Lauric acid

Last updated
Lauric acid
Lauric acid.svg
Lauric-acid-3D-balls.png
Names
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 205-582-1
KEGG
PubChem CID
UNII
  • InChI=1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14) X mark.svgN
    Key: POULHZVOKOAJMA-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14)
    Key: POULHZVOKOAJMA-UHFFFAOYAP
  • O=C(O)CCCCCCCCCCC
Properties
C12H24O2
Molar mass 200.322 g·mol−1
AppearanceWhite 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]
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]
a = 9.524 Å, b = 4.965 Å, c = 35.39 Å (α-form) [8]
α = 90°, β = 129.22°, γ = 90°
Thermochemistry
404.28 J/mol·K [4]
−775.6 kJ/mol [6]
7377 kJ/mol
7425.8 kJ/mol (292 K) [4]
Hazards
GHS labelling:
GHS-pictogram-acid.svg
Danger
H412 [7]
P273 [7]
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
1
1
1
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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. [6] 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.

Contents

Occurrence

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]

In various plants

Insect

Uses

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. [6]

Nutritional and medical aspects

Although 95% of medium-chain triglycerides are absorbed through the portal vein, only 25–30% of lauric acid is absorbed through it. [14] [15] Lauric acid induces apoptosis in cancer and promotes the proliferation of normal cells by maintaining cellular redox homeostasis. [16]

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". [17] In general, a lower total/HDL serum lipoprotein ratio correlates with a decrease in atherosclerotic incidence. [18] 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. [19] A 2016 review of coconut oil (which is nearly half lauric acid) was similarly inconclusive about the effects on cardiovascular disease incidence. [15]

Related Research Articles

<span class="mw-page-title-main">Fat</span> Esters of fatty acid or triglycerides

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.

<span class="mw-page-title-main">Copra</span> Dried meat or kernel of the coconut

Copra is the dried, white flesh of the coconut from which coconut oil is extracted. Traditionally, the coconuts are sun-dried, especially for export, before the oil, also known as copra oil, is pressed out. The oil extracted from copra is rich in lauric acid, making it an important commodity in the preparation of lauryl alcohol, soaps, fatty acids, cosmetics, etc. and thus a lucrative product for many coconut-producing countries. The palatable oil cake, known as copra cake, obtained as a residue in the production of copra oil is used in animal feeds. The ground cake is known as coconut or copra meal.

<span class="mw-page-title-main">Margarine</span> Semi-solid oily spread often used as a butter substitute

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.

<span class="mw-page-title-main">Coconut oil</span> Edible oil derived from coconut

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 between the carbon atoms. 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.

<span class="mw-page-title-main">Palmitic acid</span> Chemical compound

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 ratio is 16:0. It is a major component of palm oil from the fruit of Elaeis guineensis, 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.

<span class="mw-page-title-main">Coconut milk</span> Liquid extracted from coconuts

Coconut milk is an opaque, milky-white liquid extracted from the grated pulp of mature coconuts. The opacity and rich taste of coconut milk are due to its high oil content, most of which is saturated fat. Coconut milk is a traditional food ingredient used in Southeast Asia, Oceania, South Asia, and East Africa. It is also used for cooking in the Caribbean, tropical Latin America, and West Africa, where coconuts were introduced during the colonial era.

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.

<span class="mw-page-title-main">Saponification value</span> Milligrams of a base required to saponify 1g of fat

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 two other 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. The name of the acyl group derived from myristic acid is myristoyl or tetradecanoyl. The acid is named after the binomial name for nutmeg, from which it was first isolated in 1841 by Lyon Playfair.

<span class="mw-page-title-main">Babassu oil</span> Vegetable oil from the seeds of the babassu palm

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:

<span class="mw-page-title-main">Medium-chain triglyceride</span> Medium-chain fatty acids

A medium-chain triglyceride (MCT) is a triglyceride with two or three fatty acids having an aliphatic tail of 6–12 carbon atoms, i.e. a medium-chain fatty acid (MCFA). Rich food sources for commercial extraction of MCTs include palm kernel oil and coconut oil.

<i>Astrocaryum murumuru</i> Species of palm

Astrocaryum murumuru is a palm native to Amazon Rainforest vegetation in Brazil, which bears edible fruits. Murumuru butter, extracted from the seeds of the plant, may be used as a moisturizer. One remarkable feature of this palm is that it is covered with spines up to twelve inches in length.

Oleochemistry is the study of vegetable oils and animal oils and fats, and oleochemicals derived from these fats and oils. The resulting product can be called oleochemicals (from Latin: oleum "olive oil"). The major product of this industry is soap, approximately 8.9×106 tons of which were produced in 1990. Other major oleochemicals include fatty acids, fatty acid methyl esters, fatty alcohols and fatty amines. Glycerol is a side product of all of these processes. Intermediate chemical substances produced from these basic oleochemical substances include alcohol ethoxylates, alcohol sulfates, alcohol ether sulfates, quaternary ammonium salts, monoacylglycerols (MAG), diacylglycerols (DAG), structured triacylglycerols (TAG), sugar esters, and other oleochemical products.

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.

In the food industry and biochemistry, interesterification (IE) is a process that rearranges the fatty acids of a fat product, typically a mixture of triglycerides. The process implies breaking and reforming the ester bonds C–O–C that connect the fatty acid chains to the glycerol hubs of the fat molecules. The reactions involve catalysts, either inorganic chemicals or enzymes.

<span class="mw-page-title-main">Cooking oil</span> Oil consumed by humans, of vegetable or animal origin

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.

<i>Attalea dubia</i> Species of palm

Attalea dubia, also known as the Indaiá plant, babassu palm, or bacuaçu palm is a flowering plant in the family Arecaceae, native to the Southern and Southeast Regions of Brazil.

References

  1. 1 2 3 4 G., Chuah T.; D., Rozanna; A., Salmiah; Y., Thomas Choong S.; M., Sa'ari (2006). "Fatty acids used as phase change materials (PCMs) for thermal energy storage in building material applications" (PDF). University Putra Malaysia. Archived from the original (PDF) on 2014-11-03. Retrieved 2014-06-22.
  2. 1 2 3 Mezaki, Reiji; Mochizuki, Masafumi; Ogawa, Kohei (2000). Engineering data on mixing (1st ed.). Elsevier Science B.V. p. 278. ISBN   0-444-82802-8.
  3. 1 2 3 4 Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN   978-1-4200-9084-0.
  4. 1 2 3 4 Dodecanoic acid in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2014-06-14)
  5. 1 2 3 4 5 6 Seidell, Atherton; Linke, William F. (1952). Solubilities of inorganic and organic compounds (3rd ed.). New York: D. Van Nostrand Company. pp. 742–743.
  6. 1 2 3 4 5 6 CID 3893 from PubChem
  7. 1 2 3 4 Sigma-Aldrich Co., Lauric acid. Retrieved on 2014-06-14.
  8. 1 2 3 4 Vand, V.; Morley, W. M.; Lomer, T. R. (1951). "The crystal structure of lauric acid". Acta Crystallographica. 4 (4): 324–329. Bibcode:1951AcCry...4..324V. doi: 10.1107/S0365110X51001069 .
  9. 1 2 3 Sydow, Erik von (1956). "On the structure of the crystal form A of lauric acid" (PDF). actachemscand.org. Acta Chemica Scandinavica. Retrieved 2014-06-14.
  10. 1 2 Beare-Rogers, J.; Dieffenbacher, A.; Holm, J.V. (2001). "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry. 73 (4): 685–744. doi: 10.1351/pac200173040685 . S2CID   84492006.
  11. 1 2 David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. doi : 10.1002/14356007.a10_245.pub2
  12. ↑ Zarifikhosroshahi; Tugba Murathan; Kafkas; Okatan (2019). "Variation in volatile and fatty acid contents among Viburnum opulus L. Fruits growing different locations". Scientia Horticulturae. 264: 109160. doi:10.1016/j.scienta.2019.109160. S2CID   213568257.
  13. ↑ Montevecchi, G.; Zanasi, L.; Masino, F.; Maistrello, L.; Antonelli, A. (2019). "Black soldier fly (Hermetia illucens L.): effect on the fat integrity using different approaches to the killing of the prepupae". Journal of Insects as Food and Feed. 6 (2): 121–131. doi:10.3920/JIFF2019.0002. S2CID   208604432.
  14. ↑ Ramya, Venkatesan; Shyam, Karuppiah Prakash; Kowsalya, Eshwaran; Balavigneswaran, Chelladurai Karthikeyan; Kadalmani, Balamuthu (2022). "Dual Roles of Coconut Oil and Its Major Component Lauric Acid on Redox Nexus: Focus on Cytoprotection and Cancer Cell Death". Frontiers in Neuroscience. 16: 833630. doi: 10.3389/fnins.2022.833630 . PMC   8963114 . PMID   35360165.
  15. 1 2 Eyres L, Eyres MF, Chisholm A, Brown RC (2016). "Coconut oil consumption and cardiovascular risk factors in humans". Nutrition Reviews . 74 (4): 267–280. doi:10.1093/nutrit/nuw002. PMC   4892314 . PMID   26946252.
  16. ↑ Ramya, Venkatesan; Shyam, Karuppiah Prakash; Angelmary, Arulanandu; Kadalmani, Balamuthu (2024). "Lauric acid epigenetically regulates lncRNA HOTAIR by remodeling chromatin H3K4 tri-methylation and modulates glucose transport in SH-SY5Y human neuroblastoma cells: Lipid switch in macrophage activation". Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids. 1869 (1): 159429. doi:10.1016/j.bbalip.2023.159429.
  17. ↑ Mensink RP, Zock PL, Kester AD, Katan MB (May 2003). "Effects of dietary fatty acids and carbohydrates on the ratio of serum total to HDL cholesterol and on serum lipids and apolipoproteins: a meta-analysis of 60 controlled trials". American Journal of Clinical Nutrition. 77 (5): 1146–1155. doi: 10.1093/ajcn/77.5.1146 . ISSN   0002-9165. PMID   12716665.
  18. ↑ Thijssen, M.A. and R.P. Mensink. (2005). Fatty Acids and Atherosclerotic Risk. In Arnold von Eckardstein (Ed.) Atherosclerosis: Diet and Drugs. Springer. pp. 171–172. ISBN   978-3-540-22569-0.
  19. ↑ Effects of dietary fatty acids and carbohydrates on the ratio of serum total to HDL cholesterol and on serum lipids and apolipoproteins: a meta-analysis of 60 controlled trials

Further reading

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