1,8-Dihydroxyanthraquinone

Description

Danthron, a natural product, was originally extracted from the roots and rhizome of Polygonaceae plant, also called Da Huang in traditional Chinese herbal medicine. Now it is synthesized in many countries, such as Germany, India, Japan, Poland, the United Kingdom, and the United States. Danthron is reasonably anticipated to be a human carcinogen.
Danthron is an anthraquinone that exists at room temperature as a red or orange crystalline powder.It is practically insoluble in water, but soluble in a variety of solvents (acetone, chloroform, diethyl ether, ethanol) and alkaline hydroxide solutions. The stability of danthron is generally good. It is stable under room temperatures and normal pressures.

Chemical Properties

orange-brown or brown powder

Uses

1,8-Dihydroxyanthraquinone can be used:

• To prepare an inclusion complex with β-cyclodextrin, applicable as a sensor in the estimation of Cu²⁺?ions in an aqueous solution.
• As a starting material in the synthesis of 1,4,5,8-tetramethoxyanthracene.
• As an aromatic scavenger in the modification of lignin, which acts as a corrosion inhibitor for steel.

Definition

ChEBI: 1,8-Dihydroxyanthraquinone is a dihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1 and 8. It has a role as an apoptosis inducer and a plant metabolite.

World Health Organization (WHO)

Dantron, an anthroquinone derivative, has been available for over twenty years and is widely used as a laxative. The results of two chronic toxicity studies in rodents, published in 1985 and 1986, have shown that administration of high doses is associated with the development of intestinal and liver tumours.

General Description

Orange crystalline powder. Almost odorless and tasteless.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

1,8-Dihydroxyanthraquinone is incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides.

Fire Hazard

Flash point data for 1,8-Dihydroxyanthraquinone are not available; however, 1,8-Dihydroxyanthraquinone is probably combustible.

Side effects

Liver injury may occur with 1,8-Dihydroxyanthraquinone when used as a laxative for one year. Symptoms disappeared after discontinuation of the drug, but recurred after resumption of the drug; none of the drugs administered alone had any effect on liver function test results. In addition, deep skin discolouration may occur with heavy use, mainly in elderly subjects, and is limited to the buttocks and thighs, with mild signs of inflammation. Skin contact with faeces or urine containing the drug appears to be a prerequisite for discolouration. Inflammation, if present, may be due to reduction of the parent compound in the colon to diol derivatives, which can irritate the intestine and skin in a way that the parent compound does not. There is also the possibility of colorectal melanosis.

Safety Profile

Confirmed carcinogen with experimental carcinogenic data. Moderately toxic by intraperitoneal route. An eye irritant. Questionable carcinogen with experimental carcinogenic and neoplastigenic data. Human mutation data reported. A laxative. When heated to decomposition it emits acrid smoke and irritating fumes.

Potential Exposure

A potential liver carcinogen and possible narcotic, this compound is no longer sold or marketed in the United States Nervous system toxin-acute effects; Respiratory toxin-acute effects other than severe or moderate irritation; Liver-acute effects; Eye irritant-mild.

Carcinogenicity

Danthron is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

Environmental Fate

Danthron can cause DNA damage particularly at guanines in the 5'-GG-3', 5'-GGGG-3', 5'-GGGGG-3' sequences in the presence of Cu(II), cytochrome P450 reductase and the nicotinamide adenine dinucleotide phosphate (NADPH)-generating system. H2O2 and Cu(I) may also be involved because this DNA damage can be inhibited by catalase and bathocuproine. The further mechanism is danthron is reduced by P450 reductase and generate reactive oxygen species through the redox cycle, leading to extensive Cu(II)-mediated DNA damage. The DNA damage also comes from similar topoisomerase II inhibitor behavior of danthron.

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Purification Methods

Crystallise Danthrone from EtOH and sublime it in a vacuum. [Beilstein 8 IV 3217.]

Incompatibilities

Keep away from strong reducing agents, such as hydrides, nitrides, alkali metals, and sulfides.

Waste Disposal

It is inappropriate and possibly dangerous to the environment to dispose of expired or waste drugs and pharmaceuticals by flushing them down the toilet or discarding them to the trash. Household quantities of expired or waste pharmaceuticals may be mixed with wet cat litter or coffee grounds, double- bagged in plastic, discard in trash. Larger quantities shall carefully take into consideration applicable DEA, EPA, and FDA regulations. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to prop- erly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.