General Description
Oily white crystalline solid.
Reactivity Profile
TETRADECANOIC ACID(544-63-8) is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in TETRADECANOIC ACID(544-63-8) to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.
Air & Water Reactions
Insoluble in water.
Fire Hazard
This chemical is probably combustible.
Description
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. 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.
Occurrence
Reported found in nutmeg, palm seed, sperm whale oil, blue cheese, burley tobacco, cooked beef and chicken,
fish, rum, apricot, banana, lemon and grapefruit juice, cranberry, guava, grapes, melon, papaya, raspberry, strawberry fruit and jam,
cucumber, tomato, many cheeses, thyme, breads, butter, milk, lamb liver, pork, hop oil, beer, cognac, whiskies, peanut oil, cocoa, tea,
coconut meat and milk, cloudberry, beans, passion fruit, mushroom, mango, starfruit, tamarind, kelp, cardamom, rice, buckwheat,
watercress, malt, wort, loquat, Bourbon vanilla, lemon balm, shrimp, nectarine, crab, scallop, squid, cape gooseberry, Chinese
quince, pawpaw and sweet grass oi
Definition
ChEBI: A straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat.
Production Methods
Myristic acid occurs naturally in nutmeg butter and in most animal
and vegetables fats. Synthetically, it may be prepared by electrolysis
of methyl hydrogen adipate and decanoic acid or by Maurer
oxidation of myristyl alcohol.
Aroma threshold values
Detection: 10 ppm
Pharmaceutical Applications
Myristic acid is used in oral and topical pharmaceutical formulations.
Myristic acid has been evaluated as a penetration enhancer in
melatonin transdermal patches in rats and bupropion formulations
on human cadaver skin.Further studies have assessed the
suitability of myristic acid in oxymorphone formulations and
clobetasol 17-propionate topical applications.Furthermore,
polyvinyl alcohol substituted with myristic acid (as well as other
fatty acids) at different substitution degrees has been used for the
preparation of biodegradable microspheres containing progesterone
or indomethacin.
Biochem/physiol Actions
Myristic acid is commonly added via a covalent linkage to the N-terminal glycine of many eukaryotic and viral proteins, a process called myristoylation. Myristoylation enables proteins to bind to cell membranes and facilitates protein-protein interactions. Myristolyation of proteins affect many cellular functions and thus has implications in health and disease .
Safety
Myristic acid is used in oral and topical pharmaceutical formulations
and is generally regarded as nontoxic and nonirritant at the
levels employed as an excipient. However, myristic acid is reported
to be an eye and skin irritant at high levels and is poisonous by
intravenous administration. Mutation data have also been
reported.
LD50 (mouse, IV): 0.043 g/kg
LD50 (rat, oral): >10 g/kg
storage
The bulk material should be stored in a well-closed container in a
cool, dry, place.
Purification Methods
Purify the acid via the methyl ester (b 153-154o/10mm, n25 1.4350), as for capric acid. [Trachtman & Miller J Am Chem Soc 84 4828 1962.] Also purify it by zone melting. It crystallises from pet ether, and is dried in a vacuum desiccator containing shredded wax. [Beilstein 2 IV 1126.]
Incompatibilities
Myristic acid is incompatible with strong oxidizing agents and
bases.
Regulatory Status
GRAS listed. Included in the FDA Inactive Ingredients Database (oral capsules). Included in nonparenteral medicines licensed in the UK.
