Palmitic acid

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Palmitic acid
Palmitic acid structure.png
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

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]


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.

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. Template:Fix/category[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. Template:Fix/category[citation needed]

Reduction of palmitic acid yields cetyl alcohol. Template:Fix/category[citation needed]

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.

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

The WHO reports "convincing" evidence that dietary intake of palmitic acid increases risk of developing cardiovascular diseases. [1] 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.[2] The controversy may be resolved by a study showing palmitic acid to have no hypercholesterolaemic effect if intake of linoleic acid was greater than 4.5% of energy, but that if the diet contained trans fatty acids, the health effects would be unfavorable (with an LDL cholesterol increase and HDL cholesterol decrease). [3]

References

  1. 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)
  2. Palm oil and blood cholesterol controversy, Wikipedia
  3. 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. 

bg:Палметинова киселина ca:Àcid palmític cs:Kyselina palmitová de:Palmitinsäure eo:Palmita acido id:Asam palmitat it:Acido palmitico lv:Palmitīnskābe nl:Palmitinezuur fi:Palmitiinihappo sv:Palmitinsyra


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