Grundinformationen
- Standard-SMILES
O=C1c2ccccc2C(=O)c2c1ccc(O)c2O- InChIKey
RGCKGOZRHPZPFP-UHFFFAOYSA-N- Summenformel
- C14H8O4
- Durchschnittliche Molmasse
- 240,21 g/mol
- Monoisotopische Masse
- 240,04225874
Überblick
Alizarin is a dihydroxyanthraquinone that is anthracene-9,10-dione in which the two hydroxy groups are located at positions 1 and 2. It has a role as a chromophore, a dye and a plant metabolite.
Namen und Bezeichner
- Bevorzugter Name
- Alizarin
- IUPAC
- 1,2-dihydroxyanthracene-9,10-dione
- Lokaler Name
- Alizarin
- Englischer Name
- Alizarin
- Summenformel
- C14H8O4
- Molmasse
- 240.21
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
72-48-0- PubChem CID
- 6293
- DTXSID
DTXSID5045960- ChEMBL
CHEMBL1206015、CHEMBL55814- ChEBI
CHEBI:16866- UNII
- 60MEW57T9G
- EC Number
- 200-782-5
- Nikkaji
- J2.816I
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,2
- Polarare Oberfläche (TPSA)
- 74,6 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 18
- Formalladung
- 0
- Komplexität
- 378
Experimentelle und physikochemische Eigenschaften
Physikochemische Eigenschaften
- Schmelzpunkt
- 287 °C · 287 °C
- Siedepunkt
- 430 °C · 430 °C
- Dichte
- 1.06 g/mL · 1.06 g/mL at 20 °C
- Brechungsindex
- 1.519 · 1.5190 (estimate)
- Flammpunkt
- 430 °C · 430°C subl.
- storage temp.
- Inert atmosphere,Room Temperature
- Löslichkeit
- Solubility Virtually insoluble in water; moderately soluble in ethanol, soluble in benzene, toluene, Ixylene, pyridine, acetic acid
- Aggregatzustand
- Fine Powder
- pka
- 6.77 · 6.77(at 25℃)
- Farbe
- Orange to orange-brown
- PH
- 5.5 · 5.5~7.2
- Wasserlöslichkeit
- Soluble in hexane and chloroform. Slightly soluble in water.
- Merck
- 14 · 14,251
- BRN
- 1914037 · 1914037
- Stabilität
- Stable. Incompatible with strong oxidizing agents, strong bases.
- Major Application
- 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
- 2.479 · 2.479 (est)
- CAS Datenbank
- 72 · 72-48-0(CAS DataBase Reference)
- NIST chemische Informationen
- Alizarin(72-48-0)
- EPA chemische Informationen
- Alizarin (72-48-0)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 10.8% (8 of 74) of reports.
Warning
H302 (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.
Gefahrenhinweise
Regulatory Information
Chemical: 9,10-Anthracenedione, 1,2-dihydroxy-
Status: Cease Manufacture Update: 15-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/23796
9,10-Anthracenedione, 1,2-dihydroxy-: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Anthraquinones are toxic by ingestion: vomiting, diarrhea, kidney and liver damage, and coma; Deaths have been reported after children ingested Rhamnus berries; [HSDB] Toxic by ingestion; An eye irritant; [Sax] An irritant; Harmful by ingestion, inhalation, or skin absorption; Toxic if swallowed; [Aldrich MSDS]
Sicherheit und Schutzausrüstung
Protective Action Criteria (PAC)
1.2 [mg/m3]
13 [mg/m3]
79 [mg/m3]
Toxikologische Informationen
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN3077
- hs_code
- 29146990
- RTECS-Nr.
- YO8300000
- risk_code
- 36/38-36/37/38
- hazard_code
- Xi
- safety_code
- 26-36-24/25-22
- hazard_class
- 9
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Aquatic Chronic 1Eye Dam. 1Skin Sens. 1A
Chemie und Industrie
Verwendung und Herstellung
Uses
Used as a pH indicator for the pH range of 5.8-7.2 and 10.2-11.8; [Ullmann] The parent chemical for many dyes, pigments, lakes, indicators, and biological stains; Naturally occurring in madder root; [Hawley]
Textiles (Printing, Dyeing, or Finishing) [Category: Industry]
Anwendungen
HistoryIn 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.
VerwendenAlizarin 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.
Darstellung
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).
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
Anbieter50 Anbieter
Ergänzende Hinweise
Definitionalizarin: An orange-red compound,C14H8O4. The compound is a derivativeof anthraquinone, with hydroxylgroups substituted at the 1and 2 positions. It is an importantdyestuff producing red or violetlakes with metal hydroxide.Alizarin occurs naturally as the glucosidein madder. It can be synthesizedby heating anthraquinone withsodium hydroxide.
Zugehörige Reaktionen
Verknüpfte Notizen
Wird geladen…