| Revision as of 00:27, 8 March 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit |
Latest revision as of 16:10, 8 June 2024 edit undoGivatbrenner (talk | contribs)241 editsm full stop |
| (237 intermediate revisions by more than 100 users not shown) |
| Line 1: |
Line 1: |
|
|
{{redir|Laurate|the honorary title|Laureate}} |
|
{{chembox |
|
{{chembox |
|
|
| Verifiedfields = changed |
|
| verifiedrevid = 417602632 |
|
|
|
| Watchedfields = changed |
|
|ImageFile=Lauric acid.png |
|
|
|
| verifiedrevid = 417697408 |
|
|ImageSize= |
|
|
|ImageFile2=Lauric-acid-3D-balls.png |
|
| ImageFile = Lauric acid.svg |
|
|
| ImageSize = |
|
|IUPACName=dodecanoic acid |
|
|
|
| ImageName = Skeletal formula of lauric acid |
|
|OtherNames=''n''-Dodecanoic acid; Dodecylic acid; Dodecoic acid; |
|
|
|
| ImageFile2 = Lauric-acid-3D-balls.png |
|
Laurostearic acid; Vulvic acid; 1-Undecanecarboxylic acid; Duodecylic acid;<br />C12:0 (]) |
|
|
|
| ImageSize1 = |
|
|Section1= {{Chembox Identifiers |
|
|
|
| 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 (]) |
|
|
|Section1={{Chembox Identifiers |
|
|
| IUPHAR_ligand = 5534 |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo=143-07-7 |
|
| CASNo = 143-07-7 |
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
| PubChem=3893 |
|
|
|
| UNII = 1160N9NU9U |
|
}} |
|
|
|
| ChEBI_Ref = {{ebicite|changed|EBI}} |
|
|Section2= {{Chembox Properties |
|
|
|
| ChEBI = 30805 |
|
| Formula=C<sub>12</sub>H<sub>24</sub>O<sub>2</sub> |
|
|
|
| ChEMBL_Ref = {{ebicite|changed|EBI}} |
|
| Structural Formula=CH<sub>3</sub>(CH<sub>2</sub>)<sub>10</sub>CO<sub>2</sub>H |
|
|
|
| ChEMBL = 108766 |
|
| MolarMass=200.31776 |
|
|
|
| PubChem = 3893 |
|
| Appearance= white powder |
|
|
|
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
|
| Odor = slight odor of ] |
|
|
|
| ChemSpiderID = 3756 |
|
| Density=0.880 g/cm<sup>3</sup> |
|
|
|
| KEGG_Ref = {{keggcite|changed|kegg}} |
|
| MeltingPt=43.2 °C<ref>{{RubberBible86th}}</ref> |
|
|
|
| KEGG = C02679 |
|
| BoilingPt=298.9 °C |
|
|
|
| SMILES = O=C(O)CCCCCCCCCCC |
|
| Viscosity = 7.30 mPa·s at 323 K |
|
|
|
| InChI = 1/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14) |
|
| RefractIndex = 1.423 |
|
|
|
| InChIKey = POULHZVOKOAJMA-UHFFFAOYAP |
|
| Solubility= insoluble |
|
|
|
| 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) |
|
|Section3= {{Chembox Hazards |
|
|
|
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
|
| MainHazards= |
|
|
|
| StdInChIKey = POULHZVOKOAJMA-UHFFFAOYSA-N |
|
| FlashPt=≥ 110 °C |
|
|
|
| EINECS = 205-582-1 |
|
| Autoignition= |
|
|
|
}} |
|
|
|Section2={{Chembox Properties |
|
|
| C=12 | H=24 | O=2 |
|
|
| Appearance= White powder |
|
|
| Odor = Slight odor of ] |
|
|
| 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 |url-status=dead |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 ]s, ], ]s, ]s, ]s<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 = ] (α-form)<ref name=csba /><br /> ], ] (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 Å |
|
|
| LattConst_b = 4.965 Å |
|
|
| LattConst_c = 35.39 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|412}}<ref name="sigma" /> |
|
|
| PPhrases = {{P-phrases|273}}<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-H = 1 |
|
| NFPA-F = 1 |
|
| NFPA-F = 1 |
|
| NFPA-R = 1 |
|
| NFPA-R = 1 |
|
| NFPA-O = |
|
| NFPA-S = |
|
|
}} |
|
|
|Section6={{Chembox Related |
|
|
| OtherCompounds = ] |
|
|
}} |
|
|
|Section8={{Chembox Related |
|
|
| OtherCompounds = ]<br />]<br />]<br />]<br />] |
|
|
}} |
|
}} |
|
}} |
|
|
'''Lauric acid''', systematically '''dodecanoic acid''', is a ] with a 12-carbon atom chain, thus having many properties of ].<ref name=pubchem/> It is a bright white, powdery solid with a faint odor of ] or soap. The ] and ]s of lauric acid are known as '''laurates'''. |
|
| Section4 = {{Chembox Other |
|
|
| OtherCpds = ]}} |
|
|
}} |
|
|
'''Lauric acid''' (systematically: dodecanoic acid), the ] ] with a 12 carbon atom chain, is a white, powdery solid with a faint odor of bay oil or soap. |
|
|
|
|
|
|
==Occurrence== |
|
==Occurrence== |
|
Lauric acid is the main acid in ] and in ] (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 |url=http://iupac.org/publications/pac/73/4/0685/ |doi=10.1351/pac200173040685 |last1=Beare-Rogers |first1=J. |last2=Dieffenbacher |first2=A. |last3=Holm |first3=J.V.}}</ref> and is believed to have antimicrobial properties.<ref>{{cite journal |author=Hoffman KL, Han IY, Dawson PL |title=Antimicrobial effects of corn zein films impregnated with nisin, lauric acid, and EDTA |journal=J. Food Prot. |volume=64 |issue=6 |pages=885–9 |year=2001|pmid=11403145}}</ref><ref>{{cite journal |author=Ouattar B, Simard RE, Piett G, Bégin A, Holley RA |title=Inhibition of surface spoilage bacteria in processed meats by application of antimicrobial films prepared with chitosan |journal=Int. J. Food Microbiol. |volume=62 |issue=1–2 |pages=139–48 |year=2000|pmid=11139014 |doi= 10.1016/S0168-1605(00)00407-4}}</ref><ref>{{cite journal|journal = ]|volume = 81|issue = 5|pages = 721–726|title = Effect of lauric acid and nisin-impregnated soy-based films on the growth of Listeria monocytogenes on turkey bologna|author = PL Dawson, GD Carl, JC Acton, and IY Han|url = http://ps.fass.org/cgi/content/abstract/81/5/721|format = Free full text|pmid = 12033424|date=1 May 2002}}</ref><ref>{{cite journal|journal = ]|year = 2000 May| volume = 182|issue = 9|pages = 2668–2671|title = Equivalence of Lauric Acid and Glycerol Monolaurate as Inhibitors of Signal Transduction in Staphylococcus aureus|author = Alexey Ruzin and Richard P. Novick|url = http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=111339|format = Free full text|doi = 10.1128/JB.182.9.2668-2671.2000|pmid = 10762277|pmc = 111339}}</ref> |
|
Lauric acid, as a component of ]s, comprises about half of the fatty-acid content in ], ], ], and ] (not to be confused with ]),<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> Otherwise, it is relatively uncommon. It is also found in human ] (6.2% of total fat), cow's milk (2.9%), and goat's milk (3.1%).<ref name="lexicon" /> |
|
It is also found in human milk (6.2% of total fat), cow's milk (2.9%), and goat's milk (3.1%).<ref name="lexicon" /> |
|
|
|
|
|
|
|
===In various plants=== |
|
It also occurs in |
|
|
*The palm tree Orbignya phalerata Mart, a species popularly known in Brazil as babassu, |
|
*The palm tree '']'', a species popularly known in Brazil as ''babassu'' – 50% in ] |
|
*Attalea cohune cohune palm (also rain tree, American oil palm, corozo palm or manaca palm), |
|
*'']'', the cohune palm (also rain tree, American oil palm, corozo palm or manaca palm) – 46.5% in ] |
|
*Astrocaryum murumuru (Arecaceae) a palm native to Amazon |
|
*'']'' (Arecaceae) a palm native to the Amazon – 47.5% in "murumuru butter" |
|
|
*] 49% |
|
*Pycanthus kombo "African Nutmeg" |
|
|
|
*'']'' (African nutmeg) |
|
*Virola surinamensis (Wild nutmeg) 7.8–11.5% |
|
|
|
*'']'' (wild nutmeg) 7.8–11.5% |
|
*Peach palm seed 10.4% |
|
|
|
*] seed 10.4% |
|
*Betel nut 9% |
|
|
|
*] 9% |
|
*Date palm seed 0.56–5.4% |
|
|
|
*] seed 0.56–5.4% |
|
*Macadamia nut 0.072–1.1% |
|
|
|
*] 0.072–1.1% |
|
*Plum 0.35–0.38% |
|
|
|
*] 0.35–0.38% |
|
*Watermelon seed 0.33% |
|
|
|
*] seed 0.33% |
|
*Citrullus lanatus (egusi melon) |
|
|
|
*'']'' 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 |page = 109160 |doi = 10.1016/j.scienta.2019.109160|s2cid = 213568257 }}</ref> |
|
*Pumpkin flower 205 ppm, seed 472 ppm |
|
|
|
*'']'' (egusi melon) |
|
|
*] flower 205 ppm, pumpkin seed 472 ppm |
|
|
|
|
|
===Insect=== |
|
|
*Black soldier fly '']'' 30–50 mg/100 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== |
|
==Uses== |
|
|
Like many other ]s, lauric acid is inexpensive, has a long shelf-life, is nontoxic, and is safe to handle. It is used mainly for the production of ]s and ]. For these purposes, lauric acid is reacted with ] to give ], which is a ]. Most commonly, sodium laurate is obtained by ] of various oils, such as coconut oil. These precursors give mixtures of sodium laurate and other soaps.<ref name="Ullmann" /> |
|
Lauric acid is inexpensive, has a long shelf-life, and is non-toxic and safe to handle. Thus, it is often used in laboratory investigations of ]. Lauric acid is a solid at room temperature but melts easily in boiling water, so liquid lauric acid can be treated with various solutes and used to determine their molecular masses. '']'' experiments have suggested that some fatty acids including lauric acid could be a useful component in a treatment for ], but no clinical trials have yet been conducted to evaluate this potential benefit in humans.<ref>{{cite journal|last1=Nakatsuji|first1=T|last2=Kao|first2=MC|last3=Fang|first3=JY|last4=Zouboulis|first4=CC|last5=Zhang|first5=L|last6=Gallo|first6=RL|last7=Huang|first7=CM|title=Antimicrobial property of lauric acid against Propionibacterium acnes: its therapeutic potential for inflammatory acne vulgaris.|journal=The Journal of investigative dermatology|volume=129|issue=10|pages=2480–8|year=2009|pmid=19387482|pmc=2772209|doi=10.1038/jid.2009.93}}</ref><ref>{{cite journal|last1 = Yang|first1 = D|last2 = Pornpattananangkul|first2 = D|last3 = Nakatsuji|first3 = T|last4 = Chan|first4 = M|last5 = Carson|first5 = D|last6 = Huang|first6 = CM|last7 = Zhang|first7 = L|title = The antimicrobial activity of liposomal lauric acids against Propionibacterium acnes.|journal = Biomaterials|volume = 30|issue = 30|pages = 6035–40|year = 2009|pmid = 19665786|pmc = 2735618|doi = 10.1016/j.biomaterials.2009.07.033}}</ref> |
|
|
|
|
|
|
|
Lauric acid is a precursor to ], a common initiator of ]s.<ref name=pubchem/> |
|
Lauric is antibacterial, antioxidant, antiviral and COX-1-2 inhibitor. It frequently occurs in traditional medicinal remedies for ] (e.g., ]).<ref>{{cite journal|last1=Veeresh Babu|first1=S.V.|last2=Veeresh|first2=B.|last3=Patil|first3=Anup A.|last4=Warke|first4=Y.B.|title=Lauric acid and myristic acid prevent testosterone induced prostatic hyperplasia in rats|journal=European Journal of Pharmacology|volume=626|pages=262|year=2010|doi=10.1016/j.ejphar.2009.09.037}}</ref> |
|
|
|
|
|
|
==Nutritional and medical aspects== |
|
|
Although 95% of medium-chain triglycerides are absorbed through the ], only 25–30% of lauric acid is absorbed through it.<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 |page = 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> <ref name="pmid26946252">{{cite journal | vauthors=Eyres L, Eyres MF, Chisholm A, Brown RC | title=Coconut oil consumption and cardiovascular risk factors in humans | journal= ] | volume=74 | issue=4 | pages=267–280 | year=2016 | doi= 10.1093/nutrit/nuw002 | pmc= 4892314 | pmid = 26946252 }}</ref> Lauric acid induces apoptosis in cancer and promotes the proliferation of normal cells by maintaining cellular redox homeostasis. <ref name = "Ramya">{{cite journal |title = Lauric acid epigenetically regulates lncRNA HOTAIR by remodeling chromatin H3K4 tri-methylation and modulates glucose transport in SH-SY5Y human neuroblastoma cells: Lipid switch in macrophage activation |year = 2024 |journal = Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids |volume = 1869 |issue = 1 |page = 159429 |url=https://www.sciencedirect.com/science/article/pii/S1388198123001531 |doi = 10.1016/j.bbalip.2023.159429 |last1 = Ramya |first1 = Venkatesan |last2 = Shyam |first2 = Karuppiah Prakash |last3 = Angelmary |first3 = Arulanandu |last4 = Kadalmani |first4 = Balamuthu }}</ref> |
|
|
|
|
|
Lauric acid increases total serum ]s more than many other fatty acids, but mostly ]. As a result, lauric acid has been characterized as having "a more favorable effect on total HDL than any other fatty acid , 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> In general, a lower total/HDL serum lipoprotein ratio correlates with a decrease in atherosclerotic incidence.<ref name=Thijssen>Thijssen, M.A. and R.P. Mensink. (2005). . In Arnold von Eckardstein (Ed.) ''Atherosclerosis: Diet and Drugs''. Springer. pp. 171–172. {{ISBN|978-3-540-22569-0}}.</ref> Nonetheless, an extensive meta-analysis on foods affecting the total ]/serum lipoprotein ratio found in 2003 that the net effects of lauric acid on coronary artery disease outcomes remained uncertain.<ref></ref> A 2016 review of coconut oil (which is nearly half lauric acid) was similarly inconclusive about the effects on ] incidence.<ref name="pmid26946252" /> |
|
|
|
|
|
==References== |
|
==References== |
|
{{reflist}} |
|
{{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. . {{ISBN|978-0-12-016437-0}}. |
|
|
|
|
|
==External links== |
|
|
{{Commons category|Lauric acid}} |
|
|
* |
|
|
|
|
|
{{Fatty acids}} |
|
{{Fatty acids}} |
|
|
{{Lipids}} |
|
|
{{Palm oil}} |
|
|
|
|
|
{{Authority control}} |
|
|
|
|
|
{{DEFAULTSORT:Lauric Acid}} |
|
{{DEFAULTSORT:Lauric Acid}} |
|
] |
|
] |
|
] |
|
] |
|
] |
|
] |
|
|
] |
|
|
|
|
|
] |
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|