Quinizarin

HCID 6688CAS 81-64-1

Basic information

Standard SMILES
O=C1c2ccccc2C(=O)c2c(O)ccc(O)c21
InChIKey
GUEIZVNYDFNHJU-UHFFFAOYSA-N
Molecular formula
C14H8O4
Average molar mass
240.21 g/mol
Monoisotopic mass
240.04225874

Overview

Quinizarin is a dihydroxyanthraquinone having the two hydroxy substituents at the 1- and 4-positions; formally derived from anthraquinone by replacement of two hydrogen atoms by hydroxy groups. It has a role as a dye.

Names & identifiers

Preferred name
Quinizarin
IUPAC
1,4-dihydroxyanthracene-9,10-dione
English name
1,4-Dihydroxyanthraquinone
Molecular formula
C14H8O4
Molecular weight
240.21

Names & synonyms

Quinizarin1,4-Dihydroxyanthraquinone81-64-11,4-dihydroxyanthracene-9,10-dioneQuinizarineChinizarinSolvent Orange 86Smoke Orange R1,4-DihydroxyanthrachinonMacrolex Orange GG1,4-Dihydroxy-9,10-anthraquinone9,10-Anthracenedione, 1,4-dihydroxy-
Show more names
DSD ACID1,4-DHAQQUINAZARINQuinizalin4-Dihydroxyanthraquinone
Anthraquinone, 1,4-dihydroxy-1,4-Dioxyanthraquinone1,4-Doa1,4-DIHYDROXY-9,10-ANTHRACENEDIONEC.I. 58050DTXSID80444648S496ZV3CSCI 58050

Database identifiers

CAS
81-64-1
PubChem CID
6688
DTXSID
DTXSID8044464
ChEMBL
CHEMBL17594
ChEBI
CHEBI:37487
UNII
8S496ZV3CS
EC Number
201-368-7
Nikkaji
J3.861J、J710.748J

Properties

Computed structural properties

XLogP
3.7
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
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
Color/Form · 2 items

ORANGE CRYSTALS FROM ACETIC ACID; ORANGE PLATES FROM ETHER; DEEP RED NEEDLES FROM ALCOHOL, BENZENE, TOLUENE, XYLENE

YELLOW RED LEAFLETS FROM ETHER; RED CRYSTALS FROM TOLUENE, ACETIC ACID

Solubility · 5 items

MODERATELY SOL IN ALCOHOL WITH RED COLOR

SOL IN ETHER WITH BROWN COLOR & YELLOW FLUORESCENCE

SOL WITH VIOLET COLOR IN AQ ALKALIES & IN AMMONIA

1 G SOL IN ABOUT 13 G OF BOILING GLACIAL ACETIC ACID

For more Solubility (Complete) data for 1,4-DIHYDROXY-9,10-ANTHRACENEDIONE (6 total), please visit the HSDB record page.

Flash Point222 °C
Melting Point196 °C

Physicochemical properties

Melting point
195 · 195-200 °C
Boiling point
450 °C · 450 °C
Density
1.3032 · 1.3032 (rough estimate)
bulk density
350 kg/m3 · 350kg/m3
vapor density
8.3 · 8.3 (vs air)
vapor pressure
1 mm · 1 mm Hg ( 196.7 °C)

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 0.3% (7 of 2238) of reports.

Warning

H315 (90.9%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2238 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Not Classified

Hazard information

Regulatory Information · 4 items

Chemical: 9,10-Anthracenedione, 1,4-dihydroxy-

9,10-Anthracenedione, 1,4-dihydroxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 9,10-Anthracenedione, 1,4-dihydroxy- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 14-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/20342

9,10-Anthracenedione, 1,4-dihydroxy-: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryA mutagen and irritant; Effects in high-dose animal studies include changes in renal tubules and weight loss; [RTECS] Emergency treatment: irritants; [HSDB] An irritant; [MSDSonline]
Hazard Classes and Categories · 2 items

Skin Irrit. 2 (90.9%)

Hazardous to the aquatic environment (Acute) - Category 1

Toxicology

Non-Human Toxicity Excerpts · 4 items

ACUTE TOXICITY OF 1,4-DIHYDROXYANTHRAQUINONE WAS TESTED IN ANIMALS & DID NOT SENSITIZE MANY, BUT PRODUCED A VERY SEVERE REACTION IN THOSE AFFECTED.

1,4-DIHYDROXYANTHRAQUINONES DID NOT ALTER COLONIC WATER ABSORPTION BUT RESTRICTED SODIUM ABSORPTION & CAUSED AN APPARENT RELEASE OF POTASSIUM INTO THE LUMEN.

IN VITRO STUDY INDICATED ANTHRAQUINONE DYES TO BE INHIBITORS OF MITOCHONDRIA ADENINE NUCLEOTIDE TRANSLOCATION & OXIDATIVE PHOSPHORYLATION. MOST OF THE DYES INHIBITED MITOCHONDRIAL (14)C-ADP UPTAKE IN A PARTIALLY COMPETITIVE-NONCOMPETITIVE MANNER.

QUINIZARIN GLUCOSIDE TETRAACETATE WAS RENDERED MUTAGENIC TO SALMONELLA TYPHIMURIUM BY ENZYME EXTRACTS OF RAT CECAL BACTERIA (APPARENTLY BY AGLYCONE FORMATION).

Safety data

PPE
Eyeshields, Faceshields, Gloves, type N95 (US)
wgk
2
tsca
TSCA listed
rtecs
CB6600000
ridadr
UN 3077 9 / PGIII
hs_code
2914 69 80

Chemistry & industry

Pharmacology

Mechanism of Action · 1 item

LAXATIVE EFFECTS OF 6 ANTHRAQUINONES WERE RELATED TO THEIR ABILITY TO UNCOUPLE PHOSPHORYLATION IN BOTH PLANT (PHASEOLUS AUREUS) & ANIMAL (GUINEA PIGS INTESTINE) MITOCHONDRIA. THE STRUCTURAL REQUIREMENTS WERE: A RIGID PLANAR STRUCTURE AND AT LEAST 1 OH GROUP, PREFERENTIALLY IN POSITION 1, 1 AND 8, 2, 3, 6, AND 7.

Uses & manufacturing

Uses · 5 items

Used as an antioxidant in synthetic lubricants and a fungicide for control of powdery mildew; [HSDB] Used in the fuel and textile processing industries and as a coloring agent and intermediate; [IUCLID]

Petroleum Production and Refining [Category: Industry]

ANTIOXIDANT IN SYNTHETIC LUBRICANTS

IN THE SYNTHESIS OF EXPERIMENTAL ANTITUMOR AGENTS

FUNGICIDE FOR CONTROL OF POWDERY MILDEW

U.S. Production2023: 75,000 - <500,000 lb
Industry UsesIntermediate
Methods of Manufacturing · 1 item

...BY DIAZOTIZING P-CHLOROANILINE, CONDENSING WITH PHTHALIC ANHYDRIDE, & HYDROLYZING: BRITISH PATENT 373,999, CA 27, 3946 (1933); BY TREATING ANTHRAQUINONE WITH AMMONIUM PERSULFATE IN SULFURIC ACID: WACKER, J PRAKT CHEM [2] 54, 90 (1896). BY HEATING P-CHLOROPHENOL, PHTHALIC ANHYDRIDE & EITHER SULFURIC ACID OR ALUMINUM CHLORIDE: REYNOLDS, BIGELOW, J AM CHEM SOC 48, 420 (1926); US PATENT 1,845,632, CA 26, 2203; ORG SYN COLL VOL I, 476 (NEW YORK, 1941).

General Manufacturing Information · 4 items

Synthetic Dye and Pigment Manufacturing

9,10-Anthracenedione, 1,4-dihydroxy-: ACTIVE

THE CONDENSATION OF ALKYLENEDIAMINES WITH QUINIZARIN GAVE COMPD MARKEDLY ACTIVE AGAINST BOTH LEUKEMIAS & SOLID TUMORS IN MICE.

1,4-DIHYDROXYANTHRAQUINONE IS FUNGICIDE @ 4000 PPM FOR CONTROL OF POWDERY MILDEW (ERYSIPHE POLYGONI) ON INOCULATED CRANBERRY BEAN SEEDLINGS.

Applications · 4 items

Uses1,4-Dihydroxyanthraquinone, also known as quinizarin, is of great importance in manufacturing disperse, acid, and vat dyes.

Uses1,4-Dihydroxyanthraquinone is used to color gasoline and some heating oils. It is used as an intermediate for the synthesis of indanthrene- and alizarin-derived dyes. It is also used to form lake pigments with calcium, barium and lead. It may be used in the synthesis of cyclopentanoids by cyclization of α,β-unsaturated aldehyde with 1,4-Dihydroxyanthraquinone. It has been studied as a long range emissive ratiometric fluorescent probe for live cell imaging.

UsesAntioxidant in synthetic lubricants, dyes.

General Description1,4-Dihydroxyanthraquinone is an organic dye molecule with an aromatic structure. It is a derivative of anthraquinone bearing hydroxyl moieties. They may find uses in pharmacological, biochemical and dye industries. Anthraquinone dye are resistant to degradation.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]

Additional notes

DefinitionChEBI: Quinizarin is a dihydroxyanthraquinone having the two hydroxy substituents at the 1- and 4-positions; formally derived from anthraquinone by replacement of two hydrogen atoms by hydroxy groups It has a role as a dye.

Related reactions

29 records

Linked notes

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