4-Methyldaphnetin

Names

[ Name ]:
4-Methyldaphnetin

[Synonym ]:
4-METHYLDAPHNETIN
7,8-dihydroxy-4-methyl-2H-1-benzopyran-2-one
7,8-Dihydroxy-4-methyl-2H-chromen-2-one
2H-1-Benzopyran-2-one, 7,8-dihydroxy-4-methyl-
EINECS 218-290-4
7,8-dihydroxy-4-methyl-chromen-2-one
7,8-DIHYDROXY-4-METHYLCOUMARIN
4-methyl-7,8-dihydroxycoumarin
Coumarin,7,8-dihydroxy-4-methyl
MFCD00016972
7,8-dihydroxy-4-methyl-2H-2-chromenone
4-Methyldaphnetine

Biological Activity

[Description]:

4-Methyldaphnetin is a precursor in the synthesis of derivatives of 4-methyl coumarin. 4-Methyldaphnetin has potent, selective anti-proliferative and apoptosis-inducing effects on several cancer cell lines. 4-Methyldaphnetin possesses radical scavenging property and strongly inhibits membrane lipid peroxidation[1][2][3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

[References]

[1]. Vázquez R, et al. Pharmacodynamic study of the 7,8-dihydroxy-4-methylcoumarin-induced selective cytotoxicity toward U-937 leukemic cells versus mature monocytes: cytoplasmic p21(Cip1/WAF1) as resistance factor. Biochem Pharmacol. 2013 Jul 15;86(2):210-21.

[2]. Jin X, et al. 7,8-Dihydroxy-4-methylcoumarin provides neuroprotection by increasing hippocalcin expression. Neurotox Res. 2015 Apr;27(3):268-74.

[3]. Raj HG, et al. Mechanism of biochemical action of substituted 4-methylbenzopyran-2-ones. Part 5: Pulse radiolysis studies on the antioxidant action of 7,8-diacetoxy-4-methylcoumarin. Bioorg Med Chem. 1999 Sep;7(9):2091-4.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
421.5±45.0 °C at 760 mmHg

[ Melting Point ]:
242-246 °C(lit.)

[ Molecular Formula ]:
C₁₀H₈O₄

[ Molecular Weight ]:
192.168

[ Flash Point ]:
176.0±22.2 °C

[ Exact Mass ]:
192.042252

[ PSA ]:
70.67000

[ LogP ]:
1.95

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.652

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GN6385000

CHEMICAL NAME :: Coumarin, 7,8-dihydroxy-4-methyl-

CAS REGISTRY NUMBER :: 2107-77-9

BEILSTEIN REFERENCE NO. :: 0177613

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C10-H8-O4

MOLECULAR WEIGHT :: 192.18

WISWESSER LINE NOTATION :: T66 BOVJ E1 IQ JQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 180 mg/kg

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

REFERENCE :: CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) Volume(issue)/page/year: NX#04864

Safety Information

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36/37

[ WGK Germany ]:
3

[ RTECS ]:
GN6385000

[ 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%