trans-9,10-Epoxystearic acid methyl ester

• CAS: 6084-76-0
• Catalog Number: ACM6084760
• Category: Main Products
• Molecular Weight: 312.49
• Molecular Formula: C₁₉H₃₆O₃
• Synonyms: (+/-)-TRANS-9,10-EPOXYOCTADECANOIC ACID METHYL ESTER;TRANS-9,10-EPOXYSTEARIC ACID METHYL ESTER;Epoxy fatty acids methyl ester;Epoxy Fatty Acid Methyl Esters
• IUPAC Name: methyl8-[(2R,3R)-3-octyloxiran-2-yl]octanoate
• SMILES: CCCCCCCCC1C(O1)CCCCCCCC(=O)OC
• InChI Key: CAMHHLOGFDZBBG-QZTJIDSGSA-N
• Boiling Point: 385.9ºC at 760 mmHg
• Flash Point: 149ºC
• Density: 0.925 g/cm³
• Exact Mass: 312.26600

Case Study

Solvent-Free Synthesis of trans-9,10-Epoxystearic Acid Methyl Ester via Chemo-Enzymatic Epoxidation

Orellana-Coca, Cecilia, et al. Biocatalysis and Biotransformation 23.6 (2005): 431-437.

The report presented an effective enzymatic procedure for synthesizing trans-9,10-epoxystearic acid methyl ester, a useful epoxy fatty ester, under solvent-free conditions. Utilizing methyl oleate as a substrate and immobilized Candida antarctica lipase B as a biocatalyst, this strategy allows for high-yield epoxidation using hydrogen peroxide as the oxidant.
Experimental Procedure
The reactions of epoxidation were performed as a solvent-free system. Methyl oleate (99%, substrate), immobilized lipase from Candida antarctica (catalyst), 30% w/w hydrogen peroxide (10% stoichiometric excess, oxidant) were shaken (800 rpm) in closed vials under 40-60°C, where hydrogen peroxide was added every 15 minutes during 4 hours. The samples were periodically taken for analysis to determine the extent of the substrate conversion and the product formation.
Key Results
Methyl oleate conversion to epoxidized products was nearly 100% after 6 hours at 40-60°C. Epoxidation was highly selective, and the main product was trans-9,10-epoxystearic acid methyl ester with only minor amounts of epoxystearic acid due to lipase-catalyzed hydrolysis. Temperature played an important role in reaction kinetics. At a higher temperature (e.g., 50-60°C) reaction time was shorter but extended durations also increased the formation of by-products.