4-methyl esculetin
2H-1-benzopyran-2-one, 6,7-dihydroxy-4-methyl-
Identification
| Name | 4-methyl esculetin |
| IUPAC | 6,7-dihydroxy-4-methylchromen-2-one |
| CAS Number | 529-84-0 |
| EINECS | 208-470-0 |
| FDA UNII | 132H8N0A91 |
| Molecular Formula | C10 H8 O4 |
| Molecular Weight | 192.17056000 |
| MDL Number | MFCD00006859 |
| Nikkaji Number | J11.701C |
| Beilstein | 0162550 |
| XlogP3 | 1.50 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Equivalence Factor for Assay | . |
| Food Chemicals Codex Listed | No |
| Boiling Point | 455.50 °C. @ 760.00 mm Hg (est) |
| Flash Point | 375.00 °F. TCC ( 190.80 °C. ) (est) |
| logP (o/w) | 0.959 (est) |
| Soluble in | water, 2.097e+004 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | oral-mouse LD50 3200 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']
Safety in Use
| Category | pharmaceuticals / chemical synthisis |
| Recommendation for 4-methyl esculetin usage levels up to | not for fragrance use. |
| Recommendation for 4-methyl esculetin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
aesculetin, 4-methyl-
2H-1-
benzopyran-2-one, 6,7-dihydroxy-4-methyl-
coumarin, 6,7-dihydroxy-4-methyl-
6,7-
dihydroxy-4-methyl-2H-1-benzopyran-2-one
6,7-
dihydroxy-4-methyl-2H-benzopyran-2-one
6,7-
dihydroxy-4-methyl-2H-chromen-2-one
6,7-
dihydroxy-4-methyl-chromen-2-one
6,7-
dihydroxy-4-methylchromen-2-one
6,7-
dihydroxy-4-methylcoumarin
4-
methyl-6,7-dihydroxycoumarin
4-
methylaesculetin
4-
methylesculetin
4-
methylesculetol
5,6,7,7a,8,9,10,11-
octahydro-4H-benzo[ef]heptalene
PubMed:
Effects of sesquiterpene, flavonoid and coumarin types of compounds from Artemisia annua L. on production of mediators of angiogenesis.
PubMed:
A selective turn-on fluorescent sensor for sulfur mustard simulants.
PubMed:
Antiarthritic and antiinflammatory propensity of 4-methylesculetin, a coumarin derivative.
PubMed:
Absence of genotoxic effects of the coumarin derivative 4-methylesculetin in vivo and its potential chemoprevention against doxorubicin-induced DNA damage.
PubMed:
Suppression of TNBS-induced colitis in rats by 4-methylesculetin, a natural coumarin: comparison with prednisolone and sulphasalazine.
PubMed:
Short- and long-term regulation of 3-hydroxy 3-methylglutaryl coenzyme A reductase by a 4-methylcoumarin.
PubMed:
Structure-activity relationship of dihydroxy-4-methylcoumarins as powerful antioxidants: correlation between experimental & theoretical data and synergistic effect.
PubMed:
Intestinal anti-inflammatory activity of esculetin and 4-methylesculetin in the trinitrobenzenesulphonic acid model of rat colitis.
PubMed:
Synthesis, characterisation and antimicrobial activity of copper(II) and manganese(II) complexes of coumarin-6,7-dioxyacetic acid (cdoaH2) and 4-methylcoumarin-6,7-dioxyacetic acid (4-MecdoaH2): X-ray crystal structures of [Cu(cdoa)(phen)2].8.8H(2)O and [Cu(4-Mecdoa)(phen)2].13H2O (phen=1,10-phenanthroline).
PubMed:
Inhibitory effect of 4-methylesculetin on hyaluronan synthesis slows the development of human pancreatic cancer in vitro and in nude mice.
PubMed:
Structural requirements of hydroxylated coumarins for in vitro anti-Helicobacter pylori activity.
PubMed:
Protection of coumarins against linoleic acid hydroperoxide-induced cytotoxicity.
PubMed:
[Sensitization and crossreaction of simple coumarins].
PubMed:
Effect of coumarins on HL-60 cell differentiation.
PubMed:
Pharmacological and biochemical actions of simple coumarins: natural products with therapeutic potential.
PubMed:
Studies on the preparation of bioactive lignans by oxidative coupling reaction. VI. Oxidation of methyl (E)-3-(4,5-dihydroxy-2-methoxyphenyl)-2-butenoate and lipid peroxidation-inhibitory effects of the produced caffeoquinone.
PubMed:
Novel sensing system for glucose based on the complex formation between phenylborate and fluorescent diol compounds.
PubMed:
The sensitizing capacity of coumarins (II).
PubMed:
The sensitizing capacity of coumarins (I).
PubMed:
Liberation of prostaglandin-like substances from the isolated coronary artery in presence of angiotensin and of 4-methylesculetin.
PubMed:
[Facilitation of the onset of tetanic responses induced by 4-methylesculetol in amphibian isolated neuromuscular preparations].
PubMed:
[Contraction of the isolated stomach of the rat as a result of stimulation of postganglionic fibers in the presence of 4-methylesculetol].
PubMed:
[Effect of a bioflavinoid (4-methylesculetin) on the response of calf hepatic arteries to serotonin in the presence of indomethacin].
PubMed:
[Effect of a flavinoid (4-methylesculetin) on the response of isolated calf coronary arteries to histamine in the presence of indomethacin].
PubMed:
[Responses of isolated hepatic artery segments to barium in the presence of a flavonoid (4-methylesculetin), indomethacin and acetylsalicylate].
PubMed:
[Influence of 4-methylesculetol on the response of segments of isolated coronary arteries to adrenaline, in presence of pyrogallol].
PubMed:
[Effect of prostaglandin-synthetase inhibitors on responses of segments of coronary arteries to 4-methylesculetol and/or to angiotensin II].
PubMed:
[Influence of bioflavonoid (4-methylesculetin) on the reaction of isolated calf hepatic artery to serotonin].
PubMed:
[Effect of a flavonoid (4-methylesculetin) on the response of isolated segments of coronary arteries to adrenaline].
PubMed:
[Effect of a flavonoid (4-methylesculetin) on the response of isolated calf coronary arteries to histamine].
PubMed:
The relation of cycling of intracellular pH to mitosis in the acellular slime mould Physarum polycephalum.
PubMed:
Methyl calcein blue and other analogues of calcein blue.
PubMed:
[Polarographic method for quantitative determination of 4-methylesculetin-6,7-disulfonic acid (water-soluble vitamin P) in pharmaceutical preparations].
PubMed:
[Polarographic determination of the bisodium salt of 4-methylesculetin-6,7-disulfuric ester. IX. Control of various pharmaceutical products].
PubMed:
[Experimental and clinical use of disodium salt of 4-methylesculetin disulfuric ester in treatment of traumatic shock in 400 cases].
PubMed:
[Endothelial permeability in the pathogenesis of experimental atherosclerosis. I. Protective effect of 4-Methylesculetin, disulfuric ester].
PubMed:
[Diseases of children with increased capillary fragility treated with a disulfuric ester of 4-methyl-esculetin].