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Myristic acid





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(Redirected from Myristic Acid)
  

Myristic acid (IUPAC name: tetradecanoic acid) is a common saturated fatty acid with the molecular formula 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 myristoylortetradecanoyl. The acid is named after the binomial name for nutmeg (Myristica fragrans), from which it was first isolated in 1841 by Lyon Playfair.[12]

Myristic acid[1]
Skeletal formula of myristic acid
Ball-and-stick model of myristic acid
Names
Preferred IUPAC name

Tetradecanoic acid

Other names

C14:0 (Lipid numbers)

Identifiers

CAS Number

3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.069 Edit this at Wikidata
EC Number
  • 208-875-2

IUPHAR/BPS

PubChem CID
RTECS number
  • QH4375000
UNII

CompTox Dashboard (EPA)

  • 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

Chemical formula

 C14H28O2
Molar mass 228.376 g·mol−1
Appearance colorless or white solid
Density 1.03 g/cm3 (−3 °C)[2]
0.99 g/cm3 (24 °C)[3]
0.8622 g/cm3 (54 °C)[4]
Melting point 54.4 °C (129.9 °F; 327.5 K)[9]
Boiling point 326.2 °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]

Solubility in water

 13 mg/L (0 °C)
20 mg/L (20 °C)
24 mg/L (30 °C)
33 mg/L (60 °C)[5]
Solubility Soluble in alcohol, acetates, C6H6, haloalkanes, phenyls, nitros[5]
Solubilityinacetone 2.75 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]
Solubilityinbenzene 6.95 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]
Solubilityinmethanol 2.8 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]
Solubilityinethyl acetate 3.4 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]
Solubilityintoluene 0.6 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]
log P 6.1[4]
Vapor pressure 0.01 kPa (118 °C)
0.27 kPa (160 °C)[6]
1 kPa (186 °C)[4]

Magnetic susceptibility (χ)

 -176·10−6cm3/mol
Thermal conductivity 0.159 W/m·K (70 °C)
0.151 W/m·K (100 °C)
0.138 W/m·K (160 °C)[7]

Refractive index (nD)

 1.4723 (70 °C)[4]
Viscosity 7.2161 cP (60 °C)
3.2173 cP (100 °C)
0.8525 cP (200 °C)
0.3164 cP (300 °C)[8]
Structure

Crystal structure

 Monoclinic (−3 °C)[2]

Space group

 P21/c[2]

Lattice constant

a = 31.559 Å, b = 4.9652 Å, c = 9.426 Å[2]

α = 90°, β = 94.432°, γ = 90°

Thermochemistry

Heat capacity (C)

 432.01 J/mol·K[4][6]

Std enthalpy of
formation (ΔfH⦵298)

 −833.5 kJ/mol[4][6]

Std enthalpy of
combustion (ΔcH⦵298)

 8675.9 kJ/mol[6]
Hazards
GHS labelling:

Pictograms

 GHS07: Exclamation mark[10]

Signal word

 Warning

Hazard statements

 H315[10]
NFPA 704 (fire diamond)
[11]
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point > 110 °C (230 °F; 383 K)[11]
Lethal dose or concentration (LD, LC):

LD50 (median dose)

 >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 their standard state (at 25 °C [77 °F], 100 kPa).

☒N verify (what is checkY☒N ?)

Infobox references

Occurrence

edit
 
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.[13] 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.[9] 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.[14][15]

Chemical behaviour

edit
See also: Myristoylation

Myristic acid acts as a lipid anchorinbiomembranes.[16]

Reduction of myristic acid yields myristyl aldehyde and myristyl alcohol.

Health effects

edit

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

See also

edit

References

edit
  1. ^ Merck Index, 11th Edition, 6246
  • ^ a b c d Bond, Andrew D. (2003). "On the crystal structures and melting point alternation of the n-alkyl carboxylic acids" (PDF). RSC.org. Royal Society of Chemistry. Retrieved 17 June 2014.
  • ^ a b Chuah, 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. Retrieved 17 June 2014.
  • ^ a b c d e f g Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
  • ^ a b c d e f g Seidell, Atherton; Linke, William F. (1940). Solubilities of Inorganic and Organic Compounds (3rd ed.). New York: D. Van Nostrand Company. pp. 762–763.
  • ^ a b c d Tetradecanoic 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)
  • ^ 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.
  • ^ Yaws, Carl L. (2009). Transport Properties of Chemicals and Hydrocarbons. New York: William Andrew Inc. p. 177. ISBN 978-0-8155-2039-9.
  • ^ a b 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. S2CID 84492006.
  • ^ a b Sigma-Aldrich Co., Myristic acid.
  • ^ a b c "Myristic Acid". ChemicalLand21.com. AroKor Holdings Inc. Retrieved 17 June 2014.
  • ^ 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.
  • ^ Beal, G. D. (1926). "Myristic Acid". Organic Syntheses. 6: 66. doi:10.15227/orgsyn.006.0066.
  • ^ Council of Europe, August 2007 Natural Sources of Flavourings, Volume 2, p. 103, at Google Books
  • ^ John Charles Sawer Odorographia a natural history of raw materials and drugs used in the perfume industry intended to serve growers, manufacturers and consumers, p. 108, at Google Books
  • ^ 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)
  • ^ Mensink, Ronald P. (2016). "Effects of saturated fatty acids on serum lipids and lipoproteins: a systematic review and regression analysis" (PDF). World Health Organization.
  • ^ 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.
    •  
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    Last edited on 27 January 2024, at 12:04  





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    ●This page was last edited on 27 January 2024, at 12:04 (UTC).
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