ARS | Publication request: Synthesis and physical properties of coriander estolide 2-ethylhexyl esters

Submitted to: American Oil Chemists' Society Meeting
Publication Type: Abstract Only
Publication Acceptance Date: February 13, 2009
Publication Date: May 3, 2009
Citation: Cermak, S.C., Isbell, T. 2009. Synthesis and physical properties of coriander estolide 2-ethylhexyl esters [abstract]. American Oil Chemists' Society Meeting. p. 87.

Technical Abstract: Coriander (Coriandrum sativum L.) is new crop that is currently being investigated for cultivation in Central Illinois by USDA-NCAUR. Coriander is an annual herb belonging to the Apiaceae (Umbelliferae) family and indigenous to the Mediterranean basin areas and the Near East. This plant is widely distributed and mainly cultivated for its seeds, which are used for different purposes (food, drugs and cosmetics). Coriander seed oil is rich in an unusual fatty acid, the petroselinic acid (C18:1, n-12), which composes as much as 85% of the total fatty acid. The fresh green leaves of coriander, commonly known as cilantro, are widely featured on the menu in China, Mexico, South America, India, and Southeast Asia. The development of a new crop often depends on the synthesis of novel compounds. Estolides are one such derivative of new crop oils which show promise in industrial applications. Estolides are formed when the carboxylic acid functionality of one fatty acid links to the site of unsaturation of another fatty acid to form esters. Estolides were derived from coriander fatty acids and various other fatty acids in the presence of an acid catalyst at 60 deg C for 24 hrs. The free acid estolides were then esterified to the 2-ethylhexyl esters under standard conditions. These new estolide esters were converted to their corresponding hydroxy fatty acid and the degrees of polymerization were determined by GC analysis. Physical properties (pour points, cloud points and viscosities) of the coriander estolide esters were compared to previously synthesized homo-estolides and coco-estolides, which have current industrial applications. These new estolides show promise as a cheap alternative bio-based material.