4-methyl daphnetin
2H-1-benzopyran-2-one, 7,8-dihydroxy-4-methyl- (9CI)
Identification
| Name | 4-methyl daphnetin |
| IUPAC | 7,8-dihydroxy-4-methylchromen-2-one |
| CAS Number | 2107-77-9 |
| EINECS | 218-290-4 |
| FDA UNII | Search |
| Molecular Formula | C10 H8 O4 |
| Molecular Weight | 192.17056000 |
| MDL Number | MFCD00016972 |
| Nikkaji Number | J67.674H |
| Beilstein | 0177613 |
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 SDS | View |
| Oral/Parenteral Toxicity | intravenous-mouse LD50 180 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not 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
| Category | natural substances and extractives |
| Recommendation for 4-methyl daphnetin usage levels up to | not for fragrance use. |
| Recommendation for 4-methyl daphnetin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
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.