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1,8-Dihydroxyanthraquinone(CAS No. 117-10-2)

1,8-Dihydroxyanthraquinone C14H8O4 (cas 117-10-2) Molecular Structure

117-10-2 Structure

Identification and Related Records

【CAS Registry number】
【Molecular Formula】
C14H8O4 (Products with the same molecular formula)
【Molecular Weight】
【Canonical SMILES】
【MOL File】

Chemical and Physical Properties

yellow to orange solid
1.54 g/cm3
【Melting Point】
【Boiling Point】
452.7 °C at 760 mmHg
8.21E-09mmHg at 25°C
【Refractive Index】
1.787 (20 C)
【Flash Point】
241.7 °C
Insoluble (Soluble in glacial acetic acid, aqueous alkali, ethanol, acetone, chloroform and ether)
Red or red-yellow needles or leaves (from alcohol)
Orange needles from alcohol
Orange powder or reddish-brown needles
Stable under normal temperatures and pressures.
【HS Code】
【Storage temp】
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
【Spectral properties】
Absorption max: 430, 250 nm (log E 4.35, 4.60)
MASS: 70813 (NIST/EPA/MSDC Mass Spectral Database 1990 version)
IR: 5147 (Coblentz Society Spectral Collection)
UV: 4318 (Sadtler Research Laboratories Spectral Collection)
【Computed Properties】
Molecular Weight:240.21092 [g/mol]
Molecular Formula:C14H8O4
H-Bond Donor:2
H-Bond Acceptor:4
Rotatable Bond Count:0
Tautomer Count:14
Exact Mass:240.042259
MonoIsotopic Mass:240.042259
Topological Polar Surface Area:74.6
Heavy Atom Count:18
Formal Charge:0
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Donor Count:2
Feature 3D Ring Count:3
Effective Rotor Count:0
Conformer Sampling RMSD:0.4
CID Conformer Count:1

Safety and Handling

【Hazard Codes】
【Risk Statements】
【Safety Statements 】

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.
Hazard Codes:
Xn: Harmful
Risk Statements about 1,8-Dihydroxyanthraquinone (117-10-2):
R40 Limited evidence of a carcinogenic effect.
Safety Statements about 1,8-Dihydroxyanthraquinone (117-10-2):
S36/37 Wear suitable protective clothing and gloves.
1. Storage: Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
2. Handling: Avoid ingestion and inhalation. Avoid contact with eyes, skin, and clothing. Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Minimize dust generation and accumulation. Keep container tightly closed.

【PackingGroup 】
【Skin, Eye, and Respiratory Irritations】
An eye irritant.
【Cleanup Methods】
PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/
Dantron is available commercially at a purity of 95-99%.
DanSunate D
Neokutin S
Scatron D
The following trade names are those of multi-ingredient preparations containing dantron: Agarol Capsules; Coloxyl; Dorbanate, Dorbanex; Dorbantyl; Doss; Doxidan; Normax.
Co-danthramer capsules contain Dantron 25 mg and Poloxamer 188 200 mg. Strong Co-danthramer capsules contain Dantron 37.5 mg and Poloxamer 188 500 mg.
【Other Preventative Measures】
SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
PRECAUTIONS FOR "CARCINOGENS": Doors leading into areas where carcinogens are used ... should be marked distinctively with appropriate labels. Access ... limited to persons involved in expt. ... A prominently displayed notice should give the name of the Scientific Investigator or other person who can advise in an emergency & who can inform others (such as firemen) on the handling of carcinogenic substances. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Rooms in which obvious contamination has occurred, such as spillage, should be decontaminated by lab personnel engaged in expt. Design of expt should ... avoid contamination of permanent equipment. ... Procedures should ensure that maintenance workers are not exposed to carcinogens. ... Particular care should be taken to avoid contamination of drains or ventilation ducts. In cleaning labs, procedures should be used which do not produce aerosols or dispersal of dust, ie, wet mop or vacuum cleaner equipped with high-efficiency particulate filter on exhaust, which are avail commercially, should be used. Sweeping, brushing & use of dry dusters or mops should be prohibited. Grossly contaminated cleaning materials should not be re-used ... If gowns or towels are contaminated, they should not be sent to laundry, but ... decontaminated or burnt, to avoid any hazard to laundry personnel. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": To eliminate risk that ... contamination in lab could build up during conduct of expt, periodic checks should be carried out on lab atmospheres, surfaces, such as walls, floors & benches, & ... interior of fume hoods & airducts. As well as regular monitoring, check must be carried out after cleaning-up of spillage. Sensitive methods are required when testing lab atmospheres. ... Methods ... should ... where possible, be simple & sensitive. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": When ... admin in diet or applied to skin, animals should be kept in cages with solid bottoms & sides & fitted with a filter top. When volatile carcinogens are given, filter tops should not be used. Cages which have been used to house animals that received carcinogens should be decontaminated. Cage-cleaning facilities should be installed in area in which carcinogens are being used, to avoid moving of ... contaminated /cages/. It is difficult to ensure that cages are decontaminated, & monitoring methods are necessary. Situations may exist in which the use of disposable cages should be recommended, depending on type & amt of carcinogen & efficiency with which it can be removed. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Principles that apply to chem or biochem lab also apply to microbiological & cell-culture labs ... Special consideration should be given to route of admin. ... Safest method of administering volatile carcinogen is by injection of a soln. Admin by topical application, gavage, or intratracheal instillation should be performed under hood. If chem will be exhaled, animals should be kept under hood during this period. Inhalation exposure requires special equipment. ... Unless specifically required, routes of admin other than in the diet should be used. Mixing of carcinogen in diet should be carried out in sealed mixers under fume hood, from which the exhaust is fitted with an efficient particulate filter. Techniques for cleaning mixer & hood should be devised before expt begun. When mixing diets, special protective clothing &, possibly, respirators may be required. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Vertical laminar-flow biological safety cabinets may be used for containment of in vitro procedures ... provided that the exhaust air flow is sufficient to provide an inward air flow at the face opening of the cabinet, & contaminated air plenums that are under positive pressure are leak-tight. Horizontal laminar-flow hoods or safety cabinets, where filtered air is blown across the working area towards the operator, should never be used ... Each cabinet or fume cupboard to be used ... should be tested before work is begun (eg, with fume bomb) & label fixed to it, giving date of test & avg air-flow measured. This test should be repeated periodically & after any structural changes. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... Clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/
【Protective Equipment and Clothing】
An eye irritant.
【Octanol/Water Partition Coefficient】
log Kow = 3.94 (est)

NTP 10th Report on Carcinogens. Reported in EPA TSCA Inventory.

【Disposal Methods】
SRP: Criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly 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.
PRECAUTIONS FOR "CARCINOGENS": Carcinogens that are alkylating, arylating or acylating agents per se can be destroyed by reaction with appropriate nucleophiles, such as water, hydroxyl ions, ammonia, thiols & thiosulfate. The reactivity of various alkylating agents varies greatly ... & is also influenced by sol of agent in the reaction medium. To facilitate the complete reaction, it is suggested that the agents be dissolved in ethanol or similar solvents. ... No method should be applied ... until it has been thoroughly tested for its effectiveness & safety on material to be inactivated. For example, in case of destruction of alkylating agents, it is possible to detect residual compounds by reaction with 4(4-nitrobenzyl)-pyridine. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... Small quantities of ... some carcinogens can be destroyed using chem reactions ... but no general rules can be given. ... As a general technique ... treatment with sodium dichromate in strong sulfuric acid can be used. The time necessary for destruction ... is seldom known ... but 1-2 days is generally considered sufficient when freshly prepd reagent is used. ... Carcinogens that are easily oxidizable can be destroyed with milder oxidative agents, such as saturated soln of potassium permanganate in acetone, which appears to be a suitable agent for destruction of hydrazines or of compounds containing isolated carbon-carbon double bonds. Concn or 50% aqueous sodium hypochlorite can also be used as an oxidizing agent. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Dantron has been prepared by several processes, including the alkaline hydrolysis of 1,8-dinitroanthraquinone, the caustic fusion of 1,8-anthraquinonedisulfonic acid, the diazotization of 1,8-diaminoanthraquinone followed by hydrolysis of the bisdiazo compound, the acid hydrolysis of 1,8-dimethoxyanthraquinone in glacial acetic acid-sulfuric acid, the alkaline hydrolysis of 1,8-anthraquinonedisulfonic acid using calcium oxide, and the reaction of 1,8-dinitroanthraquinone with sodium formate or potassium formate.
U.S. Production

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. Year Production Range (pounds) 1986 10 thousand - 500 thousand 1990 No Reports 1994 No Reports 1998 No Reports 2002 No Reports
Intermediate in the production of alizarin and indanthrene dyestuffs.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Agents that are used to stimulate evacuation of the bowels.
- Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes.
【Therapeutic Uses】
Danthron has been widely used since the beginning of this century as a laxative. In 1987, the FDA ordered its withdrawal from the market for its use as a laxative, and U.S. manufacturers voluntarily withdrew production of all human drug products containing the compound. /Former use in US/
Therapeutic Indications: Constipation in terminally ill patients.
【Biomedical Effects and Toxicity】
Following its administration within 24 hr of the induction of labor in 12 women, dantron was found in maternal urine, neonatal urine and amniotic fluide. Most of the drug appeared as a glucuronide in both mothers and babies.
Male Wistar rats were given the sodium salt of dantron intravenously at 4.8, 22 or 58 umol/kg (1.2, 5.3 or 14 mg/kg) bw or at 12 umol/kg (28.8 mg/kg) bw by gastric tube. ... Following intravenous administration, about 80% of the dantron conjugates in bile were excreted after 1 hr; the dose fractions found after 5 hr represented about 20%, 30% and 40% of the low-; intermediate- and high-dose levels, respectively. The corresponding fractions in urine were 16%, 12% and 10%, giving rise to bile:urine excretion ratios of 1.3, 2.7 and 4.0, respectively. Only 30-50% of the dose could be accounted for by conjugates. Earlier studies also showed that after oral administration of dantron only 30-40% of the total dose administered could be recovered in feces and urine, mostly during the first 24 hr. /Dantron sodium salt/
Like other anthraquinone compounds, dantron is partially absorbed from the small intestine.
Rats were infused with danthron (I) at doses of 0.48, 2.2 and 5.8 umol/100 g body weight, or given 12 umol/100 g with gastric tube. TLC of bile and urine demonstrated a number of metabolites, at both administration routes. These included danthron monosulfate (II) and -glucuronide (III), two other phase 2 metabolites which behaved as the corresponding diconjugates, and several phase 1 metabolites (IV) in conjugated form. ... Following infusion, about 80% of the danthron conjugates in bile were excreted after 1 hour; the dose fractions found after 5 hours represented about 20%, 30%, and 40% at the low, intermediate and high dose level, respectively. The corresponding fractions in urine were 16%, 12% and 10%, giving rise to bile:urine excretion ratios of 1.3, 2.7 and 4.0, respectively. This change in excretion pattern was associated with changes in metabolite muster, which involved a decrease in the balance of IV:I conjugates, as well as an increase in III:II ratio. IV was more abundantly present in bile than in urine, and showed a more sustained excretion than the danthron conjugates. By intragastric administration, the cumulated excretion (bile + urine) of I conjugates were only 6%, 8% and 5% of dose, in three consecutive 6 hours' periods (0-6, 6-12 and 12-18 hours after dosing). The bile:urine excretion ratios seemed to decrease with time, as did the III:II ratio... [Sund RB; Pharmacol Toxicol 61 (2): 130-7 (1987). Available from, as of November 16, 2009:] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 8,600(SRC), determined from a structure estimation method(2), indicates that 1,8-dihydroxyanthraquinone is expected to be immobile in soil(SRC). An estimated pKa value of 1,8-dihydroxyanthraquinone is 8.45(3), indicating that this compound will exist partially in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of 1,8-dihydroxyanthraquinone from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.4X10-11 atm-cu m/mole(SRC), using a fragment constant estimation method(5). 1,8-Dihydroxyanthraquinone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 8.6X10-10 mm Hg(SRC), determined from a fragment constant method(6). Biodegradation data were not available(SRC, 2009).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 8,600(SRC), determined from a structure estimation method(2), indicates that 1,8-dihydroxyanthraquinone is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 5.4X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 50(SRC), from an estimated log Kow of 3.9(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). 1,8-Dihydroxyanthraquinone is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Biodegradation data were not available(SRC, 2009).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,8-dihydroxyanthraquinone, which has an estimated vapor pressure of 8.6X10-10 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase 1,8-dihydroxyanthraquinone may be removed from the air by wet or dry deposition(SRC). 1,8-Dihydroxyanthraquinone absorbs light at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).

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