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Palmitic acid[1]
Identifiers
CAS number 57-10-3 Yes check.svgY
PubChem 985
SMILES
Properties
Molecular formula C16H32O2
Molar mass 256.42 g/mol
Appearance White crystals
Density 0.853 g/cm3 at 62 °C
Melting point

62.9 °C[2]

Boiling point

351-352 °C[3]
215 °C at 15 mmHg

Solubility in water Insoluble
 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Palmitic acid,CH3(CH2)14COOH or hexadecanoic acid in IUPAC nomenclature, is one of the most common saturated fatty acids found in animals and plants.[2] As its name indicates, it is a major component of the oil from palm trees (palm oil and palm kernel oil). The word palmitic is from the French "palmitique", the pith of the palm tree. Palmitic acid was discovered by Edmond Frémy in 1840, in saponified palm oil.[4] Butter, cheese, milk and meat also contain this fatty acid.[2][5]

Palmitate is a term for the salts or esters of palmitic acid.

Contents

Biochemistry

Palmitic acid is the first fatty acid produced during lipogenesis (fatty acid synthesis) and from which longer fatty acids can be produced. Palmitate negatively feeds back on acetyl-CoA carboxylase (ACC) which is responsible for converting acetyl-CoA to malonyl-CoA which is used to add to the growing acyl chain, thus preventing further palmitate generation.[6]

Reduction of palmitic acid yields cetyl alcohol.

Uses

Derivatives of palmitic acid were used in combination with naphtha during World War II to produce napalm (aluminum naphthenate and aluminum palmitate).[7]

The World Health Organization claims there is convincing evidence that dietary intake of palmitic acid increases risk of developing cardiovascular diseases.[8] However, possibly less-disinterested studies have shown no ill effect, or even a favorable effect, of dietary consumption of palmitic acid on blood lipids and cardiovascular disease, so that the WHO finding may be deemed controversial.[9] However, another study showed that palmitic acid has no hypercholesterolaemic effect if intake of linoleic acid is greater than 4.5% of energy. On the other hand, it was shown that, if the diet contains trans fatty acids, the health effects are negative, causing an LDL cholesterol increase and HDL cholesterol decrease.[10]

Recently, a long-acting anti-psychotic medication, paliperidone palmitate (marketed as INVEGA Sustenna), used in the treatment of schizophrenia, has been synthesized using the oily palmitate ester as a long-acting release carrier medium when injected intramuscularly. The underlying method of drug delivery is similar to that used with decanoic acid to deliver long-acting depot medication, in particular, neuroleptics such as haloperidol decanoate.

See also

References

  1. ^ Merck Index, 12th Edition, 7128.
  2. ^ a b c "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry 73 (4): 685–744. 2001. doi:10.1351/pac200173040685. http://iupac.org/publications/pac/73/4/0685/. 
  3. ^ Palmitic acid at Inchem.org
  4. ^ E. Frémy, Memoire sur les produits de la saponification de l’huile de palme, Journal de Pharmacie et de Chimie XII (1842), p. 757.
  5. ^ The Importance of Saturated Fats for Biological Functions by Mary Enig, PhD. Wise Traditions in Food, Farming and the Healing Arts (the quarterly magazine of the Weston A. Price Foundation). Spring 2004.
  6. ^ Fatty acid biosynthesis - Reference pathway
  7. ^ Napalm
  8. ^ DIET, NUTRITION AND THE PREVENTION OF CHRONIC DISEASES, WHO Technical Report Series 916, Report of a Joint WHO/FAO Expert Consultation, World Health Organization, Geneva, 2003, p. 88 (Table)
  9. ^ Palm oil and blood cholesterol controversy, Wikipedia
  10. ^ French MA, Sundram K, Clandinin MT (2002). "Cholesterolaemic effect of palmitic acid in relation to other dietary fatty acids". Asia Pacific journal of clinical nutrition 11 Suppl 7: S401–7. doi:10.1046/j.1440-6047.11.s.7.3.x. PMID 12492626. 
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