Myristic Acid

Title: Myristic Acid
CAS Registry Number: 544-63-8
CAS Name: Tetradecanoic acid
Molecular Formula: C14H28O2
Molecular Weight: 228.37
Percent Composition: C 73.63%, H 12.36%, O 14.01%
Line Formula: CH3(CH2)12COOH
Literature References: Occurs in nutmeg butter (Myristica fragrans Houtt.) to the extent of 70-80%; predominates in the fats of the Myristicaceae; in palm seed fats it may comprise 20% of the total fatty acids; in milk fats between 8-12% of the total acids. Occurs in most animal and vegetable fats; has been found in considerable amounts (up to 15%) in sperm whale oil, see Markley, Fatty Acids (New York, 1947). Prepn: G. D. Beal, Org. Synth. coll. vol. I, 379 (2nd ed., 1941). Prepn from tall-oil fatty acids: Segessmann, Molnar, US 2481356 (1949); from 9-ketotetradecanoic acid: Ames et al., J. Chem. Soc. 1950, 174; by electrolysis of methyl hydrogen adipate + decanoic acid: Greaves et al., ibid. 1950, 3326; by Maurer oxidation of myristyl alc: Langenbeck, Richter, Ber. 89, 202 (1956); from cetanol: Selwitz, US 2969380 (1961 to Gulf). Wide-line NMR spectrum: A. V. Bailey, R. A. Pittman, J. Am. Oil Chem. Soc. 48, 775 (1971). Toxicity study: L. Orö, A. Wretlind, Acta Pharmacol. Toxicol. 18, 141 (1961).
Properties: Crystals from methanol, mp 58.5°. bp100 250.5°; bp16 199°; bp4 184°. d454 0.8622. d470 0.8528. d490 0.8394. nD60 1.4305; nD70 1.4273. Soluble in abs alcohol, methanol, ether, petr ether, benzene, chloroform. Neutralization value: 245.68. Absorption spectrum: Markley, op. cit. LD50 i.v. in mice: 432.6 mg/kg (Orö, Wretlind).
Melting point: mp 58.5°
Boiling point: bp100 250.5°; bp16 199°; bp4 184°
Index of refraction: nD60 1.4305; nD70 1.4273
Density: d454 0.8622; d470 0.8528; d490 0.8394
Toxicity data: LD50 i.v. in mice: 432.6 mg/kg (Orö, Wretlind)
Derivative Type: Ethyl ester
Additional Names: Ethyl myristate
Molecular Formula: C16H32O2
Molecular Weight: 256.42
Percent Composition: C 74.94%, H 12.58%, O 12.48%
Properties: Liquid, mp 12°; bp 295°; bp30 195°. d420 0.856. Insol in water. Sol in alcohol; slightly sol in ether.
Melting point: mp 12°
Boiling point: bp 295°; bp30 195°
Density: d420 0.856
Use: As ingredient in soaps and shaving creams; in lubricants; in coatings for anodized aluminum.
Myristicin Myristyl Alcohol Myristyltrimethylammonium Bromide Myrtecaine Myrtol

Myristic acid[1]
Myristic acid.svg
Identifiers
CAS number 544-63-8 YesY
PubChem 11005
ChemSpider 10539 N
ChEBI CHEBI:28875 N
ChEMBL CHEMBL111077 N
Jmol-3D images Image 1
Properties
Molecular formula C14H28O2
Molar mass 228.37092
Density 0.8622 g/cm3
Melting point 54.4 °C[2]
Boiling point 250.5 °C at 100 mmHg
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Myristic acid, also called tetradecanoic acid, is a common saturated fatty acid with the molecular formula CH3(CH2)12COOH. A myristate is a salt or ester of myristic acid.

Myristic acid is named after the nutmeg Myristica fragrans. Nutmeg butter is 75% trimyristin, the triglyceride of myristic acid. Besides nutmeg, myristic acid is also found in palm kernel oil, coconut oil, butter fat and is a minor component of many other animal fats.[2] It is also found in spermaceti, the crystallized fraction of oil from the sperm whale.

Myristic acid is also commonly added co-translationally to the penultimate, nitrogen-terminus, glycine in receptor-associated kinases to confer the membrane localisation of the enzyme. The myristic acid has a sufficiently high hydrophobicity to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasma membrane of the eukaryotic cell. In this way, myristic acid acts as a lipid anchor in biomembranes.

The ester isopropyl myristate is used in cosmetic and topical medicinal preparations where good absorption through the skin is desired.

Reduction of myristic acid yields myristyl aldehyde and myristyl alcohol.