Fatty acid esters

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Fatty acid esters are an extensive group of organic-chemical compounds that contain an ester group , are derived from fatty acids - long-chain carboxylic acids - and are therefore among the carboxylic acid esters .

Example of the acid-catalyzed transesterification of a natural triglyceride (above) in fats and oils. The fatty acid residue marked blue is saturated, the green marked is single, the red marked triple unsaturated . In the equilibrium reaction, glycerine is split off and FAME (bottom) is formed, a mixture of fatty acid methyl esters, in the example three different ones.

Occurrence

Fats and oils - widespread in nature and often used as food - are fatty acid esters, more precisely triglycerides , i.e. triesters of the trihydric alcohol glycerine .

Myricyl palmitate - an ingredient in beeswax.
Beeswax

The fatty acid residues in the triglycerides can be the same or different. The main components of beeswax are saturated fatty acid esters of cerotic acid and palmitic acid of a fatty alcohol with the empirical formula C 30 H 62 O. Cholesterol is transported and stored in the human body as a fatty acid ester .

Manufacturing

Fatty acid esters, which are not triesters of glycerine, are mainly made from naturally occurring fats or oils. The most important fatty acid esters are the fatty acid methyl esters (FAME), which are synthesized from triglycerides by transesterification .

use

Natural products that are of considerable importance as food are, for example, coconut fat , olive oil , palm oil , rapeseed oil and sunflower oil . The saponification of natural fats and oils with caustic soda provides sodium soap ( curd soap ), which is widely used as a cleaning agent and in cosmetics. Glycerine is also produced. The catalytic hydrogenation of triglycerides yields glycerine and fatty alcohols . The latter are an important raw material for the synthesis of surfactants for cosmetic applications. Mixtures of fatty acid methyl esters ( FAME ) are added as biodiesel or diesel fuel .

Structural formula of sucrose stearate a sugar ester of stearic acid .

Zuckerester of fatty acids are used as emulsifiers or a flour treatment agent in baked goods ( cakes , puff pastry ), and including for confectionery , ice cream , alcoholic and non-alcoholic beverages (except beer and wine, as this specific legal provisions prohibit) and for the surface treatment of Used fruit . In the EU , sugar esters of fatty acids are permitted as food additives with the number E 473 .

Monoglyceride, here with a saturated fatty acid residue ( marked in blue ).

It is also used as a biomarker for the consumption of ethanol .

Diglyceride, here with a saturated fatty acid residue ( marked in blue ) and an unsaturated fatty acid residue ( marked in green ).

Mono- and diglycerides of fatty acids are mainly used as emulsifiers in the production of baked goods and confectionery, chocolate products, margarine, baby food, cocoa powder, milk powder, mashed potatoes, rice and pasta.

Individual evidence

  1. ^ Siegfried Hauptmann : Organic Chemistry , 2nd edition, VEB Deutscher Verlag für Grundstoffindustrie, Leipzig, 1985, p. 654, ISBN 3-342-00280-8 .
  2. ^ Albert Gossauer: Structure and reactivity of biomolecules , Verlag Helvetica Chimica Acta, Zurich, 2006, p. 399, ISBN 978-3-906390-29-1 .
  3. ^ Albert Gossauer: Structure and reactivity of biomolecules , Verlag Helvetica Chimica Acta, Zurich, 2006, p. 400, ISBN 978-3-906390-29-1 .
  4. ↑ Joachim Buddrus: Fundamentals of Organic Chemistry , 4th edition, de Gruyter Verlag, Berlin, 2011, pp. 790–791, ISBN 978-3-11-024894-4 .
  5. ↑ Fritz Pragst , Michel Yegles: Determination of Fatty Acid Ethyl Ester (FAEE) and ethyl glucuronide (EtG) in Hair: A Promising Way for Retrospective Detection of Alcohol Abuse During Pregnancy? In: Therapeutic Drug Monitoring . tape 30 , no. 2 , April 2008, ISSN  0163-4356 , p. 255–263 , doi : 10.1097 / ftd.0b013e318167d602 ( ovid.com [accessed May 11, 2018]).