Myristic acid

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Myristic acid[1]
Skeletal formula of myristic acid
Ball-and-stick model of myristic acid
Names
IUPAC name
Tetradecanoic acid
Other names
Identifiers
544-63-8 YesY
ChEBI CHEBI:28875 N
ChEMBL ChEMBL111077 N
ChemSpider 10539 N
EC Number 208-875-2
2806
Jmol 3D model Interactive image
PubChem 11005
RTECS number QH4375000
UNII 0I3V7S25AW N
  • 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 228.38 g·mol−1
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]
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]
−833.5 kJ/mol[4][6]
8675.9 kJ/mol[6]
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Myristic acid, also called tetradecanoic acid, is a common saturated fatty acid with the molecular formula CH3(CH2)12COOH. A myristate is a salt or ester of myristic acid. Myristic acid is named after the nutmeg Myristica fragrans.

Occurrence

Myristica fragrans fruit contains myristic acid

Nutmeg butter has 75% trimyristin, the triglyceride of myristic acid. Besides nutmeg, myristic acid is also found in palm kernel oil, coconut oil, butter fat and is a minor component of many other animal fats.[9] It is also 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.[10][11]

Uses

Myristic acid is commonly added co-translationally to the penultimate, nitrogen-terminus, glycine in receptor-associated kinases to confer the membrane localisation of the enzyme.[citation needed] The myristic acid has a sufficiently high hydrophobicity to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasma membrane of the eukaryotic cell. In this way, myristic acid acts as a lipid anchor in biomembranes.[citation needed]

The ester isopropyl myristate is used in cosmetic and topical medicinal preparations where good absorption through the skin is desired[citation needed].

Reduction of myristic acid yields myristyl aldehyde and myristyl alcohol.

References

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External links

  1. ↑ Merck Index, 11th Edition, 6246
  2. ↑ 2.0 2.1 2.2 2.3 Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ 3.0 3.1 Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ 4.0 4.1 4.2 4.3 4.4 4.5 4.6 Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ 5.0 5.1 5.2 5.3 5.4 5.5 5.6 Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ 6.0 6.1 6.2 6.3 Tetradecanoic acid in Linstrom, P.J.; Mallard, W.G. (eds.) NIST Chemistry WebBook, NIST Standard Reference Database Number 69. National Institute of Standards and Technology, Gaithersburg MD. http://webbook.nist.gov (retrieved 2014-06-17)
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ 9.0 9.1 Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Council of Europe, August 2007 Natural Sources of Flavourings, Volume 2, p. 103, at Google Books
  11. ↑ 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
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