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Another example of this is the relationship between oleic acid and elaidic acid; oleic acid, the cis isomer, has a melting point of 13.4 °C, making it a liquid at room temperature, while the trans isomer, elaidic acid, has the much higher melting point of 43 °C, due to the straighter trans isomer being able to pack more tightly, and is solid ...
The trans isomer of oleic acid is called elaidic acid or trans-9-octadecenoic acid. These isomers have distinct physical properties and biochemical properties. Elaidic acid, the most abundant trans fatty acid in diet, appears to have an adverse effect on health. [21] A reaction that converts oleic acid to elaidic acid is called elaidinization.
Elaidic acid has 18 carbons and is a trans-9-mono-unsaturated fatty acid. It is also a trans isomer of oleic acid. C 17 H 33 CO 2 H, IUPAC organization name (E)-octadec-9-enoic acid, numerical representation 18:1 (9), n-9, molecular weight 282.46, melting point 43–45 °C. CAS Registry Number 112-79-8.
Comparison of the trans isomer elaidic acid (top) and the cis isomer oleic acid (bottom) Fatty acids are classified in many ways: by length, by saturation vs unsaturation, by even vs odd carbon content, and by linear vs branched.
Any molecule with a C=C double bond can be either a trans or a cis fatty acid depending on the configuration of the double bond. For example, oleic acid and elaidic acid are both unsaturated fatty acids with the chemical formula C 9 H 17 C 9 H 17 O 2. [36] They both have a double bond located midway along the carbon chain.
Oleic acid Elaidic acid; Oleic acid is a cis unsaturated fatty acid, a common component of natural vegetable oils. Elaidic acid is a trans unsaturated fatty acid often created by partial hydrogenation or elaidinisation of vegetable oils. These fatty acids are isomers (chemically identical except for the orientation of the double bond).
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. [1] It is the trans isomer of oleic acid. The name of the elaidinization reaction comes from elaidic acid.
Traditionally, double bond stereochemistry was described as either cis (Latin, on this side) or trans (Latin, across), in reference to the relative position of substituents on either side of a double bond. A simple example of cis–trans isomerism is the 1,2-disubstituted ethenes, like the dichloroethene (C 2 H 2 Cl 2) isomers shown below. [7]