TETRADECANOIC ACID

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 Tetradecanoic acid.
Tetradecanoic acid is named after the nutmeg Myristica fragrans. 

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

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 Tetradecanoic acid 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 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.
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. 
Tetradecanoic acid is named after the binomial name for nutmeg (Myristica fragrans), from which it was first isolated in 1841 by Lyon Playfair.

Tetradecanoic acid, also known as tetradecanoic acid or C14:0, belongs to the class of organic compounds known as long-chain fatty acids. 
These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Tetradecanoic acid (its ester is called myristate) is a saturated fatty acid that has 14 carbons; as such, Tetradecanoic acid is a very hydrophobic molecule that is practically insoluble in water. 
Tetradecanoic acid exists as an oily white crystalline solid. 

Tetradecanoic acid is found in all living organisms ranging from bacteria to plants to animals, and is found in most animal and vegetable fats, particularly butterfat, as well as coconut, palm, and nutmeg oils. 
Industrially, Tetradecanoic acid is used to synthesize a variety of flavour compounds and as an ingredient in soaps and cosmetics (Dorland, 28th ed). 
Within eukaryotic cells, Tetradecanoic acid is also commonly conjugated to a penultimate N-terminal glycine residue in receptor-associated kinases to confer membrane localization of these enzymes (a post-translational modification called myristoylation via the enzyme N-myristoyltransferase). 

Tetradecanoic acid has a high enough hydrophobicity to allow the myristoylated protein to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasma membrane of eukaryotic cells. 
Also, this fatty acid is known because Tetradecanoic acid accumulates as fat in the body; however, its consumption also impacts positively on cardiovascular health(see, for example, PMID:15936650 ). 
Tetradecanoic acid is named after the scientific name for nutmeg, Myristica fragrans, from which it was first isolated in 1841 by Lyon Playfair.

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
Form: Flakes, Powder, Chunks or Crystalline Mass
pkA: 4.78±0.10(Predicted)
Color: White
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.
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. 
Tetradecanoic acid contains about 70% to 80% while other kinds of coconut oil, palm kernel oil also contain it.
Prepared from the fatty acid mixture of palm seed oil.
Tetradecanoic acid has a faint, waxy, oily odor.
Tetradecanoic acid occurs as an oily white crystalline solid with a faint odor.

Uses
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 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.

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 common saturated fatty acid found in nutmeg, palm kernel oil, coconut oil and butter fat.

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.

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 myristic acid in oxymorphone formulations and clobetasol 17-propionate topical applications.
Furthermore, polyvinyl alcohol substituted with Tetradecanoic acid (as well as other fatty acids) 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 myristic 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. 
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.
 
Tetradecanoic acid 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 Tetradecanoic acid dissociate to an extent in water to yield hydrogen ions. 
The pH of solutions of Tetradecanoic acid 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. 

Tetradecanoic acid 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 Tetradecanoic acid as well, but are slow if the solid acid remains dry. 
Even "insoluble" Tetradecanoic acid 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 acid, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. 
The reaction is slower for dry, solid Tetradecanoic acid. 
Insoluble Tetradecanoic acid 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. 
Tetradecanoic acid, 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 acid 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 acid may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.

Synonyms
Tetradecanoic acid
MYRISTIC ACID
544-63-8
n-Tetradecanoic acid
n-Tetradecan-1-oic acid
Crodacid
n-Tetradecoic acid
1-Tridecanecarboxylic acid
Myristate
tetradecoic acid
Hydrofol acid 1495
Univol U 316S
Emery 655
Myristinsaeure
Hystrene 9014
FEMA No. 2764
Myristic acid, pure
n-Myristic acid
Myristic acid (natural)
Tetradecanoate
acide tetradecanoique
NSC 5028
CCRIS 4724
CH3-[CH2]12-COOH
HSDB 5686
C14:0
Philacid 1400
CHEBI:28875
AI3-15381
Prifac 2942
NSC-5028
1-tetradecanecarboxylic acid
PHILACID-1400
PRIFRAC-2942
0I3V7S25AW
CHEMBL111077
NSC5028
n-tetradecan-1-oate
32112-52-0
CAS-544-63-8
Myristic acid [NF]
EINECS 208-875-2
BRN 0508624
myristoate
UNII-0I3V7S25AW
myristoic acid
n-Tetradecanoate
Tetradecanoicacid
3usx
Myristic acid pure
Myristic Acid Flake
MFCD00002744
Hystrene 9514
Edenor C 14
Myristic Acid 655
1-Tridecanecarboxylate
MAGNESIUMARSENATE
Myristic acid, 95%
Myristic acid, natural
tridecanecarboxylic acid
Myristic acid (8CI)
Myristic Acid, Reagent
3v2n
3w9k
Myristic acid, puriss.
Tetradecanoic acid (9CI)
bmse000737
Epitope ID:176772
MYRISTIC ACID [II]
MYRISTIC ACID [MI]
SCHEMBL6374
MYRISTIC ACID [FCC]
Myristic acid-[14-13C]
MYRISTIC ACID [FHFI]
MYRISTIC ACID [HSDB]
MYRISTIC ACID [INCI]
4-02-00-01126 (Beilstein Handbook Reference)
MLS002152942
WLN: QV13
Tetradecanoic (Myristic) acid
MYRISTIC ACID [MART.]
GTPL2806
MYRISTIC ACID [USP-RS]
DTXSID6021666
HMS3039E15
HMS3648O20
Myristic acid, analytical standard
HY-N2041
ZINC1530417
EINECS 250-924-5
Myristic acid, >=98.0% (GC)
Tox21_201852
Tox21_302781
BDBM50147581
LMFA01010014
s5617
STL185697
Myristic acid, >=95%, FCC, FG
Myristic acid, Sigma Grade, >=99%
AKOS009156714
CCG-266785
DB08231
DS-3833
FA 14:0
NSC 122834
NCGC00091068-01
NCGC00091068-02
NCGC00091068-03
NCGC00256547-01
NCGC00259401-01
AC-34674
BP-27915
SMR001224536
CS-0018531
FT-0602832
FT-0770860
M0476
EN300-78099
C06424
Myristic acid, Vetec(TM) reagent grade, 98%
Q422658
SR-01000854525
SR-01000854525-3
W-109088
F8889-5016
Z1954802504
EDAE4876-C383-4AD4-A419-10C0550931DB
MYRISTIC ACID (CONSTITUENT OF SAW PALMETTO) [DSC]
Myristic acid, United States Pharmacopeia (USP) Reference Standard
Tetradecanoic acid; 1-Tridecanecarboxylic acid; n-Tetradecanoic acid
Myristic acid, Pharmaceutical Secondary Standard; Certified Reference Material