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Lauric acid

From Wikipedia, the free encyclopedia
"Laurate" redirects here. For the honorary title, seeLaureate.
Lauric acid
Skeletal formula of lauric acid
Skeletal formula of lauric acid
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 InfoCard100.005.075Edit this at Wikidata
EC Number
  • 205-582-1
KEGG
UNII
  • 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 mass200.322 g·mol−1
AppearanceWhite powder
OdorSlight odor ofbay oil
Density1.007 g/cm3 (24 °C)[1]
0.8744 g/cm3 (41.5 °C)[2]
0.8679 g/cm3 (50 °C)[3]
Melting point43.8 °C (110.8 °F; 316.9 K)[3]
Boiling point297.9 °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]
SolubilitySoluble inalcohols,diethyl ether,phenyls,haloalkanes,acetates[5]
Solubility inmethanol12.7 g/100 g (0 °C)
120 g/100 g (20 °C)
2250 g/100 g (40 °C)[5]
Solubility inacetone8.95 g/100 g (0 °C)
60.5 g/100 g (20 °C)
1590 g/100 g (40 °C)[5]
Solubility inethyl acetate9.4 g/100 g (0 °C)
52 g/100 g (20°C)
1250 g/100 g (40°C)[5]
Solubility intoluene15.3 g/100 g (0 °C)
97 g/100 g (20°C)
1410 g/100 g (40°C)[5]
logP4.6[6]
Vapor pressure2.13·10−6 kPa (25 °C)[6]
0.42 kPa (150 °C)[4]
6.67 kPa (210 °C)[7]
Acidity (pKa)5.3 (20 °C)[6]
Thermal conductivity0.442 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]
Viscosity6.88 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:
GHS05: Corrosive
Danger
H318[7]
P280,P305+P351+P338[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 theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Lauric acid, systematicallydodecanoic acid, is asaturated fatty acid with a 12-carbon atom chain, thus having many properties ofmedium-chain fatty acids.[6] It is a bright white, powdery solid with a faint odor ofbay oil or soap. Thesalts andesters of lauric acid are known aslaurates. Lauric acid accounts for nearly half of thefat incoconut oil andpalm oil.

Occurrence

[edit]

Lauric acid, as a component oftriglycerides, comprises about half of the fatty-acid content incoconut milk, coconut oil,laurel oil, andpalm kernel oil (not to be confused with palm oil).[10][11][12] Oils with high levels of lauric acid are known aslauric oils.[13][14] Otherwise, it is relatively uncommon. It is also found in humanbreast milk (6.2% of total fat), cow's milk (2.9%), and goat's milk (3.1%).[10]

In various plants

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Insect

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Uses

[edit]

Like many otherfatty acids, lauric acid is inexpensive, has a long shelf-life, is nontoxic, and is safe to handle. It is used mainly for the production ofsoaps andcosmetics. For these purposes, lauric acid is reacted withsodium hydroxide to givesodium laurate, which is asoap. Most commonly, sodium laurate is obtained bysaponification of various oils, such as coconut oil. These precursors give mixtures of sodium laurate and other soaps.[11]

Lauric acid is a precursor todilauroyl peroxide, a commercial initiator ofpolymerizations.[6]

Production and reactions

[edit]

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 (O=C(C11H23)2).[17] Ittransesterifies withvinyl acetate.[18] Treatment withsulfur trioxide gives the α-sulfonic acid.[19]

As a dietary fat and cardiovascular risk factor

[edit]

Lauric acid increases total serumlipoproteins more than many other fatty acids, includingLDL andhigh-density lipoprotein (HDL), making it arisk factor forcardiovascular 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 and coconut oil (about 47% of total fat), replacing dietary coconut oil and its high lauric acid content with oils containing mostlyunsaturated fats would alter total blood lipids in a way that reduces cardiovascular disease risk.[12]

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

References

[edit]
  1. ^abcdG., 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 fromthe original(PDF) on 2014-11-03. Retrieved2014-06-22.
  2. ^abcMezaki, Reiji; Mochizuki, Masafumi; Ogawa, Kohei (2000).Engineering data on mixing (1st ed.). Elsevier Science B.V. p. 278.ISBN 0-444-82802-8.
  3. ^abcdLide, David R., ed. (2009).CRC Handbook of Chemistry and Physics (90th ed.).Boca Raton, Florida:CRC Press.ISBN 978-1-4200-9084-0.
  4. ^abcdDodecanoic 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. ^abcdefSeidell, Atherton; Linke, William F. (1952).Solubilities of inorganic and organic compounds (3rd ed.). New York: D. Van Nostrand Company. pp. 742–743.
  6. ^abcdefCID 3893 fromPubChem
  7. ^abcdSigma-Aldrich Co.,Lauric acid. Retrieved on 2014-06-14.
  8. ^abcdVand, 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. ^abcSydow, Erik von (1956)."On the structure of the crystal form A of lauric acid"(PDF).actachemscand.org. Acta Chemica Scandinavica. Retrieved2014-06-14.
  10. ^abBeare-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. ^abcDavid 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. ^abcdEyres 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. ^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. ^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. ^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. ^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. ^J. C. Sauer (1951). "Laurone".Organic Syntheses.31: 68.doi:10.15227/orgsyn.031.0068.
  18. ^Swern, Daniel; Jordan, Jr, E. F. (1950). "Vinyl Laurate and Other Vinyl Esters".Organic Syntheses.30: 106.doi:10.15227/orgsyn.030.0106.
  19. ^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. ^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.ISBN 978-3-540-22569-0.
  22. ^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

[edit]
  • 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.ISBN 978-0-12-016437-0.

External links

[edit]
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Saturated
ω−3 Unsaturated
ω−5 Unsaturated
ω−6 Unsaturated
ω−7 Unsaturated
ω−9 Unsaturated
ω−10 Unsaturated
ω−11 Unsaturated
ω−12 Unsaturated
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