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H46805

Sigma-Aldrich

2-Hydroxy-1,4-naphthoquinone

≥96.5% purity, powder

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Synonym(s):
Lawsone, Natural Orange 6
Empirical Formula (Hill Notation):
C10H6O3
CAS Number:
83-72-7
Molecular Weight:
174.15
Colour Index Number:
75480
Beilstein:
1565260
EC Number:
201-496-3
MDL number:
MFCD00001678
UNSPSC Code:
12171500
PubChem Substance ID:
24895653
NACRES:
NA.47

Quality Level

200

Assay

97%

form

powder

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
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

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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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
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)
Pablo J Almeida et al.
Contact dermatitis, 66(1), 33-37 (2011-10-07)
Very few studies are available in which the components of henna products used by tattoo artists have been analysed. The aim of this study was to quantify the amounts of lawsone (2-hydroxy-1,4-naphthoquinone, the active ingredient in henna) and p-phenylenediamine (PPD)
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
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
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