Methyl 4-O-demethylbarbatate

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Methyl 4-O-demethylbarbatate
Category Others
Catalog number BBF-05417
CAS 5038-46-0
Molecular Weight 360.36
Molecular Formula C19H20O7

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Description

It is a new depside from Erioderma Lichens.

Specification

Synonyms Benzoic acid, 2,4-dihydroxy-3,6-dimethyl-, 3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl ester; methyl 4-(2,4-dihydroxy-3,6-dimethylbenzoyloxy)-2-hydroxy-3,6-dimethylbenzoate; 4-(2,4-Dihydroxy-3,6-dimethylbenzoyloxy)-2-hydroxy-3,6-dimethylbenzoic acid methyl ester
IUPAC Name 3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl 2,4-dihydroxy-3,6-dimethylbenzoate
Canonical SMILES CC1=CC(=C(C(=C1C(=O)OC2=C(C(=C(C(=C2)C)C(=O)OC)O)C)O)C)O
InChI InChI=1S/C19H20O7/c1-8-6-12(20)10(3)16(21)15(8)19(24)26-13-7-9(2)14(18(23)25-5)17(22)11(13)4/h6-7,20-22H,1-5H3
InChI Key ODMVDRJFBPXTRQ-UHFFFAOYSA-N

Properties

Boiling Point 568.9±50.0°C at 760 mmHg
Melting Point 132-134°C (dichloromethane)
Density 1.3±0.1 g/cm3

Reference Reading

1. O-Methylation of carboxylic acids with streptozotocin
Li-Yan Zeng, Yang Liu, Jiakun Han, Jinhong Chen, Shuwen Liu, Baomin Xi Org Biomol Chem. 2022 Jul 6;20(26):5230-5233. doi: 10.1039/d2ob00578f.
The clinically used DNA-alkylating drug streptozotocin (STZ) was investigated using a simple work-up as an O-methylating agent to transform various carboxylic acids, sulfonic acids and phosphorous acids into corresponding methyl esters, and did so with yields of up to 97% in 4 h at room temperature. Good substrate tolerance was observed, and benefited from the mild conditions and compatibility of the reaction with water.
2. Ribosomal RNA 2'- O-methylations regulate translation by impacting ribosome dynamics
Sohail Khoshnevis, R Elizabeth Dreggors-Walker, Virginie Marchand, Yuri Motorin, Homa Ghalei Proc Natl Acad Sci U S A. 2022 Mar 22;119(12):e2117334119. doi: 10.1073/pnas.2117334119. Epub 2022 Mar 16.
SignificanceThe presence of RNA chemical modifications has long been known, but their precise molecular consequences remain unknown. 2'-O-methylation is an abundant modification that exists in RNA in all domains of life. Ribosomal RNA (rRNA) represents a functionally important RNA that is heavily modified by 2'-O-methylations. Although abundant at functionally important regions of the rRNA, the contribution of 2'-O-methylations to ribosome activities is unknown. By establishing a method to disturb rRNA 2'-O-methylation patterns, we show that rRNA 2'-O-methylations affect the function and fidelity of the ribosome and change the balance between different ribosome conformational states. Our work links 2'-O-methylation to ribosome dynamics and defines a set of critical rRNA 2'-O-methylations required for ribosome biogenesis and others that are dispensable.
3. Microbial mercury transformations: Molecules, functions and organisms
Ri-Qing Yu, Tamar Barkay Adv Appl Microbiol. 2022;118:31-90. doi: 10.1016/bs.aambs.2022.03.001. Epub 2022 Apr 13.
Mercury (Hg) methylation, methylmercury (MeHg) demethylation, and inorganic redox transformations of Hg are microbe-mediating processes that determine the fate and cycling of Hg and MeHg in many environments, and by doing so influence the health of humans and wild life. The discovery of the Hg methylation genes, hgcAB, in the last decade together with advances in high throughput and genome sequencing methods, have resulted in an expanded appreciation of the diversity of Hg methylating microbes. This review aims to describe experimentally confirmed and recently discovered hgcAB gene-carrying Hg methylating microbes; phylogenetic and taxonomic analyses are presented. In addition, the current knowledge on transformation mechanisms, the organisms that carry them out, and the impact of environmental parameters on Hg methylation, MeHg demethylation, and inorganic Hg reduction and oxidation is summarized. This knowledge provides a foundation for future action toward mitigating the impact of environmental Hg pollution.

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