Quinizarin

Names

[ CAS No. ]:
81-64-1

[ Name ]:
Quinizarin

[Synonym ]:
MFCD00001209
EINECS 201-368-7
1,4-hydroxyanthraquinone
QUINIZARINE
DSD ACID
smokeoranger
1,4-Dihydroxy-9,10-anthraquinone
Quinizarin
Chinizarin
1,4-Dihydroxy-9,10-anthracene-dione
1,4-Dihydroxyanthraquinone
9,10-Anthracenedione, 1,4-dihydroxy-
Quinizalin
QUINAZARIN
1,4-Doa
1,4-dihydroxyanthracene-9,10-dione
quiniazarine

Biological Activity

[Description]:

Quinizarin (1,4-Dihydroxyanthraquinone), a part of the anticancer agents such as Doxorubicin, Daunorubicin, and Adriamycin, interacts with DNA by intercalating mode (Kd=86.1 μM). Quinizarin is used as a fungicide and pesticide chemical and has shown the ability to inhibit tumor cell growth[1][2].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis

Signaling Pathways >> Anti-infection >> Fungal

[In Vitro]

1,4-Dihydroxyanthraquinone (1,4-DHAQ, a fluorophore) doped cellulose (CL) (denoted as 1,4-DHAQ@CL) microporous nanofiber film has been achieved via simple electrospinning and subsequent deacetylating, and used for highly sensitive and selective fluorescence detection of Cu(2+) in aqueous solution[1].

[References]

[1]. Verebová V, et al. Anthraquinones quinizarin and danthron unwind negatively supercoiled DNA and lengthen linear DNA. Biochem Biophys Res Commun. 2014;444(1):50-55.

[2]. Dominic Cheuk, et al. Investigation into solid and solution properties of quinizarin.

[3]. Wang M, et al. Electrospun 1,4-DHAQ-doped cellulose nanofiber films for reusable fluorescence detection of trace Cu2+ and further for Cr3+. Environ Sci Technol. 2012;46(1):367-373.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
465.3±40.0 °C at 760 mmHg

[ Melting Point ]:
198-199 °C(lit.)

[ Molecular Formula ]:
C₁₄H₈O₄

[ Molecular Weight ]:
240.211

[ Flash Point ]:
249.3±23.8 °C

[ Exact Mass ]:
240.042252

[ PSA ]:
74.60000

[ LogP ]:
4.47

[ Vapour density ]:
8.3 (vs air)

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.733

[ Water Solubility ]:
<1 g/L (20 ºC)

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CB6600000

CHEMICAL NAME :: Anthraquinone, 1,4-dihydroxy-

CAS REGISTRY NUMBER :: 81-64-1

LAST UPDATED :: 199701

DATA ITEMS CITED :: 8

MOLECULAR FORMULA :: C14-H8-O4

MOLECULAR WEIGHT :: 240.22

WISWESSER LINE NOTATION :: L C666 BV IVJ DQ GQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration into the eye

SPECIES OBSERVED :: Rodent - rabbit

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >10 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 320 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Salmonella typhimurium

DOSE/DURATION :: 100 ug/plate

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 40,203,1976 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 82067 No. of Facilities: 563 (estimated) No. of Industries: 10 No. of Occupations: 9 No. of Employees: 6634 (estimated)

Safety Information

[ Symbol ]:

GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H410

[ Precautionary Statements ]:
P273-P501

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
UN 3077 9 / PGIII

[ WGK Germany ]:
2

[ RTECS ]:
CB6600000

[ Packaging Group ]:
II; III

[ Hazard Class ]:
4.1

[ HS Code ]:
2914610000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914610000

[ Summary ]:
2914610000 anthracene-9,10-dione。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。Lowest tariff:5.5%。General tariff:30.0%

Articles

In vitro inhibition of Streptococcus mutans biofilm formation on hydroxyapatite by subinhibitory concentrations of anthraquinones.

Antimicrob. Agents Chemother. 51 , 1541-4, (2007)

We report that certain anthraquinones (AQs) reduce Streptococcus mutans biofilm formation on hydroxyapatite at concentrations below the MIC. Although AQs are known to generate reactive oxygen species,...

Synthesis and activity of substituted anthraquinones against a human filarial parasite, Brugia malayi.

J. Med. Chem. 48 , 2822-30, (2005)

Lymphatic filariasis (elephantiasis) is a global public health problem caused by the parasitic nematodes Wuchereria bancrofti and Brugia malayi. We have previously reported anthraquinones from daylily...

Synthesis of glycoside derivatives of hydroxyanthraquinone with ability to dissolve and inhibit formation of crystals of calcium oxalate. Potential compounds in kidney stone therapy.

Eur. J. Med. Chem. 45 , 1001-7, (2010)

Synthesis of glycosyl derivatives of hydroxyanthraquinones (6-10) potentially useful for kidney stone therapy is presented. These compounds were analyzed as inhibitors of calcium oxalate crystals form...