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%

Articles

Non-animal photosafety screening for complex cosmetic ingredients with photochemical and photobiochemical assessment tools.

Regul Toxicol Pharmacol 72 , 578-85, (2015)

Previously, a non-animal screening approach was proposed for evaluating photosafety of cosmetic ingredients by means of in vitro photochemical and photobiochemical assays; however, complex cosmetic in...

An efficient and economical MTT assay for determining the antioxidant activity of plant natural product extracts and pure compounds.

J. Nat. Prod. 73 , 1193-5, (2010)

Antioxidants scavenge free radicals, singlet oxygen, and electrons in cellular redox reactions. The yellow MTT [3-(4,5-dimethylthiazole-2-yl)-2,5-diphenyltetrazolium bromide] is reduced to a purple fo...

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...

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.