Myristic acid

Myristic acid[1]
Names
IUPAC name
Tetradecanoic acid
Other names
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
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) [5]
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)[6]
Solubility Soluble in alcohol, acetates, C6H6, haloalkanes, phenyls, nitros[6]
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)[6]
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)[6]
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)[6]
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)[6]
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)[6]
log P 6.1[4]
Vapor pressure 0.01 kPa (118 °C)
0.27 kPa (160 °C)[7]
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)[8]
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)[9]
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][7]
−833.5 kJ/mol[4][7]
8675.9 kJ/mol[7]
Hazards
GHS pictograms [10]
GHS signal word Warning
H315[10]
NFPA 704
Flash point > 110 °C (230 °F; 383 K) [11]
Lethal dose or concentration (LD, LC):
>10 g/kg (rats, oral)[11]
Related compounds
Related compounds
 Tridecanoic acid, 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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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

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, butterfat, 8–14% of bovine milk, and 8.6% of breast milk as well as being a minor component of many other animal fats.[5] 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] It also comprises 14.49% of the fats from the fruit of the Durian species Durio graveolens.[15]

Uses

Myristic acid is commonly added co-translationally to the penultimate, nitrogen-terminus, glycine in receptor-associated kinases to confer the membrane localization of the enzyme. 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.

Various "human epidemiological studies have shown that myristic acid and lauric acid were the saturated fatty acids most strongly related to the average serum cholesterol concentrations in humans",[16] meaning they were positively correlated with higher cholesterol levels as well as raising triglycerides in plasma by some 20% increasing the risk for cardiovascular disease, although some research points to myristic acid's positive effects on HDL cholesterol and hence improving HDL (good cholesterol) to total cholesterol ratio.[17]

Reduction of myristic acid yields myristyl aldehyde and myristyl alcohol.

See also

References

  1. ↑ Merck Index, 11th Edition, 6246
  2. 1 2 3 4 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. 1 2 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 17 June 2014.
  4. 1 2 3 4 5 6 7 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. 1 2 Beare-Rogers, J. L; Dieffenbacher, A; Holm, J. V (2001). "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry. 73 (4): 685–744. doi:10.1351/pac200173040685.
  6. 1 2 3 4 5 6 7 Seidell, Atherton; Linke, William F. (1940). Solubilities of Inorganic and Organic Compounds (3rd ed.). New York: D. Van Nostrand Company. pp. 762–763.
  7. 1 2 3 4 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), http://webbook.nist.gov
  8. ↑ 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.
  9. ↑ Yaws, Carl L. (2009). Transport Properties of Chemicals and Hydrocarbons. New York: William Andrew Inc. p. 177. ISBN 978-0-8155-2039-9.
  10. 1 2 Sigma-Aldrich Co., Myristic acid.
  11. 1 2 3 "MYRISTIC ACID". ChemicalLand21.com. AroKor Holdings Inc. Retrieved 17 June 2014.
  12. ↑ Playfair, Lyon (2009). "XX. On a new fat acid in the butter of nutmegs". Philosophical Magazine. Series 3. 18 (115): 102–113. doi:10.1080/14786444108650255. ISSN 1941-5966.
  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
  15. ↑ Nasaruddin, Mohd hanif; Noor, Noor Qhairul Izzreen Mohd; Mamat, Hasmadi (2013). "Komposisi Proksimat dan Komponen Asid Lemak Durian Kuning (Durio graveolens) Sabah" [Proximate and Fatty Acid Composition of Sabah Yellow Durian (Durio graveolens)] (PDF). Sains Malaysiana (in Malay). 42 (9): 1283–1288. ISSN 0126-6039. OCLC 857479186. Retrieved 28 November 2017.
  16. ↑ German JB, Dillard CJ. "Saturated fats: a perspective from lactation and milk composition". Lipids. 2010;45(10):915–923
  17. ↑ Kromhout, Daan; et al. (1995). "Dietary Saturated and transFatty Acids and Cholesterol and 25-Year Mortality from Coronary Heart Disease: The Seven Countries Study". Preventive Medicine. 24 (3): 308–315. doi:10.1006/pmed.1995.1049. PMID 7644455.
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