{{redir|Laurate|the honorary title|Laureate}} {{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 417697408 | ImageFile = Lauric acid.svg | ImageClass = skin-invert | ImageSize = | ImageName = Skeletal formula of lauric acid | ImageFile2 = Lauric-acid-3D-balls.png | ImageClass2 = bg-transparent | ImageSize1 = | ImageName1 = Ball-and-stick model of lauric acid | PIN = Dodecanoic acid | OtherNames =''n''-Dodecanoic acid, Dodecylic acid, Dodecoic acid, Laurostearic acid, Vulvic acid, 1-Undecanecarboxylic acid, Duodecylic acid, C12:0 (Lipid numbers) |Section1={{Chembox Identifiers | IUPHAR_ligand = 5534 | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 143-07-7 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 1160N9NU9U | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 30805 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 108766 | PubChem = 3893 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 3756 | KEGG_Ref = {{keggcite|changed|kegg}} | KEGG = C02679 | SMILES = O=C(O)CCCCCCCCCCC | InChI = 1/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14) | InChIKey = POULHZVOKOAJMA-UHFFFAOYAP | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14) | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = POULHZVOKOAJMA-UHFFFAOYSA-N | EINECS = 205-582-1 }} |Section2={{Chembox Properties | C=12 | H=24 | O=2 | Appearance= White powder | Odor = Slight odor of bay oil | Density = 1.007 g/cm<sup>3</sup> (24 °C)<ref name=dspace /><br /> 0.8744 g/cm<sup>3</sup> (41.5 °C)<ref name=edm /><br /> 0.8679 g/cm<sup>3</sup> (50 °C)<ref name=crc /> | MeltingPtC = 43.8 | MeltingPt_ref = <ref name=crc>{{CRC90}}</ref> | BoilingPtC = 297.9 | BoilingPt_notes = <br /> {{convert|282.5|C|F K}}<br /> at 512 mmHg<ref name=dspace>{{cite web|url=http://dspace.unimap.edu.my/dspace/bitstream/123456789/14118/1/008_010_012_014-015_fatty%20a.pdf |title=Fatty acids used as phase change materials (PCMs) for thermal energy storage in building material applications |last1=G. |first1=Chuah T. |last2=D. |first2=Rozanna |last3=A. |first3=Salmiah |last4=Y. |first4=Thomas Choong S. |last5=M. |first5=Sa'ari |publisher=University Putra Malaysia |access-date=2014-06-22 |year=2006 |archive-url=https://web.archive.org/web/20141103225311/http://dspace.unimap.edu.my/dspace/bitstream/123456789/14118/1/008_010_012_014-015_fatty%20a.pdf |archive-date=2014-11-03 }}</ref><br /> {{convert|225.1|C|F K}}<br /> at 100 mmHg<ref name=crc /><ref name=nist /> | Viscosity = 6.88 cP (50 °C)<br /> 5.37 cP (60 °C)<ref name=edm /> | RefractIndex = 1.423 (70 °C)<ref name=dspace /><br /> 1.4183 (82 °C)<ref name=crc /> | Solubility= 37 mg/L (0 °C)<br /> 55 mg/L (20 °C)<br /> 63 mg/L (30 °C)<br /> 72 mg/L (45 °C)<br /> 83 mg/L (100 °C)<ref name=sioc>{{cite book|last1 = Seidell|first1 = Atherton|last2 = Linke|first2 = William F.|year = 1952|title = Solubilities of inorganic and organic compounds|publisher = D. Van Nostrand Company|place = New York|edition = 3rd|pages = 742–743}}</ref> | VaporPressure = 2.13·10<sup>−6</sup> kPa (25 °C)<ref name=pubchem /><br /> 0.42 kPa (150 °C)<ref name=nist /><br /> 6.67 kPa (210 °C)<ref name="sigma" /> | pKa = 5.3 (20 °C)<ref name=pubchem>{{PubChemLink|3893}}</ref> | LogP = 4.6<ref name=pubchem /> | Solubility1 = 12.7 g/100 g (0 °C)<br /> 120 g/100 g (20 °C)<br /> 2250 g/100 g (40 °C)<ref name=sioc /> | Solvent1 = methanol | Solubility2 = 8.95 g/100 g (0 °C)<br /> 60.5 g/100 g (20 °C)<br /> 1590 g/100 g (40 °C)<ref name=sioc /> | Solvent2 = acetone | Solubility3 = 9.4 g/100 g (0 °C)<br /> 52 g/100 g (20°C)<br /> 1250 g/100 g (40°C)<ref name=sioc /> | Solvent3 = ethyl acetate | Solubility4 = 15.3 g/100 g (0 °C)<br /> 97 g/100 g (20°C)<br /> 1410 g/100 g (40°C)<ref name=sioc /> | Solvent4 = toluene | SolubleOther = Soluble in alcohols, diethyl ether, phenyls, haloalkanes, acetates<ref name=sioc /> | ThermalConductivity = 0.442 W/m·K (solid)<ref name=edm>{{cite book|last1 = Mezaki|first1 = Reiji|last2 = Mochizuki|first2 = Masafumi|last3 = Ogawa|first3 = Kohei|year = 2000|title = Engineering data on mixing|publisher = Elsevier Science B.V.|isbn = 0-444-82802-8|page = 278|url = https://books.google.com/books?id=6PDnxdmwlKUC&pg=PA278|edition = 1st}}</ref><br /> 0.1921 W/m·K (72.5 °C)<br /> 0.1748 W/m·K (106 °C)<ref name=dspace /> }} |Section3={{Chembox Structure | Dipole = | CrystalStruct = Monoclinic (α-form)<ref name=csba /><br /> Triclinic, aP228 (γ-form)<ref name=acta>{{cite web|url = http://actachemscand.org/pdf/acta_vol_10_p0001-0008.pdf|title = On the structure of the crystal form A of lauric acid|last = Sydow|first = Erik von|website = actachemscand.org|publisher = Acta Chemica Scandinavica|access-date = 2014-06-14|year = 1956|volume = 10}}</ref> | SpaceGroup = P2<sub>1</sub>/a, No. 14 (α-form)<ref name=csba /><br /> P{{overline|1}}, No. 2 (γ-form)<ref name=acta /> | PointGroup = 2/m (α-form)<ref name=csba /><br /> {{overline|1}} (γ-form)<ref name=acta /> | LattConst_a = 9.524&nbsp;Å | LattConst_b = 4.965&nbsp;Å | LattConst_c = 35.39&nbsp;Å (α-form)<ref name=csba>{{Cite journal | doi = 10.1107/S0365110X51001069| title = The crystal structure of lauric acid| journal = Acta Crystallographica| volume = 4| issue = 4| pages = 324–329| year = 1951| last1 = Vand | first1 = V.| last2 = Morley | first2 = W. M.| last3 = Lomer | first3 = T. R.| doi-access = free| bibcode = 1951AcCry...4..324V}}</ref> | LattConst_alpha = | LattConst_beta = 129.22 | LattConst_gamma = }} |Section4={{Chembox Thermochemistry | DeltaHc = 7377 kJ/mol<br /> 7425.8 kJ/mol (292 K)<ref name=nist>{{nist|name=Dodecanoic acid|id=C143077|accessdate=2014-06-14|mask=FFFF|units=SI}}</ref> | HeatCapacity = 404.28 J/mol·K<ref name=nist /> | DeltaHf = −775.6 kJ/mol<ref name=pubchem /> }} |Section5={{Chembox Hazards | MainHazards = | GHSPictograms = {{GHS05}} | GHSSignalWord = Danger | HPhrases = {{H-phrases|318}}<ref name="sigma" /> | PPhrases = {{P-phrases|280|305+351+338}}<ref name="sigma" /> | FlashPtC = 113 | FlashPt = > | FlashPt_ref = <ref name="sigma">{{Sigma-Aldrich|id=w261416|name=Lauric acid|accessdate=2014-06-14}}</ref> | AutoignitionPt = | NFPA-H = 1 | NFPA-F = 1 | NFPA-R = 1 | NFPA-S = }} |Section6={{Chembox Related | OtherCompounds = Glyceryl laurate }} |Section8={{Chembox Related | OtherCompounds = Undecanoic acid<br />Tridecanoic acid<br />Dodecanol<br />Dodecanal<br />Sodium lauryl sulfate }} }} '''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.<ref name=pubchem/> 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).<ref name="lexicon">{{cite journal |year=2001 |title=Lexicon of lipid nutrition (IUPAC Technical Report) |journal=Pure and Applied Chemistry |volume=73 |issue=4 |pages=685–744 |doi=10.1351/pac200173040685 |doi-access=free |last1=Beare-Rogers |first1=J. |last2=Dieffenbacher |first2=A. |last3=Holm |first3=J.V. |s2cid=84492006 }}</ref><ref name=Ullmann>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}}</ref><ref name=eyres/> Oils with high levels of lauric acid are known as ''lauric oils''.<ref>{{cite encyclopedia|encyclopedia=Encyclopedia of Food and Health |last=Dijkstra |first=D.J. |title=Lauric Oils |doi=10.1016/B978-0-12-384947-2.00513-4 |date=2015|pages=517–522 |isbn=978-0-12-384953-3 }}</ref><ref>{{cite book |chapter=The Lauric (Coconut and Palm Kernel) Oils |last=Amri |first=Ibrahim Nuzul |editor-last=Gunstone |editor-first=Frank D. |title=Vegetable Oils in Food Technology: Composition, Properties and Uses |edition=2 |date=2011 |pages=169–197 |doi=10.1002/9781444339925.ch6|isbn=978-1-4443-3268-1 }}</ref> 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%).<ref name="lexicon" />

===In various plants=== *The palm tree ''Attalea speciosa'', a species 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 oil 47-49% *''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% *''Viburnum opulus'' 0.24-0.33%<ref name = viburnumopulus_fatcomp2019>{{cite journal |title = Variation in volatile and fatty acid contents among Viburnum opulus L. Fruits growing different locations |year = 2019 |last1 = Zarifikhosroshahi |last2 = Tugba Murathan |last3 = Kafkas |last4 = Okatan |journal = Scientia Horticulturae |volume = 264 |article-number = 109160 |doi = 10.1016/j.scienta.2019.109160|s2cid = 213568257 }}</ref> *''Citrullus lanatus'' (egusi melon) *Pumpkin flower 205 ppm, pumpkin seed 472 ppm

===Insect=== *Black soldier fly ''Hermetia illucens'' 30–50&nbsp;mg/100&nbsp;mg fat.<ref name="Montevecchi">{{cite journal |year=2019 |title=Black soldier fly (Hermetia illucens L.): effect on the fat integrity using different approaches to the killing of the prepupae. |journal=Journal of Insects as Food and Feed |url=https://www.wageningenacademic.com/doi/abs/10.3920/JIFF2019.0002 |doi=10.3920/JIFF2019.0002 |last1=Montevecchi |first1=G. |last2=Zanasi |first2=L. |last3=Masino |first3=F. |last4=Maistrello |first4=L. |last5=Antonelli |first5=A.|volume=6 |issue=2 |pages=121–131 |s2cid=208604432 }}</ref>

==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.<ref name="Ullmann" />

Lauric acid is a precursor to dilauroyl peroxide, a commercial initiator of polymerizations.<ref name=pubchem/>

==Production and reactions== Lauric acid is mainly isolated from natural sources.<ref name=Ullmann/> Its reactions are representative of those of similar long chain, saturated fatty acids. It can be converted to the symmetrical fatty ketone called laurone ({{chem2|O\dC(C_{11}H_{23})2}}).<ref>{{cite journal |author=J. C. Sauer|doi=10.15227/orgsyn.031.0068 |title=Laurone |journal=Organic Syntheses |date=1951 |volume=31 |page=68 }}</ref> It transesterifies with vinyl acetate.<ref>{{cite journal |doi=10.15227/orgsyn.030.0106 |title=Vinyl Laurate and Other Vinyl Esters |journal=Organic Syntheses |date=1950 |volume=30 |page=106|first1=Daniel|last1=Swern|first2=E. F.|last2=Jordan, Jr }}</ref> Treatment with sulfur trioxide gives the α-sulfonic acid.<ref>{{cite journal |doi=10.15227/orgsyn.036.0083 |title=α-Sulfopalmitic Acid |journal=Organic Syntheses |date=1956 |volume=36 |page=83| first1=J. K.|last1=Weil|first2=R. G.|last2=Bistline, Jr.|first3=A. J.|last3=Stirton }}</ref>

==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.<ref name="eyres">{{cite journal | vauthors=Eyres L, Eyres MF, Chisholm A, Brown RC | title=Coconut oil consumption and cardiovascular risk factors in humans | journal= Nutrition Reviews | volume=74 | issue=4 | pages=267–280 | year=2016 | doi= 10.1093/nutrit/nuw002 | pmc= 4892314 | pmid = 26946252 }}</ref> Lauric acid has been characterized as having "a more favorable effect on total HDL than any other fatty acid [examined], either saturated or unsaturated",<ref name=Mensink2003>{{cite journal | title = 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 | url=http://www.ajcn.org/content/77/5/1146.full?ijkey=846a72387ebc0d82545acd5442a0c3a9e9fc3566 | journal =American Journal of Clinical Nutrition |vauthors=Mensink RP, Zock PL, Kester AD, Katan MB | volume=77 | issue=5 | pages = 1146–1155 |date=May 2003 | issn = 0002-9165 | pmid = 12716665|doi = 10.1093/ajcn/77.5.1146| doi-access =free }}</ref> which may favor a lower cardiovascular disease risk.<ref name=Thijssen>Thijssen, M.A. and R.P. Mensink. (2005). [https://books.google.com/books?id=kvo6BN1AGNAC&pg=PA171 Fatty Acids and Atherosclerotic Risk]. In Arnold von Eckardstein (Ed.) ''Atherosclerosis: Diet and Drugs''. Springer. pp. 171–172. {{ISBN|978-3-540-22569-0}}.</ref> 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.<ref name=eyres/>

Although 95% of medium-chain triglycerides are absorbed through the portal vein, only 25–30% of lauric acid is absorbed through this vein.<ref name=eyres/><ref name = "RamyaFrontiers">{{cite journal |title = Dual Roles of Coconut Oil and Its Major Component Lauric Acid on Redox Nexus: Focus on Cytoprotection and Cancer Cell Death |year = 2022 |journal = Frontiers in Neuroscience |volume = 16 |article-number = 833630 |doi = 10.3389/fnins.2022.833630 |doi-access = free |last1 = Ramya |first1 = Venkatesan |last2 = Shyam |first2 = Karuppiah Prakash |last3 = Kowsalya |first3 = Eshwaran |last4 = Balavigneswaran |first4 = Chelladurai Karthikeyan |last5 = Kadalmani |first5 = Balamuthu |pmid = 35360165 |pmc = 8963114 }}</ref>

==References== {{reflist}}

==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. [https://books.google.com/books?id=wflcBD1PKx8C&pg=PA159 159–166]. {{ISBN|978-0-12-016437-0}}.

==External links== {{Commons category|Lauric acid}} * [http://gmd.mpimp-golm.mpg.de/Spectrums/82155059-5257-4809-a5d5-c30751495378.aspx Lauric acid MS Spectrum]

{{Fatty acids}} {{Lipids}} {{Palm oil}}

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{{DEFAULTSORT:Lauric Acid}} Category:Fatty acids Category:Nutrition Category:Palm oil Category:Laurates Category:Alkanoic acids