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Palmitic acid



Palmitic acid
IUPAC name hexadecanoic acid
Identifiers
CAS number 57-10-3
PubChem 985
SMILES CCCCCCCCCCCCCCCC(=O)O
Properties
Molecular formula C16H32O2
Molar mass 256.42408
Density 0.853 g/cm3 at 62 °C
Melting point

63-64 °C

Boiling point

21 °C at 15 mmHg

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Palmitic acid, or hexadecanoic acid in IUPAC nomenclature, is one of the most common saturated fatty acids found in animals and plants. 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. Butter, cheese, milk and meat also contain this fatty acid. [1]

Additional recommended knowledge

Palmitate is a term for the salts or esters of palmitic acid. The palmitate anion is the observed form of palmitic acid at physiological pH.[citation needed]

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-ACP to malonyl-ACP on the growing acyl chain, thus preventing further palmitate generation. [1]

Reduction of palmitic acid yields cetyl alcohol.


Uses

Palmitate is an antioxidant and a vitamin A compound added to low-fat milk to replace the vitamin content lost through the removal of milk fat. Palmitate is attached to the alcohol form of vitamin A, retinol, in order to make vitamin A stable in milk.[citation needed]

Derivatives of palmitic acid were used in combination with naphtha during World War II to produce napalm (naphthenic and palmitic acids). [2]

The WHO reports "convincing" evidence that dietary intake of palmitic acid increases risk of developing cardiovascular diseases. [3] 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.[4] 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. [5]

References

  1. ^ Fatty acid biosynthesis - Reference pathway
  2. ^ http://www.globalsecurity.org/military/systems/munitions/napalm.htm
  3. ^ 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)
  4. ^ Palm oil and blood cholesterol controversy, Wikipedia
  5. ^ 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. PMID 12492626.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Palmitic_acid". A list of authors is available in Wikipedia.
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