- Lauric acid
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Lauric acid 
dodecanoic acidOther namesn-Dodecanoic acid; Dodecylic acid; Dodecoic acid; Laurostearic acid; Vulvic acid; 1-Undecanecarboxylic acid; Duodecylic acid;
C12:0 (Lipid numbers)Identifiers CAS number 143-07-7 
PubChem 3893 ChEMBL CHEMBL108766 
Properties Molecular formula C12H24O2 Molar mass 200.31776 Appearance white powder Odor slight odor of bay oil Density 0.880 g/cm3 Melting point 43.2 °C[1]
Boiling point 298.9 °C
Solubility in water 0.006 g/100 mL (20 °C) Refractive index (nD) 1.423 Viscosity 7.30 mPa·s at 323 K Hazards NFPA 704 
111Flash point ≥ 110 °C Related compounds Related compounds Glyceryl laurate 
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)Infobox references Lauric acid (systematically: dodecanoic acid), the saturated fatty acid with a 12-carbon atom chain, is a white, powdery solid with a faint odor of bay oil or soap.
Contents
Occurrence
Lauric acid, as a component of triglycerides, comprises about half of the fatty acid content in coconut oil and in palm kernel oil (not to be confused with palm oil),[2][3] 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%).[2]
Properties
Like many other fatty acids, lauric acid is inexpensive, has a long shelf-life, and is non-toxic and safe to handle. It is mainly used for the production of soaps and cosmetics. For these purposes, lauric acid is neutralized 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.[3]
Niche uses
In the laboratory, lauric acid is often used to investigate the molar mass of an unknown substance via the freezing-point depression. Lauric acid is convenient because its melting point when pure is relatively high (43.9 °C). Its cryoscopic constant is 3.9 K/kg/mol. By melting lauric acid with the unknown substance, allowing it to cool, and recording the temperature at which the mixture freezes, the molar mass of the unknown compound may be determined.[4]
Potential medicinal properties
Lauric acid has been claimed to have antimicrobial properties.[5][6][7][8]
Lauric acid has been found to increase total cholesterol the most of all fatty acids. But most of the increase is attributable to an increase in high-density lipoprotein (HDL) "good" cholesterol. As a result, lauric acid has "a more favorable effect on total:HDL cholesterol than any other fatty acid, either saturated or unsaturated";[9] a lower total/HDL cholesterol ratio suggests a decrease in atherosclerotic risk.[10]
References
- ^ Lide, D. R., ed (2005). CRC Handbook of Chemistry and Physics (86th ed.). Boca Raton (FL): CRC Press. ISBN 0-8493-0486-5.
- ^ a b 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. http://iupac.org/publications/pac/73/4/0685/.
- ^ a b 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
- ^ "Using Freezing Point Depression to find Molecular Weight". University of California, Irvine. 2010-04-12. https://eee.uci.edu/programs/gchem/02MANfrzptdep.pdf.
- ^ Hoffman KL, Han IY, Dawson PL (2001). "Antimicrobial effects of corn zein films impregnated with nisin, lauric acid, and EDTA". J. Food Prot. 64 (6): 885–9. PMID 11403145.
- ^ Ouattar B, Simard RE, Piett G, Bégin A, Holley RA (2000). "Inhibition of surface spoilage bacteria in processed meats by application of antimicrobial films prepared with chitosan". Int. J. Food Microbiol. 62 (1–2): 139–48. doi:10.1016/S0168-1605(00)00407-4. PMID 11139014.
- ^ PL Dawson, GD Carl, JC Acton, and IY Han (1 May 2002). "Effect of lauric acid and nisin-impregnated soy-based films on the growth of Listeria monocytogenes on turkey bologna" (Free full text). Poultry Science 81 (5): 721–726. PMID 12033424. http://ps.fass.org/cgi/content/abstract/81/5/721.
- ^ Alexey Ruzin and Richard P. Novick (May 2000). "Equivalence of Lauric Acid and Glycerol Monolaurate as Inhibitors of Signal Transduction in Staphylococcus aureus" (Free full text). J Bacteriol 182 (9): 2668–2671. doi:10.1128/JB.182.9.2668-2671.2000. PMC 111339. PMID 10762277. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=111339.
- ^ Mensink RP, Zock PL, Kester ADM, 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. ISSN 0002-9165. PMID 12716665. http://www.ajcn.org/content/77/5/1146.full?ijkey=846a72387ebc0d82545acd5442a0c3a9e9fc3566.
- ^ 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 9783540225690.
Appendix: occurrence of lauric acid in various foods
- The palm tree Orbignya phalerata Mart, a species popularly known in Brazil as babassu
- Attalea cohune, the cohune palm (also rain tree, American oil palm, corozo palm or manaca palm)
- Astrocaryum murumuru (Arecaceae) a palm native to the Amazon
- Pycnanthus kombo (African nutmeg)
- Virola surinamensis (wild nutmeg) 7.8–11.5%
- Peach palm seed 10.4%
- Betel nut 9%
- Date palm seed 0.56–5.4%
- Macadamia nut 0.072–1.1%
- Plum 0.35–0.38%
- Watermelon seed 0.33%
- Citrullus lanatus (egusi melon)
- Pumpkin flower 205 ppm, pumpkin seed 472 ppm
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. ISBN 9780120164370.
- Kabara, Jon J. (1978). The Pharmacological Effect of Lipids. Champaign IL: American Oil Chemist's Society. ISBN 9991817697.
- Kabara, Jon J. (2008). Fats Are Good for You and Other Secrets – How Saturated Fat and Cholesterol Actually Benefit the Body. North Atlantic Books. ISBN 1556436904.
Lipids: fatty acids Saturated VFA: Acetic (C2) · Propionic (C3) · Butyric (C4) · Valeric (C5) · Caproic (C6) · Enanthic (C7) · Caprylic (C8) · Pelargonic (C9) · Capric (C10) · Undecylic (C11) · Lauric (C12) · Tridecylic (C13) · Myristic (C14) · Pentadecanoic (C15) · Palmitic (C16) · Margaric (C17) · Stearic (C18) · Nonadecylic (C19) · Arachidic (C20) · Heneicosylic (C21) · Behenic (C22) · Tricosylic (C23) · Lignoceric (C24) · Pentacosylic (C25) · Cerotic (C26) · Heptacosylic (C27) · Montanic (C28) · Nonacosylic (C29) · Melissic (C30) · Hentriacontylic (C31) · Lacceroic (C32) · Psyllic (C33) · Geddic (C34) · Ceroplastic (C35) · Hexatriacontylic (C36)n−3 Unsaturated n−6 Unsaturated n−9 Unsaturated biochemical families: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) · amac/i · ncbs/i · ttpy/i
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