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Myristic acid

Myristic acid

0.8622 g/cm3 (54 °C) 250 C at 100 mmHg 218.3 C at 32 mmHg 20 mg/L (20 °C) 24 mg/L (30 °C) 33 mg/L (60 °C) 15.9 g/100 g (20 °C) 42.5 g/100 g (30 °C) 149 g/100 g (40 °C) 29.2 g/100 g (20 °C) 87.4 g/100 g (30 °C) 1.29 kg/100 g (50 °C) 17.3 g/100 g (20 °C) 75 g/100 g (30 °C) 2.67 kg/100 g (50 °C) 15.3 g/100 g (20 °C) 44.7 g/100 g (30 °C) 1.35 kg/100 g (40 °C) 3.2 g/100 g (0 °C) 30.4 g/100 g (20 °C) 1.35 kg/100 g (50 °C) 3.2173 cP (100 °C) 0.8525 cP (200 °C) 0.3164 cP (300 °C) 0.27 kPa (160 °C) 1 kPa (186 °C) 0.151 W/m·K (100 °C) 0.138 W/m·K (160 °C) | NFPA-H = 2 | NFPA-F = 1 | NFPA-R = 0 Phorbol myristate acetate Myristylbenzylmorphine Dimyristoylphosphatidylethanolamine

Myristic acid (IUPAC name: tetradecanoic acid) is a common saturated fatty acid with the molecular formula . 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.

Occurrence

''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. 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. 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.

Chemical behaviour

Myristic acid acts as a lipid anchor in biomembranes.

Reduction of myristic acid yields myristyl aldehyde and myristyl alcohol.

Health effects

Myristic acid consumption raises low-density lipoprotein (LDL) cholesterol.

References

References

  1. ''Merck Index'', 11th Edition, '''6246'''
  2. (2006). "Fatty Acids used as Phase Change Materials (PCMs) for Thermal Energy Storage in Building Material Applications". University Putra Malaysia.
  3. (2001). "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry.
  4. (1940). "Solubilities of Inorganic and Organic Compounds". D. Van Nostrand Company.
  5. Yaws, Carl L.. (2009). "Transport Properties of Chemicals and Hydrocarbons". William Andrew Inc..
  6. {{CRC90
  7. Vargaftik, Natan B.. (1993). "Handbook of Thermal Conductivity of Liquids and Gases". CRC Press.
  8. Bond, Andrew D.. (2003). "On the crystal structures and melting point alternation of the n-alkyl carboxylic acids". Royal Society of Chemistry.
  9. {{nist
  10. {{Sigma-Aldrich
  11. "Myristic Acid". AroKor Holdings Inc..
  12. (2009). "XX. On a new fat acid in the butter of nutmegs". Philosophical Magazine.
  13. Beal, G. D.. (1926). "Myristic Acid". [[Organic Syntheses]].
  14. Council of Europe, August 2007 {{Google books. e8OwTIHMJDAC. Natural Sources of Flavourings, Volume 2
  15. John Charles Sawer {{Google books. J_cJAwAAQBAJ. Odorographia a natural history of raw materials and drugs used in the perfume industry intended to serve growers, manufacturers and consumers
  16. Cox, David L. Nelson, Michael M.. (2005). "Lehninger principles of biochemistry". W.H. Freeman.
  17. Mensink, Ronald P.. (2016). "Effects of saturated fatty acids on serum lipids and lipoproteins: a systematic review and regression analysis". World Health Organization.
  18. (2018). "Effects of oils and solid fats on blood lipids: a systematic review and network meta-analysis". J Lipid Res.
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