TETRADECANOIC ACID

Tetradecanoic Acid is a common saturated fatty acid with the molecular formula CH3(CH2)12COOH. 
Tetradecanoic Acid's salts and esters are commonly referred to as myristates or tetradecanoates. 
The name of the acyl group derived from Tetradecanoic Acid is myristoyl or tetradecanoyl. 

CAS:    544-63-8
MF:    C14H28O2
MW:    228.37
EINECS:    208-875-2

Synonyms
Myristinsαure;NAA104;NAA142;Neo-Fat 14;neo-fat14;n-Myristicacid;n-Tetradecan-1-oic acid;n-tetradecan-1-oicacid

The acid is named after the binomial name for nutmeg (Myristica fragrans), from which Tetradecanoic Acid was first isolated in 1841 by Lyon Playfair.
Tetradecanoic Acid is a fatty acid that is produced by plants and animals. 
Tetradecanoic Acid is important for cell membrane structure and function, as well as for energy metabolism and the production of various compounds. 
Tetradecanoic Acid can be metabolized in the body to produce a number of compounds, including methyl myristate, which has been shown to inhibit the growth of cancer cells. 
Tetradecanoic Acid also binds to DNA through covalent linkages and has significant cytotoxicity against polymorphonuclear leucocytes (PMN) in vitro. 
This activity may be due to its ability to bind with toll-like receptors on PMN cells.
Tetradecanoic Acid is a 14-carbon saturated fatty acid. 
Tetradecanoic Acid is incorporated into myristoyl coenzyme A (myristoyl-CoA) and transferred by N-myristoyltransferase to the N-terminal glycine of certain proteins either during translation to modify protein activity or post-translationally in apoptotic cells.

Tetradecanoic 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 Tetradecanoic Acid.
Tetradecanoic Acid is named after the nutmeg Myristica fragrans. 
Nutmeg butter is 75 % trimyristin, the triglyceride of Tetradecanoic Acid. 
Besides nutmeg, Tetradecanoic Acid is also found in palm kernel oil, coconut oil, butter fat and is a minor component of many other animal fats. 
Tetradecanoic Acid is also found in spermaceti, the crystallized fraction of oil from the sperm whale.
Tetradecanoic 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 Tetradecanoic 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, Tetradecanoic 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 Tetradecanoic Acid yields myristyl aldehyde and myristyl alcohol.
Tetradecanoic Acid is a common saturated fatty acid found in nutmeg, palm kernel oil, coconut oil and butter fat.
A straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat.
Tetradecanoic Acid is a common saturated fatty acid with the molecular formula CH3(CH2)12COOH. 
Tetradecanoic Acid's salts and esters are commonly referred to as myristates or tetradecanoates. 
The name of the acyl group derived from Tetradecanoic Acid is myristoyl or tetradecanoyl. 
The acid is named after the binomial name for nutmeg (Myristica fragrans), from which Tetradecanoic Acid was first isolated in 1841 by Lyon Playfair.
Tetradecanoic Acid acts as a lipid anchor in biomembranes.
Reduction of Tetradecanoic Acid yields myristyl aldehyde and myristyl alcohol.

Tetradecanoic Acid Chemical Properties
Melting point: 52-54 °C(lit.)
Boiling point: 250 °C100 mm Hg(lit.)
Density: 0.862
Vapor pressure: <0.01 hPa (20 °C)
FEMA: 2764 | MYRISTIC ACID
Refractive index: nD60 1.4305; nD70 1.4273
Fp: >230 °F
Storage temp.: room temp
Solubility: 1.07mg/l
Pka: 4.78±0.10(Predicted)
Form: Flakes, Powder, Chunks or Crystalline Mass
Color: White
Odor: at 100.00 %. waxy fatty soapy coconut
Odor Type: waxy
Biological source: synthetic
Water Solubility: <0.1 g/100 mL at 18 ºC
Merck: 14,6333
JECFA Number: 113
BRN: 508624
Stability: Stable. Incompatible with strong oxidizing agents, bases.
LogP: 5.79
CAS DataBase Reference: 544-63-8(CAS DataBase Reference)
NIST Chemistry Reference: Tetradecanoic Acid(544-63-8)
EPA Substance Registry System: Tetradecanoic Acid (544-63-8)

Tetradecanoic Acid appears as white to yellowish white solid, sometimes appearing as shiny crystalline solid, or white to yellowish white powder. 
Tetradecanoic Acid has a relative density of 0.8739 (80 ℃), melting point of 54.5 ℃ and the boiling point of 326.2 ℃. 
Tetradecanoic Acid's refractive index (nD60) is 1.4310. 
Tetradecanoic Acid is not soluble in water but soluble in ethanol, ether and chloroform. 
Myristin contains about 70% to 80% while other kinds of coconut oil, palm kernel oil also contain Tetradecanoic Acid.

Application    
Tetradecanoic Acid can be used as a chemical agent, also for the synthesis of spices and organic matter
Tetradecanoic Acid can be used in the manufacture of emulsifiers, waterproofing agents, curing agents, PVC heat stabilizers and plasticizers, and also used as the raw materials of spices and pharmaceutical.
Tetradecanoic Acid is mainly used as raw materials for the production of surfactants for the production of sorbitan fatty acid esters, glycerol fatty acid esters, ethylene glycol or propylene glycol fatty acid esters. 
Tetradecanoic Acid can also be used for the production of isopropyl myristate and so on. 
Tetradecanoic Acid can also be used for defoamers and flavoring agent. 

According to the provision of China GB2760-89, Tetradecanoic Acid can be used to prepare a variety of food spices.
Tetradecanoic Acid is a fatty acid obtained from coconut oil and other fats. 
Tetradecanoic Acid has poor water solubility but is soluble in alcohol, chloro- form, and ether. 
Tetradecanoic Acid is used as a lubricant, binder, and defoaming agent.
Tetradecanoic Acid is a 14-carbon saturated (14:0) fatty acid. 
In vivo, Tetradecanoic Acid is commonly added covalently to the N-terminus of proteins in a co-translational process termed N-myristoylation. 

In addition, there are examples where N-myristoylation occurs post-translationally, when a hidden myristoylation pattern is exposed.
Tetradecanoic Acid is a surfactant and cleansing agent. 
When combined with potassium, Tetradecanoic Acid soap provides very good, abundant lather. 
Tetradecanoic Acid is a solid organic acid naturally occurring in butter acids such as nutmeg, oil of lovage, coconut oil, mace oil, and most animal and vegetable fats. 
Although some sources cite Tetradecanoic Acid as having no irritation potential, they do indicate comedogenicity potential.

Pharmaceutical Applications    
Tetradecanoic Acid is used in oral and topical pharmaceutical formulations. 
Tetradecanoic 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 Tetradecanoic Acid in oxymorphone formulations and clobetasol 17-propionate topical applications.
Furthermore, polyvinyl alcohol substituted with Tetradecanoic Acid at different substitution degrees has been used for the preparation of biodegradable microspheres containing progesterone or indomethacin.

Preparation    
To prepare the Tetradecanoic Acid, the methyl ester of the mixed fatty acids or mixed fatty acid methyl ester obtained from the coconut oil or palm kernel oil is subject to vacuum fractionation, obtaining myristic acid. 
For laboratory preparation, glycerol tris (tetradecanoate) is subject to saponification with 10% sodium hydroxide solution, further being acidified with hydrochloric acid to obtain the free Tetradecanoic Acid. 
Tetradecanoic Acid can also be made from tetradecanol.

Production Methods    
Tetradecanoic Acid occurs naturally in nutmeg butter and in most animal and vegetables fats. 
Synthetically, Tetradecanoic Acid may be prepared by electrolysis of methyl hydrogen adipate and decanoic acid or by Maurer oxidation of myristyl alcohol.

Biochem/physiol Actions    
Tetradecanoic 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 .

Reactivity Profile    
Tetradecanoic Acid is a carboxylic acid. 
Tetradecanoic Acid's 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. 
Tetradecanoic Acid's 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 Tetradecanoic Acid's is therefore less than 7.0. 

Many insoluble Tetradecanoic Acid's 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 Tetradecanoic Acid's can react with active metals to form gaseous hydrogen and a metal salt. 
Such reactions occur in principle for solid Tetradecanoic Acid's as well, but are slow if the solid acid remains dry. 
Even "insoluble" Tetradecanoic Acid's may absorb enough water from the air and dissolve sufficiently in Tetradecanoic Acid to corrode or dissolve iron, steel, and aluminum parts and containers. 
Tetradecanoic Acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. 
The reaction is slower for dry, solid carboxylic acids. 
Insoluble Tetradecanoic 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 Tetradecanoic Acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Tetradecanoic 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, Tetradecanoic 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, Tetradecanoic Acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.