164014-40-8

Basic information

• Product Name: Methanesulfonic acid, trifluoro-, 2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-5-yl ester
• CAS NO: 164014-40-8
• Molecular Formula: C11H9F3O6S
• Molecular Weight: 326.25
• Mol File: 164014-40-8.mol

Chemical Properties

• CAS DataBase Reference: Methanesulfonic acid, trifluoro-, 2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-5-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Methanesulfonic acid, trifluoro-, 2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-5-yl ester(164014-40-8)
• EPA Substance Registry System: Methanesulfonic acid, trifluoro-, 2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-5-yl ester(164014-40-8)

Safety Data

• Hazardous Substances Data: 164014-40-8(Hazardous Substances Data)

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 154714-19-9 5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 
• 1107631-27-5 C₁₀H₉FO₄ 

Downstream Products

• 185698-58-2 5-[4-(tert-Butyl-dimethyl-silanyloxy)-phenylethynyl]-2,2-dimethyl-benzo[1,3]dioxin-4-one 
• 936352-38-4 5-(3-benzyloxy-phenyl)-2,2-dimethyl-benzo[1,3]dioxin-4-one 
• 1196985-67-7 5-(5-hydroxy-2-methylphenyl)-2,2-dimethyl-4H-1,3-benzodioxin-4-one 
• 378242-08-1 2,2-dimethyl-5-vinyl-4H-benzo[d][1,3]dioxin-4-one 
• 1240382-67-5 (E)-2,2-dimethyl-5-(2-(trimethylsilyl)vinyl)-4H-benzo[d][1,3]dioxin-4-one 
• 154714-19-9 5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 
• 1357170-93-4 5-((4-(2-methoxyethoxy)phenyl)ethynyl)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 
• 1357170-94-5 5-((3-acetyl-4-(pentyloxy)phenyl)ethynyl)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 
• 1357171-00-6 5-(3-acetyl-4-(pentyloxy)phenethyl)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 
• 1357171-01-7 5-(3-(1-hydroxyethyl)-4-(pentyloxy)phenethyl)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 
• 1357171-02-8 5-(3-ethyl-4-(pentyloxy)phenethyl)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 
• 1357171-10-8 2-(3-acetyl-4-(pentyloxy)phenethyl)-6-hydroxybenzoic acid 
• 1357171-11-9 2-hydroxy-6-(3-(1-hydroxyethyl)-4-(pentyloxy)phenethyl)benzoic acid 
• 1357171-12-0 2-(3-ethyl-4-(pentyloxy)phenethyl)-6-hydroxybenzoic acid 

Relevant articles and documents

Novel chemical synthesis of ginkgolic acid (13:0) and evaluation of its tyrosinase inhibitory activity

A novel efficient synthesis of ginkgolic acid (13:0) from abundant 2,6-dihydroxybenzoic acid was successfully developed through a state-of-the-art palladium-catalyzed cross-coupling reaction and catalytic hydrogenation with an overall yield of 34% in five steps. The identity of the synthesized ginkgolic acid (13:0) was confirmed by nuclear magnetic resonance, mass spectrometry, infrared, and high-performance liquid chromatography. The reaction sequence of this method can be readily extended to the synthesis of other ginkgolic acids. The synthesized ginkgolic acid (13:0) exhibited promising anti-tyrosinase activity (IC50 = 2.8 mg/mL) that was not correlated to antioxidant activity as probed by 1,1-diphenyl-2-picrylhydrazyl, 2,2′-azino-bis(3- ethylbenzothiazoline-6-sulfonic acid), ferric reducing ability of plasma, and oxygen radical absorbance capacity assays. The synthetic strategy developed in this work will significantly facilitate biological studies of ginkgolic acids that have great potential applications in food and pharmaceuticals.

Synthesis and Structure-Activity Relationship of Xenocoumacin 1 and Analogues as Inhibitors of Ribosomal Protein Synthesis

Ribosomal protein synthesis is an important target in antibacterial drug discovery. Numerous natural products have served as starting points for the development of antibiotics. We report here the total synthesis of xenocoumacin 1, a natural product that binds to 16S ribosomal RNA at a highly conserved region, as well as analogues thereof. Preliminary structure–activity relationship studies were aimed at understanding and modulating the selectivity between eukaryotic and prokaryotic ribosomes. Modifications were mainly tolerated in the aromatic region. Whole-cell activity against Gram-negative bacteria is limited by efflux and penetration, as demonstrated in genetically modified strains of E. coli. Analogues with high selectivity for eukaryotic ribosomes were identified, but it was not possible to obtain inhibitors selective for bacterial protein synthesis. Achieving high selectivity (albeit not the desired one) was thus possible despite the high homology between eukaryotic and prokaryotic ribosomes in the binding region.

Divinylcarbinol Desymmetrization Strategy: A Concise and Reliable Approach to Chiral Hydroxylated Fatty Acid Derivatives

By the aid of the catalytic desymmetrization of divinylcarbinol as one-pot asymmetric induction and protection of olefin, asymmetric total syntheses of two chiral hydroxylated fatty acid derivatives were successfully achieved. The desired stereoisomers could be concisely prepared in mild conditions in a highly convergent manner. Thus, this novel strategy can help stereochemical elucidations of natural products, which have difficulties in spectroscopic stereochemical analyses due to their local symmetries in the vicinities of the stereogenic secondary hydroxyl units.

Synthesis and Evaluation of Ginkgolic Acid Derivatives as SUMOylation Inhibitors

SUMOylation has emerged as an important post-translational modification that has been shown to modulate protein activity associated with various signaling pathways, and consequently, it has emerged as an important therapeutic target. While several natural products have been shown to inhibit enzymes involved in the SUMOylation process, there has been little progress toward the development of more selective and potent SUMOylation inhibitors. Ginkgolic acid was one of the first natural products discovered to inhibit the SUMO E1 enzyme. Despite its use to mechanistically investigate the SUMOylation process, ginkgolic acid also modulates other pathways as well. In this Letter, preliminary structure-activity relationships for ginkgolic acid as a SUMOylation inhibitor are presented.

A Heck-Based Strategy to Generate Anacardic Acids and Related Phenolic Lipids for Isoform-Specific Bioactivity Profiling

A synthetic strategy for phenolic lipids such as anacardic acid and ginkgolic acid derivatives using an efficient and selective redox-relay Heck reaction followed by a stereoselective olefination is reported. This approach controls both the alkene position and stereochemistry, allowing the synthesis of natural and unnatural unsaturated lipids as single isomers. By this strategy, the activities of different anacardic acid and ginkgolic acid derivatives have been examined in a matrix metalloproteinase inhibition assay.

Structure-inspired design of a sphingolipid mimic sphingosine-1-phosphate receptor agonist from a naturally occurring sphingomyelin synthase inhibitor

Ginkgolic acid obtained as a sphingomyelin synthase inhibitor from a plant extract library inspired the concept of sphingolipid mimics. Ginkgolic acid-derived N-acyl anilines and ginkgolic acid 2-phosphate (GA2P) respectively mimic ceramide and sphingosine 1-phosphate (S1P) in structure and function. The GA2P-induced phosphorylation of ERK and internalization of S1P receptor 1 (S1P1) indicated potent agonist activity. Docking studies revealed that GA2P adopts a similar binding conformation to the bound ligand ML5, which is a strong antagonist of S1P1.

Gold(I)-Catalyzed Cyclization for the Synthesis of 8-Hydroxy-3- substituted Isocoumarins: Total Synthesis of Exserolide F

A highly regioselective gold(I)-catalyzed 6-endo-dig cyclization of 2,2-dimethyl-5-(alkynyl)-4H-benzo[d][1,3]dioxin-4-ones for the synthesis of 8-hydroxy-3-substituted isocoumarins is described. Key features of the reaction include the broad substrate scope, scalability, and tolerance for protecting groups. The synthetic utility of this novel method is demonstrated by the first total synthesis of exserolide F, an isocoumarin-containing polyol natural product.

Enantioselective Chemical Syntheses of the Furanosteroids (-)-Viridin and (-)-Viridiol

Herein we describe concise enantioselective chemical syntheses of (-)-viridin and (-)-viridiol. Our convergent approach couples two achiral fragments of similar complexity and employs an enantioselective intramolecular Heck reaction to set the absolute stereochemical configuration of an all-carbon quaternary stereocenter. To complete the syntheses of these base- and nucleophile-sensitive natural products, we conduct carefully orchestrated site- and diastereoselective oxidations and other transformations. Our work is the first to generate these targets as single enantiomers.

Synthesis and structure-activity studies of the V-ATPase inhibitor saliphenylhalamide (SaliPhe) and simplified analogs

An efficient total synthesis of the potent V-ATPase inhibitor saliphenylhalamide (SaliPhe), a synthetic variant of the natural product salicylihalamide A (SaliA), has been accomplished aimed at facilitating the development of SaliPhe as an anticancer and antiviral agent. This new approach enabled facile access to derivatives for structure-activity relationship studies, leading to simplified analogs that maintain SaliPhe's biological properties. These studies will provide a solid foundation for the continued evaluation of SaliPhe and analogs as potential anticancer and antiviral agents.

First enantioselective total synthesis of penicimarin B, aspergillumarins A and B

A convergent enantioselective synthesis of penicimarin B, aspergillumarin A and B has been reported using Brown's allylation, DeBrabander-Bhattacharjee lactonization and Grubbs cross coupling metathesis. During this synthesis we have standardized the conditions for DeBrabande-Bhattacharjee lactonization to obtain excellent yield (>90%).