Ethyl oleate

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Ethyl oleate
Ethyl oleate.png
Names
Preferred IUPAC name
Ethyl (9Z)-octadec-9-enoate
Other names
Oleic acid ethyl ester
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.536 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C20H38O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22-4-2/h11-12H,3-10,13-19H2,1-2H3/b12-11- Yes check.svgY
    Key: LVGKNOAMLMIIKO-QXMHVHEDSA-N Yes check.svgY
  • O=C(OCC)CCCCCCC\C=C/CCCCCCCC
Properties
C20H38O2
Molar mass 310.522 g·mol−1
AppearanceColorless to light yellow liquid [1]
Density 0.87 g/cm3 [1]
Melting point −32 °C (−26 °F; 241 K) [1]
Boiling point 216–218 °C (421–424 °F; 489–491 K) [1] (15 hPa)
Insoluble [1]
Hazards
Flash point > 113 °C [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.

Contents

Use and occurrence

Additive

Ethyl oleate is used by compounding pharmacies as a vehicle for intramuscular drug delivery, in some cases to prepare the daily doses of progesterone in support of pregnancy. Studies that document the safe use of ethyl oleate in pregnancy for both the mother and the fetus have never been performed. It is regulated as a food additive in the U.S. by the Food and Drug Administration. [2] Ethyl oleate is used as a solvent for pharmaceutical drug preparations involving lipophilic substances such as steroids. [3] It also finds use as a lubricant and a plasticizer. Louis Bouveault used ethyl oleate to demonstrate Bouveault–Blanc reduction, producing oleyl alcohol and ethanol, [4] a method which was subsequently refined and published in Organic Syntheses . [5]

Occurrence

Ethyl oleate has been identified as a primer pheromone in honeybees. [6]

Precursor to other chemicals

By the process of ethenolysis, the methyl ester of oleic acid, converts to 1-decene and methyl 9-decenoate: [7]

CH3(CH2)7CH=CH(CH2)7CO2Me +CH2=CH2 → CH3(CH2)7CH=CH2 + MeO2C(CH2)7CH=CH2

Medical aspects

Ethyl oleate is produced by the body during ethanol intoxication. [8] It is one of the fatty acid ethyl esters (FAEE) produced after ingestion of ethanol. Some research literature implicates FAEEs such as ethyl oleate as the toxic mediators of ethanol in the body (pancreas, liver, heart, and brain). [9] [10] Ethyl oleate may be the toxic mediator of alcohol in fetal alcohol syndrome. [9] The oral ingestion of ethyl oleate has been carefully studied and due to rapid degradation in the digestive tract it appears safe for oral ingestion. [11]

See also

Related Research Articles

<span class="mw-page-title-main">Alcohol (chemistry)</span> Organic compound with at least one hydroxyl (–OH) group

In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl functional group bound to a saturated carbon atom. Alcohols range from the simple, like methanol and ethanol, to complex, like sucrose and cholesterol. The presence of an OH group strongly modifies the properties of hydrocarbons, conferring hydrophilic (water-loving) properties. The OH group provides a site at which many reactions can occur.

<span class="mw-page-title-main">Ether</span> Organic compounds made of alkyl/aryl groups bound to oxygen (R–O–R)

In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula R−O−R′, where R and R′ represent the alkyl or aryl groups. Ethers can again be classified into two varieties: if the alkyl or aryl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the solvent and anaesthetic diethyl ether, commonly referred to simply as "ether". Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin.

<span class="mw-page-title-main">Ester</span> Compound derived from an acid

In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

<span class="mw-page-title-main">Ketone</span> Organic compounds of the form >C=O

In organic chemistry, a ketone is an organic compound with the structure R−C(=O)−R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group −C(=O)−. The simplest ketone is acetone, with the formula (CH3)2CO. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.

<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.

Erucic acid is a monounsaturated omega-9 fatty acid, denoted 22:1ω9. It has the chemical formula :CH3(CH2)7CH=CH(CH2)11CO2H. It is prevalent in wallflower seed and other plants in the family Brassicaceae, with a reported content of 20 to 54% in high erucic acid rapeseed oil and 42% in mustard oil. Erucic acid is also known as cis-13-docosenoic acid and the trans isomer is known as brassidic acid.

<span class="mw-page-title-main">Oleic acid</span> Monounsaturated omega-9 fatty acid

Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish. In chemical terms, oleic acid is classified as a monounsaturated omega-9 fatty acid, abbreviated with a lipid number of 18:1 cis-9, and a main product of Δ9-desaturase. It has the formula CH3−(CH2)7−CH=CH−(CH2)7−COOH. The name derives from the Latin word oleum, which means oil. It is the most common fatty acid in nature. The salts and esters of oleic acid are called oleates. It is part of many oils and thus used in a lot of artificial food, as well as for soap.

<span class="mw-page-title-main">Oleyl alcohol</span> Chemical compound

Oleyl alcohol, or cis-9-octadecen-1-ol, is an unsaturated fatty alcohol with the molecular formula C18H36O or the condensed structural formula CH3(CH2)7−CH=CH−(CH2)8OH. It is a colorless oil, mainly used in cosmetics.

In organic chemistry, ozonolysis is an organic reaction where the unsaturated bonds are cleaved with ozone. Multiple carbon–carbon bond are replaced by carbonyl groups, such as aldehydes, ketones, and carboxylic acids. The reaction is predominantly applied to alkenes, but alkynes and azo compounds are also susceptible to cleavage. The outcome of the reaction depends on the type of multiple bond being oxidized and the work-up conditions.

The Bouveault–Blanc reduction is a chemical reaction in which an ester is reduced to primary alcohols using absolute ethanol and sodium metal. It was first reported by Louis Bouveault and Gustave Louis Blanc in 1903. Bouveault and Blanc demonstrated the reduction of ethyl oleate and n-butyl oleate to oleyl alcohol. Modified versions of which were subsequently refined and published in Organic Syntheses.

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

Ethyl sulfate, also known as sulfovinic acid, is an organic chemical compound used as an intermediate in the production of ethanol from ethylene. It is the ethyl ester of sulfuric acid.

1-Tetradecanol, or commonly myristyl alcohol (from Myristica fragrans – the nutmeg plant), is a straight-chain saturated fatty alcohol, with the molecular formula CH3(CH2)12CH2OH. It is a white waxy solid that is practically insoluble in water, soluble in diethyl ether, and slightly soluble in ethanol.

Pelargonic acid, also called nonanoic acid, is an organic compound with structural formula CH3(CH2)7CO2H. It is a nine-carbon fatty acid. Nonanoic acid is a colorless oily liquid with an unpleasant, rancid odor. It is nearly insoluble in water, but very soluble in organic solvents. The esters and salts of pelargonic acid are called pelargonates or nonanoates.

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

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.

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.

Decene is an organic compound with the chemical formula C10H20. Decene contains a chain of ten carbon atoms with one double bond, making it an alkene. There are many isomers of decene depending on the position and geometry of the double bond. Dec-1-ene is the only isomer of industrial importance. As an alpha olefin, it is used as a comonomer in copolymers and is an intermediate in the production of epoxides, amines, oxo alcohols, synthetic lubricants, synthetic fatty acids and alkylated aromatics.

The enzyme fatty-acyl-ethyl-ester synthase (EC 3.1.1.67) catalyzes the reaction

Ethyl octanoate, also known as ethyl caprylate, is a fatty acid ester formed from caprylic acid and ethanol. A colorless liquid at room temperature, it has the semi-developed formula of CH3(CH2)6COOCH2CH3, and is used in food industries as a flavoring and in the perfume industry as a scent additive. It is present in many fruits and alcoholic beverages, and has a strong odor of fruit and flowers. It is used in the creation of synthetic fruity scents.

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

Ethyl vinyl ether is an organic compound with the chemical formula CH3CH2OCH=CH2. It is the simplest enol ether that is liquid at room temperature. It is used as a synthetic building block and a monomer.

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


Butyl oleate is a fatty acid ester and an organic chemical found in liquid form. It has the formula C22H42O2 and the CAS Registry Number 142-77-8. It is REACH registered and produced or imported into the European Union with the EC number of 205-559-6.

References

  1. 1 2 3 4 5 6 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ↑ "Food Additives Permitted for Direct Addition to Food for Human Consumption", 21CFR172.515
  3. ↑ Ory SJ, Hammond CB, Yancy SG, Hendren RW, Pitt CG (1983). "The effect of a biodegradable contraceptive capsule (Capronor) containing levonorgestrel on gonadotropin, estrogen, and progesterone levels". Am. J. Obstet. Gynecol. 145 (5): 600–5. doi:10.1016/0002-9378(83)91204-8. PMID   6402933.
  4. ↑ Bouveault, Louis; Blanc, Gustave Louis (1904). "Hydrogénation des éthers des acides possédant en outre les fonctions éther-oxyde ou acétal" [Hydrogenation of the ether of the acids furthermore possessing the ether-oxide or acetal functions]. Bull. Soc. Chim. Fr. (in French). 31 (3): 1210–1213.
  5. ↑ Adkins, Homer; Gillespie, R. H. (1949). "Oleyl alcohol". Organic Syntheses . 29: 80. doi:10.15227/orgsyn.029.0080.; Collective Volume, vol. 3, p. 671
  6. ↑ Leoncini I.; Le Conte, Y; Costagliola, G; Plettner, E; Toth, AL; Wang, M; Huang, Z; Bécard, JM; et al. (2004). "Regulation of behavioral maturation by a primer pheromone produced by adult worker honey bees". Proc. Natl. Acad. Sci. U.S.A. 101 (50): 17559–17564. doi: 10.1073/pnas.0407652101 . PMC   536028 . PMID   15572455.
  7. ↑ Marinescu, Smaranda C.; Schrock, Richard R.; Müller, Peter; Hoveyda, Amir H. (2009). "Ethenolysis Reactions Catalyzed by Imido Alkylidene Monoaryloxide Monopyrrolide (MAP) Complexes of Molybdenum". J. Am. Chem. Soc. 131 (31): 10840–10841. doi:10.1021/ja904786y. PMID   19618951.
  8. ↑ Dan L, Laposata M (1997). "Ethyl palmitate and ethyl oleate are the predominant fatty acid ethyl esters in the blood after ethanol ingestion and their synthesis is differentially influenced by the extracellular concentrations of their corresponding fatty acids". Alcohol. Clin. Exp. Res. 21 (2): 286–92. doi:10.1111/j.1530-0277.1997.tb03762.x. PMID   9113265.
  9. 1 2 Laposata M. (1998). "Fatty acid ethyl esters: nonoxidative metabolites of ethanol". Addiction Biology . 3 (1): 5–14. doi: 10.1080/13556219872308 . PMID   26736076. S2CID   22486675.
  10. ↑ Laposata M, et al. (2002). "Fatty acid ethyl esters: recent observations". Prostaglandins, Leukotrienes, and Essential Fatty Acids. 67 (2–3): 193–196. doi:10.1054/plef.2002.0418. PMID   12324241.
  11. ↑ Saghir M. (1997). "Rapid in vivo hydrolysis of fatty acid ethyl esters, toxic nonoxidative ethanol metabolites". Am J Physiol. 273 (1 Pt 1): G184–190. doi:10.1152/ajpgi.1997.273.1.G184. PMID   9252525.
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