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H46805

Sigma-Aldrich

2-Hydroxy-1,4-naphthoquinone

≥96.5% purity, powder

Synonyme(s) :

Lawsone, Natural Orange 6

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About This Item

Formule empirique (notation de Hill):
C10H6O3
Numéro CAS:
83-72-7
Poids moléculaire :
174.15
Numéro C.I. (Colour Index):
75480
Numéro Beilstein :
1565260
Numéro CE :
201-496-3
Numéro MDL:
MFCD00001678
Code UNSPSC :
12171500
ID de substance PubChem :
24895653
Nomenclature NACRES :
NA.47

product name

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

Niveau de qualité

200

Pureté

97%

Forme

powder

Couleur

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

Pf

192-195 °C (dec.) (lit.)

λmax

452 nm

Application(s)

diagnostic assay manufacturing
hematology
histology

Température de stockage

room temp

Chaîne SMILES 

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

Clé InChI

CSFWPUWCSPOLJW-UHFFFAOYSA-N

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Catégories apparentées

Description générale

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
STBJ7322
STBG0780V
STBD7466V
STBD5846V
STBD2253V

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Sigma-Aldrich

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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)
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
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)
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