Naphthazarin

Names

[ CAS No. ]:
475-38-7

[ Name ]:
Naphthazarin

[Synonym ]:
5,8-Dihydroxy-1,4-naphthalenedione
EINECS 207-495-4
MFCD00001685
5,8-Dihydroxy-1,4-naphthoquinone
5,8-dihydroxynaphthalene-1,4-dione
Naphthazarin

Biological Activity

[Description]:

Naphthazarin (DHNQ) is a naturally occurring compound. Naphthazarin is effective by various cellular mechanisms including oxidative stress, activation of mitochondrial apoptosis-inducing factor (AIF), depolymerization of microtubules, interference with lysosomal function and p53-dependent p21 activation. Naphthazarin triggers apoptosis and has anti-tumor effects[1][2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Research Areas >> Neurological Disease

[References]

[1]. Seon Young Choi, et al. Naphthazarin has a protective effect on the 1-methyl-4-phenyl-1,2,3,4-tetrahydropyridine-induced Parkinson's disease model. J Neurosci Res. 2012 Sep;90(9):1842-9.

[2]. Omar Aljanadi, et al. Stimulation of Suicidal Erythrocyte Death by Naphthazarin. Basic Clin Pharmacol Toxicol. 2015 Dec;117(6):369-74.

Chemical & Physical Properties

[ Density]:
1.592g/cm3

[ Boiling Point ]:
498.2ºC at 760mmHg

[ Melting Point ]:
220-230 °C(lit.)

[ Molecular Formula ]:
C₁₀H₆O₄

[ Molecular Weight ]:
190.15200

[ Flash Point ]:
269.2ºC

[ Exact Mass ]:
190.02700

[ PSA ]:
74.60000

[ LogP ]:
1.03300

[ Vapour Pressure ]:
1.51E-10mmHg at 25°C

[ Index of Refraction ]:
1.71

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QL7970000

CHEMICAL NAME :: 1,4-Naphthoquinone, 5,8-dihydroxy-

CAS REGISTRY NUMBER :: 475-38-7

LAST UPDATED :: 199410

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C10-H6-O4

MOLECULAR WEIGHT :: 190.16

WISWESSER LINE NOTATION :: L66 BV EVJ GQ JQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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: 124,25,1983

Safety Information

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

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S22-S24/25-S37/39-S26

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
QL7970000

[ HS Code ]:
2914690090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914690090

[ Summary ]:
2914690090 other quinones。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%

Articles

Stimulation of Suicidal Erythrocyte Death by Naphthazarin.

Basic Clin Pharmacol Toxicol. 117 , 369-74, (2016)

The 1,4-naphthoquinone derivative naphthazarin may trigger apoptosis and is thus considered for the treatment of malignancy. On the other hand, naphthazarin decreases neurotoxicity. In analogy to apop...

Bioactivities of simplified adociaquinone B and naphthoquinone derivatives against Cdc25B, MKP-1, and MKP-3 phosphatases.

Bioorg. Med. Chem. 17 , 2276-81, (2009)

Some simplified adociaquinone B analogs and a series of 1,4-naphthoquinone derivatives were synthesized and tested against the three enzymes Cdc25B, MKP-1, and MKP-3. Cdc25B and MKP-1 in particular ar...

Naphthazarin enhances ionizing radiation-induced cell cycle arrest and apoptosis in human breast cancer cells.

Int. J. Oncol. 46(4) , 1659-66, (2015)

Naphthazarin (Naph, DHNQ, 5,8-dihydroxy-l,4-naphthoquinone) is one of the naturally available 1,4-naphthoquinone derivatives that are well-known for their anti-inflammatory, antioxidant, antibacterial...

Related Compounds

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