Methyl cis-9,10-epoxystearate

Base Information

• Chemical Name: Methyl cis-9,10-epoxystearate
• CAS No.: 2566-91-8
• Molecular Formula: C19H36 O3
• Molecular Weight: 312.493
• Nikkaji Number: J512.929J
• Wikidata: Q104951498
• Mol file: 2566-91-8.mol

Synonyms:cis-9,10-epoxystearate methyl ester;methyl 9,10-epoxystearate;methyl 9,10-epoxystearate, (2R-cis)-isomer;methyl 9,10-epoxystearate, (2R-trans)-isomer;methyl 9,10-epoxystearate, (2S-cis)-isomer;methyl 9,10-epoxystearate, (cis)-isomer;methyl 9,10-epoxystearate, (trans)-isomer;methyl 9,10-epoxystearate, carboxy 14C-labeled, (cis)-isomer;methyl cis-9,10-epoxystearate;trans-9,10-epoxystearate methyl ester

Chemical Property of Methyl cis-9,10-epoxystearate

Chemical Property:

• Vapor Pressure: 3.67E-06mmHg at 25°C
• Boiling Point: 385.9°Cat760mmHg
• Flash Point: 149°C
• PSA: 38.83000
• Density: 0.925g/cm³
• LogP: 5.40810
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 16
• Exact Mass: 312.26644501
• Heavy Atom Count: 22
• Complexity: 278

Purity/Quality:

99% ^*data from raw suppliers

cis-9,10-EpoxystearicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC1C(O1)CCCCCCCC(=O)OC
• Isomeric SMILES: CCCCCCCC[C@@H]1[C@@H](O1)CCCCCCCC(=O)OC
• Uses: cis-9,10-Epoxystearic Acid Methyl Ester can be used as an inhibitor of soybean lipoxygenase. It is also an intermediate used to synthesize biobased polyurethane from oleic and ricinoleic acids as renewable resources.

Technology Process of Methyl cis-9,10-epoxystearate

There total 46 articles about Methyl cis-9,10-epoxystearate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.8%

Methyl oleate (112-62-9) → (Z)-9,10-epoxyoctadecanoic acid methyl ester (2500-59-6,2566-91-8,6084-76-0,38003-69-9,38003-75-7,38003-77-9,79854-41-4,112244-28-7)

Guidance literature:

With formic acid; dihydrogen peroxide; In water; at 0 - 23 ℃; for 24h;

DOI:10.1007/s11746-009-1441-0

Reference yield: 96.0%

methyl (9E)-octadec-9-enoate (2462-84-2) → (E)-9,10-epoxyoctadecanoic acid methyl ester (2500-59-6,2566-91-8,6084-76-0,38003-69-9,38003-75-7,38003-77-9,79854-41-4,112244-28-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 21h;

DOI:10.1039/b202891c

Reference yield: 82.0%

Methyl oleate (112-62-9) → methyl 9,10-dihydroxy stearate (1115-01-1) + epoxidized methyl oleate (2566-91-8)

Guidance literature:

With R Amano K lipase; 1-butyl-3-methylimidazolium hexafluorophosphate; dihydrogen peroxide; at 30 ℃; for 5h; Enzymatic reaction;

DOI:10.1016/j.molcatb.2010.09.019

upstream raw materials:

octadec-9-enoic acid methyl ester

methanol

trans-9,10-epoxystearic acid

methyl (9E)-octadec-9-enoate

Downstream raw materials:

trans-9,10-epoxystearic acid

cis-9,10-epoxystearic acid

9-hydroxy-octadecanoic acid methyl ester

Methyl stearate

Refernces

• 1、 Abdullah, Luqman Chuah,Ariffin, Hidayah,Biak, Dayang Radiah Awang,Hoong, Seng Soi,Kamairudin, Norsuhaili. "Optimisation of epoxide ring-opening reaction for the synthesis of bio-polyol from palm oil derivative using response surface methodology". . . Retrieved 2021.
• 2、 Baluch, Dosten,Charalambous, John,Haines, L. Ian B.. "Manganese Complexes of 1,2-Naphthoquinone Mono-oximes (2-Nitrosophenols) as Catalysts for Alkene Epoxidation". . p. 1178 - 1179. Retrieved 1988.
• 3、 Bigot, Sandra,Kébir, Nasreddine,Plasseraud, Laurent,Burel, Fabrice. "Organocatalytic synthesis of new telechelic polycarbonates and study of their chemical reactivity". . p. 127 - 134. Retrieved 2015.
• 4、 Turco, Rosa,Pischetola, Chiara,Tesser, Riccardo,Andini, Salvatore,Di Serio, Martino. "New findings on soybean and methylester epoxidation with alumina as the catalyst". . p. 31647 - 31652. Retrieved 2016.
• 5、 Turco, Rosa,Aronne, Antonio,Carniti, Paolo,Gervasini, Antonella,Minieri, Luciana,Pernice, Pasquale,Tesser, Riccardo,Vitiello, Rosa,Di Serio, Martino. "Influence of preparation methods and structure of niobium oxide-based catalysts in the epoxidation reaction". . p. 99 - 103. Retrieved 2015.
• 6、 Peyrton, Julien,Chambaretaud, Clémence,Avérous, Luc. "New insight on the study of the kinetic of biobased polyurethanes synthesis based on oleo-chemistry". . . Retrieved 2019.
• 7、 Gamelas, Carla A.,Romao, Carlos C.,Neves, Patricia,Gomes, Ana C.,Valente, Anabela A.,Goncalves, Isabel S.,Pillinger, Martyn. "Molybdenum(II) diiodo-tricarbonyl complexes containing nitrogen donor ligands as catalyst precursors for the epoxidation of methyl oleate". . p. 1218 - 1224,7. Retrieved 2012.
• 8、 Poli, Evelyne,Bion, Nicolas,Barrault, Jo?l,Casciato, Stefano,Dubois, Vincent,Pouilloux, Yannick,Clacens, Jean-Marc. "Selective epoxidation of unsaturated fatty esters over peroxophosphotungstic catalysts (POW) under solvent free conditions: Study of the POW catalyst's mechanism". . p. 371 - 377. Retrieved 2010.
• 9、 Guerrero, Isabel,Romero, Isabel,Teixidor, Francesc,Vi?as, Clara. "A stand-alone cobalt bis(dicarbollide) photoredox catalyst epoxidates alkenes in water at extremely low catalyst load". . p. 10123 - 10131. Retrieved 2021/12/27.