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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/REAXYS Number:
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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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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
Trivedi PC
Medicinal Plants: Traditional Knowledge (2006)
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

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