MYRISTIC ACID
MYRISTIC ACID
Myristic acid (IUPAC name: tetradecanoic acid) is a common saturated fatty acid with the molecular formula CH3(CH2)12COOH.
Its salts and esters are commonly referred to as myristates or tetradecanoates. It is named after the binomial name for nutmeg (Myristica fragrans), from which it was first isolated in 1841 by Lyon Playfair.
EC / List no.: 208-875-2
CAS no.: 544-63-8
Mol. formula: C14H28O2
Myristic acid, also known as 14 or tetradecanoate, 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. Myristic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Myristic Acid is a saturated long-chain fatty acid with a 14-carbon backbone. Myristic acid is found naturally in palm oil, coconut oil and butter fat.
Name
Tetradecanoic acid;
Tetradecanoate;
Myristic acid
1-Tridecanecarboxylic acid
C14 fatty acid
Crodacid
Emery 655
Hydrofol acid 1495
Other
Hystrene 9014
myristic acid
n-Tetradecan-1-oic acid
n-Tetradecanoic acid
n-Tetradecoic acid
Neo-fat 14
Univol U 316S
IUPAC names
MYRISTIC ACID
Tetradecanoic acid
Myristic acid — also known as tetradecanoic acid — is a saturated fatty acid with 14 carbon atoms that has many industrial applications
Myristic acid is an oily, white crystalline solid. It is soluble in alcohol and ether, and insoluble in water.
Myristic acid has many uses including soaps, cosmetics, synthesis of esters for flavors and perfumes, and a component of food-grade additives.
Myristic acid, a long-chain saturated fatty acid (14:0), is one of the most abundant fatty acids in milk fat (above 10%) (Verruck et al., 2019).
This fatty acid is known because it accumulates fat in the body, however, its consumption also impacts positively on cardiovascular health.
This behavior is largely influenced by the balance between saturated fatty acid and simple dietary carbohydrates in the diet (Ruiz-Núñez, Dijck-Brouwer, & Muskiet, 2016).
Myristic acid is directly involved in post-translational protein changes and mechanisms that control important metabolic processes in the human body (Legrand & Rioux, 2015; Ruiz-Núñez et al., 2016).
Dabadie, Peuchant, Bernard, Leruyet, and Mendy (2005) reported that moderate myristic acid consumption improves long-chain omega-3 fatty acids levels in plasma phospholipids, which could exert improvement of cardiovascular health parameters in humans.
Another research by the same group reported that the consumption of myristic acid from dairy fat increased HDL cholesterol and decreased triacylglycerides levels, while no changes in LDL cholesterol were observed.
Additional immunomodulatory functions are exerted by myristic acid through the increase of a specific protein involved in activation of macrophages in murine with high levels of myristic acid intake (Hubbard, Socolich, & Erickson, 1996).
The fatty acid profile in virgin olive oil may contain between 14 (myristic acid) and 24 (lignoceric acid) carbon atoms.
Myristic acid is a 14-carbon saturated fatty acid.
It 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 has a wide range of uses in various industries and manufacturing processes.
You can find it in foods and beverages, in which it is used as a flow agent and emulsifier.
Myristic acid is a surfactant in soaps, detergents and textiles, as well as an intermediate, internal or external lubricant in plastics.
Isopropyl myristate, an ester of myristic acid, is used in the preparation of pharmaceuticals, cosmetics and personal care products to promote absorption through the skin.
Myristic Acid is a common natural organic saturated fatty acid which is found in plants and animals sources such as nutmeg, coconut oil, palm oil, butter fat
Applications :
Myristic acid is a 100% natural source material used in particular by the cosmetic industry and in many other applications.
Myristic acid allows cosmetic oils to penetrate the skin more easily and help regenerate the protective function of the skin.
Myristic is an emulsifying agent in the form of esters, also used as a cleaning or perfuming agent.
ChEBI Name: tetradecanoic acid
ChEBI ID: CHEBI:28875
1-tetradecanecarboxylate
1-tetradecanecarboxylic acid
1-Tridecanecarboxylate
1-Tridecanecarboxylic acid
12-O-Tetradecanoylphorbol 13-acetate
12-Tetradecanoylphorbol 13-acetate
Acide Myristique
acide tetradecanoique
Crodacid
Isopropyl myristate (NF)
myristate
Myristic acid
Myristinsaeure
myristoate
myristoic acid
n-Tetradecan-1-oate
n-Tetradecan-1-oic acid
n-Tetradecanoate
n-Tetradecanoic acid
n-tetradecoate
n-Tetradecoic acid
Phorbol 12-myristate 13-acetate
Tetradecanoate
Tetradecanoic acid
tetradecoate
tetradecoic acid
14
14:0
14:00
C14
CH3-[CH2]12-COOH
Myristic acid pure
Tetradecanoic (myristic) acid
Acid, tetradecanoic
Acid, myristic
FA(14:0)
Myristic Acid is a straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat.
Cosmetics and Pharmaceuticals use: Oil base for creams, lotions, lipsticks, powders, skin ointments, face cleaners, body shampoos, soaps etc,.
Myristic acid has many uses including soaps, cosmetics, synthesis of esters for flavors and perfumes, and a component of food-grade additives
Myristic acid was discovered in the nutmeg that is the seed of the tropical tree Myristica fragrans.
Myristic acid is a saturated fatty acid member of the sub-group called long-chain fatty acids.
Myristic acid occurs, as glycerol ester, in most animal and vegetable fats and oils.
Myristic acid is mostly found in milk fat. Myristic acid is hypercholesterolemic and raises both LDL and HDL cholesterol concentrations compared with oleic acid in healthy subjects.
Myristic acid delays gastric emptying. It may act as a trigger, for the release of a hormone or hormones, which can delay gastric emptying.
Myristic acid is used as ingredient in soaps, cosmetic and shaving creams, often in the form of the ester isopropyl myristate.
Myristic acid is safe as cosmetic ingredients in the current practices of use and concentration.
Tetradecanoic acid is an oily white crystalline solid.
Fractionated distillation (or thermal fractionation) allows the separation of fatty acids mixtures into a narrower cuts or even individual component, based on different boiling point characteristics of components.
Solubility of lauric acid and myristic acid at 10°C in toluene is >400 and 100 times higher, respectively, than that of stearic acid
Myristic acid is indeed directly and specifically involved in protein N-terminal myristoylation, that refers to the highly specific covalent attachment of myristic acid by an amide linkage to the NH2-terminal glycine residue of an increasing number of eukaryotic and viral proteins
Lauric acid and myristic acid are saturated fatty acids. Their formal names are dodecanoic acid and tetradecanoic acid, respectively.
Both are white solids that are very slightly soluble in water.
Lauric acid esters (principally triglycerides) are found only in vegetable fats, primarily from coconut milk and oil, laurel oil, and palm kernel oil.
In contrast, myristic acid triglycerides occur in plants and animals, notably in nutmeg butter, coconut oil, and mammalian milk.
Myristic acid is a 14 carbon length fatty acid that can be naturally found in nutmeg, palm kernel oil, coconut oil and butter fat. It’s used as a foam building cleansing agent
Myristic acid Chemical Properties,Uses,Production
Chemical properties
Myristic acid 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.
Application
Myristic acid can be used as a chemical agent, also for the synthesis of spices and organic matter
Myristic 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.
Myristic 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. It can also be used for the production of isopropyl myristate and so on. It can also be used for defoamers and flavoring agent. According to the provision of China GB2760-89, it can be used to prepare a variety of food spices.
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.
What foods contain Myristic Acid
Nutmeg butter has 75% trimyristin, the triglyceride of myristic acid. Besides nutmeg, myristic acid is 16% of coconut oil and palm kernel oil, 7-12% of butter fat, 2-4% of beef and lamb fat, 3% of salmon fat, 2% of lard, and less than 1% of chicken.
Myristic Acid and Cholesterol Levels
Myristic acid (C14:0), apparently raises LDL cholesterol concentrations somewhat more than does palmitic acid, which is the predominant saturated fatty acid in most diets
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.
Myristic acid Preparation Products And Raw materials
Raw materials
PALM KERNEL OIL 7-ETHYL-2-METHYL-4-UNDECANOL FATTY ACID MIXTURE Metaclazepam Coconut oil ammonium myristate 14-Octacosanone, 15-hydroxy- 1,2-DIMYRISTOYL-SN-GLYCERO-3-PHOSPHOETHANOLAMINE 1-PENTADECENE 6-Bromohexanoic acid 1-Bromooctane
Preparation Products
Orris oil METHYL MYRISTATE ETHOXYLATEDMONO-ANDDI-GLYCERIDES alkoxy ethanolamido sulfosuccinate sodium salt Ethyl myristate 1-Tetradecanol FEMA 2763 Isopropyl myristate
Other names: Myristic acid; n-Tetradecanoic acid; n-Tetradecoic acid; Neo-Fat 14; Univol U 316S; 1-Tridecanecarboxylic acid; Crodacid; Emery 655; Hydrofol acid 1495; Hystrene 9014; n-Tetradecan-1-oic acid; Hystrene 9514; Philacid 1400; Prifac 2942; Prifrac 2942; NSC 5028; Tetradecanoic acid (myristic acid); Acide Myristique; Tetradecanoic (Myristic) acid; Myristic acid (tetradecanoic acid); Tetradecanoic acid (=Myristic acid)
What Is It?
Myristic Acid is a fatty acid that occurs naturally in some foods. Purified Myristic Acid occurs as a hard, white or faintly yellow, glossy crystalline solid, or as a white or yellow-white powder. Salts of Myristic Acid (Aluminum Dimyristate, Aluminum Isostearates/Myristate, Aluminum Myristate, Aluminum Myristates/Palmitates, Calcium Myristate, Magnesium Myristate, Potassium Myristate, Sodium Myristate, Zinc Myristate) and esters of Myristic Acid (Butyl Myristate, Cetyl Myristate, Decyl Myristate, Ethylhexyl Myristate, Ethyl Myristate, Glyceryl Dimyristate, Glyceryl Isostearate/Myristate, Glyceryl Myristate, Isobutyl Myristate, Isocetyl Myristate, Isodecyl Myristate, Isopropyl Myristate, Isostearyl Myristate, Isotridecyl Myristate, Lauryl Myristate, Methyl Myristate, Myristyl Myristate, Octyldodecyl Myristate, Oleyl Myristate, Propylene Glycol Myristate, Tetradecyloctadecyl Myristate, Tridecyl Myristate) may also be used in cosmetics and personal care products. Myristic Acid and its salts and esters may be used in eye makeup, soaps and detergents, hair care products, nail care products, shaving products and other skin care products.
Why is it used in cosmetics and personal care products?
The following functions have been reported for Myristic Acid and its salts and esters.
Anticaking agent – Aluminum Dimyristate, Aluminum Isostearates/Myristates, Aluminum Myristate, Aluminum Myristates/Palmitates, Calcium Myristate, Magnesium Myristate, Zinc Myristate
Binder – Isopropyl Myristate, Isostearyl Myristate, Tetradecyloctyldecyl Myristate
Emulsion stabilizer – Aluminum Dimyristate, Aluminum Isostearates/Myristates, Aluminum Myristate, Aluminum Myristates/Palmitates, Calcium Myristate, Tetradecyloctyldecyl Myristate
Film former – Tetradecyloctyldecyl Myristate
Hair conditioning agent – Ethyl Myristate, Isotridecyl Myristate, Lauryl Myristate, Oleyl Myristate
Opacifying agent – Myristic Acid, Tetradecyloctyldecyl Myristate
Slip modifier – Magnesium Myristate, Zinc Myristate
Skin-Conditioning Agent – Emollient – Butyl Myristate, Ethylhexyl Myristate, Ethyl Myristate, Glyceryl Dimyristate, Glyceryl Isostearate/Myristate, Glyceryl Myristate, Isobutyl Myristate, Isodecyl Myristate, Isopropyl Myristate, Isostearyl Myristate, Methyl Myristate, Propylene Glycol Myristate
Skin-conditioning agent – occlusive – Cetyl Myristate, Decyl Myristate, Isocetyl Myristate, Isotridecyl Myristate, Lauryl Myristate, Myristyl Myristate, Octyldodecyl Myristate, Oleyl Myristate, Tetradecyloctyldecyl Myristate, Tridecyl Myristate
Surfactant – cleansing agent – Myristic Acid, Potassium Myristate, Sodium Myristate
Surfactant – emulsifying agent – Potassium Myristate, Sodium Myristate, Glyceryl Isostearate/Myristate, Glyceryl Myristate, Propylene Glycol Myristate
Viscosity increasing agent – nonaqueous – Aluminum Dimyristate, Aluminum Isostearates/Myristates, Aluminum Myristate, Aluminum Myristates/Palmitates, Calcium Myristate, Magnesium Myristate, Zinc Myristate
Scientific Facts:
Myristic Acid, also called tetradecanoic acid, occurs naturally in vegetable or animal fats and oils with relatively high levels found in nutmeg, palm oil, coconut oil and butter fat. The salts of Myristic acid are formed by reaction with base materials such as sodium or potassium hydroxide. The esters of Myristic Acid are derived from Myristic Acid and an alcohol. For example, Isopropyl Myristate is derived from Myristic Acid and isopropyl alcohol, and Butyl Myristate is derived from Myristic Acid and butyl alcohol.
Occurrence
Myristica fragrans fruit contains myristic acid
Nutmeg butter has 75% trimyristin, the triglyceride of myristic acid.
Besides nutmeg, myristic acid is also found in palm kernel oil, coconut oil, butterfat, 8–14% of bovine milk, and 8.6% of breast milk as well as being a minor component of many other animal fats.
Myristic acid is also found in the rhizomes of the Iris, including Orris root.
It also comprises 14.49% of the fats from the fruit of the Durian species Durio graveolens.
Uses
Myristic acid is commonly added to the N-terminus glycine in receptor-associated kinases to confer the membrane localization 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.
Various “human epidemiological studies have shown that myristic acid and lauric acid were the saturated fatty acids most strongly related to the average serum cholesterol concentrations in humans”, meaning they were positively correlated with higher cholesterol levels as well as raising triglycerides in plasma by some 20% increasing the risk for cardiovascular disease, although some research points to myristic acid’s positive effects on HDL cholesterol and hence improving HDL (good cholesterol) to total cholesterol ratio.
Reduction of myristic acid yields myristyl aldehyde and myristyl alcohol.
Tetradecanoic acid is a straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat. It has a role as a human metabolite, an EC 3.1.1.1 (carboxylesterase) inhibitor, a Daphnia magna metabolite and an algal metabolite. It is a long-chain fatty acid and a straight-chain saturated fatty acid. It is a conjugate acid of a tetradecanoate.
Preferred IUPAC name: Tetradecanoic acid
Other names: C14:0 (Lipid numbers)
Identifiers
CAS Number: 544-63-8
EC Number: 208-875-2
Properties
Chemical formula: C14H28O2
Molar mass: 228.376 g·mol−1
Density: 1.03 g/cm3 (−3 °C)
0.99 g/cm3 (24 °C)
0.8622 g/cm3 (54 °C)
Melting point: 54.4 °C (129.9 °F; 327.5 K)
Boiling point: 326.2 °C (619.2 °F; 599.3 K) at 760 mmHg
250 °C (482 °F; 523 K) at 100 mmHg
218.3 °C (424.9 °F; 491.4 K) at 32 mmHg
Solubility in water: 13 mg/L (0 °C)
20 mg/L (20 °C)
24 mg/L (30 °C)
33 mg/L (60 °C)
Solubility: Soluble in alcohol, acetates, C6H6, haloalkanes, phenyls, nitros
Solubility in acetone: 2.75 g/100 g (0 °C)
15.9 g/100 g (20 °C)
42.5 g/100 g (30 °C)
149 g/100 g (40 °C)
Solubility in benzene: 6.95 g/100 g (10 °C)
29.2 g/100 g (20 °C)
87.4 g/100 g (30 °C)
1.29 kg/100 g (50 °C)
Solubility in methanol: 2.8 g/100 g (0 °C)
17.3 g/100 g (20 °C)
75 g/100 g (30 °C)
2.67 kg/100 g (50 °C)[5]
Solubility in ethyl acetate: 3.4 g/100 g (0 °C)
15.3 g/100 g (20 °C)
44.7 g/100 g (30 °C)
1.35 kg/100 g (40 °C)[5]
Solubility in toluene: 0.6 g/100 g (−10 °C)
3.2 g/100 g (0 °C)
30.4 g/100 g (20 °C)
1.35 kg/100 g (50 °C)
log P 6.1
Vapor pressure: 0.01 kPa (118 °C)
0.27 kPa (160 °C)
1 kPa (186 °C)
Magnetic susceptibility (χ): -176·10−6 cm3/mol
Thermal conductivity: 0.159 W/m·K (70 °C)
0.151 W/m·K (100 °C)
0.138 W/m·K (160 °C)
Refractive index (nD): 1.4723 (70 °C)
Viscosity: 7.2161 cP (60 °C)
3.2173 cP (100 °C)
0.8525 cP (200 °C)
0.3164 cP (300 °C)
Structure
Crystal structure: Monoclinic (−3 °C)
Space group: P21/c
Lattice constant
a = 31.559 Å, b = 4.9652 Å, c = 9.426 Å
α = 90°, β = 94.432°, γ = 90°
Thermochemistry
Heat capacity (C): 432.01 J/mol·K
Std enthalpy of formation (ΔfH⦵298): −833.5 kJ/mol
Std enthalpy of combustion (ΔcH⦵298): 8675.9 kJ/mol[6]
Tetradecanoic acid
MYRISTIC ACID
544-63-8
n-Tetradecanoic acid
Crodacid
n-Tetradecoic acid
1-Tridecanecarboxylic acid
n-Tetradecan-1-oic acid
Hydrofol acid 1495
Univol U 316S
Emery 655
Myristinsaeure
Myristate
tetradecoic acid
Hystrene 9014
Neo-fat 14
Myristic acid (natural)
C14 fatty acid
Myristic acid, pure
n-Myristic acid
Tetradecanoate
acide tetradecanoique
NSC 5028
FEMA No. 2764
CCRIS 4724
CH3-[CH2]12-COOH
HSDB 5686
C14:0
UNII-0I3V7S25AW
Philacid 1400
CHEBI:28875
AI3-15381
Prifac 2942
MFCD00002744
1-tetradecanecarboxylic acid
0I3V7S25AW
CHEMBL111077
NSC5028
Myristic acid, 99%
DSSTox_CID_1666
n-tetradecan-1-oate
DSSTox_RID_76274
DSSTox_GSID_21666
CAS-544-63-8
Myristic acid [NF]
EINECS 208-875-2
BRN 0508624
myristoate
myristoic acid
Lead dimyristate
n-Tetradecanoate
3usx
Myristic acid pure
Myristic Acid Flake
Hystrene 9514
Kortacid 1499
Edenor C 14
Myristic Acid 655
1-Tridecanecarboxylate
Prifrac 2942
MAGNESIUMARSENATE
Myristic acid, 95%
Myristic acid, natural
Saturated fatty acids occur in the diet in different chain lengths, with lauric, myristic, palmitic, and stearic acids as the major ones.
Trans fatty acids predominantly occur as monounsaturated fatty acids with the trans double bond at different positions in the carbon chain.
Dietary saturated and trans fatty acids have important effects on health.
In particular, epidemiological studies and randomized controlled trials on hard clinical end-points indicate that reducing the intake of saturated and trans fatty acids would reduce the risk of Coronary Heart Disease [“CHD”].
The most important metabolic effect by which saturated and trans fatty acids increase CHD risk is through an adverse influence on blood lipid levels.
High levels of total blood cholesterol and of cholesterol in Low-Density Lipoproteins [“LDL”] raise the risk for CHD, whereas a high level of cholesterol in High-Density Lipoproteins [“HDL”] lowers it.
Dietary saturated fatty acids strongly raise total and LDL cholesterol levels in blood.
Trans fatty acids not only raise LDL cholesterol, but also lower HDL cholesterol.
Different saturated fatty acids can have different effects on lipoprotein cholesterol levels, but it is unclear if this translates to different effects on CHD risk.
1-tetradecanoic acid
1-Tridecanecarboxylic acid
208-875-2 [EINECS]
508624 [Beilstein]
544-63-8 [RN]
Acide myristique [French] [ACD/IUPAC Name]
Acide tétradécanoïque [French]
myristic acid [ACD/IUPAC Name]
Myristinsäure [German] [ACD/IUPAC Name]
n-Myristic acid
n-TETRADECANOIC ACID
Tetradecanoic acid [ACD/Index Name]
1-Tridecanecarboxylate
n-Tetradecan-1-oate
n-Tetradecanoate
1,2-DIMYRISTOYL-RAC-GLYCERO-3-PHOSPHOCHOLINE
12-O-Tetradecanoylphorbol 13-acetate
12-Tetradecanoylphorbol 13-acetate
13-Tetradecynoic acid [ACD/Index Name] [ACD/IUPAC Name]
1-tetradecanecarboxylate
1-tetradecanecarboxylic acid
4-02-00-01126 [Beilstein]
82909-47-5 [RN]
Crodacid
DS-3833
Methyl 11-methyldodecanoate [ACD/IUPAC Name]
Myristic Acid 655
Myristinsaeure
Myristoate
Myristoic acid
n-Tetradecan-1-oic acid
n-tetradecoate
n-Tetradecoic acid
QV13 [WLN]
tetradecanoate
TetradecanoicAcid
tetradecoate
tetradecoic acid
Membrane Proteins
William Stillwell, in An Introduction to Biological Membranes, 2013
1 Myristoylated lipid-anchored proteins
The 14-carbon saturated fatty acid, myristic acid (14:0), is often employed as a lipid anchor for proteins.
Myristoylation is a lipid modification involving the addition of a 14-carbon unsaturated fatty acid, myristic acid, to the N-terminal glycine of a subset of proteins
myristic acid has role Daphnia magna metabolite
myristic acid has role algal metabolite
myristic acid has role EC 3.1.1.1 (carboxylesterase) inhibitor
myristic acid has role human metabolite
myristic acid is a long-chain fatty acid
myristic acid is a straight-chain saturated fatty acid
myristic acid is conjugate acid of tetradecanoate
Incoming
β-D-galactosyl-(1→4)-β-D-glucosyl-(1↔1)-N-tetradecanoylsphingosine has functional parent myristic acid
(13R)-13-hydroxymyristic acid (CHEBI:78989) has functional parent myristic acid
(R)-3-hydroxymyristic acid (CHEBI:42539) has functional parent myristic acid
(S)-3-hydroxymyristic acid (CHEBI:37374) has functional parent myristic acid
1,2-ditetradecanoyl-3-(6-sulfoquinovopyranosyl)glycerol has functional parent myristic acid
1,2-ditetradecanoyl-sn-glycero-3-cytidine 5′-diphosphate has functional parent myristic acid
1,2-ditetradecanoyl-sn-glycerol has functional parent myristic acid
1-(1Z-hexadecenyl)-2-tetradecanoyl-sn-glycero-3-phosphocholine has functional parent myristic acid
1-O-(α-D-galactopyranosyl)-N-tetradecanoylphytosphingosine has functional parent myristic acid
1-docosanoyl-2-tetradecanoyl-sn-glycero-3-phosphoethanolamine has functional parent myristic acid
1-icosanoyl-2-tetradecanoyl-sn-glycero-3-phosphocholine has functional parent myristic acid
1-naphthyl tetradecanoate has functional parent myristic acid
1-tetradecanoyl-2,3-dihexadecanoyl-sn-glycerol has functional parent myristic acid
1-tetradecanoyl-2-docosanoyl-sn-glycero-3-phosphoethanolamine has functional parent myristic acid
1-tetradecanoyl-2-icosanoyl-sn-glycero-3-phosphocholine has functional parent myristic acid
10-hydroxymyristic acid has functional parent myristic acid
10-methylmyristic acid has functional parent myristic acid
11-hydroxymyristic acid has functional parent myristic acid
12-hydroxymyristic acid has functional parent myristic acid
13-hydroxymyristic acid has functional parent myristic acid
14-hydroxymyristic acid has functional parent myristic acid
3-hydroxymyristic acid has functional parent myristic acid
3-oxomyristic acid has functional parent myristic acid
9-hydroxymyristic acid has functional parent myristic acid
N,N-dimethyltetradecanamide has functional parent myristic acid
N-(tetradecanoyl)ethanolamine has functional parent myristic acid
N-myristoyl-1,2-dioleoyl-sn-glycero-3-phosphoethanolamine has functional parent myristic acid
N-myristoylglycine (CHEBI:87142) has functional parent myristic acid
N-myristoylsphingosine-1-phosphocholine has functional parent myristic acid
N-tetradecanoyl-(2S)-hydroxyglycine has functional parent myristic acid
N-tetradecanoylsphingosine has functional parent myristic acid
N-tetradecanoylsphingosine 1-phosphate has functional parent myristic acid
N-tetradecanoyltaurine has functional parent myristic acid
S-tetradecanoyl-4ʼ-phosphopantetheine has functional parent tetradecanoic acid
acrophiarin has functional parent tetradecanoic acid
klymollin F has functional parent tetradecanoic acid
methyl tetradecanoate has functional parent tetradecanoic acid
monoacylglycerol 14:0 has functional parent tetradecanoic acid
myristamide has functional parent tetradecanoic acid
myristoyl-CoA has functional parent tetradecanoic acid
tetradecanoate ester has functional parent tetradecanoic acid
tetradecanoic-d27 acid has functional parent tetradecanoic acid
tetradecanoyl-AMP has functional parent tetradecanoic acid
tetradecanoate is conjugate base of tetradecanoic acid
tetradecanoyl group is substituent group from tetradecanoic acid
IUPAC Name
myristic acid
Synonyms Sources
1-tetradecanecarboxylic acid ChEBI
14 ChEBI
14:0 ChEBI
14:00 ChEBI
acide tétradécanoïque Français ChEBI
C14 ChEBI
CH3‒[CH2]12‒COOH IUPAC
Myristic acid KEGG COMPOUND
MYRISTIC ACID PDBeChem
Myristic acid KEGG COMPOUND
Myristinsäure Deutsch ChEBI
n-Tetradecan-1-oic acid ChemIDplus
n-tetradecanoic acid NIST Chemistry WebBook
n-Tetradecoic acid ChemIDplus
Tetradecanoic acid KEGG COMPOUND
tetradecoic acid
Alternative Parents
Straight chain fatty acids
Monocarboxylic acids and derivatives
Carboxylic acids
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
Substituents
Long-chain fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound
• Myristinsαure
• NAA104
• NAA142
• Neo-Fat 14
• neo-fat14
• n-Myristicacid
• n-Tetradecan-1-oic acid
• n-tetradecan-1-oicacid
• n-Tetradecoic acid
• n-tetradecoicacid
• Philacid 1400
• Philacid1400
• Prifac 2940
• Prifrac 2940
• Tetradecanoic (Myristic) acid
• Tetradecansαure
• Univol U 3165
• Univol U 316S
• Univol U320
• univolu316s
• MYRISTIC ACID, STANDARD FOR GC
• MYRISTIC ACID NATURAL FCC
• MYRISTIC ACID, 99.5+%
• MYRISTIC ACID FCC
• MYRISTIC ACID SIGMA GRADE
• MYRISTIC ACID BIOTECH GRADE
• MyristicAcid>95%
• Tetradecanoicacid,98%
• N-TETRADECANOIC ACID ( MYRISTIC ACID)
• Tetradcanoic acid
• myristic acid, pure
• MYRISTICACID,REAGENT
• MYRISTIC ACID(SG)
• MIRISTICACID
• Tetradecanoic acid;Myristic acid
• MYRISTIC ACID (TETRADECANOIC ACID)
• MYRISTIC ACID WITH GC
• Myristic acid Vetec(TM) reagent grade, 98%
• NSC 5028
• MYRISTIC ACID >= 98.0% (GC)
• MYRISTIC ACID, VETEC
• 1-tridecanecarboxylic acid
• C14:0 ACID
• CARBOXYLIC ACID C14
• FEMA 2764
• TETRADECANOIC ACID
• TETRADECYLIC ACID
• RARECHEM AL BO 0367
• N-TETRADECANOIC ACID
• MYRISTIC ACID
• Myristic acid, ≥99.5%(GC)
• Myristic acid, ≥99%(GC)
• Tetradecanoic Acid(C14:0)
• acidemyristique
• acidetetradecanoique
• Crodacid
• EdenorC14
• Emery 654
Food sources of myristic acid
MYRISTIC ACID occurs, as glycerol ester, in most animal and vegetable fats and oils.
In animal fats, such as meat, eggs, milk, fish, shellfish, and crustacean fats, it is present in small quantities, <1.5 g/100 g of edible portion (maximum content: 1.4 g/100 g of edible portion in eel, and 1 g in herring).
The exception is represented by the fat in dairy products, such as:
cheeses, especially the seasoned types (a good source is Parmigiano, with 3.4 g/100 g of edible portion);
butter, the richest source, 8.3 g/100 g of edible portion.
Among vegetable fats and oils, a particularly rich source is coconut oil, with about 17 g/100 g of edible portion.
In the other vegetable oils, only palm oil has concentrations that reach 1 g/100 g of edible portion, whereas it does not exceed 0.86 g/100 g of edible portion in margarine (it is absent in peanut butter).
It should be noted that nutmeg butter is 75% trimyristin, the triglyceride of myristic acid (myristic acid predominates in the fats of the Myristicaceae).
In fruit, MYRISTIC ACID is present in high amounts only in dried and fresh coconut, like lauric acid, 9.5 and 5.4 g/100 g of edible portion, respectively.
MYRISTIC ACID is present in small amounts in a few cereals (maize, 0.28 g/100 g of edible portion, is the richest one).
MYRISTIC ACID is absent in legumes.
Uses in cosmetics
MYRISTIC ACID is used as an ingredient in soaps and shaving creams, often in the form of the esterester isopropyl myristate.
Myristic acid, also named tetradecanoic acid, is a saturated fatty acid with 14 carbon atoms (C14). It is found especially in coconut oil and palm kernel oil, which are vegetable oils very rich in myristic acid and lauric acid. It is also found in large quantities in milk fat.
Applications :
Myristic acid is a 100% natural source material used in particular by the cosmetic industry and in many other applications.
Myristic acid allows cosmetic oils to penetrate the skin more easily and help regenerate the protective function of the skin.
It is an emulsifying agent, also used as a cleaning or perfuming agent.
MYRISTIC ACID
CAS number: 544-63-8
Other language: Acide tétradécanoïque (Acide myristique)
INCI name: MYRISTIC ACID
EINECS/ELINCS number: 208-875-2
Comedogenic potential (pc): 3
Bio-compatible (COSMOS Reference)
Its functions (INCI)
Cleansing : Helps to keep a clean surface
Emulsifying : Promotes the formation of intimate mixtures between immiscible liquids by modifying the interfacial tension (water and oil)
Perfuming : Used for perfume and aromatic raw materials
MYRISTIC ACID is classified as :
Cleansing
Emulsifying
Perfuming
CAS Number 544-63-8
EINECS/ELINCS No: 208-875-2
COSING REF No: 35442
Chem/IUPAC Name: Tetradecanoic acid
Myristic acid (MA), a free fatty acid highly abundant in copra/palmist oils, is a predictor of nonalcoholic steatohepatitis (NASH) and stimulates ceramide synthesis
Myristic acid molecular formula: CH3(CH2)12COOCH
Things to Know About Myristic Acid!
-Melting point=129.9F
-Covalently attached to the- alpha-amino group of an N-ternual glycine residue (myristolation)
-68 safe
-Considered neurotoxin
-Located in cytoplasm, membrane, blood, saliva and urine
-Organic compound
– used to synthesize flavor
– substituent= carboxylic
– occurs in most animals and vegetable facts
– Myristic acid is added to penultimate nitrogen terminus glycine in receptor-associated kinases
Nature products and man made products
-Cows milk
-Dairy Products
-Coconut, palm and nut meg oils
-butter fat
Uses
-cosmetics
-Medical preparations
Myristic acid is obtained from the fractionation of a lauric-type oil.