Myristic acid

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Myristic acid[1]
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Template:Longitem Template:Chembox Elements/molecular formula
Molar mass Template:Chem molar mass
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 Template:Chembox CalcTemperatures
Boiling point Template:Chembox CalcTemperatures
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]
Template:Longitem −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]
Template:Longitem 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]
Template:Longitem Monoclinic (−3 °C)[2]
Template:Longitem P21/c[2]
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a = 31.559 Å, b = 4.9652 Å, c = 9.426 Å[2]
α = 90°, β = 94.432°, γ = 90°
Template:Longitem 432.01 J/mol·K[4][6]
Template:Longitem −833.5 kJ/mol[4][6]
Template:Longitem 8675.9 kJ/mol[6]
NFPA 704 (fire diamond) Template:NFPA 704 diamond
Flash point Template:Chembox CalcTemperatures
Template:Longitem Isopropyl myristate
Phorbol myristate acetate
Myristylbenzylmorphine
Dimyristoylphosphatidylethanolamine
Template:Longitem Tridecanoic acid, Pentadecanoic acid

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Myristic acid (IUPAC name: tetradecanoic acid) is a common saturated fatty acid with the molecular formula Template:Chem2. 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.[11]

Occurrence

File:Myristica fragrans.JPG
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.[12] 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.[13] 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

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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

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  1. ↑ Merck Index, 11th Edition, 6246
  2. ↑ a b c d Script error: No such module "citation/CS1".
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  4. ↑ a b c d e f g Template:CRC90
  5. ↑ a b c d e f g Script error: No such module "citation/CS1".
  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. ↑ Script error: No such module "citation/CS1".
  8. ↑ Script error: No such module "citation/CS1".
  9. ↑ a b Sigma-Aldrich Co., Myristic acid.
  10. ↑ Script error: No such module "citation/CS1".
  11. ↑ Script error: No such module "Citation/CS1".
  12. ↑ Script error: No such module "Citation/CS1".
  13. ↑ Cite error: Script error: No such module "Namespace detect".Script error: No such module "Namespace detect".
  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. ↑ Script error: No such module "citation/CS1".
  17. ↑ Script error: No such module "Citation/CS1".
  18. ↑ Script error: No such module "Citation/CS1".

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