria is extensively grown in India 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, 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.

References
  • "Morindone". NCBI PubChem. Retrieved 2008-12-27.
  • Gmelin, Leopold (1864). "Hand book of chemistry". Hand-Book of Chemistry. Vol. V. XVI. Translated by Henry Watts. London: Cavendish Society. p. 189. Retrieved 2008-12-27. Note that the chemical formula given here is incorrect; this reference was used only for physical properties and preparation of substance.
  • Aobchey, Paitoon; Supawadee Sriyam; Worawit Praharnripoorab; Sorasak Lhieochaiphant; Suree Phutrakul (January–April 2002). "Production of Red Pigment from the Root of Morinda angustifolia Roxb. var. scabridula Craib. by Root Cell Culture" (PDF). Chiang Mai University Journal. 1 (1): 66–78. Archived from the original (PDF) on 2009-02-21. Retrieved 2009-01-05.
  • "Morinda citrifolia". World Agroforestry Centre. Archived from the original on 2011-09-30. Retrieved 2009-01-05.
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