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Myristic Acid (C14) is a common saturated fatty acid with the molecular formula CH3(CH2)12COOH.
Myristic Acid (C14)'s salts and esters are commonly referred to as myristates or tetradecanoates.
The name of the acyl group derived from Myristic Acid (C14) 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;Tetradecanoic acid;MYRISTIC ACID;544-63-8;n-Tetradecanoic acid;n-Tetradecan-1-oic acid;n-Tetradecoic acid;Crodacid;1-Tridecanecarboxylic acid;Hydrofol acid 1495;Myristinsaeure;Univol U 316S;Emery 655;Myristate;tetradecoic acid;Hystrene 9014;Myristic acid, pure;FEMA No. 2764;Myristic acid (natural);acide tetradecanoique;nMyristic acid;NSC 5028;CCRIS 4724;HSDB 5686;Philacid 1400;C14:0;Prifac 2942;CH3-[CH2]12-COOH;CHEBI:28875;AI3-15381;NSC-5028;1-tetradecanecarboxylic acid;EINECS 208-875-2;PHILACID-1400;UNII-0I3V7S25AW;PRIFRAC-2942;BRN 0508624;0I3V7S25AW;DTXSID6021666;Edenor C 14;Acid, Myristic;MFCD00002744;CHEMBL111077;DTXCID501666;MYRISTIC-14-13C ACID;NSC5028;4-02-00-01126 (Beilstein Handbook Reference);FA 14:0;MyristicAcid-13C14;MYRISTIC ACID (II);MYRISTIC ACID [II];32112-52-0;MYRISTIC ACID (MART.);MYRISTIC ACID [MART.];MYRISTIC ACID (USP-RS);MYRISTIC ACID [USP-RS];CH3-(CH2)12-COOH;CAS-544-63-8;Acid, Tetradecanoic;Myristic acid [NF];62217-70-3;myristoate;myristoic acid;n-Tetradecanoate;Tetradecanoicacid;3usx;Myristic acid pure;fatty acid 14:0;Hystrene 9514;TETRADECANSAEURE;1-Tridecanecarboxylate;ACIDO MYNISTICO;Myristic acid, 95%;Myristic acid, natural;tridecanecarboxylic acid;Myristic acid (8CI);Myristic Acid, Reagent;3v2n;3w9k;Myristic acid, puriss.;Univol U 3165;Myristic acid, ?99%;Myristic acid (Standard);Tetradecanoic acid (9CI);bmse000737;Epitope ID:176772;MYRISTIC ACID [MI];SCHEMBL6374;MYRISTIC ACID [FCC];MYRISTIC ACID [FHFI];MYRISTIC ACID [HSDB];MLS002152942;WLN: QV13;Tetradecanoic (Myristic) acid;GTPL2806;HY-N2041R;NAA 104;NAA 142;IS_D27-TETRADECANOIC ACID;HMS3039E15;HMS3648O20;Myristic acid, analytical standard;HY-N2041;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;FM62595;NSC 122834;NCGC00091068-01;NCGC00091068-02;NCGC00091068-03;NCGC00256547-01;NCGC00259401-01;AC-34674;BP-27915;SMR001224536;CS-0018531;M0476;NS00010444;EN300-78099;C06424;G74510;Myristic acid, Vetec(TM) reagent grade, 98%;Q422658;SR-01000854525;MYRISTIC ACID (CONSTITUENT OF SAW PALMETTO);SR-01000854525-3;F8889-5016;Z1954802504;EDAE4876-C383-4AD4-A419-10C0550931DB;MYRISTIC ACID (CONSTITUENT OF SAW PALMETTO) [DSC];Myristic acid, United States Pharmacopeia (USP) Reference Standard;Myristic acid, Pharmaceutical Secondary Standard; Certified Reference Material
208-875-2
The acid is named after the binomial name for nutmeg (Myristica fragrans), from which Myristic Acid (C14) was first isolated in 1841 by Lyon Playfair.
Myristic Acid (C14) is a fatty acid that is produced by plants and animals.
Myristic Acid (C14) is important for cell membrane structure and function, as well as for energy metabolism and the production of various compounds.
Myristic Acid (C14) 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.
Myristic Acid (C14) 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.
Myristic Acid (C14) is a 14-carbon saturated fatty acid.
Myristic Acid (C14) 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.
Myristic Acid (C14), also called tetradecanoic acid , is a common saturated fatty acid with the molecular formula CH3(CH2)12COOH.
Myristic Acid (C14) is a salt or ester of myristic acid.
Myristic Acid (C14) is named after the nutmeg Myristica fragrans.
Nutmeg butter is 75 % trimyristin, the triglyceride of myristic acid.
Besides nutmeg, Myristic Acid (C14) is also found in palm kernel oil, coconut oil, butter fat and is a minor component of many other animal fats.
Myristic Acid (C14) is also found in spermaceti, the crystallized fraction of oil from the sperm whale.
Myristic Acid (C14) 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 (C14) 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 (C14) acts as a lipid anchor in biomembranes.
The ester Myristic Acid (C14) is used in cosmetic and topical medicinal preparations where good absorption through the skin is desired.
Reduction of Myristic Acid (C14) yields myristyl aldehyde and myristyl alcohol.
A straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat.
Myristic Acid (C14) is a straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat.
Myristic Acid (C14) has a role as a human metabolite, an EC 3.1.1.1 (carboxylesterase) inhibitor, a Daphnia magna metabolite and an algal metabolite.
Myristic Acid (C14) is a long-chain fatty acid and a straight-chain saturated fatty acid.
Myristic Acid (C14) is a conjugate acid of a tetradecanoate.
Myristic Acid (C14) 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: Myristic Acid (C14)(544-63-8)
EPA Substance Registry System: Myristic acid (544-63-8)
Myristic Acid (C14) appears as white to yellowish white solid, sometimes appearing as shiny crystalline solid, or white to yellowish white powder.
Myristic Acid (C14) has a relative density of 0.8739 (80 ℃), melting point of 54.5 ℃ and the boiling point of 326.2 ℃.
Myristic Acid (C14)'s refractive index (nD60) is 1.4310.
Myristic Acid (C14) is not soluble in water but soluble in ethanol, ether and chloroform.
Myristic Acid (C14) 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.
Myristic Acid (C14) has a faint, waxy, oily odor
Myristic Acid (C14) occurs as an oily white crystalline solid with a faint odor.
Application
Myristic Acid (C14) can be used as a chemical agent, also for the synthesis of spices and organic matter
Myristic Acid (C14) 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.
Myristic Acid (C14) 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.
Myristic Acid (C14) can also be used for the production of isopropyl myristate and so on.
Myristic Acid (C14) can also be used for defoamers and flavoring agent.
According to the provision of China GB2760-89, Myristic Acid (C14) can be used to prepare a variety of food spices.
Myristic Acid (C14) is a common saturated fatty acid found in nutmeg, palm kernel oil, coconut oil and butter fat.
Myristic Acid (C14) is a fatty acid obtained from coconut oil and other fats.
Myristic Acid (C14) has poor water solubility but is soluble in alcohol, chloro- form, and ether.
Myristic Acid (C14) is used as a lubricant, binder, and defoaming agent.
Myristic Acid (C14) is a 14-carbon saturated (14:0) fatty acid.
In vivo, Myristic Acid (C14) 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.
Myristic Acid (C14) is a surfactant and cleansing agent.
When combined with potassium, Myristic Acid (C14) soap provides very good, abundant lather.
Myristic Acid (C14) 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 Myristic Acid (C14) as having no irritation potential, they do indicate comedogenicity potential.
Pharmaceutical Applications
Myristic Acid (C14) is used in oral and topical pharmaceutical formulations.
Myristic Acid (C14) 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 (C14) in oxymorphone formulations and clobetasol 17-propionate topical applications.
Furthermore, polyvinyl alcohol substituted with Myristic Acid (C14) (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 Myristic Acid (C14), 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 (C14).
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.
Myristic Acid (C14) can also be made from tetradecanol.
Production Methods
Myristic Acid (C14) occurs naturally in nutmeg butter and in most animal and vegetables fats.
Synthetically, Myristic Acid (C14) may be prepared by electrolysis of methyl hydrogen adipate and decanoic acid or by Maurer oxidation of myristyl alcohol.
Reactivity Profile
Myristic Acid (C14) 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 Myristic Acid (C14) 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.
Biochem/physiol Actions
Myristic Acid (C14) 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.
