Names | |
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Preferred IUPAC name Dodecanoic acid | |
Other names n-Dodecanoic acid, Dodecylic acid, Dodecoic acid, Laurostearic acid, Vulvic acid, 1-Undecanecarboxylic acid, Duodecylic acid, C12:0 (Lipid numbers) | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.005.075 |
EC Number |
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KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C12H24O2 | |
Molar mass | 200.322 g·mol−1 |
Appearance | White powder |
Odor | Slight odor of bay oil |
Density | 1.007 g/cm3 (24 °C) [1] 0.8744 g/cm3 (41.5 °C) [2] 0.8679 g/cm3 (50 °C) [3] |
Melting point | 43.8 °C (110.8 °F; 316.9 K) [3] |
Boiling point | 297.9 °C (568.2 °F; 571.0 K) 282.5 °C (540.5 °F; 555.6 K) at 512 mmHg [1] 225.1 °C (437.2 °F; 498.2 K) at 100 mmHg [3] [4] |
37 mg/L (0 °C) 55 mg/L (20 °C) 63 mg/L (30 °C) 72 mg/L (45 °C) 83 mg/L (100 °C) [5] | |
Solubility | Soluble in alcohols, diethyl ether, phenyls, haloalkanes, acetates [5] |
Solubility in methanol | 12.7 g/100 g (0 °C) 120 g/100 g (20 °C) 2250 g/100 g (40 °C) [5] |
Solubility in acetone | 8.95 g/100 g (0 °C) 60.5 g/100 g (20 °C) 1590 g/100 g (40 °C) [5] |
Solubility in ethyl acetate | 9.4 g/100 g (0 °C) 52 g/100 g (20°C) 1250 g/100 g (40°C) [5] |
Solubility in toluene | 15.3 g/100 g (0 °C) 97 g/100 g (20°C) 1410 g/100 g (40°C) [5] |
log P | 4.6 [6] |
Vapor pressure | 2.13·10−6 kPa (25 °C) [6] 0.42 kPa (150 °C) [4] 6.67 kPa (210 °C) [7] |
Acidity (pKa) | 5.3 (20 °C) [6] |
Thermal conductivity | 0.442 W/m·K (solid) [2] 0.1921 W/m·K (72.5 °C) 0.1748 W/m·K (106 °C) [1] |
Refractive index (nD) | 1.423 (70 °C) [1] 1.4183 (82 °C) [3] |
Viscosity | 6.88 cP (50 °C) 5.37 cP (60 °C) [2] |
Structure | |
Monoclinic (α-form) [8] Triclinic, aP228 (γ-form) [9] | |
P21/a, No. 14 (α-form) [8] P1, No. 2 (γ-form) [9] | |
2/m (α-form) [8] 1 (γ-form) [9] | |
α = 90°, β = 129.22°, γ = 90° | |
Thermochemistry | |
Heat capacity (C) | 404.28 J/mol·K [4] |
Std enthalpy of formation (ΔfH⦵298) | −775.6 kJ/mol [6] |
Std enthalpy of combustion (ΔcH⦵298) | 7377 kJ/mol 7425.8 kJ/mol (292 K) [4] |
Hazards | |
GHS labelling: | |
Danger | |
H412 [7] | |
P273 [7] | |
NFPA 704 (fire diamond) | |
Flash point | >113 °C (235 °F; 386 K) [7] |
Related compounds | |
Related compounds | Glyceryl laurate |
Related compounds | |
Related compounds | Undecanoic acid Tridecanoic acid Dodecanol Dodecanal Sodium lauryl sulfate |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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.
Lauric acid, as a component of triglycerides, comprises about half of the fatty-acid content in coconut milk, coconut oil, laurel oil, and palm kernel oil (not to be confused with palm oil), [10] [11] Otherwise, it is relatively uncommon. It is also found in human breast milk (6.2% of total fat), cow's milk (2.9%), and goat's milk (3.1%). [10]
Like many other fatty acids, lauric acid is inexpensive, has a long shelf-life, is nontoxic, and is safe to handle. It is used mainly for the production of soaps and cosmetics. For these purposes, lauric acid is reacted with sodium hydroxide to give sodium laurate, which is a soap. Most commonly, sodium laurate is obtained by saponification of various oils, such as coconut oil. These precursors give mixtures of sodium laurate and other soaps. [11]
Lauric acid is a precursor to dilauroyl peroxide, a common initiator of polymerizations.
Although 95% of medium-chain triglycerides are absorbed through the portal vein, only 25–30% of lauric acid is absorbed through it. [14]
Lauric acid increases total serum lipoproteins more than many other fatty acids, but mostly high-density lipoprotein (HDL). As a result, lauric acid has been characterized as having "a more favorable effect on total HDL than any other fatty acid [examined], either saturated or unsaturated". [15] In general, a lower total/HDL serum lipoprotein ratio correlates with a decrease in atherosclerotic incidence. [16] Nonetheless, an extensive meta-analysis on foods affecting the total LDL/serum lipoprotein ratio found in 2003 that the net effects of lauric acid on coronary artery disease outcomes remained uncertain. [17] A 2016 review of coconut oil (which is nearly half lauric acid) was similarly inconclusive about the effects on cardiovascular disease incidence. [14]
Cholesterol is the principal sterol of all higher animals, distributed in body tissues, especially the brain and spinal cord, and in animal fats and oils.
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.
High-density lipoprotein (HDL) is one of the five major groups of lipoproteins. Lipoproteins are complex particles composed of multiple proteins which transport all fat molecules (lipids) around the body within the water outside cells. They are typically composed of 80–100 proteins per particle. HDL particles enlarge while circulating in the blood, aggregating more fat molecules and transporting up to hundreds of fat molecules per particle.
A lipoprotein is a biochemical assembly whose primary function is to transport hydrophobic lipid molecules in water, as in blood plasma or other extracellular fluids. They consist of a triglyceride and cholesterol center, surrounded by a phospholipid outer shell, with the hydrophilic portions oriented outward toward the surrounding water and lipophilic portions oriented inward toward the lipid center. A special kind of protein, called apolipoprotein, is embedded in the outer shell, both stabilising the complex and giving it a functional identity that determines its role.
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.
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). Palmitic acid is the most common SFA found in plants, animals, and many microorganisms. Major sources of C16:0 are palm oil, palm kernel oil, coconut oil, and milk fat.
In biochemistry and nutrition, monounsaturated fats are fatty acids that have one double bond in the fatty acid chain with all of the remainder carbon atoms being single-bonded. By contrast, polyunsaturated fatty acids (PUFAs) have more than one double bond.
Stanol esters is a heterogeneous group of chemical compounds known to reduce the level of low-density lipoprotein (LDL) cholesterol in blood when ingested, though to a much lesser degree than prescription drugs such as statins. The starting material is phytosterols from plants. These are first hydrogenated to give a plant stanol which is then esterified with a mixture of fatty acids also derived from plants. Plant stanol esters are found naturally occurring in small quantities in fruits, vegetables, nuts, seeds, cereals, legumes, and vegetable oils.
Saponification value or saponification number represents the number of milligrams of potassium hydroxide (KOH) or sodium hydroxide (NaOH) required to saponify one gram of fat under the conditions specified. It is a measure of the average molecular weight of all the fatty acids present in the sample in form of triglycerides. The higher the saponification value, the lower the fatty acids average length, the lighter the mean molecular weight of triglycerides and vice versa. Practically, fats or oils with high saponification value are more suitable for soap making.
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.
Myristic 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, from which it was first isolated in 1841 by Lyon Playfair.
Babassu oil or cusi oil is a clear light yellow vegetable oil extracted from the seeds of the babassu palm which grows in the Amazon region of South America. It is a non-drying oil used in food, cleaners and skin products. This oil has properties similar to coconut oil and is used in much the same context. It is increasingly being used as a substitute for coconut oil. Babassu oil is about 70% lipids, in the following proportions:
Medium-chain triglycerides (MCTs) are triglycerides with two or three fatty acids having an aliphatic tail of 6–12 carbon atoms, i.e. medium-chain fatty acids (MCFAs). Rich food sources for commercial extraction of MCTs include palm kernel oil and coconut oil.
Vaccenic acid is a naturally occurring trans 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.
Blood lipids are lipids in the blood, either free or bound to other molecules. They are mostly transported in a phospholipid capsule, and the type of protein embedded in this outer shell determines the fate of the particle and its influence on metabolism. Examples of these lipids include cholesterol and triglycerides. The concentration of blood lipids depends on intake and excretion from the intestine, and uptake and secretion from cells. Hyperlipidemia is the presence of elevated or abnormal levels of lipids and/or lipoproteins in the blood, and is a major risk factor for cardiovascular disease.
Monolaurin (abbreviated GML; also called glycerol monolaurate, glyceryl laurate, and 1-lauroyl-glycerol) is a monoglyceride. It is the mono-ester formed from glycerol and lauric acid. Its chemical formula is C15H30O4.
The chronic endothelial injury hypothesis is one of two major mechanisms postulated to explain the underlying cause of atherosclerosis and coronary heart disease (CHD), the other being the lipid hypothesis. Although an ongoing debate involving connection between dietary lipids and CHD sometimes portrays the two hypotheses as being opposed, they are in no way mutually exclusive. Moreover, since the discovery of the role of LDL cholesterol (LDL-C) in the pathogenesis of atherosclerosis, the two hypotheses have become tightly linked by a number of molecular and cellular processes.
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.