Tariric acid
- 6- octadecinic acid (IUPAC)
White powder
Fixed
49-50 ° C
178-180 ° C (40 Pa)
Template: Infobox chemical / molecular formula search available
Tariric is considered the first proven natural material with triple bond. Your systematic name is 6- octadecinic acid ( delta-6- octadecinic acid ); It is also known as omega -12 octadecinic acid. The fatty acid is an isomer of linoleic acid.
Occurrence
Tariric occurs in specific vegetable oils and fats. It was first isolated in 1892 from the seed oil of a Picramnia type. Further evidence were made in Picramnia camboita from Brazil in Picramnia carpinterae from Guatemala and Picramnia lindeniana from Mexico. The biosynthesis of tariric carried out petroselinic acid; both fatty acids were detected in Picramnia and Alvaradoa types side by side.
The occurrence of tariric as the main fatty acid is considered to be characteristic of the species Picramniaceae.
Production and representation
Fatty acids can be obtained by alkaline hydrolysis of the corresponding triacylglycerols by the corresponding fats or oils are boiled with bases. The hydrolysis itself initially provides their salts. The free fatty acids are obtained by neutralization with (mineral) acid. As the natural fats and oils contain many different fatty acids always includes in the control separation of the resulting mixture of.
Synthetic tariric is prepared from commercially available in pure form petroselinic acid.
Properties
Physical Properties
Pure tariric is solid at room temperature (melting point 40 degrees Celsius). The molar mass is 280 g · mol -1. The fatty acid is insoluble in water but soluble in methanol.
Chemical Properties
The triple bond is the most reactive part of the tariric. The acid and its salts in particular are amphiphilic, meaning they contain both a polar, hydrophilic part ( the carboxyl group ) and a non-polar, lipophilic portion ( hydrocarbon chain).
The synthesis of pure tariric via bromination and dehydrohalogenation with potassium hydroxide of petroselinic acid, the purity is detected by capillary gas chromatography, the identity by NMR spectroscopy, by selective hydrogenation followed by ozonolysis.
Biological Properties
Tariric exerts a stronger inhibitory effect on microorganisms as petroselinic acid. Unlike petroselinic tariric acid can not be completely degraded in Säugetierkatabolismus.
Proof
The detection and assay of tariric as well as other fatty acids in the fats is carried out usually by gas chromatography of the methyl esters; supplement can be a separation of unsaturated fatty acids with silver nitrate thin layer chromatography.
A second detection method would be to Bromwasserprobe multiple bonds.
Use
Tariric is not currently used commercially.