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Quinizarin

Quinizarin structure

CAS No:
81-64-1
Formula:
C14H8O4
Chemical Name:
Quinizarin
Synonyms:
9,10-Anthracenedione,1,4-dihydroxy-;Anthraquinone,1,4-dihydroxy-;1,4-Dihydroxy-9,10-anthracenedione;C.I. 58050;Chinizarin;Quinizarin;Quinizarine;Smoke Orange R;1,4-Dihydroxyanthraquinone;1,4-Dihydroxy-9,10-anthraquinone;NSC 15367;DAQ;Solvent Orange 86;C.I. Solvent Orange 86;Macrolex Orange GG;C.I. Solvent Orange 100;Solvent Orange 100;Smoke Orange 18;NSC 229036;NSC 40899;NSC 646569;103220-12-8
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

orange to red-brown crystalline powder

DryPowder

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.

Quinizarin Basic Attributes

Molecular Weight：

240.21100

Exact Mass：

240.21

EC Number：

201-368-7

UNII：

8S496ZV3CS

NSC Number：

646569|229036|40899|15367

DSSTox ID：

DTXSID8044464

Color/Form：

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

HScode：

2914610000

Characteristics

PSA：

74.60000

XLogP3：

3.7

Appearance：

DryPowder

Density：

1.52 g/cm³

Melting Point：

196 °C

Boiling Point：

450ºC

Flash Point：

222ºC

Refractive Index：

1.732

Water Solubility：

H2O: <1 g/L (20 ºC);SOL IN POTASSIUM HYDROXIDE & SULFURIC ACID

Storage Conditions：

Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances.

Vapor Pressure：

1 mm Hg ( 196.7 °C)

Vapor Density：

8.3 (vs air)

Toxicity：

LD50 orally in Rabbit: > 5000 mg/kg

Experimental Properties：

UV: 1-545 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York) /1,5-Dihydroxyanthraquinone/

Safety Information

Packing level：

II; III

Hazard category：

4.1

Transport codes：

UN 3077 9 / PGIII

wgk germany：

hazard class code：

R36/37/38

safety instructions：

S24/25

RTECS Number：

CB6600000

Marks：

Stability/Shelf Life：

BLACK PPT WITH CO2; SUBLIMES @ HIGH VACUUM

Precautionary statement(s)：

P273-P501

Hazard Statements：

H410

GHS Classification：

|Warning|H315 (96.58%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 2144 companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Not Classified

Drug Information

Mechanism of Action：

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.

MeSH Entry Terms：

1,4-dihydroxy-9,10-anthraquinone

Quinizarin Use and Manufacturing

Methods of Manufacturing

...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).

Uses

Antioxidant in synthetic lubricants.

Intermediates

Manufacturing Info：

All other basic organic chemical 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.

Laboratory Methods：

HPLC IS EMPLOYED FOR ANALYSIS OF QUINIZARIN IN D&C GREEN #6.

Computed Properties

Molecular Weight:240.21
XLogP3:3.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Exact Mass:240.04225873
Monoisotopic Mass:240.04225873
Topological Polar Surface Area:74.6
Heavy Atom Count:18
Complexity:342
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Quinone

Hydroquinone

Phthalic anhydride

Phthaloyl chloride

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