6333. Myristic Acid

Nomenclature

CAS number: 544-63-8
Tetradecanoic acid; 1-tridecanecarboxylic acid.
C14H28O2; mol wt 228.37.
C 73.63%, H 12.36%, O 14.01%.

Description and 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. Or"o, A. Wretlind, Acta Pharmacol. Toxicol. 18, 141 (1961).

Chemical structure

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 (Or"o, Wretlind).

Derivative

Ethyl ester.

Nomenclature

CAS number: 124-06-1
Ethyl myristate; ethyl tetradecanoate.
C16H32O2; mol wt 256.42.
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.

Use

As ingredient in soaps and shaving creams; in lubricants; in coatings for anodized aluminum.