4-methyl daphnetin

2H-1-benzopyran-2-one, 7,8-dihydroxy-4-methyl- (9CI)

CAS: 2107-77-9 C10 H8 O4 MW: 192.17056000

Identification

Name4-methyl daphnetin
IUPAC7,8-dihydroxy-4-methylchromen-2-one
CAS Number2107-77-9
EINECS218-290-4
FDA UNIISearch
Molecular FormulaC10 H8 O4
Molecular Weight192.17056000
MDL NumberMFCD00016972
Nikkaji NumberJ67.674H
Beilstein0177613

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Flash Point 32.00 °F. TCC ( 0.00 °C. ) (est)
Soluble in water, 2.097e+004 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityintravenous-mouse LD50 180 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements', 'U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04864,']

Safety in Use

Categorynatural substances and extractives
Recommendation for 4-methyl daphnetin usage levels up tonot for fragrance use.
Recommendation for 4-methyl daphnetin flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

found in nature

Synonyms

2H-1- benzopyran-2-one, 7,8-dihydroxy-4-methyl- (9CI) coumarin, 7,8-dihydroxy-4-methyl- 7,8- dihydroxy-4-methyl-2-benzopyrone 7,8- dihydroxy-4-methyl-2H-1-benzopyran-2-one 7,8- dihydroxy-4-methylchromen-2-one 7,8- dihydroxy-4-methylcoumarin 4- methyl-7,8-dihydroxycoumarin 4- methyldaphnetin 4- methyldaphnetine PubMed: DNA cleavage, antibacterial, antifungal and anthelmintic studies of Co(II), Ni(II) and Cu(II) complexes of coumarin Schiff bases: Synthesis and spectral approach. PubMed: Infrared, Raman and NMR spectra, conformational stability and vibrational assignment of 7,8-Dihydroxy-4-Methylcoumarin. PubMed: An efficient catalytic system based on 7,8-dihydroxy-4-methylcoumarin and copper(II) for the click synthesis of diverse 1,4-disubstituted-1,2,3-triazoles under green conditions. PubMed: 4-Methylcoumarin derivatives with anti-inflammatory effects in activated microglial cells. PubMed: 4-methylcoumarin derivatives inhibit human neutrophil oxidative metabolism and elastase activity. PubMed: 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. PubMed: Evaluation of the antioxidant capacity of synthesized coumarins. PubMed: A spectroelectrochemical and chemical study on oxidation of 7,8-dihydroxy-4-methylcoumarin (DHMC) and some related compounds in aprotic medium. PubMed: Structure-activity relationship of dihydroxy-4-methylcoumarins as powerful antioxidants: correlation between experimental & theoretical data and synergistic effect. PubMed: 4-methylcoumarins as antioxidants: scavenging of peroxyl radicals and inhibition of human low-density lipoprotein oxidation. PubMed: Antioxidant properties of 4-methylcoumarins in in vitro cell-free systems. PubMed: In vitro interactions of coumarins with iron. PubMed: Biochemical mechanisms underlying the pro-apoptotic activity of 7,8-dihydroxy-4-methylcoumarin in human leukemic cells. PubMed: 7,8-Dihydroxy-4-methylcoumarin induces apoptosis of human lung adenocarcinoma cells by ROS-independent mitochondrial pathway through partial inhibition of ERK/MAPK signaling. PubMed: Inhibitory activity of polyhydroxycarboxylate chelators against recombinant NF-kappaB p50 protein-DNA binding. PubMed: Novel thiocoumarins as inhibitors of TNF-alpha induced ICAM-1 expression on human umbilical vein endothelial cells (HUVECs) and microsomal lipid peroxidation. PubMed: DNA damage in healthy term neonate. PubMed: Acetoxy drug: protein transacetylase of buffalo liver-characterization and mass spectrometry of the acetylated protein product. PubMed: Crystal structure of 7,8-dihydroxy-4-methylcoumarin. PubMed: Daphnetin methylation by a novel O-methyltransferase is associated with cold acclimation and photosystem II excitation pressure in rye. PubMed: Acetoxy-4-methylcoumarins confer differential protection from aflatoxin B(1)-induced micronuclei and apoptosis in lung and bone marrow cells. PubMed: Chemoprevention of benzene-induced bone marrow and pulmonary genotoxicity. PubMed: Mechanism of biochemical action of substituted 4-methylbenzopyran-2-ones. Part 7: Assay and characterization of 7,8-diacetoxy-4-methylcoumarin:protein transacetylase from rat liver microsomes based on the irreversible inhibition of cytosolic glutathione S-transferase. PubMed: Antioxidative and prooxidative effects of coumarin derivatives on free radical initiated and photosensitized peroxidation of human low-density lipoprotein. PubMed: 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. PubMed: Mechanism of biochemical action of substituted 4-methylbenzopyran-2-ones. Part 4: hyperbolic activation of rat liver microsomal NADPH-cytochrome C reductase by the novel acetylator 7,8-diacetoxy-4-methylcoumarin. PubMed: Mechanism of biochemical action of substituted 4-methylbenzopyran-2-ones. Part 3: A novel mechanism for the inhibition of biological membrane lipid peroxidation by dioxygenated 4-methylcoumarins mediated by the formation of a stable ADP-Fe-inhibitor mixed ligand complex. PubMed: Mechanism of biochemical action of substituted 4-methylbenzopyran-2-ones. Part II: Mechanism-based inhibition of rat liver microsome-mediated aflatoxin B1-DNA binding by the candidate antimutagen 7,8-diacetoxy-4-methylcoumarin. PubMed: Mechanism of biochemical action of substituted 4-methylbenzopyran-2-ones. Part I: Dioxygenated 4-methyl coumarins as superb antioxidant and radical scavenging agents. PubMed: Pharmacological and biochemical actions of simple coumarins: natural products with therapeutic potential. PubMed: Spectrophotometric determination of molybdenum with 7,8-dihydroxy-4-methylcoumarin and cetyltrimethylammonium bromide.