Morindone

Last updated
Morindone
Moridone Structural Formulae V.1.svg
Morindone-3D-balls.png
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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 Yes check.svgY
    Key: BATFHSIVMJJJAF-UHFFFAOYSA-N Yes check.svgY
  • 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
Appearancered needle-like crystals
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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.

Related Research Articles

<span class="mw-page-title-main">Dye</span> Soluble chemical substance or natural material which can impart color to other materials

A dye is a colored substance that chemically bonds to the substrate to which it is being applied. This distinguishes dyes from pigments which do not chemically bind to the material they color. Dye is generally applied in an aqueous solution and may require a mordant to improve the fastness of the dye on the fiber.

<i>Alkanna tinctoria</i> Species of flowering plant

Alkanna tinctoria, the dyer's alkanet or simply alkanet, is a herbaceous flowering plant in the borage family Boraginaceae. Its roots are used to produce a red dye. The plant is also known as dyers' bugloss, orchanet, Spanish bugloss, or Languedoc bugloss. It is native to the Mediterranean region. A. tinctoria has 30 chromosomes and is regarded as a dysploid at the tetraploid level.

<span class="mw-page-title-main">Indigo dye</span> Chemical compound, food additive and dye

Indigo dye is an organic compound with a distinctive blue color. Indigo is a natural dye extracted from the leaves of some plants of the Indigofera genus, in particular Indigofera tinctoria; dye-bearing Indigofera plants were commonly grown and used throughout the world, in Asia in particular, as an important crop, with the production of indigo dyestuff economically important due to the historical rarity of other blue dyestuffs

<span class="mw-page-title-main">Alizarin</span> Chemical compound and histologic stain

Alizarin is an organic compound with formula C
14
H
8
O
4
that has been used throughout history as a prominent red dye, principally for dyeing textile fabrics. Historically it was derived from the roots of plants of the madder genus. In 1869, it became the first natural dye to be produced synthetically.

<span class="mw-page-title-main">Mordant</span> Substance used for binding dyes to fabrics

A mordant or dye fixative is a substance used to set dyes on fabrics. It does this by forming a coordination complex with the dye, which then attaches to the fabric. It may be used for dyeing fabrics or for intensifying stains in cell or tissue preparations. Although mordants are still used, especially by small batch dyers, it has been largely displaced in industry by directs.

A lake pigment is a pigment made by precipitating a dye with an inert binder, or mordant, usually a metallic salt. Unlike vermilion, ultramarine, and other pigments made from ground minerals, lake pigments are organic. Manufacturers and suppliers to artists and industry frequently omit the lake designation in the name. Many lake pigments are fugitive because the dyes involved are not lightfast. Red lakes were particularly important in Renaissance and Baroque paintings; they were often used as translucent glazes to portray the colors of rich fabrics and draperies.

<span class="mw-page-title-main">Staining</span> Technique used to enhance visual contrast of specimens observed under a microscope

Staining is a technique used to enhance contrast in samples, generally at the microscopic level. Stains and dyes are frequently used in histology, in cytology, and in the medical fields of histopathology, hematology, and cytopathology that focus on the study and diagnoses of diseases at the microscopic level. Stains may be used to define biological tissues, cell populations, or organelles within individual cells.

<i>Morinda citrifolia</i> Species of plant

Morinda citrifolia is a fruit-bearing tree in the coffee family, Rubiaceae. Its native range extends across Southeast Asia and Australasia, and was spread across the Pacific by Polynesian sailors. The species is now cultivated throughout the tropics and widely naturalized. Among some 100 names for the fruit across different regions are the more common English names of great morinda, Indian mulberry, noni, beach mulberry, vomit fruit, awl tree and cheese fruit.

<i>Maclura tinctoria</i> Species of tree

Maclura tinctoria, known as old fustic and dyer's mulberry, is a medium to large tree of the Neotropics, from Mexico to Argentina. It produces a yellow dye called fustic primarily known for coloring khaki fabric for U.S. military apparel during World War I. This dye contains the flavonoid morin. It is dioecious, so both male and female plants are needed to set seed.

<i>Morinda tinctoria</i> Species of flowering plant

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

<span class="mw-page-title-main">Anthraquinones</span>

For the parent molecule 9,10-anthraquinone, see anthraquinone

<i>Cibotium menziesii</i> Species of fern

Cibotium menziesii, the hāpuʻu ʻiʻi or Hawaiian tree fern, is a species of tree fern that is endemic to the islands of Hawaiʻi. It is named after the Scottish naturalist Archibald Menzies. It is also known as the male tree fern, and Cibotium glaucum is deemed the female tree fern due to differences in color.

<i>Rubia tinctorum</i> Species of flowering plant (rose madder)

Rubia tinctorum, the rose madder or common madder or dyer's madder, is a herbaceous perennial plant species belonging to the bedstraw and coffee family Rubiaceae.

<span class="mw-page-title-main">Damnacanthal</span> Chemical compound

Damnacanthal is an anthraquinone isolated from the root of Morinda citrifolia, using water or organic solvents.

<span class="mw-page-title-main">Alkannin</span> Chemical compound

Alkannin is a natural dye that is obtained from the extracts of plants from the borage family Alkanna tinctoria that are found in the south of France. The dye is used as a food colouring and in cosmetics. It is used as a red-brown food additive in regions such as Australia. Alkannin is deep red in an acid and blue in an alkaline environment. The chemical structure as a naphthoquinone derivative was first determined by Brockmann in 1936. The R-enantiomer of alkannin is known as shikonin, and the racemic mixture of the two is known as shikalkin.

<span class="mw-page-title-main">Natural dye</span> Dye extracted from plant or animal sources

Natural dyes are dyes or colorants derived from plants, invertebrates, or minerals. The majority of natural dyes are vegetable dyes from plant sources—roots, berries, bark, leaves, and wood—and other biological sources such as fungi.

<span class="mw-page-title-main">Glossary of dyeing terms</span>

Dyeing is the craft of imparting colors to textiles in loose fiber, yarn, cloth or garment form by treatment with a dye. Archaeologists have found evidence of textile dyeing with natural dyes dating back to the Neolithic period. In China, dyeing with plants, barks and insects has been traced back more than 5,000 years. Natural insect dyes such as Tyrian purple and kermes and plant-based dyes such as woad, indigo and madder were important elements of the economies of Asia and Europe until the discovery of man-made synthetic dyes in the mid-19th century. Synthetic dyes quickly superseded natural dyes for the large-scale commercial textile production enabled by the industrial revolution, but natural dyes remained in use by traditional cultures around the world.

<i>Lithospermum erythrorhizon</i> Species of flowering plant in the borage family Boraginaceae

Lithospermum erythrorhizon, commonly called purple gromwell, red stoneroot, red gromwell, red-root gromwell and redroot lithospermum, is a plant species in the genus Lithospermum. It is called zǐcǎo (紫草) in Chinese, jichi (지치) in Korean, and murasaki in Japanese.

Kotpad Handloom is a vegetable-dyed fabric woven by the tribal weavers of the Mirgan community of Kotpad village in Koraput district, Odisha, India. Cotton sarees with solid border and Pata Anchal, duppatta with typical Buties / motifs, Scolrfs on cotton, silk, handloom stoles, and dress materials are all dyed with organic dyes. The natural dye is manufactured from the aul tree grown in this area. The Kotpad tussar silk saree with tribal art and Kotpad handloom fabrics with natural color is its specialty.

<span class="mw-page-title-main">Morindin</span> Chemical compound

Morindin is an anthraquinone glycoside present in several Morinda species, especially M. tinctoria and M. citrifolia (noni). Chemical or enzymatic hydrolysis of morindin yields its bright red aglycone, morindone.

References