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388513

Sigma-Aldrich

5,8-Dihydroxy-1,4-naphthoquinone

technical grade

Synonym(s):

Naphthazarin

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About This Item

Empirical Formula (Hill Notation):
C10H6O4
CAS Number:
Molecular Weight:
190.15
Beilstein:
880561
EC Number:
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.23

grade

technical grade

mp

220-230 °C (lit.)

SMILES string

Oc1ccc(O)c2C(=O)C=CC(=O)c12

InChI

1S/C10H6O4/c11-5-1-2-6(12)10-8(14)4-3-7(13)9(5)10/h1-4,11-12H

InChI key

RQNVIKXOOKXAJQ-UHFFFAOYSA-N

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Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Régis Millet et al.
Journal of medicinal chemistry, 48(22), 7024-7039 (2005-10-28)
The human selenoprotein thioredoxin reductase is involved in antioxidant defense and DNA synthesis. As increased thioredoxin reductase levels are associated with drug sensitivity to cisplatin and drug resistance in tumor cells, this enzyme represents a promising target for the development
Brígida R Pinho et al.
PloS one, 6(8), e24098-e24098 (2011-09-03)
The search of new anti-inflammatory drugs has been a current preoccupation, due to the need of effective drugs, with less adverse reactions than those used nowadays. Several naphthoquinones (plumbagin, naphthazarin, juglone, menadione, diosquinone and 1,4-naphthoquinone), plus p-hydroquinone and p-benzoquinone were
Vishnu K Tandon et al.
Bioorganic & medicinal chemistry letters, 15(13), 3288-3291 (2005-05-26)
A series of (1,4)-naphthoquinono [3,2-c]-1H-pyrazoles and their (1,4)-naphthohydroquinone derivatives 2-7 were synthesized and evaluated for antifungal, antibacterial, and anticancer activities. The structure-activity relationship of these compounds was studied and the results show that the compound 2b exhibited in vitro antifungal
Gulseren Pekin et al.
Planta medica, 73(3), 267-272 (2007-02-24)
The quantification of free and total alkannins in 13 endemic Anatolian Alkanna species is described for the first time. Extraction of the samples was performed by sonication with hexane, followed by hydrolysis in 1 N NaOH. For analysis, a new
Bipul R Acharya et al.
Apoptosis : an international journal on programmed cell death, 16(9), 924-939 (2011-06-15)
Naphthazarin (DHNQ, 5,8-dihydroxy-l,4-naphthoquinone) is a naturally available 1,4-naphthoquinone derivatives. In this study, we focused on elucidating the cytotoxic mechanism of naphthazarin in A549 non-small cell lung carcinoma cells. Naphthazarin reduced the A549 cell viability considerably with an IC(50) of 16.4 ± 1.6 μM.

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