Palmitic acid 542488 209447813 2008-05-01T13:07:09Z 81.172.122.195 {{Chembox new |Reference=<ref>''[[Merck Index]]'', 12th Edition, '''7128'''.</ref> |ImageFile=Palmitic acid structure.png |ImageSize=350px |IUPACName=hexadecanoic acid |Section1= {{Chembox Identifiers | CASNo=57-10-3 | PubChem=985 | SMILES=CCCCCCCCCCCCCCCC(=O)O }} |Section2= {{Chembox Properties | Formula=C<sub>16</sub>H<sub>32</sub>O<sub>2</sub> | MolarMass=256.42 g/mol | Appearance=White crystals | Density=0.853 g/cm<sup>3</sup> at 62 °C | MeltingPt=63-64 °C | BoilingPt=351-352 °C<ref>[http://www.inchem.org/documents/icsc/icsc/eics0530.htm Palmitic acid] at Inchem.org</ref><br>215 °C at 15 mmHg | Solubility=Insoluble }} |Section3= {{Chembox Hazards | MainHazards= | FlashPt= | Autoignition= }} }} '''Palmitic acid''', or hexadecanoic acid in [[IUPAC nomenclature]], is one of the most common saturated [[fatty acid]]s found in animals and plants. As its name indicates, it is a major component of the oil from [[palm tree]]s ([[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 [[Saponification|saponified]] palm oil.<ref>E. Frémy, Memoire sur les produits de la saponification de l’huile de palme, Journal de Pharmacie et de Chimie XII (1842), p. 757.</ref> [[Butter]], [[cheese]], [[milk]] and [[meat]] also contain this fatty acid. <ref>[http://www.westonaprice.org/knowyourfats/import_sat_fat.html 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.</ref> '''Palmitate''' is a term for the salts or [[ester]]s of palmitic acid. The palmitate anion is the observed form of palmitic acid at physiological pH. {{Fact|date=July 2007}} ==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. <ref>[http://www.genome.jp/kegg/pathway/map/map00061.html Fatty acid biosynthesis - Reference pathway]</ref> Reduction of palmitic acid yields [[cetyl alcohol]]. ==Uses== Retinyl 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. {{Fact|date=July 2007}} Derivatives of palmitic acid were used in combination with [[naphtha]] during [[World War II]] to produce [[napalm]] ('''''na'''''phthenic and '''''palm'''''itic acids). <ref name="GS Napalm">[http://www.globalsecurity.org/military/systems/munitions/napalm.htm Napalm<!-- Bot generated title -->]</ref> The [[WHO]] claims there is convincing evidence that dietary intake of palmitic acid increases risk of developing cardiovascular diseases. <ref>[http://www.who.int/hpr/NPH/docs/who_fao_expert_report.pdf 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)</ref> 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.<ref>[[Palm oil#Blood cholesterol controversy|Palm oil and blood cholesterol controversy]], Wikipedia</ref> 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. <ref>{{cite journal |author=French MA, Sundram K, Clandinin MT |title=Cholesterolaemic effect of palmitic acid in relation to other dietary fatty acids |journal=Asia Pacific journal of clinical nutrition |volume=11 Suppl 7 |issue= |pages=S401–7 |year=2002 |pmid=12492626 |doi=}}</ref> ==References== {{Reflist}} {{Fatty acids}} [[Category:Fatty acids]] [[Category:Palmitates]] [[bg:Палмитинова киселина]] [[ca:Àcid palmític]] [[cs:Kyselina palmitová]] [[de:Palmitinsäure]] [[es:Ácido palmítico]] [[eo:Palmita acido]] [[fr:Acide palmitique]] [[id:Asam palmitat]] [[it:Acido palmitico]] [[lv:Palmitīnskābe]] [[nl:Palmitinezuur]] [[ja:パルミチン酸]] [[no:Palmitinsyre]] [[pl:Kwas palmitynowy]] [[pt:Ácido palmítico]] [[ru:Пальмитиновая кислота]] [[sk:Kyselina palmitová]] [[fi:Palmitiinihappo]] [[sv:Palmitinsyra]] [[tr:Palmitik asit]] [[zh:棕櫚酸]]