Methyl trans-9,12-octadecadienoateMethyl trans-9,12-octadecadienoate
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Methyl trans-9,12-octadecadienoate

Methyl linoelaidate; C18:2 (all trans-9,12) Methyl ester

This product is the high purity methyl ester form of linoelaidic acid (the trans isomer of linoleic acid) and is an ideal standard for gas chromatography and for biological studies. The process of producing partially hydrogenated fats converts the cis double bonds of linoleic acid into trans double bonds and the resulting linoelaidic acid can comprise a significant percentage of the unsaturated fatty acids in some partially hydrogenated fats. trans-Fatty acids have become widely studied due to the link between these fatty acids and coronary heart disease. Whereas some trans isomers of linoleic acid are metabolized or converted to other polyunsaturated fatty acids, linoelaidic acid appears not to undergo such processes. Although linoelaidic acid is incorporated into triacylglycerols as readily as linoleic acid it is discriminated against in cholesterol esters.1 At high temperatures, such as are used in cooking and frying, the triacylglycerols of linoelaidic acid are easily converted to other isomers of linoleic acid and conjugated linoleic acid.2 Some cis-unsaturated fatty acids are activators for protein kinase C (PKC) and most of their corresponding trans-isomers have greatly reduced activating properties; however, linoelaidic acid demonstrates approximately the same degree of activation of PKC as its natural linoleic isomer.3 Linoelaidic acid (as well as trans elaidic acid) induce apoptosis through its effect on Caspase-3 activity and on intracellular reactive oxygen species production and may play a role in causing damage and death of vascular endothelial cells in atherosclerosis.4
Cat# Size Price Qty Buy
1152 100 mg £71.40

Additional Information

Property Value or Rating
Product Size 100 mg
Manufacturer Matreya, LLC
Empirical Formula C19H34O2
CAS# 2566-97-4
Formula Weight 294.5
Source semisynthetic
Purity 99%
Analytical Methods GC, TLC
Natural Source Plant|Semi-synthetic
Solubility chloroform, hexane, ethyl ether
Physical Appearance A neat liquid
Storage -20°C

1. A. Lanser et al. “Metabolism of Linoleate versus Linoelaidate in the Laying Hen” Lipids, vol. 13 pp. 103-109, 1978 
2. A. Christy “Thermally Induced Isomerization of Trilinolein and Trilinoelaidin at 250 _C: Analysis of Products by Gas Chromatography and Infrared Spectroscopy” Lipids, vol. 44 pp. 1105-1112, 2009 
3. H.-H. Lo et al. “In vitro activation of mouse skin protein kinase C by fatty acids and their hydroxylated metabolites” Lipids, vol. 29 pp. 547-553, 1994 
4. D. Zapolska-Downar et al. “Trans Fatty Acids Induce Apoptosis in Human Endothelial Cells” Journal of Physiology and Pharmacology, vol. 56 pp. 611- 625, 2005

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