{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 396344370 | Reference = <ref>''Merck Index'', 11th Edition, '''6246'''</ref> | ImageFile = Myristic acid.svg | ImageClass = skin-invert | ImageSize = | ImageName = Skeletal formula of myristic acid | ImageFile1 = Myristic-acid-3D-balls.png | ImageClass1 = bg-transparent | ImageSize1 = | ImageName1 = Ball-and-stick model of myristic acid | PIN = Tetradecanoic acid | OtherNames = C14:0 (Lipid numbers) |Section1={{Chembox Identifiers | IUPHAR_ligand = 2806 | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 544-63-8 | UNII_Ref = {{fdacite|changed|FDA}} | UNII = 0I3V7S25AW | PubChem = 11005 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 28875 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 111077 | SMILES = CCCCCCCCCCCCCC(=O)O | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 10539 | InChI = 1/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16) | InChIKey = TUNFSRHWOTWDNC-UHFFFAOYAZ | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16) | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = TUNFSRHWOTWDNC-UHFFFAOYSA-N | RTECS = QH4375000 | EINECS = 208-875-2 }} |Section2={{Chembox Properties | C=14 | H=28 | O=2 | Appearance = colorless or white solid | Density = 1.03 g/cm<sup>3</sup> (−3 °C)<ref name=adb /><br/> 0.99 g/cm<sup>3</sup> (24 °C)<ref name=dspace>{{cite web|url = http://dspace.unimap.edu.my/bitstream/handle/123456789/14118/008_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 = Chuah|first1 = T.G.|last2 = Rozanna|first2 = D.|last3 = Salmiah|first3 = A.|last4 = Thomas|first4 = Choong S.Y.|last5 = Sa’ari|first5 = M.|publisher = University Putra Malaysia|access-date = 17 June 2014|year = 2006}}</ref><br/> 0.8622 g/cm<sup>3</sup> (54 °C)<ref name=crc /> | MeltingPtC = 54.4 | MeltingPt_ref = <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.L. |last2=Dieffenbacher |first2=A. |last3=Holm |first3=J.V. |s2cid=84492006 }}</ref> | BoilingPtC = 326.2 | BoilingPt_notes = at 760 mmHg<br/> {{convert|250|C|F K}}<br/> at 100 mmHg<ref name=crc /><br/> {{convert|218.3|C|F K}}<br/> at 32 mmHg<ref name=dspace /> | Solubility = 13 mg/L (0 °C)<br/> 20 mg/L (20 °C)<br/> 24 mg/L (30 °C)<br/> 33 mg/L (60 °C)<ref name=sioc>{{cite book|last1 = Seidell|first1 = Atherton|last2 = Linke|first2 = William F.|year = 1940|title = Solubilities of Inorganic and Organic Compounds|publisher = D. Van Nostrand Company|place = New York|edition = 3rd|url = http://babel.hathitrust.org/cgi/pt?id=mdp.39015082385801;view=1up;seq=770|pages = 762–763}}</ref> | SolubleOther = Soluble in alcohol, acetates, C<sub>6</sub>H<sub>6</sub>, haloalkanes, phenyls, nitros<ref name=sioc /> | Solubility1 = 2.75 g/100 g (0 °C)<br /> 15.9 g/100 g (20 °C)<br/> 42.5 g/100 g (30 °C)<br/> 149 g/100 g (40 °C)<ref name=sioc /> | Solvent1 = acetone | Solubility2 = 6.95 g/100 g (10 °C)<br/> 29.2 g/100 g (20 °C)<br/> 87.4 g/100 g (30 °C)<br/> 1.29 kg/100 g (50 °C)<ref name=sioc /> | Solvent2 = benzene | Solubility3 = 2.8 g/100 g (0 °C)<br/> 17.3 g/100 g (20 °C)<br /> 75 g/100 g (30 °C)<br /> 2.67 kg/100 g (50 °C)<ref name=sioc /> | Solvent3 = methanol | Solubility4 = 3.4 g/100 g (0 °C)<br/> 15.3 g/100 g (20 °C)<br/> 44.7 g/100 g (30 °C)<br/> 1.35 kg/100 g (40 °C)<ref name=sioc /> | Solvent4 = ethyl acetate | Solubility5 = 0.6 g/100 g (−10 °C)<br/> 3.2 g/100 g (0 °C)<br/> 30.4 g/100 g (20 °C)<br/> 1.35 kg/100 g (50 °C)<ref name=sioc /> | Solvent5 = toluene | Viscosity = 7.2161 cP (60 °C)<br/> 3.2173 cP (100 °C)<br/> 0.8525 cP (200 °C)<br/> 0.3164 cP (300 °C)<ref name="trp">{{cite book|last = Yaws|first = Carl L.|year = 2009|title = Transport Properties of Chemicals and Hydrocarbons|publisher = William Andrew Inc.|place = New York|url = https://books.google.com/books?id=NbvExWe30YsC&pg=PA177|page = 177|isbn = 978-0-8155-2039-9}}</ref> | LogP = 6.1<ref name=crc>{{CRC90}}</ref> | RefractIndex = 1.4723 (70 °C)<ref name=crc /> | VaporPressure = 0.01 kPa (118 °C)<br/> 0.27 kPa (160 °C)<ref name="nist" /><br/> 1 kPa (186 °C)<ref name="crc" /> | ThermalConductivity = 0.159 W/m·K (70 °C)<br/> 0.151 W/m·K (100 °C)<br/> 0.138 W/m·K (160 °C)<ref>{{cite book|last = Vargaftik|first = Natan B.|year = 1993|title = Handbook of Thermal Conductivity of Liquids and Gases|publisher = CRC Press|edition = illustrated|isbn = 978-0-8493-9345-7|url = https://books.google.com/books?id=DFo1sZBwdNgC&pg=PA305|page = 305|display-authors=etal}}</ref> | MagSus = −176·10<sup>−6</sup> cm<sup>3</sup>/mol }} |Section3={{Chembox Structure | CrystalStruct = Monoclinic (−3 °C)<ref name=adb>{{cite web|url = http://www.rsc.org/suppdata/nj/b3/b307208h/b307208h.pdf|title = On the crystal structures and melting point alternation of the n-alkyl carboxylic acids|last = Bond|first = Andrew D.|website = RSC.org|publisher = Royal Society of Chemistry|access-date = 17 June 2014|year = 2003}}</ref> | SpaceGroup = P2<sub>1</sub>/c<ref name="adb" /> | PointGroup = | LattConst_a = 31.559&nbsp;Å | LattConst_b = 4.9652&nbsp;Å | LattConst_c = 9.426&nbsp;Å<ref name="adb" /> | LattConst_alpha = | LattConst_beta = 94.432 | LattConst_gamma = }} |Section4={{Chembox Thermochemistry | DeltaHc = 8675.9 kJ/mol<ref name="nist">{{nist|name=Tetradecanoic acid|id=C544638|access-date=17 June 2014|mask=FFFF|units=SI}}</ref> | HeatCapacity = 432.01 J/mol·K<ref name="crc" /><ref name="nist" /> | DeltaHf = −833.5 kJ/mol<ref name="crc" /><ref name="nist" /> }} |Section7={{Chembox Hazards | GHSPictograms = {{GHS07}}<ref name="sigma">{{Sigma-Aldrich|id=w276405|name=Myristic acid|access-date=17 June 2014}}</ref> | GHSSignalWord = Warning | HPhrases = {{H-phrases|315}}<ref name="sigma" /> | FlashPt = > | FlashPtC = 110 | FlashPt_ref = <ref name="fca" /> | NFPA-H = 2 | NFPA-F = 1 | NFPA-R = 0 | NFPA_ref = <ref name="fca" /> | LD50 = >10 g/kg (rats, oral)<ref name="fca">{{cite web|url = http://www.chemicalland21.com/industrialchem/organic/MYRISTIC%20ACID.htm|title = Myristic Acid |website = ChemicalLand21.com |access-date = 17 June 2014|publisher = AroKor Holdings Inc.}}</ref> }} |Section8={{Chembox Related | OtherCompounds = Tridecanoic acid, Pentadecanoic acid | OtherFunction = Isopropyl myristate<br/>Phorbol myristate acetate<br/>Myristylbenzylmorphine<br/>Dimyristoylphosphatidylethanolamine | OtherFunction_label = esters of myristic acid }} }}

'''Myristic acid''' (IUPAC name: '''tetradecanoic acid''') is a common saturated fatty acid with the molecular formula {{chem2|CH3(CH2)12COOH}}. Its salts and esters are commonly referred to as '''myristates''' or tetradecanoates. The name of the acyl group derived from myristic acid is '''myristoyl''' or '''tetradecanoyl'''. The acid is named after the binomial name for nutmeg (''Myristica fragrans''), from which it was first isolated in 1841 by Lyon Playfair.<ref name="Playfair2009">{{cite journal|last1=Playfair|first1=Lyon|title=XX. On a new fat acid in the butter of nutmegs|journal=Philosophical Magazine |series=Series 3|volume=18|issue=115|year=2009|pages=102–113|issn=1941-5966|doi=10.1080/14786444108650255|url=https://zenodo.org/record/1431027}}</ref>

==Occurrence== 200px|thumbnail|left|''Myristica fragrans'' (nutmeg) fruit contains myristic acid Nutmeg butter has 75% trimyristin, the triglyceride of myristic acid and a source from which it can be synthesised.<ref>{{cite journal|first = G. D.|last = Beal|url = http://www.orgsyn.org/demo.aspx?prep=CV1P0379|doi = 10.15227/orgsyn.006.0066|title = Myristic Acid|journal = Organic Syntheses|volume = 6|pages = 66|year = 1926|url-access = subscription}}</ref> Besides nutmeg, myristic acid is found in palm kernel oil, coconut oil, butterfat, 8–14% of bovine milk, and 8.6% of breast milk as well as being a minor component of many other animal fats.<ref name="lexicon" /> It is found in spermaceti, the crystallized fraction of oil from the sperm whale. It is also found in the rhizomes of the Iris, including Orris root.<ref>Council of Europe, August 2007 {{Google books|e8OwTIHMJDAC|Natural Sources of Flavourings, Volume 2|page=103}}</ref><ref>John Charles Sawer {{Google books|J_cJAwAAQBAJ| Odorographia a natural history of raw materials and drugs used in the perfume industry intended to serve growers, manufacturers and consumers|page=108}}</ref>

==Chemical behaviour== {{see also|Myristoylation}} Myristic acid acts as a lipid anchor in biomembranes.<ref name="Lehninger Textbook">{{cite book|last=Cox|first=David L. Nelson, Michael M.|title=Lehninger principles of biochemistry|year=2005|publisher=W.H. Freeman|location=New York|isbn=978-0716743392|edition=4th|url-access=registration|url=https://archive.org/details/lehningerprincip00lehn_0}}</ref>

Reduction of myristic acid yields myristyl aldehyde and myristyl alcohol.

==Health effects==

Myristic acid consumption raises low-density lipoprotein (LDL) cholesterol.<ref>{{cite journal|author=Mensink, Ronald P.|year=2016|title=Effects of saturated fatty acids on serum lipids and lipoproteins: a systematic review and regression analysis|journal=World Health Organization|url=https://apps.who.int/iris/bitstream/handle/10665/246104/9789241565349-eng.pdf|volume=|issue=|pages=}}</ref><ref>{{cite journal|vauthors=Schwingshackl L, Bogensberger B, Benčič A, Knüppel S, Boeing H, Hoffmann G |year=2018|title=Effects of oils and solid fats on blood lipids: a systematic review and network meta-analysis|journal=J Lipid Res|volume=59|issue=9|pages=1771–1782|doi=10.1194/jlr.P085522|pmid=30006369|doi-access=free|pmc=6121943}}</ref>

==See also== * Saturated fat * Myristyl myristate * List of saturated fatty acids

==References== {{reflist|30em}} {{Commons category|Myristic acid|position=left}} {{Fatty acids}}

Category:Fatty acids Category:Alkanoic acids