Naphthazarin

Modify Date: 2026-07-01 16:41:45

Naphthazarin Structure
Naphthazarin structure
Common Name Naphthazarin
CAS Number 475-38-7 Molecular Weight 190.15200
Density 1.592g/cm3 Boiling Point 498.2ºC at 760mmHg
Molecular Formula C10H6O4 Melting Point 220-230 °C(lit.)
MSDS Chinese USA Flash Point 269.2ºC

 Use of Naphthazarin


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].

 Names

Name naphthazarin
Synonym More Synonyms

 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
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
InChIKey RQNVIKXOOKXAJQ-UHFFFAOYSA-N
SMILES O=C1C=CC(=O)c2c(O)ccc(O)c21

 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

 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%

 Articles32

More 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...

 NaphthazarinBioassay

View more

Name: Inhibition of recombinant human CYP1B1 expressed in baker's yeast-derived microsomes ...
Source: ChEMBL
Target: Cytochrome P450 1B1
External Id: CHEMBL4257966
Name: Inhibition of recombinant human CYP1A2 expressed in baker's yeast-derived microsomes ...
Source: ChEMBL
Target: Cytochrome P450 1A2
External Id: CHEMBL4257965
Name: Inhibition of recombinant human CYP3A4 expressed in baker's yeast-derived microsomes ...
Source: ChEMBL
Target: Cytochrome P450 3A4
External Id: CHEMBL4257968
Name: Inhibition of recombinant human CYP2D6 expressed in baker's yeast-derived microsomes ...
Source: ChEMBL
Target: Cytochrome P450 2D6
External Id: CHEMBL4257967
Name: Induction of apoptosis in human HCT-116 cells assessed as late apoptotic cells at 2.5...
Source: ChEMBL
Target: HCT-116
External Id: CHEMBL5124647
Name: Anticancer activity against Walker 256 carcinosarcoma in rats at a dose of 10 mg/kg [...
Source: ChEMBL
Target: Rattus norvegicus
External Id: CHEMBL835349
Name: Induction of apoptosis in human HCT-116 cells assessed as early apoptotic cells at 5 ...
Source: ChEMBL
Target: HCT-116
External Id: CHEMBL5124648
Name: Induction of apoptosis in human HCT-116 cells assessed as late apoptotic cells at 5 u...
Source: ChEMBL
Target: HCT-116
External Id: CHEMBL5124649
Name: Inhibition of recombinant human CYP1A1 expressed in baker's yeast-derived microsomes ...
Source: ChEMBL
Target: Cytochrome P450 1A1
External Id: CHEMBL4257963
Name: Induction of abnormal mitosis in human A549 cells assessed as formation of misaligned...
Source: ChEMBL
Target: A549
External Id: CHEMBL5124643
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 Synonyms

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