Myristic acid

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Myristic acid[1]
Skeletal formula of myristic acid
Ball-and-stick model of myristic acid
Identifiers
CAS number 544-63-8 YesY
PubChem 11005
ChemSpider 10539 N
UNII 0I3V7S25AW N
EC number 208-875-2
ChEBI CHEBI:28875 N
ChEMBL CHEMBL111077 N
RTECS number QH4375000
Jmol-3D images Image 1
Properties
Molecular formula C14H28O2
Molar mass 228.37 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]
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]
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]
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]
Lattice constant α = 90°, β = 94.432°, γ = 90°
Thermochemistry
Specific
heat capacity
C
432.01 J/mol·K[4][6]
Std enthalpy of
formation
ΔfHo298
−833.5 kJ/mol[4][6]
Std enthalpy of
combustion
ΔcHo298
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
GHS hazard statements H315[10]
EU classification Irritant Xi
R-phrases R36/37/38
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]
LD50 10 mg/kg (rats, oral)[11]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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[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.

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.

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". http://www.rsc.org. Royal Society of Chemistry. Retrieved 2014-06-17. 
  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". 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 links[edit]