1234694-20-2

Usage

Uses

Used in Pharmaceutical Industry:
(+)-trans-C75 is used as a potential therapeutic agent for obesity and weight management due to its ability to induce weight loss and feeding inhibition in obese mice.
Used in Oncology:
(+)-trans-C75 is used as a cytotoxic agent against various human cancer cell lines, particularly those with an upregulated FASN pathway. Its mechanism of action involves the accumulation of malonyl-coenzyme A in cancer cells, leading to cell death.
Used in Cancer Research:
(+)-trans-C75 serves as a valuable tool in cancer research for studying the role of FASN in cancer cell growth and the potential of FASN inhibitors as therapeutic agents.
Used in Drug Development:
(+)-trans-C75 can be utilized in the development of novel drugs targeting FASN, which may have applications in treating obesity, cancer, and other FASN-related conditions.

Upstream product

• 7338-27-4 4-methoxy-2-methylene-4-oxobutanoic acid 
• 124-19-6 nonan-1-al 
• 60427-77-2 4-((4-methoxybenzyl)oxy)-2-methylene-4-oxobutanoic acid 
• 58588-90-2 α-bromomethyl-γ-butene lactone 
• 547-65-9 α-methylene-γ-butyrolactone 
• 1234694-21-3 methyl (2S,3R)-4-methylene-5-oxo-2-octyltetrahydrofuran-3-carboxylate 

Relevant academic research and scientific papers

Total syntheses of paraconic acids and 1,10-seco-guaianolides via a barbier allylation/translactonization cascade of 3-(Bromomethyl)-2(5H)-furanone

A palladium-catalyzed Barbier allylation/translactonization cascade reaction was established for the rapid construction of β,γdisubstituted α-exo-methylene-γ-butyrolactone, an important motif in sesquiterpenes. Dimethyl zinc played significant roles in bo

Enzymatic resolution of α-methyleneparaconic acids and evaluation of their biological activity

Both enantiomers of three biologically relevant paraconic acids-MB-3, methylenolactocin, and C75-were obtained with enantioselectivities up to 99% by kinetic enzymatic resolutions. Good enantiomeric excesses were obtained for MB-3 and methylenolactocin, using α-chymotrypsin and aminoacylase as enantiocomplementary enzymes, while C75 was resolved with aminoacylase. They all were evaluated for their antiproliferative, antibacterial, and antifungal activities, showing weak effects and practically no difference between enantiomers in each case. At high concentrations (16-64μg/mL), (-)- C75 acted as an antimicrobial agent against Gram-positive bacteria.

The first kinetic enzymatic resolution of methyl ester of C75

Enantioselective hydrolysis of methyl ester of (±)-C75 was successfully accomplished by means of Acylase I from Aspergillus to afford (2,R,3S)-(+)-C75 with 96% e.e. The unreacted methyl ester was recovered with >99% e.e. This latter compound was either chemically or enzymatically hydrolyzed to furnish (2S,3,R)-(-)-C75 with >99% e.e.

INHIBITION OF FATTY ACID SYNTHASE AS A MEANS TO REDUCE ADIPOCYTE MASS

Weight loss was noted in nude mice treated with cerulenin, a non-competitive inhibitor of FAS. Sustained reduction of adipocyte mass in humans without toxicity would significantly impact disease prevention worldwide. Aside from psychological and self-este