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Sigma-Aldrich

1,4-Naphthoquinone

97%

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Synonym(s):
α-Naphthoquinone
Empirical Formula (Hill Notation):
C10H6O2
CAS Number:
130-15-4
Molecular Weight:
158.15
Beilstein:
878524
EC Number:
204-977-6
MDL number:
MFCD00001676
PubChem Substance ID:
24849257

Quality Level

200

Assay

97%

form

powder

mp

119-122 °C (lit.)

SMILES string

O=C1C=CC(=O)c2ccccc12

InChI

1S/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H

InChI key

FRASJONUBLZVQX-UHFFFAOYSA-N

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Application

1,4-Naphthoquinone was used as a potential inhibitor of monoamine oxidase and DNA topoisomerase activities. It was also used to inhibit the acetyltransferase activity.

Signal Word

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Skin Corr. 1C - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

285.8 °F

Flash Point(C)

141 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Eduardo Coelho-Cerqueira et al.
Chemical biology & drug design, 83(4), 401-410 (2013-10-30)
Monoamine oxidase (MAO) action has been involved in the regulation of neurotransmitters levels, cell signaling, cellular growth, and differentiation as well as in the balance of the intracellular polyamine levels. Although so far obscure, MAO inhibitors are believed to have
Daniela M Santos et al.
Molecular neurobiology, 47(1), 313-324 (2012-10-12)
Naphthoquinones are bioactive compounds widespread in nature that impact on several cellular pathways, including cell proliferation and survival, by acting as prooxidants and electrophiles. We have previously described the role of the synthetic isoxazole condensed 1,4-naphthoquinone derivative 1a in preventing
Paula F Carneiro et al.
Bioorganic & medicinal chemistry, 20(16), 4995-5000 (2012-07-17)
New oxirane derivatives were synthesized using six naphthoquinones as the starting materials. Our biological results showed that these oxiranes acted as trypanocidal agents against Trypanosoma cruzi with minimal cytotoxicity in the VERO cell line compared to naphthoquinones. In particular, oxirane
Yu Shang et al.
Environmental science & technology, 46(5), 2935-2942 (2012-02-01)
Airborne quinones contribute to adverse health effects of ambient particles probably because of their ability to generate hydroxyl radicals (·OH) via redox cycling, but the mechanisms remain unclear. We examined the chemical mechanisms through which 1,4-naphthoquinone (1,4-NQ) induced ·OH, and
Barbara Krajewska et al.
Bioorganic & medicinal chemistry, 15(12), 4144-4151 (2007-04-10)
In their inhibition-inducing interactions with enzymes, quinones primarily utilize two mechanisms, arylation and oxidation of enzyme thiol groups. In this work, we investigated the interactions of 1,4-naphthoquinone with urease in an effort to estimate the contribution of the two mechanisms
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