Myristic acid CAS:544-63-8 CAS:Myristic acid,544-63-8 Basic information
|Product Name:||Myristic acid|
|Synonyms:||acidemyristique;acidetetradecanoique;Crodacid;EdenorC14;Emery 654;Emery 655;emery655;Hydrofol acid 1495|
|Product Categories:||Alkylcarboxylic Acids;Biochemistry;Color Former & Related Compounds;Functional Materials;Higher Fatty Acids & Higher Alcohols;Monofunctional & alpha,omega-Bifunctional Alkanes;Monofunctional Alkanes;Saturated Higher Fatty Acids;Sensitizer;Miscellaneous Na|
Myristic acid CAS:544-63-8 CAS:Myristic acid,544-63-8 Chemical Properties
|Melting point:||52-54 °C(lit.)|
|Boiling point:||250 °C100 mm Hg(lit.)|
|form:||Flakes, Powder, Chunks or Crystalline Mass|
|Water Solubility:||<0.1 g/100 mL at 18 ºC|
|refractive index:||nD60 1.4305; nD70 1.4273|
|NIST Chemistry Reference:||Tetradecanoic acid(544-63-8)|
|Stability:||Stable. Incompatible with strong oxidizing agents, bases.|
|vapor pressure:||<0.01 hPa (20 °C)|
|FEMA:||2764 | MYRISTIC ACID|
|CAS DataBase Reference:||544-63-8(CAS DataBase Reference)|
|EPA Substance Registry System:||Myristic acid (544-63-8)|
White to light yellow white hard solid
White to light yellow white hard solid
|Myristic acid Usage And Synthesis|
|Chemical properties||It appears as white to yellowish white solid, sometimes appearing as shiny crystalline solid, or white to yellowish white powder. It has a relative density of 0.8739 (80 ℃), melting point of 54.5 ℃ and the boiling point of 326.2 ℃. Its refractive index (nD60) is 1.4310. It 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 it.
|Preparation||To prepare the myristic 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. It can also be made from tetradecanol.|
|Toxicity||Natural fatty acids, non-toxic|
Can be safely used for food (FDA, § 172.860; 2000).
LD50:43 mg/kg (mouse, transdermal).
|Use limit||FEMA (mg/kg): soft drinks 5.3, cold drinks 2.6~10, candy 4.1, baked goods 5.3, pudding class 0.10.|
|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.
|Chemical Properties||Prepared from the fatty acid mixture of palm seed oil.|
|Chemical Properties||Myristic acid has a faint, waxy, oily odor|
|Chemical Properties||white solid|
|Chemical Properties||Myristic acid occurs as an oily white crystalline solid with a faint odor.|
|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|
|Uses||myristic acid is a surfactant and cleansing agent. When combined with potassium, myristic acid soap provides very good, abundant lather. This 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 it as having no irritation potential, they do indicate comedogenicity potential.|
|Uses||Myristic Acid is a fatty acid obtained from coconut oil and other fats. it has poor water solubility but is soluble in alcohol, chloro- form, and ether. it is used as a lubricant, binder, and defoaming agent.|
|Uses||Myristic Acid is a common saturated fatty acid found in nutmeg, palm kernel oil, coconut oil and butter fat.|
|Uses||Myristic acid is a 14-carbon saturated (14:0) fatty acid. In vivo, it 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.|
|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.|
|Preparation||From fatty acid mixture of palm seed oil|
|Aroma threshold values||Detection: 10 ppm|
|General Description||Oily white crystalline solid.|
|Air & Water Reactions||Insoluble in water.|
|Reactivity Profile||Myristic 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. 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 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.|
|Fire Hazard||Myristic acid is probably combustible.|
|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.|
|Safety Profile||Poison by intravenous route. Mutation data reported. An eye and human skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.|
|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.|