7-Methoxycoumarin

Names

[ CAS No. ]:
531-59-9

[ Name ]:
7-Methoxycoumarin

[Synonym ]:
Coumarin, 7-methoxy-
Herniarin
7-Methoxycoumarin
Coumarin, 7-methoxy- (8CI)
Methyl umbelliferyl ether
EINECS 208-513-3
7-methoxychromen-2-one
7-Methoxy-2H-chromen-2-one
2H-1-Benzopyran-2-one, 7-methoxy-
Herniarin (6CI)
MFCD00006876

Biological Activity

[Description]:

Herniarin is a natural coumarin occurs in some flowering plants, with antitumor effect.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Natural Products >> Phenylpropanoids

Research Areas >> Cancer

[In Vitro]

Herniarin is cytotoxic to breast carcinoma cell line MCF-7 with an IC50 of 207.6 µM. Herniarin (100 µM) also induces apoptosis in MCF-7 cells[1]. Herniarin alone has no obvious cytotoxicity on transitional cell carcinoma (TCC) cells, but when in combination with 5 µg/mL cisplatin, Herniarin (80 µg/mL) potently enhances the antitumor effect of cisplatin, and increases chromatin condensation[2].

[Cell Assay]

Briefly, the cells are seeded (104 cells per well) onto flat-bottomed 96-well culture plates and allowed to grow 72 h after treatment with various concentration of auraptene, Herniarin, umbelliferone, and umbelliprenin. After removing the medium, MTT solution (5 mg/mL in PBS) is added and incubated for 4 h and the resulting formazan is solubilized with DMSO (100 mL). The absorption is measured at 570 nm (620 nm as a reference) in an ELISA reader[1].

[References]

[1]. Mousavi SH, et al. Comparative analysis of the cytotoxic effect of 7-prenyloxycoumarin compounds and herniarin on MCF-7 cell line. Avicenna J Phytomed. 2015 Nov-Dec;5(6):520-30.

[2]. Haghighitalab A, et al. Enhancement of cisplatin cytotoxicity in combination with herniarin in vitro. Drug Chem Toxicol. 2014 Apr;37(2):156-62.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
335.3±37.0 °C at 760 mmHg

[ Melting Point ]:
117-121 °C(lit.)

[ Molecular Formula ]:
C₁₀H₈O₃

[ Molecular Weight ]:
176.169

[ Flash Point ]:
138.6±21.1 °C

[ Exact Mass ]:
176.047348

[ PSA ]:
39.44000

[ LogP ]:
1.78

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.572

[ Water Solubility ]:
MISCIBLE

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DJ3100380

CHEMICAL NAME :: 2H-1-Benzopyran-2-one, 7-methoxy-

CAS REGISTRY NUMBER :: 531-59-9

BEILSTEIN REFERENCE NO. :: 0141728

LAST UPDATED :: 199701

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C10-H8-O3

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4300 mg/kg

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

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 26,375,1988

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

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: >5 gm/kg

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

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 26,375,1988

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
DJ3100380

[ HS Code ]:
2932209090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932209090

[ Summary ]:
2932209090. other lactones. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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7-substituted coumarins inhibit proliferation and migration of laryngeal cancer cells in vitro.

Anticancer Res. 33(10) , 4347-56, (2013)

Coumarins are a large group of naturally-occurring compounds with a wide range of biological properties, including anticancer activity. 7-Substituted coumarins (umbelliferone, scoparone, and herniarin...