{{위키데이터 속성 추적}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 396344370
| Reference =<ref>''Merck Index'', 11th Edition, '''6246'''</ref>
| ImageFile = Myristic acid.svg
| ImageSize = 
| ImageName = Skeletal formula of myristic acid
| ImageFile1 = Myristic-acid-3D-balls.png
| ImageSize1 =
| ImageName1 = Ball-and-stick model of myristic acid
| IUPACName = Tetradecanoic acid
| OtherNames = C14:0 ([[Lipid number]]s)
|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 = 
| 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>{{웹 인용|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|last = G.|first = 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 = 17 June 2014|year = 2006|archive-date = 2014-11-03|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}}</ref><br/> 0.8622 g/cm<sup>3</sup> (54 °C)<ref name=crc />
| MeltingPtC = 54.4
| MeltingPt_notes =<ref name="lexicon">{{저널 인용|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 |last1=Beare-Rogers |first1=J. L |last2=Dieffenbacher |first2=A |last3=Holm |first3=J. V }}</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>{{서적 인용|last = Seidell|first = 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]], [[acetate]]s, [[벤젠|C<sub>6</sub>H<sub>6</sub>]], [[haloalkane]]s, [[phenyl group|phenyl]]s, [[nitro compound|nitro]]s<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">{{서적 인용|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>{{서적 인용|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 crystal system|Monoclinic]] (−3 °C)<ref name=adb>{{웹 인용|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=미리스트산<br>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_notes =<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">{{웹 인용|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]]
 }}
}}
'''미리스트산'''({{llang|en|myristic acid}}) 또는 '''테트라데칸산'''은 화학식이 CH<sub>3</sub>(CH<sub>2</sub>)<sub>12</sub>COOH인 포화 [[지방산]]이다. 미리스트산의 [[염]]과 [[에스터]](에스테르)는 일반적으로 미리스테이트라고 한다. 미리스트산은 [[육두구]](''Myristica fragrans'')의 [[학명]]을 따서 명명되었으며, 1841년에 스코틀랜드의 과학자인 라이언 플레이페어(Lyon Playfair)에 의해 최초로 분리되었다.<ref name="Playfair2009">{{저널 인용|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}}</ref>

== 발견 ==
[[파일:Myristica fragrans.JPG|200px|thumbnail|left|''Myristica fragrans''의 열매에는 미리스트산이 포함되어 있다.]]
육두구 버터는 트라이미리스틴(미리스트산의 [[트라이글리세라이드]])의 함량이 75%이다. 미리스트산은 육두구 외에도 [[팜핵유]], [[코코넛오일]], [[유지방]], [[우유]](8~14%), [[모유]](8.6%)에서 발견되며, 다른 많은 동물성 지방의 부수적 성분이다.<ref>Beare-Rogers, J. L; 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</ref> 미리스트산은 [[향유고래]] 머리 부분에서 얻은 기름을 냉각, 압축해서 얻는 [[경랍]]에서도 발견된다. [[붓꽃속|아이리스]]의 뿌리, 뿌리줄기에서도 발견되고,<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> [[두리안]]의 일종인 ''Durio graveolens''의 열매 지방의 14.49%를 차지한다.<ref name="Nasaruddin">{{저널 인용|last1=Nasaruddin|first1=Mohd hanif|last2=Noor|first2=Noor Qhairul Izzreen Mohd|last3=Mamat|first3=Hasmadi|title=Komposisi Proksimat dan Komponen Asid Lemak Durian Kuning (Durio graveolens) Sabah|journal=Sains Malaysiana|date=2013|volume=42|issue=9|pages=1283–1288|url=http://www.ukm.my/jsm/pdf_files/SM-PDF-42-9-2013/11%20Mohd%20Hanif.pdf|accessdate=28 November 2017|trans-title=Proximate and Fatty Acid Composition of Sabah Yellow Durian (Durio graveolens)|language=말레이어|format=PDF|issn=0126-6039|oclc=857479186}}</ref>

== 용도 ==
미리스트산은 [[진핵세포]] 세포막의 [[인지질]] 이중층의 지방산 아실 코어 속으로 섞여 들어가기에 충분히 큰 [[소수성]]을 갖는다. 이러한 방식으로 미리스트산은 생체막에서 지질 닻으로 작용한다.

인간에 대한 다양한 역학(疫學) 연구에 따르면 미리스트산과 [[라우르산]]은 인간의 혈장 [[콜레스테롤]] 농도와 가장 밀접한 관련이 있는 포화 지방산인데,<ref>German JB, Dillard CJ. "Saturated fats: a perspective from lactation and milk composition". ''Lipids''. 2010;45(10):915–923</ref> 이는 [[혈장]]에서 [[지방|중성지방]]의 증가는 혈장 콜레스테롤 [[농도]] 증가와 상관관계가 있음을 의미하며 [[심혈관계 질환]]의 위험을 20%가량 증가시킨다. 일부 연구에서는 미리스트산이 HDL 콜레스테롤에 긍정적인 영향을 미치므로 전체 콜레스테롤 중 HDL(high density lipoprotein)의 비율을 향상시키는 것으로 나타났다.<ref>{{저널 인용|last1=Kromhout|first1=Daan|last2=Menotti|first2=A.|last3=Bloemberg|first3=B.|last4=Aravanis|first4=C.|last5=Blackburn|first5=H.|last6=Buzina|first6=R.|last7=Dontas|first7=A.S.|last8=Fidanza|first8=F.|last9=Giaipaoli|first9=S.|display-authors=1|title=Dietary Saturated and transFatty Acids and Cholesterol and 25-Year Mortality from Coronary Heart Disease: The Seven Countries Study|journal=Preventive Medicine|date=1995|volume=24|issue=3|pages=308–315|doi=10.1006/pmed.1995.1049|pmid=7644455}}</ref>

에스터인 이소프로필 미리스테이트는 피부를 통한 흡수가 요구되는 화장품 및 국소용 의약품에 사용된다.

미리스트산을 환원시키면 [[미리스틸 알데하이드]]와 [[미리스틸 알코올]]이 생성된다.

== 같이 보기 ==
{{위키공용분류}}
* [[미리스틸 알코올]](1-테트라데칸올) : 해당되는 알코올
* [[미리스틸 알데하이드]] : 해당되는 알데하이드

== 각주 ==
{{각주|2}}

{{지질}}
{{지방산}}

{{전거 통제}}

[[분류:지방산]]