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H46805

Sigma-Aldrich

2-Hydroxy-1,4-naphthoquinone

≥96.5% purity, powder

Synonym(s):

Lawsone, Natural Orange 6

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About This Item

Empirical Formula (Hill Notation):
C10H6O3
CAS Number:
Molecular Weight:
174.15
Colour Index Number:
75480
Beilstein:
1565260
EC Number:
MDL number:
UNSPSC Code:
12171500
PubChem Substance ID:
NACRES:
NA.47

product name

2-Hydroxy-1,4-naphthoquinone, 97%

Quality Level

Assay

97%

form

powder

color

faint yellow to dark yellow, and Faint Orange to Dark Orange

mp

192-195 °C (dec.) (lit.)

λmax

452 nm

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

room temp

SMILES string

OC1=CC(=O)c2ccccc2C1=O

InChI

1S/C10H6O3/c11-8-5-9(12)10(13)7-4-2-1-3-6(7)8/h1-5,12H

InChI key

CSFWPUWCSPOLJW-UHFFFAOYSA-N

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General description

2-Hydroxy-1,4-naphthoquinone is one among the forensic reagents used for fingerprint detection.
2-Hydroxy-1,4-naphthoquinone, produced from Lawsonia inermis, is an orange dye. It belongs to the class of naphthoquinone dyes. 2-Hydroxy-1,4-naphthoquinone is used to dye hair and to color textiles. It has antibacterial, antifungal, anti-inflammatory, antiviral and antineoplastic properties. 2-Hydroxy-1,4-naphthoquinone inhibits tumor cell growth. It stimulates the production of reactive oxygen species (ROS).

Application

2-Hydroxy-1,4-naphthoquinone has been used as a compound for the culture of schistosome worms.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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

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Applications of DNA-electrochemical biosensors in cancer research
Chiorcea-Paquim AM, et al.
Past, Present and Future Challenges of Biosensors and Bioanalytical Tools in Analytical Chemistry: A Tribute to Professor Marco Mascini, 77, 287-336 (2017)
Alessia Coletti et al.
The Journal of organic chemistry, 77(16), 6873-6879 (2012-07-28)
A new class of pentacyclic diquinoid compounds has been synthesized with a facile one-pot reaction of two molecules of 2-hydroxynaphthoquinone and 1-bromoalkanes in the presence of ferrocene. These molecules were isolated as enol tautomers that exhibit intramolecular hydrogen bond and
Trivedi PC
Medicinal Plants: Traditional Knowledge (2006)
Yamin Yasin et al.
Journal of biomedical nanotechnology, 7(3), 486-488 (2011-08-13)
A drug-inorganic nanostructured material involving pharmaceutically active compound lawsone intercalated Zn-Al layered double hydroxides (Law-LDHs) with Zn/AI = 4 has been assembled by co-precipitation and ion exchange methods. Powder X-ray diffraction (XRD) and Fourier transform infrared spectra (FTIR) analysis indicate
Francisco L S Bustamante et al.
Inorganic chemistry, 52(3), 1167-1169 (2013-01-25)
Dimerization of lawsone occurs upon reaction with Co(BF(4))(2)·6H(2)O and N,N'-bis(pyridin-2-ylmethyl)ethylenediamine (py(2)en) to produce the mononuclear complex [Co(III)(bhnq)(py(2)en)]BF(4)·H(2)O (1). This complex has been investigated as a prototype of a bioreductive prodrug, where the bhnq(2-) ligand acts as a model for cytotoxic

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