544-63-8 Usage
Chemical Description
Myristic acid is a fatty acid that is also conjugated with glutamate ester to form myristoylated conjugates.
Description
Myristic acid, also known as tetradecanoic acid, is a common saturated fatty acid with the molecular formula CH3(CH2)12COOH. It is a 14-carbon saturated fatty acid that occurs naturally in various plant and animal sources, such as nutmeg, palm kernel oil, coconut oil, and butter fat. Myristic acid is an oily white crystalline solid with a faint, waxy, oily odor and is named after the nutmeg Myristica fragrans. It has a melting point of 54.5 ℃ and a boiling point of 326.2 ℃. Myristic acid is not soluble in water but is soluble in ethanol, ether, and chloroform. It is used in various applications across different industries due to its unique properties.
Uses
Used in Cosmetics and Personal Care Industry:
Myristic acid is used as a surfactant and cleansing agent for the production of sorbitan fatty acid esters, glycerol fatty acid esters, ethylene glycol or propylene glycol fatty acid esters. It provides very good, abundant lather when combined with potassium, making it suitable for soap production. The ester isopropyl myristate, derived from myristic acid, is used in cosmetic and topical medicinal preparations where good absorption through the skin is desired.
Used in Pharmaceutical Industry:
Myristic acid is used as a lubricant, binder, and defoaming agent in the pharmaceutical industry. It is also involved in the co-translational process termed N-myristoylation, where it is added to the N-terminus of proteins to modify their activity or localization in cells.
Used in Food Industry:
Myristic acid can be used as a chemical agent and for the synthesis of spices and organic matter. It is used in the manufacture of emulsifiers, waterproofing agents, curing agents, PVC heat stabilizers, and plasticizers. According to the provision of China GB2760-89, it can be used to prepare a variety of food spices.
Used in Chemical Industry:
Myristic acid is used as a raw material for the production of various chemicals, including surfactants, defoamers, and flavoring agents. It is also used in the synthesis of isopropyl myristate and other compounds.
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.
Preparation
From fatty acid mixture of palm seed oil
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.
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.
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.
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 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
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.
Check Digit Verification of cas no
The CAS Registry Mumber 544-63-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,4 and 4 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 544-63:
(5*5)+(4*4)+(3*4)+(2*6)+(1*3)=68
68 % 10 = 8
So 544-63-8 is a valid CAS Registry Number.
InChI:InChI=1/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16)
544-63-8Relevant articles and documents
Isolation of a lupane triterpene fatty acid ester with antibacterial activity from the leaves of Finlaysonia obovata
Mishra, Pravat Manjari,Sree,Panigrahi, Mallika
, p. 161 - 163 (2012)
-
Long-chain fatty acid acylated derivatives of isoflavone glycosides from the rhizomes of Iris domestica
Li, Jiayuan,Liu, Yanfei,Ni, Gang,Wang, Renzhong,Yu, Dequan
, (2021/11/01)
Six undescribed long-chain fatty acid esters of isoflavone glycosides were obtained from the rhizomes of Iris domestica (L.). Their structures were elucidated by comprehensive spectroscopic data, alkaline hydrolysis, and acid hydrolysis. This is the first report of the long-chain (C14–C18) fatty acid derivatives of isoflavone glycosides from natural products. Belamcandnoate B and D exhibited moderate cytotoxic activities against HCT-116, HepG2, and BGC823 cell lines with IC50 values of 1.69–6.86 μM. Belamcandnoate B and E exhibited 72.27 and 58.98% inhibitory activities, respectively, against Fe2+/cysteine-induced liver microsomal lipid peroxidation at a concentration of 10 μM.
Highly luminescent and multi-sensing aggregates co-assembled from Eu-containing polyoxometalate and an enzyme-responsive surfactant in water
Lei, Nana,Shen, Dazhong,Chen, Xiao
, p. 399 - 407 (2019/01/24)
Hybrid co-assembly of polyoxometalates (POMs) with cationic organic matrices offers a preferable way to greatly enhance POM functionality as well as processability. Thus, multi-stimulus responsive supramolecular materials based on lanthanide-containing POMs with improved luminescence may be fabricated from appropriate components through this convenient strategy. Herein, we reported that the co-assembly of Na9(EuW10O36)·32H2O (EuW10) and a commercially available cationic surfactant, myristoylcholine chloride (Myr), in water could produce enhanced red-emitting luminescent aggregates, with their photophysical properties highly dependent on the molar ratio (R) between Myr and EuW10. The R of 36 was finally selected owing to the displayed superior luminescence intensity and good aggregate stability. The Myr/EuW10 hybrids induced by electrostatic and hydrophobic forces presented practically as multilamellar spheres with diameters varying from 80 to 300 nm. Compared to an aqueous solution of EuW10 nanoclusters, a 12-fold increase in absolute luminescence quantum yield (~23.3%) was observed for the hybrid spheres, which was ascribed to the efficient shielding of water molecules. An unusual aggregation arrangement mechanism and the excellent photophysical properties of these aggregates were thoroughly investigated. Both the enzyme substrate character of Myr and the sensitive coordination structure of EuW10 to the surrounding environment made Myr/EuW10 aggregates exhibit multi-stimulus responsiveness to enzymes, pH, and transition metal ions, thus providing potential applications in fluorescence sensing, targeted-release, and optoelectronics.
Synthesis of α,β-unsaturated aldehydes as potential substrates for bacterial luciferases
Brodl, Eveline,Ivkovic, Jakov,Tabib, Chaitanya R.,Breinbauer, Rolf,Macheroux, Peter
, p. 1487 - 1495 (2017/02/18)
Bacterial luciferase catalyzes the monooxygenation of long-chain aldehydes such as tetradecanal to the corresponding acid accompanied by light emission with a maximum at 490?nm. In this study even numbered aldehydes with eight, ten, twelve and fourteen carbon atoms were compared with analogs having a double bond at the α,β-position. These α,β-unsaturated aldehydes were synthesized in three steps and were examined as potential substrates in vitro. The luciferase of Photobacterium leiognathi was found to convert these analogs and showed a reduced but significant bioluminescence activity compared to tetradecanal. This study showed the trend that aldehydes, both saturated and unsaturated, with longer chain lengths had higher activity in terms of bioluminescence than shorter chain lengths. The maximal light intensity of (E)-tetradec-2-enal was approximately half with luciferase of P. leiognathi, compared to tetradecanal. Luciferases of Vibrio harveyi and Aliivibrio fisheri accepted these newly synthesized substrates but light emission dropped drastically compared to saturated aldehydes. The onset and the decay rate of bioluminescence were much slower, when using unsaturated substrates, indicating a kinetic effect. As a result the duration of the light emission is doubled. These results suggest that the substrate scope of bacterial luciferases is broader than previously reported.