Lauric acid

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Lauric acid
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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
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3D model (JSmol)
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  • InChI=1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14) ☒N
    Key: POULHZVOKOAJMA-UHFFFAOYSA-N ☒N
  • 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
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]
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
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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).
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Template:Chembox Footer/trackingTemplate:Short description

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. Lauric acid accounts for nearly half of the fat in coconut oil and palm kernel oil.

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][12] Oils with high levels of lauric acid are known as lauric oils.[13][14] 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 commercial initiator of polymerizations.[6]

Production and reactions

Lauric acid is mainly isolated from natural sources.[11] Its reactions are representative of those of similar long chain, saturated fatty acids. It can be converted to the symmetrical fatty ketone called laurone (Page Module:Chem2/styles.css has no content.O=C(C11H23)2).[17] It transesterifies with vinyl acetate.[18] Treatment with sulfur trioxide gives the α-sulfonic acid.[19]

As a dietary fat and cardiovascular risk factor

Lauric acid increases total serum lipoproteins more than many other fatty acids, including LDL and high-density lipoprotein (HDL), making it a risk factor for cardiovascular diseases.[12] Lauric acid has been characterized as having "a more favorable effect on total HDL than any other fatty acid [examined], either saturated or unsaturated",[20] which may favor a lower cardiovascular disease risk.[21] However, given the prominence of lauric acid in palm kernel and coconut oil (about 47% of total fat), replacing dietary coconut oil and its high lauric acid content with oils containing mostly unsaturated fats would alter total blood lipids in a way that reduces cardiovascular disease risk.[12]

Although 95% of medium-chain triglycerides are absorbed through the portal vein, only 25–30% of lauric acid is absorbed through this vein.[12][22]

References

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  1. ^ a b c d Page Module:Citation/CS1/styles.css has no content.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. ^ a b c Page Module:Citation/CS1/styles.css has no content.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. ^ a b c d Page Module:Citation/CS1/styles.css has no content.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. ^ a b c d Template:Nist
  5. ^ a b c d e f Page Module:Citation/CS1/styles.css has no content.Seidell, Atherton; Linke, William F. (1952). Solubilities of inorganic and organic compounds (3rd ed.). New York: D. Van Nostrand Company. pp. 742–743.
  6. ^ a b c d e f CID 3893 from PubChemTemplate:EditAtWikidataTemplate:WikidataCheck
  7. ^ a b c d Sigma-Aldrich Co., Lauric acid. Retrieved on 2014-06-14.
  8. ^ a b c d Page Module:Citation/CS1/styles.css has no content.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. ^ a b c Page Module:Citation/CS1/styles.css has no content.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. ^ a b Page Module:Citation/CS1/styles.css has no content.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. ^ a b c 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. Script error: No such module "CS1 identifiers".
  12. ^ a b c d Page Module:Citation/CS1/styles.css has no content.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.
  13. ^ Page Module:Citation/CS1/styles.css has no content.Dijkstra, D.J. (2015). "Lauric Oils". Encyclopedia of Food and Health. pp. 517–522. doi:10.1016/B978-0-12-384947-2.00513-4. ISBN 978-0-12-384953-3.
  14. ^ Page Module:Citation/CS1/styles.css has no content.Amri, Ibrahim Nuzul (2011). "The Lauric (Coconut and Palm Kernel) Oils". In Gunstone, Frank D. (ed.). Vegetable Oils in Food Technology: Composition, Properties and Uses (2 ed.). pp. 169–197. doi:10.1002/9781444339925.ch6. ISBN 978-1-4443-3268-1.
  15. ^ Page Module:Citation/CS1/styles.css has no content.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.
  16. ^ Page Module:Citation/CS1/styles.css has no content.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.
  17. ^ Page Module:Citation/CS1/styles.css has no content.J. C. Sauer (1951). "Laurone". Organic Syntheses. 31: 68. doi:10.15227/orgsyn.031.0068.
  18. ^ Page Module:Citation/CS1/styles.css has no content.Swern, Daniel; Jordan, Jr, E. F. (1950). "Vinyl Laurate and Other Vinyl Esters". Organic Syntheses. 30: 106. doi:10.15227/orgsyn.030.0106.
  19. ^ Page Module:Citation/CS1/styles.css has no content.Weil, J. K.; Bistline, Jr., R. G.; Stirton, A. J. (1956). "α-Sulfopalmitic Acid". Organic Syntheses. 36: 83. doi:10.15227/orgsyn.036.0083.
  20. ^ Page Module:Citation/CS1/styles.css has no content.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.
  21. ^ 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. Template:ISBN.
  22. ^ Page Module:Citation/CS1/styles.css has no content.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.

Further reading

  • Berner, Louise A. (1993). Defining the Role of Milkfat in Balanced Diets. In John E. Kinsella (Ed.) Advances in Food and Nutrition Research – Volume 37. Academic Press. pp. 159–166. Template:ISBN.

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