Description
Myristic acid is a saturated fatty acid commonly found in animal and vegetable fats that is frequently used in cosmetics, soaps, perfumes, and flavorings. It increases low density lipoprotein cholesterol making it one of the most hypercholesterolemic of the saturated fatty acids. Myristic acid ethyl ester (Ethyl myristate) is a more hydrophobic form of the free acid. It is a marker of excessive ethanol consumption that can be isolated from the hair of an individual.
Chemical Properties
Clear colorless liquid, solidifying in the cold
Chemical Properties
Ethyl myristate has a mild, waxy, soapy odor reminiscent of orris.
Occurrence
Reported found in apricot, grape, pear, capsicum, beef, beer, rum, tea, guava, Vitis vinifera, ginger, Gruyere
cheese, blue cheese, boiled mutton, cognac, whiskey, sparkling wine, cocoa, coconut meat, mango, corn oil, elderberry and mastic
gum leaf oil.
Uses
Ethyl myristate may be used as an analytical standard for the determination of the analyte as an alcohol biomarker in dried blood spots and hair samples by chromatography based techniques. Ethyl myristate may also be used as an analytical standard in the determination of the analyte in selected beer flavors by stir bar sorptive extraction and solvent back extraction.
Uses
Ethyl myristate is a labeled component from essential oil of natural hawthorn perfume. It is also frequently used in cosmetics, soaps, and flavorings.
Definition
ChEBI: A long-chain fatty acid ethyl ester resulting from the formal condensation of the carboxy group of myristic acid with the hydroxy group of ethanol.
Preparation
By esterification of the acid with ethyl alcohol in the presence of gaseous HCl.
Aroma threshold values
Detection: 4 ppm
Taste threshold values
Taste characteristics at 60 ppm: sweet, waxy and creamy.
General Description
Ethyl myristate is a fatty acid ethyl ester (FAEE) that can be formed in the body due to non-oxidative metabolism of ethanol. It also occurs in vegetable oils. Ethyl myristate, along with other FAEEs are used as alcohol markers in hair.
Safety Profile
Combustible liquid.
When heated to decomposition it emits
acrid smoke and irritating fumes.
Synthesis
The general procedure for the synthesis of ethyl tetradecanoate from ethanol and myristic acid was as follows: myristic acid (12 g, 53 mmol) was dissolved in an ethanol solution (50 mL) containing 4% wt sulfuric acid, and the mixture was sonicated for 4.5 h using a Branson 1210 ultrasonic cleaner (Branson, Danbury, CT, USA) to promote the esterification reaction. After completion of the reaction, the solvent was removed by rotary evaporator. The residue was diluted with ethyl acetate (40 mL) and subsequently washed to neutrality with 5% wt sodium hydroxide solution. The organic layer was dried with anhydrous sodium sulfate, filtered and the solvent was evaporated to give 13.25 g of ethyl tetradecanoate as a pale yellow liquid in 98.43% yield. The product was analyzed by FT-IR showing characteristic absorption peaks: 2924 cm^-1 (C-H stretching vibration), 1735 cm^-1 (C=O ester group stretching vibration), 1458 cm^-1 (CH2 bending vibration), 1180 cm^-1 (C-O ester group stretching vibration). gC analysis showed that the product had a purity of 98.90%, retention time (tR) was 34.4 minutes, and the molecular ion peak [M-15]+ = 256 was detected by mass spectrometry.
References
[1] Molecules, 2018, vol. 23, # 12,
[2] Journal of Organic Chemistry, 1996, vol. 61, # 6, p. 1962 - 1974
[3] Journal of Molecular Catalysis A: Chemical, 2014, vol. 392, p. 76 - 82
[4] Tetrahedron Asymmetry, 2010, vol. 21, # 8, p. 952 - 956
[5] Catalysis Today, 2015, vol. 255, p. 27 - 32
