Names | |
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Preferred IUPAC name Tetradecanoic acid | |
Other names C14:0 (Lipid numbers) | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.008.069 |
EC Number |
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PubChem CID | |
RTECS number |
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UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C14H28O2 | |
Molar mass | 228.376 g·mol−1 |
Appearance | colorless or white solid |
Density | 1.03 g/cm3 (−3 °C) [2] 0.99 g/cm3 (24 °C) [3] 0.8622 g/cm3 (54 °C) [4] |
Melting point | 54.4 °C (129.9 °F; 327.5 K) [5] |
Boiling point | 326.2 °C (619.2 °F; 599.3 K) at 760 mmHg 250 °C (482 °F; 523 K) at 100 mmHg [4] 218.3 °C (424.9 °F; 491.4 K) at 32 mmHg [3] |
13 mg/L (0 °C) 20 mg/L (20 °C) 24 mg/L (30 °C) 33 mg/L (60 °C) [6] | |
Solubility | Soluble in alcohol, acetates, C6H6, haloalkanes, phenyls, nitros [6] |
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) [6] |
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) [6] |
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) [6] |
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) [6] |
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) [6] |
log P | 6.1 [4] |
Vapor pressure | 0.01 kPa (118 °C) 0.27 kPa (160 °C) [7] 1 kPa (186 °C) [4] |
-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) [8] |
Refractive index (nD) | 1.4723 (70 °C) [4] |
Viscosity | 7.2161 cP (60 °C) 3.2173 cP (100 °C) 0.8525 cP (200 °C) 0.3164 cP (300 °C) [9] |
Structure | |
Monoclinic (−3 °C) [2] | |
P21/c [2] | |
α = 90°, β = 94.432°, γ = 90° | |
Thermochemistry | |
Heat capacity (C) | 432.01 J/mol·K [4] [7] |
Std enthalpy of formation (ΔfH⦵298) | −833.5 kJ/mol [4] [7] |
Std enthalpy of combustion (ΔcH⦵298) | 8675.9 kJ/mol [7] |
Hazards | |
GHS labelling: | |
[10] | |
Warning | |
H315 [10] | |
NFPA 704 (fire diamond) | |
Flash point | >110 °C (230 °F; 383 K) [11] |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | >10 g/kg (rats, oral) [11] |
Related compounds | |
Related esters of myristic acid | Isopropyl myristate Phorbol myristate acetate Myristylbenzylmorphine Dimyristoylphosphatidylethanolamine |
Related compounds | Tridecanoic acid, Pentadecanoic acid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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. The name of the acyl group derived from myristic acid is myristoyl or tetradecanoyl. The acid is named after the binomial name for nutmeg ( Myristica fragrans ), from which it was first isolated in 1841 by Lyon Playfair. [12]
Nutmeg butter has 75% trimyristin, the triglyceride of myristic acid and a source from which it can be synthesised. [13] Besides nutmeg, myristic acid is 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. [5] It is found in spermaceti, the crystallized fraction of oil from the sperm whale. It is also found in the rhizomes of the Iris, including Orris root. [14] [15]
Myristic acid acts as a lipid anchor in biomembranes. [16]
Reduction of myristic acid yields myristyl aldehyde and myristyl alcohol.
Myristic acid consumption raises low-density lipoprotein (LDL) cholesterol. [17] [18]
In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, from 4 to 28. Fatty acids are a major component of the lipids in some species such as microalgae but in some other organisms are not found in their standalone form, but instead exist as three main classes of esters: triglycerides, phospholipids, and cholesteryl esters. In any of these forms, fatty acids are both important dietary sources of fuel for animals and important structural components for cells.
In nutrition, biology, and chemistry, fat usually means any ester of fatty acids, or a mixture of such compounds, most commonly those that occur in living beings or in food.
A triglyceride is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other vertebrates, as well as vegetable fat. They are also present in the blood to enable the bidirectional transference of adipose fat and blood glucose from the liver, and are a major component of human skin oils.
Margarine is a spread used for flavoring, baking, and cooking. It is most often used as a substitute for butter. Although originally made from animal fats, most margarine consumed today is made from vegetable oil. The spread was originally named oleomargarine from Latin for oleum and Greek margarite. The name was later shortened to margarine.
Coconut oil is an edible oil derived from the kernels, meat, and milk of the coconut palm fruit. Coconut oil is a white solid fat below around 25 °C (77 °F), and a clear thin liquid oil in warmer climates. Unrefined varieties have a distinct coconut aroma. Coconut oil is used as a food oil, and in industrial applications for cosmetics and detergent production. The oil is rich in medium-chain fatty acids.
A saturated fat is a type of fat in which the fatty acid chains have all single bonds. A fat known as a glyceride is made of two kinds of smaller molecules: a short glycerol backbone and fatty acids that each contain a long linear or branched chain of carbon (C) atoms. Along the chain, some carbon atoms are linked by single bonds (-C-C-) and others are linked by double bonds (-C=C-). A double bond along the carbon chain can react with a pair of hydrogen atoms to change into a single -C-C- bond, with each H atom now bonded to one of the two C atoms. Glyceride fats without any carbon chain double bonds are called saturated because they are "saturated with" hydrogen atoms, having no double bonds available to react with more hydrogen.
Stearic acid is a saturated fatty acid with an 18-carbon chain. The IUPAC name is octadecanoic acid. It is a soft waxy solid with the formula CH3(CH2)16CO2H. The triglyceride derived from three molecules of stearic acid is called stearin. Stearic acid is a prevalent fatty-acid in nature, found in many animal and vegetable fats, but is usually higher in animal fat than vegetable fat. It has a melting point of 69.4 °C and a pKa of 4.50.
Palmitic acid is a fatty acid with a 16-carbon chain. It is the most common saturated fatty acid found in animals, plants and microorganisms. Its chemical formula is CH3(CH2)14COOH, and its C:D is 16:0. It is a major component of the oil from the fruit of oil palms, making up to 44% of total fats. Meats, cheeses, butter, and other dairy products also contain palmitic acid, amounting to 50–60% of total fats. Palmitates are the salts and esters of palmitic acid. The palmitate anion is the observed form of palmitic acid at physiologic pH (7.4). Major sources of C16:0 are palm oil, palm kernel oil, coconut oil, and milk fat.
Arachidic acid, also known as icosanoic acid, is a saturated fatty acid with a 20-carbon chain. It is a minor constituent of cupuaçu butter (7%), perilla oil (0–1%), peanut oil (1.1–1.7%), corn oil (3%), and cocoa butter (1%). The salts and esters of arachidic acid are known as arachidates.
In biochemistry and nutrition, a monounsaturated fat is a fat that contains a monounsaturated fatty acid (MUFA), a subclass of fatty acid characterized by having a double bond in the fatty acid chain with all of the remaining carbon atoms being single-bonded. By contrast, polyunsaturated fatty acids (PUFAs) have more than one double bond.
Lauric acid, systematically dodecanoic acid, is a saturated fatty acid with a 12-carbon atom chain, thus having many properties of medium-chain fatty acids. It is a bright white, powdery solid with a faint odor of bay oil or soap. The salts and esters of lauric acid are known as laurates.
Palm kernel oil is an edible plant oil derived from the kernel of the oil palm tree Elaeis guineensis. It is related to other two edible oils: palm oil, extracted from the fruit pulp of the oil palm, and coconut oil, extracted from the kernel of the coconut.
Capric acid, also known as decanoic acid or decylic acid, is a saturated fatty acid, medium-chain fatty acid (MCFA), and carboxylic acid. Its formula is CH3(CH2)8COOH. Salts and esters of decanoic acid are called caprates or decanoates. The term capric acid is derived from the Latin "caper / capra" (goat) because the sweaty, unpleasant smell of the compound is reminiscent of goats.
Trimyristin is a saturated fat and the triglyceride of myristic acid with the chemical formula C45H86O6. Trimyristin is a white to yellowish-gray solid that is insoluble in water, but soluble in ethanol, acetone, benzene, chloroform, dichloromethane, ether, and TBME.
Caprylic acid, also known under the systematic name octanoic acid or C8 Acid, is a saturated fatty acid, medium-chain fatty acid (MCFA). It has the structural formula H3C−(CH2)6−COOH, and is a colorless oily liquid that is minimally soluble in water with a slightly unpleasant rancid-like smell and taste. Salts and esters of octanoic acid are known as octanoates or caprylates. It is a common industrial chemical, which is produced by oxidation of the C8 aldehyde. Its compounds are found naturally in the milk of various mammals and as a minor constituent of coconut oil and palm kernel oil.
1-Tetradecanol, or commonly myristyl alcohol (from Myristica fragrans – the nutmeg plant), is a straight-chain saturated fatty alcohol, with the molecular formula CH3(CH2)12CH2OH. It is a white waxy solid that is practically insoluble in water, soluble in diethyl ether, and slightly soluble in ethanol.
Monoglycerides are a class of glycerides which are composed of a molecule of glycerol linked to a fatty acid via an ester bond. As glycerol contains both primary and secondary alcohol groups two different types of monoglycerides may be formed; 1-monoacylglycerols where the fatty acid is attached to a primary alcohol, or a 2-monoacylglycerols where the fatty acid is attached to the secondary alcohol.
Vaccenic acid is a naturally occurring trans fatty acid and an omega-7 fatty acid. It is the predominant kind of trans-fatty acid found in human milk, in the fat of ruminants, and in dairy products such as milk, butter, and yogurt. Trans fat in human milk may depend on trans fat content in food.
Tripalmitin is a triglyceride derived from the fatty acid palmitic acid.
Cooking oil is a plant or animal liquid fat used in frying, baking, and other types of cooking. Oil allows higher cooking temperatures than water, making cooking faster and more flavorful, while likewise distributing heat, reducing burning and uneven cooking. It sometimes imparts its own flavor. Cooking oil is also used in food preparation and flavoring not involving heat, such as salad dressings and bread dips.
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