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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.069
EC Number 208-875-2
RTECS number QH4375000
UNII
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]
-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]
−833.5 kJ/mol[4][6]
8675.9 kJ/mol[6]
Hazards
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)[10]
GHS signal word Warning
H315[10]
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point > 110 °C (230 °F; 383 K) [11]
Lethal dose or concentration (LD, LC):
>10 g/kg (rats, oral)[11]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Myristic acid, (IUPAC systematic name: 1-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. It is named after the binomial name for nutmeg (Myristica fragrans), from which it was first isolated in 1841 by Lyon Playfair.[12]

Occurrence[edit]

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.[13][14]

Uses[edit]

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.

See also[edit]

References[edit]

  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). http://www.rsc.org. Royal Society of Chemistry. Retrieved 2014-06-17.  External link in |website= (help)
  3. ^ a b G., Chuah T.; D., Rozanna; A., Salmiah; Y., Thomas Choong S.; M., Sa'ari (2006). "Fatty Acids used as Phase Change Materials (PCMs) for Thermal Energy Storage in Building Material Applications" (PDF). University Putra Malaysia. Retrieved 2014-06-17. 
  4. ^ 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. 
  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, 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. ^ Vargaftik, Natan B.; et al. (1993). Handbook of Thermal Conductivity of Liquids and Gases (illustrated ed.). CRC Press. p. 305. ISBN 0-8493-9345-0. 
  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. ^ a b "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry. 73 (4): 685–744. 2001. doi:10.1351/pac200173040685. 
  10. ^ a b Sigma-Aldrich Co., Myristic acid. Retrieved on 2014-06-17.
  11. ^ a b c "MYRISTIC ACID". https://www.chemicalland21.com. AroKor Holdings Inc. Retrieved 2014-06-17.  External link in |website= (help)
  12. ^ Playfair, Lyon (2009). "XX. On a new fat acid in the butter of nutmegs". Philosophical Magazine Series 3. 18 (115): 102–113. ISSN 1941-5966. doi:10.1080/14786444108650255. 
  13. ^ Council of Europe, August 2007 Natural Sources of Flavourings, Volume 2, p. 103, at Google Books
  14. ^ 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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