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 Methyl Linoleate.png
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]

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Related Research Articles

<span class="mw-page-title-main">Fatty acid</span> Carboxylic acid

In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, from 4 to 28. Fatty acids are a major component of the lipids in some species such as microalgae but in some other organisms are not found in their standalone form, but instead exist as three main classes of esters: triglycerides, phospholipids, and cholesteryl esters. In any of these forms, fatty acids are both important dietary sources of fuel for animals and important structural components for cells.

<span class="mw-page-title-main">Fat</span> Esters of fatty acid or triglycerides

In nutrition, biology, and chemistry, fat usually means any ester of fatty acids, or a mixture of such compounds, most commonly those that occur in living beings or in food.

<span class="mw-page-title-main">Lipid</span> Substance of biological origin that is soluble in nonpolar solvents

Lipids are a broad group of organic compounds which include fats, waxes, sterols, fat-soluble vitamins, monoglycerides, diglycerides, phospholipids, and others. The functions of lipids include storing energy, signaling, and acting as structural components of cell membranes. Lipids have applications in the cosmetic and food industries, and in nanotechnology.

<span class="mw-page-title-main">Triglyceride</span> Any ester of glycerol having all three hydroxyl groups esterified with fatty acids

A triglyceride is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other vertebrates, as well as vegetable fat. They are also present in the blood to enable the bidirectional transference of adipose fat and blood glucose from the liver, and are a major component of human skin oils.

<span class="mw-page-title-main">Glycerol</span> Chemical compound widely used in food and pharmaceuticals

Glycerol, also called glycerine or glycerin, is a simple triol compound. It is a colorless, odorless, viscous liquid that is sweet-tasting and non-toxic. The glycerol backbone is found in lipids known as glycerides. Because it has antimicrobial and antiviral properties, it is widely used in wound and burn treatments approved by the U.S. Food and Drug Administration. Conversely, it is also used as a bacterial culture medium. Its presence in blood can be used as an effective marker to measure liver disease. It is also widely used as a sweetener in the food industry and as a humectant in pharmaceutical formulations. Because of its three hydroxyl groups, glycerol is miscible with water and is hygroscopic in nature.

Transesterification is the process of exchanging the organic functional group R″ of an ester with the organic group R' of an alcohol. These reactions are often catalyzed by the addition of an acid or base catalyst. The reaction can also be accomplished with the help of other enzymes, particularly lipases.

Saponification is a process of converting esters into soaps and alcohols by the action of aqueous alkali. Soaps are salts of fatty acids, which in turn are carboxylic acids with long carbon chains. Sodium stearate is a typical soap.

Biodiesel production is the process of producing the biofuel, biodiesel, through the chemical reactions of transesterification and esterification. This involves vegetable or animal fats and oils being reacted with short-chain alcohols. The alcohols used should be of low molecular weight. Ethanol is the most used because of its low cost, however, greater conversions into biodiesel can be reached using methanol. Although the transesterification reaction can be catalyzed by either acids or bases, the base-catalyzed reaction is more common. This path has lower reaction times and catalyst cost than those acid catalysis. However, alkaline catalysis has the disadvantage of high sensitivity to both water and free fatty acids present in the oils.August 10th is international biodiesel day

<span class="mw-page-title-main">Saponification value</span> Milligrams of a base required to saponify 1g of fat

Saponification value or saponification number represents the number of milligrams of potassium hydroxide (KOH) or sodium hydroxide (NaOH) required to saponify one gram of fat under the conditions specified. It is a measure of the average molecular weight of all the fatty acids present in the sample in form of triglycerides. The higher the saponification value, the lower the fatty acids average length, the lighter the mean molecular weight of triglycerides and vice versa. Practically, fats or oils with high saponification value are more suitable for soap making.

<span class="mw-page-title-main">Ethyl oleate</span> Chemical compound

Ethyl oleate is a fatty acid ester formed by the condensation of oleic acid and ethanol. It is a colorless oil although degraded samples can appear yellow.

In chemistry, solvolysis is a type of nucleophilic substitution (SN1/SN2) or elimination where the nucleophile is a solvent molecule. Characteristic of SN1 reactions, solvolysis of a chiral reactant affords the racemate. Sometimes however, the stereochemical course is complicated by intimate ion pairs, whereby the leaving anion remains close to the carbocation, effectively shielding it from an attack by the nucleophile. Particularly fast reactions can occur by neighbour group participation, with nonclassical ions as intermediates or transition states.

In chemistry, acid value is a number used to quantify the acidity of a given chemical substance. It is the quantity of base, expressed as milligrams of KOH required to neutralize the acidic constituents in 1 gram of a sample.

<span class="mw-page-title-main">Jojoba oil</span> Oil extracted from jojoba seeds

Jojoba oil is the liquid produced in the seed of the Simmondsia chinensis (jojoba) plant, a shrub, which is native to southern Arizona, southern California, and northwestern Mexico. The oil makes up approximately 50% of the jojoba seed by weight. The terms "jojoba oil" and "jojoba wax" are often used interchangeably because the wax visually appears to be a mobile oil, but as a wax it is composed almost entirely (~97%) of mono-esters of long-chain fatty acids (wax ester) and alcohols, accompanied by only a tiny fraction of triglyceride esters. This composition accounts for its extreme shelf-life stability and extraordinary resistance to high temperatures, compared with true vegetable oils.

<span class="mw-page-title-main">Monoglyceride</span>

Monoglycerides are a class of glycerides which are composed of a molecule of glycerol linked to a fatty acid via an ester bond. As glycerol contains both primary and secondary alcohol groups two different types of monoglycerides may be formed; 1-monoacylglycerols where the fatty acid is attached to a primary alcohol, or a 2-monoacylglycerols where the fatty acid is attached to the secondary alcohol.

EN 14214 is a standard published by the European Committee for Standardization that describes the requirements and test methods for FAME - the most common type of biodiesel.

Oleochemistry is the study of vegetable oils and animal oils and fats, and oleochemicals derived from these fats and oils. The resulting product can be called oleochemicals (from Latin: oleum "olive oil"). The major product of this industry is soap, approximately 8.9×106 tons of which were produced in 1990. Other major oleochemicals include fatty acids, fatty acid methyl esters, fatty alcohols and fatty amines. Glycerol is a side product of all of these processes. Intermediate chemical substances produced from these basic oleochemical substances include alcohol ethoxylates, alcohol sulfates, alcohol ether sulfates, quaternary ammonium salts, monoacylglycerols (MAG), diacylglycerols (DAG), structured triacylglycerols (TAG), sugar esters, and other oleochemical products.

<span class="mw-page-title-main">Ethyl glucuronide</span>

Ethyl glucuronide (EtG) is a metabolite of ethanol which is formed in the body by glucuronidation following exposure to ethanol, usually from drinking alcoholic beverages. It is used as a biomarker to test for ethanol use and to monitor alcohol abstinence in situations where drinking is prohibited, such as by the military, in alcohol treatment programs, in professional monitoring programs, in schools, liver transplant clinics, or in recovering alcoholic patients. In addition to its use to monitor abstinence and detect drinking, EtG also has potential for monitoring the amount of alcohol use over time because it can be detected in hair and nails, though the effectiveness of this has not yet been proven.

<span class="mw-page-title-main">Phosphatidylethanol</span> Class of chemical compounds

Phosphatidylethanols (PEth) are a group of phospholipids formed only in the presence of ethanol via the action of phospholipase D (PLD). The lipid accumulates in the human body and competes at agonists sites of lipid-gated ion channels contributing to alcohol intoxication. The chemical similarity of PEth to phosphatidic acid (PA) and phosphatidylinositol 4,5-bisphosphate (PIP2) suggest a likely broad perturbation to lipid signaling; the exact role of PEth as a competitive lipid ligand has not been studied extensively.

<span class="mw-page-title-main">Diglyceride</span> Type of fat derived from glycerol and two fatty acids

A diglyceride, or diacylglycerol (DAG), is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Two possible forms exist, 1,2-diacylglycerols and 1,3-diacylglycerols. DAGs can act as surfactants and are commonly used as emulsifiers in processed foods. DAG-enriched oil has been investigated extensively as a fat substitute due to its ability to suppress the accumulation of body fat; with total annual sales of approximately USD 200 million in Japan since its introduction in the late 1990s till 2009.

<i>N</i>-Acetyltaurine Chemical compound

N-Acetyltaurine (NAcT) is an endogenous metabolite. Biochemically, N-acetyltaurine is formed as a result of an acetylation of taurine. The main substrate for this reaction is acetate. An increase of endogenous N-acetyltaurine concentrations was observed after the consumption of alcohol and after extended physical activity (ketoacidosis).

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.