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189162

Sigma-Aldrich

2-Methoxy-1,4-naphthoquinone

98%

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About This Item

Empirical Formula (Hill Notation):
C11H8O3
CAS Number:
Molecular Weight:
188.18
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

98%

mp

184-187 °C (lit.)

functional group

ether
ketone

SMILES string

COC1=CC(=O)c2ccccc2C1=O

InChI

1S/C11H8O3/c1-14-10-6-9(12)7-4-2-3-5-8(7)11(10)13/h2-6H,1H3

InChI key

OBGBGHKYJAOXRR-UHFFFAOYSA-N

General description

2-Methoxy-1,4-naphthoquinone is a potential candidate for Helicobacter pylori infection related disease therapy. It is isolated from the leaves of Impatiens glandulifera.

Application

2-Methoxy-1,4-naphthoquinone was used in the preparation of 2-(4-X-phenylene)amine-1,4-naphthoquinones (X= ferrocenyl, OMe, Me, I, Cl and NO2).

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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Naomi Mori et al.
Journal of natural medicines, 65(1), 234-236 (2010-10-05)
A screening study using a luciferase assay to identify natural products which inhibit Wnt signaling was carried out. The bioassay-guided fractionation of aerial parts of a plant, Impatiens balsamina, led to the isolation of 2-methoxy-1,4-naphthoquinone (1) as an active compound.
Yuan-Chuen Wang et al.
Fitoterapia, 83(8), 1336-1344 (2012-04-21)
2-Methoxy-1,4-naphthoquinone (MeONQ) from Impatiens balsamina L. exhibited strong anti-H. pylori activity in our previous study. In this study, we investigated the cytotoxicity of MeONQ against gastric adenocarcinoma (MKN45 cell line) and propose the relevant mechanisms. MeONQ resulted in serious necrosis
X Yang et al.
Phytotherapy research : PTR, 15(8), 676-680 (2001-12-18)
By using brine shrimp (Artemia salina) lethality test-guided fractionation, a single bioactive compound (LC(50)=26 ppm) was isolated from the 95% ethanol extract of the dried aerial parts of Impatiens balsamina L. and subsequently identified as 2-methoxy-1,4-naphthoquinone (MNQ). The structure of
General method for the high yield preparation of 2-(4-X-phenylene) amine-1, 4-naphthoquinones (X= ferrocenyl, OMe, Me, I, Cl, and NO2) from 2-methoxy-1, 4-naphthoquinone and investigation of H+ and Mg2+ catalysts with DFT calculations.
Francisco AI, et al.
Journal of Molecular Structure, 891(1), 228-232 (2008)
Aldana L Zalazar et al.
Food research international (Ottawa, Ont.), 116, 916-924 (2019-02-06)
Probabilistic microbial modelling using logistic regression was used to predict the growth/no growth (G/NG) interfaces of Zygosaccharomyces bailii in simulated acid sauces as a function of natamycin, xanthan gum (XG) and sodium chloride concentrations. The growth was assessed colorimetrically by

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