1,8-Dihydroxyanthraquinone CAS 117-10-2
Introduction：Basic information about 1,8-Dihydroxyanthraquinone CAS 117-10-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
1,8-Dihydroxyanthraquinone Basic information
| Product Name: | 1,8-Dihydroxyanthraquinone |
| Synonyms: | NSC 38626;NSC 646568;NSC 7210;Danthron1,8-DihydroxyanthraquinoneIstizine;1,4,5,8-tetroxyantraquinone;Dionone;Dorbane;Dorbanex |
| CAS: | 117-10-2 |
| MF: | C14H8O4 |
| MW: | 240.21 |
| EINECS: | 204-173-5 |
| Product Categories: | Inhibitors;DORBANE;Aloe Vera;Building Blocks;C13 to C14;Carbonyl Compounds;Chemical Synthesis;Ketones;Nutrition Research;Organic Building Blocks;Phytochemicals by Plant (Food/Spice/Herb);Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Intermediates of Dyes and Pigments;Anthraquinones;Hydroxyanthraquinones;bc0001;117-10-2 |
| Mol File: | 117-10-2.mol |
1,8-Dihydroxyanthraquinone Chemical Properties
| 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) |
| Fp | >200°C |
| storage temp. | Sealed in dry,2-8°C |
| solubility | very faint turbidity in hot Acetic acid |
| form | Powder |
| pka | 6.27±0.20(Predicted) |
| color | Orange-brown or brown |
| Water Solubility | insoluble |
| Merck | 14,2815 |
| BRN | 2054727 |
| InChI | 1S/C14H8O4/c15-9-5-1-3-7-11(9)14(18)12-8(13(7)17)4-2-6-10(12)16/h1-6,15-16H |
| InChIKey | QBPFLULOKWLNNW-UHFFFAOYSA-N |
| SMILES | Oc1cccc2C(=O)c3cccc(O)c3C(=O)c12 |
| 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) |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 40 |
| Safety Statements | 36/37-36-22 |
| RIDADR | 2811 |
| WGK Germany | 1 |
| RTECS | CB6650000 |
| TSCA | TSCA listed |
| HazardClass | IRRITANT |
| HS Code | 29146990 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Carc. 2 Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
| Hazardous Substances Data | 117-10-2(Hazardous Substances Data) |
| Toxicity | LD50 orally in mice: <7 g/kg (Case) |
| Description | Danthron, a natural product, was originally extracted fromthe roots and rhizome of Polygonaceae plant, alsocalled 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 UnitedStates. Danthron is reasonably anticipated to be a humancarcinogen. Danthron is an anthraquinone that exists at room temperatureas a red or orange crystalline powder.It is practicallyinsoluble in water, but soluble in a variety of solvents(acetone, chloroform, diethyl ether, ethanol) and alkalinehydroxide solutions. The stability of danthron is generallygood. It is stable under room temperatures and normal pressures. |
| Chemical Properties | orange-brown or brown powder |
| Chemical Properties | Red-orange to orange crystalline powder orreddish-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:
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| 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 overtwenty years and is widely used as a laxative. The results of two chronic toxicitystudies in rodents, published in 1985 and 1986, have shown that administration ofhigh 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 preparedby replacing SO3H, by directlyreplacing nitro groups in sulfolane inthe presence of calcium oxide , or, better,via 1,8-dimethoxyanthraquinone and subsequenthydrolysis of the ether . |
| Potential Exposure | A potential liver carcinogen andpossible narcotic, this compound is no longer sold ormarketed in the United States Nervous system toxin-acuteeffects; Respiratory toxin-acute effects other than severe ormoderate 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 the5'-GG-3', 5'-GGGG-3', 5'-GGGGG-3' sequences in the presenceof Cu(II), cytochrome P450 reductase and the nicotinamideadenine dinucleotide phosphate (NADPH)-generating system.H2O2 and Cu(I) may also be involved because this DNAdamage can be inhibited by catalase and bathocuproine. Thefurther mechanism is danthron is reduced by P450 reductaseand generate reactive oxygen species through the redox cycle,leading to extensive Cu(II)-mediated DNA damage. The DNAdamage also comes from similar topoisomerase II inhibitorbehavior of danthron. |
| Shipping | UN2811 Toxic solids, organic, n.o.s., HazardClass: 6.1; Labels: 6.1-Poisonous materials, TechnicalName 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 semifuscataharvested in Madagascar, and roots of Da Huang,a Chinese traditional herbal medicine. Danthron also appearsto be biosynthesized by some insects. The presence of danthronin insects may be a way of protection from predators. Danthroncan be manually synthesized by many countries. In the UnitedStates, danthron was available from 12 suppliers. If released to the atmosphere, danthron will exist in boththe vapor phase and the particulate phase. Vapor phase danthronhas an estimated half-life of 11 days. Particulate phasedanthron can be physically removed from air by wet and dry deposition. It is expected to biodegrade with 68% degradationwithin 3 months. If released to water, danthron is expected to adsorb to thesurface of solid particle and sediment. Biodegradation is alsoa major pathway processed in water. It was reported that 82%of the added danthron was degraded by fresh water within3 days. If added to seawater, 91% of danthron was reported asdegraded. 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 andpossibly dangerous to the environment to dispose ofexpired or waste drugs and pharmaceuticals by flushingthem down the toilet or discarding them to the trash.Household quantities of expired or waste pharmaceuticalsmay be mixed with wet cat litter or coffee grounds, double-bagged in plastic, discard in trash. Larger quantities shallcarefully take into consideration applicable DEA, EPA, andFDA regulations. If possible return the pharmaceutical tothe manufacturer for proper disposal being careful to prop-erly label and securely package the material. Alternatively,the waste pharmaceutical shall be labeled, securelypackaged and transported by a state licensed medical wastecontractor to dispose by burial in a licensed hazardous ortoxic waste landfill or incinerator. |
1,8-Dihydroxyanthraquinone Preparation Products And Raw materials
| Raw materials | 9,10-Anthracenedione, 1,8-bis(2-propyn-1-yloxy)--->1,8-DIACETOXYANTHRAQUINONE-->3-Nitrophthalic anhydride |
| Preparation Products | 1,4,5,8-TETRAHYDROXYANTHRAQUINONE-->disodium 4,5-diamino-9,10-dihydro-1,8-dihydroxy-9,10-dioxoanthracene-2,7-disulphonate |
