Methyl linoleate

Base Information

• Chemical Name: Methyl linoleate
• CAS No.: 112-63-0
• Deprecated CAS: 1198018-53-9
• Molecular Formula: C19H34O2
• Molecular Weight: 294.478
• Hs Code.: 2916190090
• European Community (EC) Number: 219-560-4,271-715-5,203-993-0
• UNII: 24N6726DE5
• DSSTox Substance ID: DTXSID7020843
• Nikkaji Number: J1.998D
• Wikidata: Q27137420
• Metabolomics Workbench ID: 130623
• ChEMBL ID: CHEMBL3183866
• Mol file: 112-63-0.mol

Synonyms:linoleic acid methyl ester;methyl linoleate;methyl linoleate, (E,E)-isomer;methyl linoleate, (E,Z)-isomer;methyl linoleate, (Z,E)-isomer;methyl linoleate, 1-(14)C-labeled, (Z,Z)-isomer

Chemical Property of Methyl linoleate

Chemical Property:

• Appearance/Colour: Clear pale to dark yellow liquid
• Vapor Pressure: 9.04E-06mmHg at 25°C
• Melting Point: -35 °C(lit.)
• Refractive Index: n20/D 1.462(lit.)
• Boiling Point: 373.3 °C at 760 mmHg
• Flash Point: 97 °C
• PSA: 26.30000
• Density: 0.884 g/cm³
• LogP: 5.84990
• XLogP3: 6.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 15
• Exact Mass: 294.255880323
• Heavy Atom Count: 21
• Complexity: 279

Purity/Quality:

Safty Information:

• Pictogram(s): F,Xn,N
• Hazard Codes: F,Xn,N

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC=CCCCCCCCC(=O)OC
• Isomeric SMILES: CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC

Technology Process of Methyl linoleate

There total 89 articles about Methyl linoleate 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: 93.8%

methanol (67-56-1) + 9,12-octadecadienoic acid (60-33-3,506-21-8,2197-37-7,2420-42-0,2420-55-5,116745-32-5,26085-09-6,64080-88-2,7049-66-3,949900-18-9,60476-23-5,6144-28-1,67922-65-0,89718-18-3) → linoleic acid methyl ester (2462-85-3,2566-97-4,20221-26-5,20221-27-6,112-63-0)

Guidance literature:

With toluene-4-sulfonic acid; at 60 ℃; for 6h; Inert atmosphere;

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 12-trimethylacetoxyoctadec-9-(Z)-enoate (942062-59-1) → (9Z,11E)-methyl octadeca-9,11-dienoate (822-10-6,13038-47-6,17675-24-0,19295-76-2,13058-52-1) + Methyl linoleate (112-63-0) + methyl ricinoleate (141-24-2)

Guidance literature:

With potassium methanolate; In methanol; at 90 - 100 ℃; for 3.5h; Product distribution / selectivity;

upstream raw materials:

methanol

chlorine

toluene-4-sulfonic acid

erythro-9,10-dihydroxyoctadecanoic acid methyl ester

Downstream raw materials:

8-(3-((3-pentyloxiran-2-yl)methyl)oxiran-2-yl)octanoic acid

cis-9,trans-11-octadecadienoic acid

trans-10,cis-12-octadecadienoic acid

(9Z,11E)-methyl octadeca-9,11-dienoate

Refernces

• 1、 Berdeaux,Christie,Gunstone,Sebedio. "Large-scale synthesis of methyl cis-9, trans-11-octadecadienoate from methyl ricinoleate". . p. 1011 - 1015. Retrieved 1997.
• 2、 Meyer, Matthew P.,Klinman, Judith P.. "Investigating inner-sphere reorganization via secondary kinetic isotope effects in the C-H cleavage reaction catalyzed by soybean lipoxygenase: Tunneling in the substrate backbone as well as the transferred hydrogen". . p. 430 - 439. Retrieved 2011.
• 3、 Schlenk,Holman. "". . p. 5001. Retrieved 1950.
• 4、 Meyer, Matthew P.,Klinman, Judith P.. "Synthesis of linoleic acids combinatorially labeled at the vinylic positions as substrates for lipoxygenases". . p. 3600 - 3603. Retrieved 2008.
• 5、 -. "Branched alkyl sulfonate anionic surfactant and preparation process thereof". Paragraph 0090-0091. . Retrieved 2021/02/10.
• 6、 Chang, Tao,Hao, Yongjing,Jinxi, Jinxi,Kai, Kai,Panchal, Balaji,Qin, Shenjun,Sun, Yuzhuang,Zhao, Cunling,Zhao, Qiaojing,Zhu, Zheng. "Novel synthesized microporous ionic polymer applications in transesterification of Jatropha curcas seed oil with short Chain alcohol". . . Retrieved 2021/09/28.