Alizarin

HCID 6293CAS 72-48-0

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

Alizarin72-48-01,2-dihydroxyanthracene-9,10-dione1,2-DihydroxyanthraquinoneMordant Red 111,2-Dihydroxy-9,10-anthracenedioneTurkey RedALIZARINEAlizarin BAlizarine Red1,2-AnthraquinonediolAlizarine B
Show more names
Alizarin RedTURKEY RED OILSULFATED CASTOR OILCI 58000Aliazrin
AlizarinaEljon MadderAlizarine NACAlizarine Red BAlizarine Red LAlizerine NACEljon Madder M1,2-Dihydroxy-9,10-anthraquinone

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

Experimental & physicochemical properties

Chemical ClassesDyes -> Anthraquinone Dyes
CosmeticsHair dyeing; Cosmetic colorant
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP2.34
Density1.54 @ 20°C
Endocrine DisruptorsPotential endocrine disrupting compound

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

Safety & regulation

GHS classification

GHS Classification · 5 items

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 · 3 items

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 · 1 item

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]

Hazard Classes and CategoriesAcute Tox. 4 (55.4%)

Safety & protection

Protective Action Criteria (PAC) · 3 items

1.2 [mg/m3]

13 [mg/m3]

79 [mg/m3]

Toxicology

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

Safety data

PPE
Eyeshields, Faceshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
rtecs
YO8300000
ridadr
UN3077
hs_code
29146990

Chemistry & industry

Uses & manufacturing

Uses · 2 items

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]

Use ClassificationCosmetics -> Hair dyeing; Cosmetic colorant
General Manufacturing Information9,10-Anthracenedione, 1,2-dihydroxy-: ACTIVE
Applications · 4 items

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 · 1 item

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).

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
山东海舟生物工程有限公司130-0567-0367 13006570367 · [email protected]
Additional notes · 3 items

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

5 records

Linked notes

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