Lawsone methyl ether

Names

[ Name ]:
Lawsone methyl ether

[Synonym ]:
2-Methoxy-p-naphthoquinone
1,4-Naphthalenedione,2-methoxy
2-methoxy-1,4-naphthalenequinone
2-methoxynaphthalene-1,4-dione
2-Methoxy-[1,4]naphthoquinone
2-methoxyl-1,4-naphthoquinone
2-Methoxynaphthoquinone
1,4-NAPHTHOQUINONE,2-METHOXY
MFCD00019539
2-Methoxy-1,4-naphthalenedione
Methoxy-1,4-naphthochinin

Biological Activity

[Description]:

Lawsone methyl ether (2-Methoxy-1,4-naphthoquinone), isolated from Impatiens balsamina L. and Swertia calycina, exhibits potent antifungal and antibacterial activities[1].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Fungal

Signaling Pathways >> Anti-infection >> Bacterial

[In Vitro]

The value of both minimal inhibitory concentration and minimal fungicidal concentration of Lawsone methyl ether (2-Methoxy-1,4-naphthoquinone) against Candida was 1.25 lg⁄ml[1].

[References]

[1]. Sritrairat N, et al. Antifungal activity of lawsone methyl ether in comparison with chlorhexidine. J Oral Pathol Med. 2011 Jan;40(1):90-6.

Chemical & Physical Properties

[ Density]:
1.28g/cm3

[ Boiling Point ]:
339.8ºC at 760mmHg

[ Melting Point ]:
184-187ºC(lit.)

[ Molecular Formula ]:
C₁₁H₈O₃

[ Molecular Weight ]:
188.17900

[ Flash Point ]:
152.7ºC

[ Exact Mass ]:
188.04700

[ PSA ]:
43.37000

[ LogP ]:
1.59590

[ Vapour Pressure ]:
8.98E-05mmHg at 25°C

[ Index of Refraction ]:
1.589

[ Storage condition ]:
-20℃

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QL8960000

CHEMICAL NAME :: 1,4-Naphthoquinone, 2-methoxy-

CAS REGISTRY NUMBER :: 2348-82-5

LAST UPDATED :: 199701

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C11-H8-O3

MOLECULAR WEIGHT :: 188.19

WISWESSER LINE NOTATION :: L66 BV EVJ CO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 320 mg/kg

TOXIC EFFECTS :: Tumorigenic - active as anti-cancer agent

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 26,570,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - wild bird species

DOSE/DURATION :: 316 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AECTCV Archives of Environmental Contamination and Toxicology. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 070944) V.1- 1973- Volume(issue)/page/year: 12,355,1983

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
S26;S36

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
QL8960000

[ HS Code ]:
2914690090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914690090

[ Summary ]:
2914690090 other quinones。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%

Articles

2-Methoxy-1,4-naphthoquinone (MNQ) induces apoptosis of A549 lung adenocarcinoma cells via oxidation-triggered JNK and p38 MAPK signaling pathways.

Life Sci. 135 , 158-64, (2015)

The compound 2-methoxy-1,4-naphthoquinone (MNQ) was previously shown to be cytotoxic against several cancer cell lines, but its mode of action is poorly understood. In this study, we aimed to explore ...

Anti-gastric adenocarcinoma activity of 2-Methoxy-1,4-naphthoquinone, an anti-Helicobacter pylori compound from Impatiens balsamina L.

Fitoterapia 83(8) , 1336-44, (2012)

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 gastri...

Effects of the compounds 2-methoxynaphthoquinone, 2-propoxynaphthoquinone, and 2-isopropoxynaphthoquinone on ecdysone 20-monooxygenase activity.

Arch. Insect Biochem. Physiol. 66(1) , 45-52, (2007)

The effects of the natural compound 2-methoxy-1,4-naphthoquinone, isolated from the leaves of Impatiens glandulifera and the synthetic compounds 2-propoxy-1,4-naphthoquinone and 2-isopropoxy-1,4-napht...