(10E,12Z)-10,12-octadecadienoic acid methyl ester

Base Information

• Chemical Name: (10E,12Z)-10,12-octadecadienoic acid methyl ester
• CAS No.: 1002-79-5
• Molecular Formula: C₁₉H₃₄O₂
• Molecular Weight: 294.478
• Mol file: 1002-79-5.mol

Synonyms:

Chemical Property of (10E,12Z)-10,12-octadecadienoic acid methyl ester

Chemical Property:

• Boiling Point: 136-142 °C(Press: 0.01 Torr)
• Density: 0.884±0.06 g/cm3(Predicted)

Purity/Quality:

ConjugatedLinoleicAcidMethylEster,90%(MixtureofIsomers) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Conjugated Linoleic Acid Methyl Ester is the methyl ester derivative of Conjugated Linoleic Acid (C685000); a compound that has reported to exhibit anticarcinogenic activity. Also a potent antioxidant.

Technology Process of (10E,12Z)-10,12-octadecadienoic acid methyl ester

There total 11 articles about (10E,12Z)-10,12-octadecadienoic acid methyl ester 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: 42.0%

methyl ricinoleate (141-24-2) → (9Z,11E)-methyl octadeca-9,11-dienoate (822-10-6,13038-47-6,17675-24-0,19295-76-2,13058-52-1) + octadeca-9,11-dienoic acid methyl ester (822-10-6,13058-52-1,17675-24-0,19295-76-2,13038-47-6) + (10E,12Z)-10,12-octadecadienoic acid methyl ester (1002-79-5,13038-48-7,13058-53-2,38433-72-6,21870-97-3) + (10E,12E)-10,12-Octadecadiensaeure-methylester (13038-48-7) + Methyl linoleate (112-63-0)

Guidance literature:

With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; potassium hydroxide; In ethylene glycol; at 180 ℃; for 0.5h; Microwave irradiation;

DOI:10.1039/c2gc35792e

Reference yield:

Methyl linoleate (112-63-0) → (9Z,11E)-methyl octadeca-9,11-dienoate (822-10-6,13038-47-6,17675-24-0,19295-76-2,13058-52-1) + (10E,12Z)-10,12-octadecadienoic acid methyl ester (1002-79-5,13038-48-7,13058-53-2,38433-72-6,21870-97-3)

Guidance literature:

2,8,9-tris(2-methylpropyl)-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane; In acetonitrile; at 40 ℃; for 49h; under 750.06 Torr; Title compound not separated from byproducts;

DOI:10.1002/adsc.200505224

Reference yield:

Methyl linoleate (112-63-0) → (9Z,11E)-methyl octadeca-9,11-dienoate (822-10-6,13038-47-6,17675-24-0,19295-76-2,13058-52-1) + octadeca-9,11-dienoic acid methyl ester (822-10-6,13058-52-1,17675-24-0,19295-76-2,13038-47-6) + (10E,12Z)-10,12-octadecadienoic acid methyl ester (1002-79-5,13038-48-7,13058-53-2,38433-72-6,21870-97-3)

Guidance literature:

With Ru/Cs-USY⁽⁴⁰⁾; In decane; at 165 ℃; for 4h; under 2625.26 Torr; Autoclave; Inert atmosphere;

DOI:10.1002/cssc.201100015

upstream raw materials:

hexylidenetriphenylphosphoran

(E)-11-Formyl-10-undecensaeure-methylester

diazomethane

linoleic acid

Refernces

• 1、 Andjelkovic, Dejan D.,Min, Byungrok,Ahn, Dong,Larock, Richard C.. "Elucidation of structural isomers from the homogeneous rhodium-catalyzed isomerization of vegetable oils". . p. 9535 - 9543. Retrieved 2006.
• 2、 Philippaerts, An,Goossens, Steven,Vermandel, Walter,Tromp, Moniek,Turner, Stuart,Geboers, Jan,Van Tendeloo, Gustaaf,Jacobs, Pierre A.,Sels, Bert F.. "Design of ru-zeolites for hydrogen-free production of conjugated linoleic acids". . p. 757 - 767. Retrieved 2011.
• 3、 Pham, Huong T.,Prendergast, Matthew B.,Dunstan, Christopher W.,Trevitt, Adam J.,Mitchell, Todd W.,Julian, Ryan R.,Blanksby, Stephen J.. "Dissociation of proton-bound complexes reveals geometry and arrangement of double bonds in unsaturated lipids". . p. 170 - 177. Retrieved 2015.
• 4、 Islam, Mohammad A.,Kim, Young S.,Oh, Tae W.,Kim, Gon S.,Won, Chung K.,Kim, Hoon G.,Choi, Myung S.,Kim, Jeong O.,Ha, Yeong L.. "Superior anticarcinogenic activity of trans, trans-conjugated linoleic acid in N-methyl-N-nitrosourea-induced rat mammary tumorigenesis". . p. 5670 - 5678. Retrieved 2010.
• 5、 Moreno, Maria,Gomez, M. Victoria,Cebrian, Cristina,Prieto, Pilar,De La Hoz, Antonio,Moreno, Andres. "Sustainable and efficient methodology for CLA synthesis and identification". . p. 2584 - 2594. Retrieved 2013/02/23.