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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 ...
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.
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.
Each double bond is preceded by a cis- or trans- prefix, indicating the configuration of the molecule around the bond. For example, linoleic acid is designated "cis-Δ 9, cis-Δ 12 octadecadienoic acid". This nomenclature has the advantage of being less verbose than systematic nomenclature, but is no more technically clear or descriptive.
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).
Examples of unsaturated fatty acids are palmitoleic acid, oleic acid, myristoleic acid, linoleic acid, and arachidonic acid. Foods containing unsaturated fats include avocado, nuts, olive oils, and vegetable oils such as canola. Meat products contain both saturated and unsaturated fats.
These include meso compounds, cis–trans isomers, E-Z isomers, and non-enantiomeric optical isomers. Diastereomers seldom have the same physical properties. In the example shown below, the meso form of tartaric acid forms a diastereomeric pair with both levo- and dextro-tartaric acids, which form an enantiomeric pair.