Methyl evernate

Methyl evernate

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Methyl evernate
Category Others
Catalog number BBF-05150
CAS 3542-22-1
Molecular Weight 346.33
Molecular Formula C18H18O7

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Specification

Synonyms 2,6-Cresotic acid, 4-methoxy-, 4-ester with methyl 6-methyl-beta-resorcylate; Benzoic acid, 2-hydroxy-4-[(2-hydroxy-4-methoxy-6-methylbenzoyl)oxy]-6-methyl-, methyl ester; β-Resorcylic acid, 6-methyl-, methyl ester, 4-(4-methoxy-2,6-cresotate)
IUPAC Name (3-hydroxy-4-methoxycarbonyl-5-methylphenyl) 2-hydroxy-4-methoxy-6-methylbenzoate
Canonical SMILES CC1=CC(=CC(=C1C(=O)OC2=CC(=C(C(=C2)C)C(=O)OC)O)O)OC
InChI InChI=1S/C18H18O7/c1-9-5-11(23-3)7-13(19)16(9)18(22)25-12-6-10(2)15(14(20)8-12)17(21)24-4/h5-8,19-20H,1-4H3
InChI Key IUAPPXZOQIJVBW-UHFFFAOYSA-N

Properties

Boiling Point 493.2±45.0°C (Predicted)
Melting Point 148°C
Density 1.311±0.06 g/cm3 (Predicted)

Reference Reading

1. Depsides and triterpenes in Pseudocyphellaria coriifolia (lichens) and biological activity against Trypanosoma cruzi
Mauricio Cuellar Fritis, Cecilia Rubio Lagos, Natalia Quiñones Sobarzo, Iván Montenegro Venegas, Cristian Salas Sánchez, Hector Carrasco Altamirano, Luis Espinoza Catalán, Wanda Quilhot Palma Nat Prod Res. 2013;27(17):1607-10. doi: 10.1080/14786419.2012.740033. Epub 2012 Nov 19.
The lichen Pseudocyphellaria coriifolia is a species endemic to southern South America. From the lichen thallus, methyl evernate, tenuiorin and three hopane triterpenoids were isolated and identified as the main lichen constituents. Their trypanocidal effects were screened against epimastigotes of Trypanosoma cruzi. The results of the biological test showed that some hopane terpenoids exhibit antiparasitic properties.
2. Biopharmaceutical Potential of Two Ramalina Lichens and their Metabolites
Svetlana Ristic, Branislav Rankovic, Marijana Kosanić, Slavisa Stamenkovic, Tatjana Stanojković, Miroslav Sovrlić, Nedeljko Manojlović Curr Pharm Biotechnol. 2016;17(7):651-8. doi: 10.2174/1389201017666160401144825.
This paper studies the phytochemical analysis of the acetone extracts of the Ramalina fraxinea and Ramalina fastigiata lichens and the antioxidant, antimicrobial and antitumour activities of these species and their constituents. The phytochemical analysis of two Ramalina species was evaluated using HPLC-UV test. The depsides (evernic acid, obtusatic acid, sekikaic acid and atranorin), depsidones (protocetraric acid) and dibenzofurane (usnic acid) were identified from these lichens. Antioxidant activity was evaluated by DPPH assay, reducing power assay and by measuring the amounts of total phenolics in extracts. Antimicrobial activity was tested towards five bacterial and 10 fungal species, using broth microdilution method to determine the minimum inhibitory concentration. Cytotoxic activity was tested using MTT method on the human epithelial carcinoma (Hela), human lung carcinoma (A549) and human colon carcinoma (LS174) cells. As a result of the study, tested samples showed strong free radical scavenging activity with I50 values within the range of 285.45-423.51 μg/mL. Absorbance for reducing power was found to be from 0.0043 to 0.1747. The total amount of phenol concentrations in extracts of Ramalina fraxinea and Ramalina fastigiata was 32.63 and 33.49 μg PE/mg, respectively. Methyl evernate showed the strongest antimicrobial properties with the least measured MIC value being 0.125 mg/mL. In addition, all samples exhibited strong anticancer activities against tested cells (I50 values were between 24.63 and 161.37 μg/mL). These results indicate that lichen appears to be a possible natural biopharmaceutical.

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