ラウリン酸 lauric acid、ラウリン酸エステル

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/07/24 00:23:20」(JST)

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Lauric acid (systematically: dodecanoic acid), the saturated fatty acid with a 12-carbon atom chain, thus falling into the medium chain fatty acids, is a white, powdery solid with a faint odor of bay oil or soap.

Occurrence[edit]

Lauric acid, as a component of triglycerides, comprises about half of the fatty acid content in coconut oil, laurel 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[edit]

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[edit]

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 (43.2 °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[edit]

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]

Lauric acid converts to the monoglyceride monolaurin in the body.

References[edit]

^ 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.
^ ^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.
^ 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.
^ 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.
^ 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.
^ 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.

Appendix: occurrence of lauric acid in various foods[edit]

The palm tree Orbignya phalerata Mart, a species popularly known in Brazil as babassu. 50% in babassu oil.
Attalea cohune, the cohune palm (also rain tree, American oil palm, corozo palm or manaca palm) 46.5% in cohune oil.
Astrocaryum murumuru (Arecaceae) a palm native to the Amazon, 47.5% in "murumuru butter".
Coconut and Coconut oil
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

English Journal

Potato protein isolates: Recovery and characterization of their properties.

Waglay A, Karboune S, Alli I.SourceDepartment of Food Science and Agricultural Chemistry, McGill University, 21, 111 Lakeshore, Ste-Anne de Bellevue, Quebec H9X 3V9, Canada.
Food chemistry.Food Chem.2014 Jan 1;142:373-82. doi: 10.1016/j.foodchem.2013.07.060. Epub 2013 Jul 20.
An imitation of industrial potato fruit juice (PFJ) was prepared, using Canadian variety of potatoes, and was characterized of being composed of 22.9% patatin, 53.3% protease inhibitors, and 23.7% high MW proteins. To isolate potato proteins from PFJ, several extraction techniques were explored incl
PMID 24001855

Synthesis and properties of fatty acid starch esters.

Winkler H, Vorwerg W, Wetzel H.SourceFraunhofer Institute for Applied Polymer Research, Division Biopolymers, Department Starch/Molecular Structure, Geiselbergstr. 69, 14476 Potsdam, Germany. Electronic address: henning.winkler@iap.fraunhofer.de.
Carbohydrate polymers.Carbohydr Polym.2013 Oct 15;98(1):208-16. doi: 10.1016/j.carbpol.2013.05.086. Epub 2013 Jun 7.
Being completely bio-based, fatty acid starch esters (FASEs) are attractive materials that represent an alternative to crude oil-based plastics. In this study, two synthesis methods were compared in terms of their efficiency, toxicity and, especially, product solubility with starch laurate (C12) as
PMID 23987337

Elution strategies for reversed-phase high-performance liquid chromatography analysis of sucrose alkanoate regioisomers with charged aerosol detection.

Lie A, Pedersen LH.SourceDepartment of Biotechnology, Chemistry and Environmental Engineering, Aalborg University, Sohngaardsholmsvej 49, 9000 Aalborg, Denmark. Electronic address: alie@bio.aau.dk.
Journal of chromatography. A.J Chromatogr A.2013 Oct 11;1311:127-33. doi: 10.1016/j.chroma.2013.08.081. Epub 2013 Aug 27.
A broad range of elution strategies for RP-HPLC analysis of sucrose alkanoate regioisomers with CAD was systematically evaluated. The HPLC analyses were investigated using design-of-experiments methodology and analysed by analysis of variance (ANOVA) and regression modelling. Isocratic elutions, iso
PMID 24011419

Japanese Journal

Swirl-Flow Membrane Emulsification for High Throughput of Dispersed Phase Flux through Shirasu Porous Glass (SPG) Membrane

SHIMODA Mitsuya,MIYAMAE Hirokazu,NISHIYAMA Kei,YUASA Tomoyuki,NOMA Seiji,IGURA Noriyuki
Journal of chemical engineering of Japan 44(1), 1-6, 2011-03-01
… Shirasu porous glass (SPG) as a micro porous membrane, methyl laurate as a dispersed oil phase, and sodium dodecyl sulfate (SDS) as an emulsifier were used. …
NAID 130000424558

Protease-Catalyzed Monoacylation of 2-O-α-D-Glucopyranosyl-L-ascorbic Acid in Three Solvent Systems

TAI Akihiro,IWAOKA Yuji,MORI Tasuku,ITO Hideyuki
Bioscience, biotechnology, and biochemistry 74(9), 1969-1971, 2010-09-23
… 6-O-Dodecanoyl-2-O-α-D-glucopyranosyl-L-ascorbic acid (6-sDode-AA-2G) was synthesized from 2-O-α-D-glucopyranosyl-L-ascorbic acid and vinyl laurate with a protease from Bacillus subtilis in 30% dimethylformamide (DMF)/dioxane with a low water content. …
NAID 10027560038

「ラウリン酸」

Lauric acid
	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
CAS number	143-07-7
PubChem	3893
ChemSpider	3756
ChEMBL	CHEMBL108766
Jmol-3D images	Image 1
	SMILES O=C(O)CCCCCCCCCCC ;
	InChI InChI=1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14) ; Key: POULHZVOKOAJMA-UHFFFAOYSA-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 ;
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
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	1 1 1
Flash point	≥ 110 °C
Related compounds
Related compounds	Glyceryl laurate
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references