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Key Documents

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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Fabiola Kind et al.
Journal der Deutschen Dermatologischen Gesellschaft = Journal of the German Society of Dermatology : JDDG, 10(8), 572-578 (2012-02-04)
The increased frequency of case reports of allergic contact dermatitis from non-permanent black henna tattoos in recent years shows the popularity of this form of body painting. Seven patients presented with allergic contact dermatitis after initial hair or eyelash dyeing.
Emerging latent fingerprint technologies: a review
Bumbrah G, et al.
Research Reports Forensic Med Sci, 6, 39-50 (2016)
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
Basma Najar et al.
Plants (Basel, Switzerland), 9(12) (2020-12-24)
The present study aimed to elucidate the salinity influence on the bioactive metabolites of Lawsonia inermis L. (henna) plants. Young henna plants were cultivated under salinity stress with two NaCl concentrations (75 mM and 150 mM) in controlled environmental conditions

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