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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:
83-72-7
Molecular Weight:
174.15
Colour Index Number:
75480
Beilstein/REAXYS Number:
1565260
EC Number:
201-496-3
MDL number:
MFCD00001678
UNSPSC Code:
12171500
PubChem Substance ID:
24895653
NACRES:
NA.47

product name

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

Quality Level

200

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
GHS07

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

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Emerging latent fingerprint technologies: a review
Bumbrah G, et al.
Research Reports Forensic Med Sci, 6, 39-50 (2016)
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.
Perry G Wang et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 879(20), 1795-1801 (2011-05-25)
A rapid method for the determination of para-phenylenediamine (PPD) in cosmetic products, such as henna tattoos has been developed and evaluated. This analytical procedure involved extracting a 10mg test portion of cosmetic product in 10 mL of ethyl acetate, followed
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
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