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. Or?, 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 (Or?, 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 (Or?, Wretlind)
Derivative Type: Ethyl ester
Synonyms: 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.
