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ChemicalBook > Product Catalog >Flavors and fragrances >Synthetic fragrances >Carboxylic acids and esters >Aliphatic dicarboxylic acid esters >Ethyl myristate

Ethyl myristate

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Ethyl myristate Basic information
Product Name:Ethyl myristate
Synonyms:Ethyl ester of tetradecanoic acid;Ethyl N-tetradecanoate;Ethylmyristat;ETHYL MYRISTATE, NATURAL;Ethyl tetradecanoate, Myristic acid ethyl ester;ETHYL MYRISTATE;FEMA 2445;Ethyl myristate~Tetradecanoic acid ethyl ester
CAS:124-06-1
MF:C16H32O2
MW:256.42
EINECS:204-675-4
Product Categories:C12 to C63;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Esters;Organic Building Blocks;Fatty Acid Derivatives & Lipids;Heterobifunctional PEGs;Materials Science;Nutrition Research;Phytochemicals by Plant (Food/Spice/Herb);Poly(ethylene glycol) and Poly(ethylene oxide);Polymer Science;Zingiber officinale (Ginger);Glycerols;124-06-1
Mol File:124-06-1.mol
Ethyl myristate Structure
Ethyl myristate Chemical Properties
Melting point 11-12 °C(lit.)
Boiling point 178-180 °C12 mm Hg(lit.)
density 0.86 g/mL at 25 °C(lit.)
refractive index n20/D 1.436(lit.)
FEMA 2445 | ETHYL MYRISTATE
Fp >230 °F
storage temp. Sealed in dry,Room Temperature
solubility Chloroform (Slightly), Methanol (Slightly)
form Liquid, Solidifying In The Cold
color Clear colorless
Odorat 100.00 %. sweet waxy violet orris
Odor Typewaxy
biological sourcesynthetic
Water Solubility Not miscible or difficult to mix with water.
Merck 14,6333
JECFA Number38
BRN 1776382
LogP7.09
CAS DataBase Reference124-06-1(CAS DataBase Reference)
NIST Chemistry ReferenceTetradecanoic acid, ethyl ester(124-06-1)
EPA Substance Registry SystemTetradecanoic acid, ethyl ester (124-06-1)
Safety Information
Safety Statements 24/25
WGK Germany 2
TSCA Yes
HS Code 29189900
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
Ethyl myristate Usage And Synthesis
DescriptionMyristic 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 PropertiesClear colorless liquid, solidifying in the cold
Chemical PropertiesEthyl myristate has a mild, waxy, soapy odor reminiscent of orris.
OccurrenceReported 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.
UsesEthyl 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.
UsesEthyl myristate is a labeled component from essential oil of natural hawthorn perfume. It is also frequently used in cosmetics, soaps, and flavorings.
DefinitionChEBI: 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.
PreparationBy esterification of the acid with ethyl alcohol in the presence of gaseous HCl.
Aroma threshold valuesDetection: 4 ppm
Taste threshold valuesTaste characteristics at 60 ppm: sweet, waxy and creamy.
General DescriptionEthyl 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 ProfileCombustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.
Synthesis
Ethanol

64-17-5

Myristic acid

544-63-8

Ethyl myristate

124-06-1

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
Ethyl myristate Preparation Products And Raw materials
Raw materialsMyristic acid-->Ethanol
Preparation ProductsN-TETRADECANAMIDE-->1-Tetradecanol
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