ChemicalBook > CAS DataBase List > 1,8-Dihydroxyanthraquinone

1,8-Dihydroxyanthraquinone

Product Name
1,8-Dihydroxyanthraquinone
CAS No.
117-10-2
Chemical Name
1,8-Dihydroxyanthraquinone
Synonyms
DANTHRON;DANTRON;CHRYSAZIN;Antrapurol;1,8-dihydroxyanthracene-9,10-dione;LTAN;Danthrone;Istin;ALTAN;Duolax
CBNumber
CB4173988
Molecular Formula
C14H8O4
Formula Weight
240.21
MOL File
117-10-2.mol
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1,8-Dihydroxyanthraquinone Property

Melting point:
191-193 °C (lit.)
Boiling point:
342.92°C (rough estimate)
Density 
1.3032 (rough estimate)
bulk density
600kg/m3
refractive index 
1.5430 (estimate)
Flash point:
>200°C
storage temp. 
Sealed in dry,2-8°C
solubility 
very faint turbidity in hot Acetic acid
pka
6.27±0.20(Predicted)
form 
Powder
color 
Orange-brown or brown
Water Solubility 
insoluble
Merck 
14,2815
BRN 
2054727
LogP
4.570 (est)
CAS DataBase Reference
117-10-2(CAS DataBase Reference)
IARC
2B (Vol. 50) 1990
NIST Chemistry Reference
1,8-Dihydroxyanthraquinone(117-10-2)
EPA Substance Registry System
Danthron (117-10-2)
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Safety

Hazard Codes 
Xn
Risk Statements 
40
Safety Statements 
36/37-36-22
RIDADR 
2811
WGK Germany 
1
RTECS 
CB6650000
TSCA 
Yes
HazardClass 
IRRITANT
HS Code 
29146990
Hazardous Substances Data
117-10-2(Hazardous Substances Data)
Toxicity
LD50 orally in mice: <7 g/kg (Case)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

H351Suspected of causing cancer

Precautionary statements

P201Obtain special instructions before use.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHL89620
Product name
Danthrone
Purity
phyproof? Reference Substance
Packaging
100MG
Price
$262
Updated
2024/03/01
Sigma-Aldrich
Product number
D108103
Product name
1,8-Dihydroxyanthraquinone
Purity
96%
Packaging
100g
Price
$101
Updated
2023/06/20
Sigma-Aldrich
Product number
D108103
Product name
1,8-Dihydroxyanthraquinone
Purity
96%
Packaging
500g
Price
$196
Updated
2023/06/20
TCI Chemical
Product number
D0563
Product name
Chrysazin
Purity
>98.0%(T)
Packaging
25g
Price
$155
Updated
2024/03/01
Alfa Aesar
Product number
A12001
Product name
1,8-Dihydroxyanthraquinone, 95%
Packaging
100g
Price
$43.65
Updated
2024/03/01
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1,8-Dihydroxyanthraquinone Chemical Properties,Usage,Production

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

Chemical Properties

Red-orange to orange crystalline powder or reddish-brown crystalline solid.

Uses

Used as a stimulant laxative, though due to its carcinogenic properties, is not widely prescribed.

Uses

cathartic

Uses

Important intermediate in the manufacture of alizarin and indanthrene dyestuffs; forms insoluble Ca, Ba, Pb lakes. Antioxidant in synthetic lubricants; fungicide.

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.

brand name

Dorbane (3M Pharmaceuticals); Istizin (Sterling Winthrop);Doss;Normax;Regulex-d.

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.

Synthesis

1,8-Dihydroxyanthraquinone is prepared by replacing SO3H, by directly replacing nitro groups in sulfolane in the presence of calcium oxide , or, better, via 1,8-dimethoxyanthraquinone and subsequent hydrolysis of the ether .

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.

target

AMPK | Antifection

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.]

Toxicity evaluation

Danthron is discovered in several species of plants and insects. It has been isolated from dried leaves and stems of Xyris semifuscata harvested in Madagascar, and roots of Da Huang, a Chinese traditional herbal medicine. Danthron also appears to be biosynthesized by some insects. The presence of danthron in insects may be a way of protection from predators. Danthron can be manually synthesized by many countries. In the United States, danthron was available from 12 suppliers.
If released to the atmosphere, danthron will exist in both the vapor phase and the particulate phase. Vapor phase danthron has an estimated half-life of 11 days. Particulate phase danthron can be physically removed from air by wet and dry deposition. It is expected to biodegrade with 68% degradation within 3 months.
If released to water, danthron is expected to adsorb to the surface of solid particle and sediment. Biodegradation is also a major pathway processed in water. It was reported that 82% of the added danthron was degraded by fresh water within 3 days. If added to seawater, 91% of danthron was reported as degraded. Danthron may bioconcentrate in aquatic organisms, such as fish and shrimps.

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.

1,8-Dihydroxyanthraquinone Preparation Products And Raw materials

Raw materials

Preparation Products

1,4,5,8-TETRAHYDROXYANTHRAQUINONE
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1,8-Dihydroxyanthraquinone Suppliers

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View Lastest Price from 1,8-Dihydroxyanthraquinone manufacturers

Hebei Zhuanglai Chemical Trading Co Ltd
Product
1,8-Dihydroxyanthraquinone 117-10-2
Price
US $45.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20 tons
Release date
2024-12-25
Wuhan Circle Star Chem-medical Technology Co.,Ltd
Product
1,8-Dihydroxyanthraquinone 117-10-2
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98
Supply Ability
1000
Release date
2024-12-25
HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
1,8-Dihydroxyanthraquinone 117-10-2
Price
US $990.00-800.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000
Release date
2024-08-19

117-10-2, 1,8-DihydroxyanthraquinoneRelated Search:

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  • NSC 38626
  • NSC 646568
  • NSC 7210
  • Danthron 1,8-Dihydroxyanthraquinone Istizine
  • 1,4,5,8-tetroxyantraquinone
  • Dionone
  • Dorbane
  • Dorbanex
  • Duolax
  • Istin
  • Laxanorm
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  • Laxipur
  • Laxipurin
  • LTAN
  • Modane
  • neokutins
  • pastomin
  • prugol
  • Regulin
  • roydan
  • scatrond
  • USAF nd-59
  • 1,8-Dihydroxyanthraquinone, synthesis grade
  • 1,8-Dihydroxyanthraquinone,Chrysazine, Danthron
  • CHRYSAZIN, PRACT
  • 1,8-Dihydroxyanthraquinone, 90-95% 100GR
  • 1,8-Dihydroxyanthraquinone, 90-95% 5GR
  • Danthron, BAN
  • 1,8-Dihydroxyanthracene-9,10-dione, 9,10-Dihydro-1,8-dihydroxy-9,10-dioxoanthracene
  • 1,8-Dihydroxyanthraquinone Vetec(TM) reagent grade, 96%
  • Diacerein Impurity 7
  • 1,8-Dihydroxyanthraquinone 98+%
  • Danthron (1,8-Dihydroxyanthraquinone)
  • 1,8-Dihydroxyanthraquinone 117-10-2
  • 8-Dihydroxyanthraquinone
  • 204-173-5
  • 1,8-Dihydroxyanthraquinone, 96%, a synthetic anthraquinone derivative
  • 1,8-dihydroxy-10-anthracenedione
  • 1,8-Dihydroxy-9,10-anthracenedione
  • 1,8-Dihydroxy-9,10-anthraquinone
  • 1,8-Dihydroxyanthra-9,10-quinone
  • 1,8-Dihydroxyanthrachinon
  • 1,8-dihydroxy-anthraquinon
  • 1,8-dihydroxyanthroquinone
  • CHRYSAZIN
  • CHRYSAZINE
  • DANTRON
  • DANTHRON
  • ISTIZIN
  • ISTIZINE
  • LABOTEST-BB LT00455159
  • 9,10-Anthracenedione, 1,8-dihydroxy-
  • 9,10-Anthracenedione,1,8-dihydroxy-
  • Anthraquinone, 1,8-dihydroxy-
  • Antrapurol
  • component of Dorbantyl
  • component of Doxan