Ethyl myristate

Ethyl myristate Property

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

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Liquid, Solidifying In The Cold

color 

Clear colorless

Odor

at 100.00 %. sweet waxy violet orris

Odor Type

waxy

biological source

synthetic

Water Solubility 

Not miscible or difficult to mix with water.

Merck 

14,6333

JECFA Number

38

BRN 

1776382

LogP

7.09

CAS DataBase Reference

124-06-1(CAS DataBase Reference)

NIST Chemistry Reference

Tetradecanoic acid, ethyl ester(124-06-1)

EPA Substance Registry System

Tetradecanoic acid, ethyl ester (124-06-1)

Safety

Safety Statements 

24/25

WGK Germany 

2

TSCA 

Yes

HS Code 

29189900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Ethyl myristate Chemical Properties,Usage,Production

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.

Preparation

By esterification of the acid with ethyl alcohol in the presence of gaseous HCl.

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.

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