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Myristic acid

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(Redirected fromMyristoyl group)
Myristic acid[1]
Skeletal formula of myristic acid
Skeletal formula of myristic acid
Ball-and-stick model of myristic acid
Ball-and-stick model of myristic acid
Names
Preferred IUPAC name
Tetradecanoic acid
Other names
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.008.069Edit this at Wikidata
EC Number
  • 208-875-2
RTECS number
  • QH4375000
UNII
  • InChI=1S/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16) ☒N
    Key: TUNFSRHWOTWDNC-UHFFFAOYSA-N ☒N
  • 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)
    Key: TUNFSRHWOTWDNC-UHFFFAOYAZ
  • CCCCCCCCCCCCCC(=O)O
Properties
C14H28O2
Molar mass228.376 g·mol−1
Appearancecolorless or white solid
Density1.03 g/cm3 (−3 °C)[2]
0.99 g/cm3 (24 °C)[3]
0.8622 g/cm3 (54 °C)[4]
Melting point54.4 °C (129.9 °F; 327.5 K)[9]
Boiling point326.2 °C (619.2 °F; 599.3 K) at 760 mmHg
250 °C (482 °F; 523 K)
at 100 mmHg[4]
218.3 °C (424.9 °F; 491.4 K)
at 32 mmHg[3]
13 mg/L (0 °C)
20 mg/L (20 °C)
24 mg/L (30 °C)
33 mg/L (60 °C)[5]
SolubilitySoluble inalcohol,acetates,C6H6,haloalkanes,phenyls,nitros[5]
Solubility inacetone2.75 g/100 g (0 °C)
15.9 g/100 g (20 °C)
42.5 g/100 g (30 °C)
149 g/100 g (40 °C)[5]
Solubility inbenzene6.95 g/100 g (10 °C)
29.2 g/100 g (20 °C)
87.4 g/100 g (30 °C)
1.29 kg/100 g (50 °C)[5]
Solubility inmethanol2.8 g/100 g (0 °C)
17.3 g/100 g (20 °C)
75 g/100 g (30 °C)
2.67 kg/100 g (50 °C)[5]
Solubility inethyl acetate3.4 g/100 g (0 °C)
15.3 g/100 g (20 °C)
44.7 g/100 g (30 °C)
1.35 kg/100 g (40 °C)[5]
Solubility intoluene0.6 g/100 g (−10 °C)
3.2 g/100 g (0 °C)
30.4 g/100 g (20 °C)
1.35 kg/100 g (50 °C)[5]
logP6.1[4]
Vapor pressure0.01 kPa (118 °C)
0.27 kPa (160 °C)[6]
1 kPa (186 °C)[4]
−176·10−6 cm3/mol
Thermal conductivity0.159 W/m·K (70 °C)
0.151 W/m·K (100 °C)
0.138 W/m·K (160 °C)[7]
1.4723 (70 °C)[4]
Viscosity7.2161 cP (60 °C)
3.2173 cP (100 °C)
0.8525 cP (200 °C)
0.3164 cP (300 °C)[8]
Structure
Monoclinic (−3 °C)[2]
P21/c[2]
a = 31.559 Å,b = 4.9652 Å,c = 9.426 Å[2]
α = 90°, β = 94.432°, γ = 90°
Thermochemistry
432.01 J/mol·K[4][6]
−833.5 kJ/mol[4][6]
8675.9 kJ/mol[6]
Hazards
GHS labelling:
GHS07: Exclamation mark[10]
Warning
H315[10]
NFPA 704 (fire diamond)
Flash point> 110 °C (230 °F; 383 K)[11]
Lethal dose or concentration (LD, LC):
>10 g/kg (rats, oral)[11]
Related compounds
Related esters of myristic acid
Isopropyl myristate
Phorbol myristate acetate
Myristylbenzylmorphine
Dimyristoylphosphatidylethanolamine
Related compounds
Tridecanoic acid,Pentadecanoic acid
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound

Myristic acid (IUPAC name:tetradecanoic acid) is a commonsaturated fatty acid with the molecular formulaCH3(CH2)12COOH. Its salts andesters are commonly referred to asmyristates or tetradecanoates. The name of theacyl group derived from myristic acid ismyristoyl ortetradecanoyl. The acid is named after thebinomial name fornutmeg (Myristica fragrans), from which it was first isolated in 1841 byLyon Playfair.[12]

Occurrence

[edit]
Myristica fragrans (nutmeg) fruit contains myristic acid

Nutmeg butter has 75%trimyristin, thetriglyceride of myristic acid and a source from which it can be synthesised.[13] Besides nutmeg, myristic acid is found inpalm kernel oil,coconut oil,butterfat, 8–14% of bovinemilk, and 8.6% ofbreast milk as well as being a minor component of many other animal fats.[9] It is found inspermaceti, the crystallized fraction of oil from thesperm whale. It is also found in the rhizomes of theIris, includingOrris root.[14][15]

Chemical behaviour

[edit]
See also:Myristoylation

Myristic acid acts as alipid anchor inbiomembranes.[16]

Reduction of myristic acid yieldsmyristyl aldehyde andmyristyl alcohol.

Health effects

[edit]

Myristic acid consumption raiseslow-density lipoprotein (LDL) cholesterol.[17][18]

See also

[edit]

References

[edit]
  1. ^Merck Index, 11th Edition,6246
  2. ^abcdBond, Andrew D. (2003)."On the crystal structures and melting point alternation of the n-alkyl carboxylic acids"(PDF).RSC.org. Royal Society of Chemistry. Retrieved17 June 2014.
  3. ^abChuah, T.G.; Rozanna, D.; Salmiah, A.; Thomas, Choong S.Y.; Sa’ari, M. (2006)."Fatty Acids used as Phase Change Materials (PCMs) for Thermal Energy Storage in Building Material Applications"(PDF). University Putra Malaysia. Retrieved17 June 2014.
  4. ^abcdefgLide, David R., ed. (2009).CRC Handbook of Chemistry and Physics (90th ed.).Boca Raton, Florida:CRC Press.ISBN 978-1-4200-9084-0.
  5. ^abcdefgSeidell, Atherton; Linke, William F. (1940).Solubilities of Inorganic and Organic Compounds (3rd ed.). New York: D. Van Nostrand Company. pp. 762–763.
  6. ^abcdTetradecanoic acid in Linstrom, Peter J.; Mallard, William G. (eds.);NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD)
  7. ^Vargaftik, Natan B.; et al. (1993).Handbook of Thermal Conductivity of Liquids and Gases (illustrated ed.). CRC Press. p. 305.ISBN 978-0-8493-9345-7.
  8. ^Yaws, Carl L. (2009).Transport Properties of Chemicals and Hydrocarbons. New York: William Andrew Inc. p. 177.ISBN 978-0-8155-2039-9.
  9. ^abBeare-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.S2CID 84492006.
  10. ^abSigma-Aldrich Co.,Myristic acid.
  11. ^abc"Myristic Acid".ChemicalLand21.com. AroKor Holdings Inc. Retrieved17 June 2014.
  12. ^Playfair, Lyon (2009)."XX. On a new fat acid in the butter of nutmegs".Philosophical Magazine. Series 3.18 (115):102–113.doi:10.1080/14786444108650255.ISSN 1941-5966.
  13. ^Beal, G. D. (1926)."Myristic Acid".Organic Syntheses.6: 66.doi:10.15227/orgsyn.006.0066.
  14. ^Council of Europe, August 2007Natural Sources of Flavourings, Volume 2, p. 103, atGoogle Books
  15. ^John Charles SawerOdorographia a natural history of raw materials and drugs used in the perfume industry intended to serve growers, manufacturers and consumers, p. 108, atGoogle Books
  16. ^Cox, David L. Nelson, Michael M. (2005).Lehninger principles of biochemistry (4th ed.). New York: W.H. Freeman.ISBN 978-0716743392.{{cite book}}: CS1 maint: multiple names: authors list (link)
  17. ^Mensink, Ronald P. (2016)."Effects of saturated fatty acids on serum lipids and lipoproteins: a systematic review and regression analysis"(PDF).World Health Organization.
  18. ^Schwingshackl L, Bogensberger B, Benčič A, Knüppel S, Boeing H, Hoffmann G (2018)."Effects of oils and solid fats on blood lipids: a systematic review and network meta-analysis".J Lipid Res.59 (9):1771–1782.doi:10.1194/jlr.P085522.PMC 6121943.PMID 30006369.
Wikimedia Commons has media related toMyristic acid.
Saturated
ω−3 Unsaturated
ω−5 Unsaturated
ω−6 Unsaturated
ω−7 Unsaturated
ω−9 Unsaturated
ω−10 Unsaturated
ω−11 Unsaturated
ω−12 Unsaturated
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