Myristic acid

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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
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.008.069 Edit this at Wikidata
EC Number
  • 208-875-2
IUPHAR/BPS
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 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]
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]
Solubility in acetone 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]
Solubility in benzene 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]
Solubility in methanol 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]
Solubility in ethyl 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]
Solubility in toluene 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]
-176·10−6 cm3/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]
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
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]
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:
GHS07: Exclamation mark[10]
Warning
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):
>10 g/kg (rats, oral)[11]
Related compounds
Related esters of myristic acid
Myristylbenzylmorphine
Dimyristoylphosphatidylethanolamine
Related compounds
Pentadecanoic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Myristic acid (

binomial name for nutmeg (Myristica fragrans), from which it was first isolated in 1841 by Lyon Playfair.[12]

Occurrence

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

See also: Myristoylation

Myristic acid acts as a

biomembranes.[16]

Reduction of myristic acid yields myristyl aldehyde and myristyl alcohol
.

Health effects

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

See also

References

  1. ^ Merck Index, 11th Edition, 6246
  2. ^ 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.
  3. ^ 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.
  4. ^
    ISBN 978-1-4200-9084-0
    .
  5. ^ 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.
  6. ^ 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)
  7. ISBN 978-0-8493-9345-7
    .
  8. ISBN 978-0-8155-2039-9
    .
  9. ^
    S2CID 84492006
    .
  10. ^ a b Sigma-Aldrich Co., Myristic acid.
  11. ^ a b c "Myristic Acid". ChemicalLand21.com. AroKor Holdings Inc. Retrieved 17 June 2014.
  12. ISSN 1941-5966
    .
  13. doi:10.15227/orgsyn.006.0066
    .
  14. ^ Council of Europe, August 2007 Natural Sources of Flavourings, Volume 2, p. 103, at Google Books
  15. ^ 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
  16. 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. PMID 30006369
    .
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