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Elaidic acid

(9E)-octadecenoic acid trans-9-octadecenoic acid 18:1 trans-9 C18:1 trans-9

Elaidic acid is a chemical compound with the formula , specifically the fatty acid with structural formula , with the double bond (between carbon atoms 9 and 10) in trans configuration. It is a colorless solid. Its salts and esters are called elaidates.

Elaidic acid is an unsaturated trans fatty acid, with code C18:1 trans-9. This compound has attracted attention because it is a major trans fat found in hydrogenated vegetable oils, and trans fats have been implicated in heart disease.

It is the trans isomer of oleic acid. The name of the elaidinization reaction comes from elaidic acid.

Etymology

The name elaidic comes from the Ancient Greek word ἔλαιον (élaion), meaning oil.

Occurrence and bioactivity

Elaidic acid occurs mostly in industrial hydrogenation of polyunsaturated fatty acids. It's also present in small amounts in goat and cow milk (very roughly 0.1% of the fatty acids) and in some meats.

Elaidic acid increases plasma cholesterylester transfer protein (CETP) activity which lowers HDL cholesterol.

References

References

  1. (2011). "Ruminant and industrial sources of trans-fat and cardiovascular and diabetic diseases". Nutrition Research Reviews.
  2. (2023). "Different Types of Industry-Produced and Ruminant Trans Fatty Acid Intake and Risk of Type 2 Diabetes: Findings From the NutriNet-Santé Prospective Cohort". Diabetes Care.
  3. (1999). "Fatty acid composition of caprine milk: major, branched-chain, and trans fatty acids". J. Dairy Sci..
  4. Stillwell, William. (2016). "An Introduction to Biological Membranes – Composition, Structure and Function". Elsevier.
  5. (1994). "Plasma cholesteryl ester transfer protein activity is increased when trans-elaidic acid is substituted for cis-oleic acid in the diet". Atherosclerosis.
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