Chemistry:Fatty acid ester

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Space-filling model of methyl linoleate, or linoleic acid methyl ester, a common methyl ester produced from soybean or canola oil and methanol

Fatty acid esters (FAEs) are a type of ester that result from the combination of a fatty acid with an alcohol. When the alcohol component is glycerol, the fatty acid esters produced can be monoglycerides, diglycerides, or triglycerides. Dietary fats are chemically triglycerides.

Esters of fatty acids are colorless, although degraded samples are sometime appear to be yellow or even brown. The triglycerides are powders, flakes, coarse powders, or granular or waxy lumps, oils or liquids. They are almost odorless.

Biodiesels are typically fatty acid esters made by the transesterification of vegetable fats and oils. In this process the glycerol component is replaced with a different alcohol. The most commonly used alcohol is methanol, producing fatty acid methyl esters (FAME). When ethanol is used fatty acid ethyl esters (FAEE) are created. Other alcohols used for the production of biodiesel include butanol and isopropanol.

Fatty acid ethyl esters are biomarkers for the consumption of ethanol (alcoholic beverages).[1][2][3]

See also

  • Fatty acid amide

References

  1. Pragst, F; Yegles, M (2008). "Determination of fatty acid ethyl esters (FAEE) and ethyl glucuronide (EtG) in hair: A promising way for retrospective detection of alcohol abuse during pregnancy?". Therapeutic Drug Monitoring 30 (2): 255–63. doi:10.1097/FTD.0b013e318167d602. PMID 18367991. 
  2. De Giovanni, N; Donadio, G; Chiarotti, M (2007). "The reliability of fatty acid ethyl esters (FAEE) as biological markers for the diagnosis of alcohol abuse". Journal of Analytical Toxicology 31 (2): 93–7. doi:10.1093/jat/31.2.93. PMID 17536744. 
  3. Cabarcos, P; Tabernero, M. J; Otero, J. L; Míguez, M; Bermejo, A. M; Martello, S; De Giovanni, N; Chiarotti, M (2014). "Quantification of fatty acid ethyl esters (FAEE) and ethyl glucuronide (EtG) in meconium for detection of alcohol abuse during pregnancy: Correlation study between both biomarkers". Journal of Pharmaceutical and Biomedical Analysis 100: 74–78. doi:10.1016/j.jpba.2014.07.023. PMID 25137651.