1,3-Dihydroxyanthraquinone
Encyclopedia
1,3-Dihydroxyanthraquinone, also called purpuroxanthin or xanthopurpurin is an organic compound
with formula that occurs in the plant Rubia cordifolia
(Indian madder
). It is one of ten dihydroxyanthraquinone
isomers. Its molecular structure can be viewed as being derived from anthraquinone
by replacement of two hydrogen
atoms (H) by hydroxyl
groups (-OH).
Xanthopurpurin occurs in small amounts (as a glycoside
) in the root of the common madder plant, Rubia tinctorum
, together with alizarin
, purpurin and other anthraquinone derivatives.
but soluble in chloroform
. It can be obtained from solutions in the latter as reddish crystals that melt at 270–273 °C.
Like many dihydroxy
- and trihydroxyanthraquinone
s, it has a purgative action, although only 1/6 as effective as 1,2,7-trihidroxyanthraquinone (anthrapurpurin).
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...
with formula that occurs in the plant Rubia cordifolia
Rubia cordifolia
Rubia cordifolia, often known as Common Madder or Indian Madder, is a species of flowering plant in the coffee family, Rubiaceae...
(Indian madder
Madder
Rubia is a genus of the madder family Rubiaceae, which contains about 60 species of perennial scrambling or climbing herbs and sub-shrubs native to the Old World, Africa, temperate Asia and America...
). It is one of ten dihydroxyanthraquinone
Dihydroxyanthraquinone
A dihydroxyanthraquinone is any of several isomeric organic compounds with formula , formally derived from an anthraquinone by replacing two hydrogen atoms by hydroxyl groups. Dihyroxyantraquinones have been studied since the early 1900s, and include some compounds of historical and current...
isomers. Its molecular structure can be viewed as being derived from 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...
by replacement of two hydrogen
Hydrogen
Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...
atoms (H) by hydroxyl
Hydroxyl
A hydroxyl is a chemical group containing an oxygen atom covalently bonded with a hydrogen atom. In inorganic chemistry, the hydroxyl group is known as the hydroxide ion, and scientists and reference works generally use these different terms though they refer to the same chemical structure in...
groups (-OH).
Xanthopurpurin occurs in small amounts (as a glycoside
Glycoside
In chemistry, a glycoside is a molecule in which a sugar is bound to a non-carbohydrate moiety, usually a small organic molecule. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme...
) in the root of the common madder plant, Rubia tinctorum
Rubia tinctorum
Rubia tinctorum, the common madder or dyer's madder, is a plant species in the genus Rubia.The plant's roots contain several polyphenolic compounds like 1,3-Dihydroxyanthraquinone , 1,4-Dihydroxyanthraquinone , 1,2,4-Trihydroxyanthraquinone and 1,2-dihydroxyanthraquinone...
, together with alizarin
Alizarin
Alizarin or 1,2-dihydroxyanthraquinone is an organic compound with formula that has been used throughout history as a prominent dye, originally derived from the roots of plants of the madder genus.Alizarin was used as a red dye for the English parliamentary "new model" army...
, purpurin and other anthraquinone derivatives.
Properties
Xanthopurpurin is insoluble in hexaneHexane
Hexane is a hydrocarbon with the chemical formula C6H14; that is, an alkane with six carbon atoms.The term may refer to any of four other structural isomers with that formula, or to a mixture of them. In the IUPAC nomenclature, however, hexane is the unbranched isomer ; the other four structures...
but soluble in chloroform
Chloroform
Chloroform is an organic compound with formula CHCl3. It is one of the four chloromethanes. The colorless, sweet-smelling, dense liquid is a trihalomethane, and is considered somewhat hazardous...
. It can be obtained from solutions in the latter as reddish crystals that melt at 270–273 °C.
Like many dihydroxy
Dihydroxyanthraquinone
A dihydroxyanthraquinone is any of several isomeric organic compounds with formula , formally derived from an anthraquinone by replacing two hydrogen atoms by hydroxyl groups. Dihyroxyantraquinones have been studied since the early 1900s, and include some compounds of historical and current...
- and trihydroxyanthraquinone
Trihydroxyanthraquinone
A trihydroxyanthraquinone or trihydroxyanthracenedione is any of several isomeric organic compounds with formula , formally derived from anthraquinone by replacing three hydrogen atoms by hydroxyl groups. They include several historically important dyes...
s, it has a purgative action, although only 1/6 as effective as 1,2,7-trihidroxyanthraquinone (anthrapurpurin).