Basic information
- Standard SMILES
O=C1c2ccccc2C(=O)c2c1ccc(O)c2O- InChIKey
RGCKGOZRHPZPFP-UHFFFAOYSA-N- Molecular formula
- C14H8O4
- Average molar mass
- 240.21 g/mol
- Monoisotopic mass
- 240.04225874
Overview
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.
Names & identifiers
- Preferred name
- Alizarin
- IUPAC
- 1,2-dihydroxyanthracene-9,10-dione
- English name
- Alizarin
- Molecular formula
- C14H8O4
- Molecular weight
- 240.21
Names & synonyms
Show more names
Database identifiers
- 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
Properties
Computed structural properties
- XLogP
- 3.2
- Topological polar surface area
- 74.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 0
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 378
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 287 °C · 287 °C
- Boiling point
- 430 °C · 430 °C
- Density
- 1.06 g/mL · 1.06 g/mL at 20 °C
- refractive index
- 1.519 · 1.5190 (estimate)
- Flash point
- 430 °C · 430°C subl.
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- Solubility Virtually insoluble in water; moderately soluble in ethanol, soluble in benzene, toluene, Ixylene, pyridine, acetic acid
- form
- Fine Powder
- Colour Index
- 58000 · 58000
- pka
- 6.77 · 6.77(at 25℃)
- color
- Orange to orange-brown
- PH
- 5.5 · 5.5~7.2
- PH Range
- Yellow (5.5) to red (6.8);Red (10.1) to purple (12.1)
- Water Solubility
- Soluble in hexane and chloroform. Slightly soluble in water.
- λmax
- 567 nm, · 567nm, 609nm
- ε(extinction coefficient)
- 13000 at · 13000 at 227-233nm in 0.1 M NaOH at 0.01g/L26000 at 268-274nm in 0.1 M NaOH at 0.01g/L
- Merck
- 14 · 14,251
- BRN
- 1914037 · 1914037
- Stability
- Stable. Incompatible with strong oxidizing agents, strong bases.
- Biological Applications
- Detecting microorganisms; treating dermatological conditions
- 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
- Cosmetics Ingredients Functions
- 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 DataBase Reference
- 72 · 72-48-0(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1-3
- FDA UNII
- 60 MEW57T9G · 60MEW57T9G
- NIST Chemistry Reference
- Alizarin(72-48-0)
- EPA Substance Registry System
- Alizarin (72-48-0)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 47 · NA.47
- Symbol(GHS)
- 5 · GHS05,GHS07,GHS09
- Signal word
- Danger
- Hazard statements
- 317 · H317-H318-H410
- Precautionary statements
- 261 · P261-P272-P273-P280-P302+P352-P305+P351+P338
- PPE
- 95 · Eyeshields, Faceshields, Gloves, type N95 (US)
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/38-36/37/38
- Safety Statements
- 26 · 26-36-24/25-22
- RIDADR
- 3077 · UN3077
- WGK Germany
- 3 · 3
- RTECS
- 8300000 · YO8300000
- TSCA
- TSCA listed
- HazardClass
- 9 · 9
- HS Code
- 29146990 · 29146990
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 1 Eye · Aquatic Chronic 1Eye Dam. 1Skin Sens. 1A
- REACH Registrations
- Inactive
- Limited Quantities
- 5 kg · 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
GHS classification
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.
Hazard information
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]
Safety & protection
Protective Action Criteria (PAC)
1.2 [mg/m3]
13 [mg/m3]
79 [mg/m3]
Toxicology
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- YO8300000
- ridadr
- UN3077
- hs_code
- 29146990
- risk_code
- 36/38-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07,GHS09
- hazard_code
- Xi
- safety_code
- 26-36-24/25-22
- hazard_class
- 9
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H317-H318-H410
- Limited Quantities
- 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- REACH Registrations
- Inactive
- Hazard Classifications
- Aquatic Chronic 1Eye Dam. 1Skin Sens. 1A
- Precautionary statements
- P261-P272-P273-P280-P302+P352-P305+P351+P338
Chemistry & industry
Uses & manufacturing
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]
Applications
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.
Usesantimutagen
UsesAlizarin has a major application in the manufacture of the madder lake pigments which is commonly called as Rose madder and Alizarin crimson. It is involved in the studies of bone growth, osteoporosis, bone marrow and calcium deposits in the vascular system. It is also used as a stain in calcite and aragonite to identify calcium carbonate, and synovial fluid to asses for basic calcium phosphate crystals. It is used in colorimetric measurements for quantification of amine extraction by model food simulants from epoxy polymer.
UsesAlizarin 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.
Preparation methods
Preparation(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).
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: A dihydroxyanthraquinone that is anthracene-9,10-dione in which the two hydroxy groups are located at positions 1 and 2.
DefinitionAn important orange-red organic compound used in the dyestuffs industry to produce red lakes. It occurs naturally in the root of the plant madder and may also be synthesized from anthraquinone.
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.
Related reactions
Linked notes
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