Alizarin
Alizarin Red · TURKEY RED OIL · Alizarine · SULFATED CASTOR OIL · 1,2-DIHYDROXYANTHRAQUINONE · CI 58000 · Alizarine Red · 1,2-dihydroxyanthracene-9,10-dione
Identifikatoren & physikalische Daten
| CAS No. | 72-48-0 |
|---|---|
| Summenformel | C14H8O4 |
| Durchschnittliche Molmasse | 240,21 g/mol |
| Monoisotopische Masse | 240,04225874 g/mol |
| SMILES | O=C1c2ccccc2C(=O)c2c1ccc(O)c2O |
| InChIKey | RGCKGOZRHPZPFP-UHFFFAOYSA-N |
| PubChem CID | 6293 |
| ChEMBL | CHEMBL1206015 |
| ChEBI | CHEBI:16866 |
| EC No. | 200-782-5 |
| DTXSID | DTXSID5045960 |
| Lokaler Name | Alizarin |
Chemische & physikalische Eigenschaften
| XLogP | 3,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 74,6 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 18 |
| Formalladung | 0 |
| Komplexität | 378 |
| Stoffklassen | Dyes -> Anthraquinone Dyes |
| Kosmetika | Hair dyeingCosmetic colorant |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| LogP (Verteilungskoeffizient) | 2.34 |
| Dichte | 1.54 @ 20°C1.06 g/mL at 20 °C |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Siedepunkt | 430 °C @760 [mm Hg] |
| Schmelzpunkt | 289 °C287 °C |
| Physical Description | Red-orange crystals slightly soluble in water[Sax] |
| Collision Cross Section | 141.4 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| Brechungsindex | 1.5190 (estimate) |
| Flammpunkt | 430°C subl. |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| Löslichkeit | Solubility Virtually insoluble in watermoderately soluble in ethanol, soluble in benzene, toluene, Ixylene, pyridine, acetic acidSoluble in hexane and chloroform. Slightly soluble in water. |
| Aggregatzustand | Fine Powder |
| pKa (Säurekonstante) | 6.77(at 25℃) |
| Farbe | Orange to orange-brown |
| pH | 5.5~7.2 |
| Merck | 14,251 |
| BRN | 1914037 |
| Stabilität | Stable. Incompatible with strong oxidizing agents, strong bases. |
| Hauptanwendungen | Plasma displays, Antireflective coatings, chemical-mechanical polishing, photoreceptors, glass coatings, paints, anticorrosion coatings, thermoplastics, wood coloring, textiles, pH sensor device, detergent, hair dyes, darkening skin, cosmetics, parasiticide, antifungal agent |
| Kosmetik-Inhaltsstoffe Funktionen | HAIR DYEINGCOLORANT |
| InChI | 1S/C14H8O4/c15-10-6-5-9-11(14(10)18)13(17)8-4-2-1-3-7(8)12(9)16/h1-6,15,18H |
| InChIKey | RGCKGOZRHPZPFP-UHFFFAOYSA-N |
| SMILES | Oc1ccc2C(=O)c3ccccc3C(=O)c2c1O |
| LogP (Verteilungskoeffizient) | 2.479 (est) |
| CAS Datenbank | 72-48-0(CAS DataBase Reference) |
| NIST chemische Informationen | Alizarin(72-48-0) |
| EPA chemische Informationen | Alizarin (72-48-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 10.8% (8 of 74) of reports.WarningH302 (55.4%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 74 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: 9,10-Anthracenedione, 1,2-dihydroxy-Status: Cease Manufacture Update: 15-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/237969,10-Anthracenedione, 1,2-dihydroxy-: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | Anthraquinones are toxic by ingestion: vomiting, diarrhea, kidney and liver damage, and comaDeaths have been reported after children ingested Rhamnus berries[HSDB] Toxic by ingestionAn eye irritant[Sax] An irritantHarmful by ingestion, inhalation, or skin absorptionToxic if swallowed[Aldrich MSDS] |
| Hazard Classes and Categories | Acute Tox. 4 (55.4%) |
| Protective Action Criteria (PAC) | 1.2 [mg/m3]13 [mg/m3]79 [mg/m3] |
| Unerwünschte Wirkungen | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN3077 |
| Zollcode | 29146990 |
| RTECS-Nr. | YO8300000 |
| R-Sätze (R) | 36/38-36/37/38 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-36-24/25-22 |
| Gefahrenklasse | 9Aquatic Chronic 1Eye Dam. 1Skin Sens. 1A |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
History
In ancient times, alizarin was the preferred red dye. Cloth dyed with it has been found in Egyptian tombs dating 6000 years ago. The dye is found in the madder plant, a member of the Rubiaceae family. In 1944 about 35 species of this plant were known, but the use of more sophisticated analytical methods led to the detection of many more species; by 1984 the number had increased to 50. Alizarin is a mordant dye forming various colored coordination complexes with different metallic salts.
Verwenden
Alizarin is used widely as a prominent red dye for textile facbrics. Alizarin red is now used in biochemical assay to determine quantitatively by colorimetry, the presence of calcific deposition by ce lls of the osteogenic lineage. Alzarine derivatives was evaluated as new inhibitors of the HIV-1 reverse transcriptase associated DNA polymerase and RNase H. Alizarin was also shown to inhibit prolife ration, tumor growth and suppress tumorigenesis in human osteosarcoma and breast cancer cell representative for bone metastasis.
Herstellung & Synthese
synthetische
(a) 2 – Bromoanthraquinone and Potassium hydroxide heating; (b) 9,10-Dioxo-9,10-dihydroanthracene-2-sulfonic acid (Sodium) and Sodium hydroxide and Sodium nitrate and Sodium chlorate heating; (C) Anthracene-9,10-dioneand Sodium hydroxide and Sodium chlorate and Sodium nitrate heating (GP 186526); (d) in the presence of Sodium nitrite and Sodium hydroxide and Anthracene-9,10-dioneand Sodium nitrate heating (GP 241806245 987); (e) in the Oxidant and Sodium sulfite and the presence of lime, anthracene in a nitrocellulose derivatives and Sodium hydroxide heating (GP 292247); (f) 2 – Anthraquinonesulfonic acid in the presence of air, with the Sodium hydroxide Etanol wetting treatment (GP 287270); (g) 2-Chloroanthracene-9,10-dione Sodium chlorate in the presence of alkali fusion for (USP 1744815); (h) 2-Methylanthracene-9,10-dione in the presence of Oxidant, with Sodium hydroxide treatment (BP 293328).