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20-September-2008 09:29:09 - Palmitic acid Palmitic acid1 IUPAC name hexadecanoic acid Identifiers CAS number 57-10-3 PubChem 985 SMILES CCCCCCCCCCCCCCCC=OO Properties Molecular formula C16H32O2 Molar mass 256.42 g/mol Appearance White crystals Density 0.853 g/cm3 at 62 °C Melting point 63-64 °C Boiling point 351-352 °C2 215 °C at 15 mmHg Solubility in water Insoluble Except where noted otherwise, data are given for materials in their standard state at 25 °C, 100 kPa Infobox 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. Palmitic acid was discovered by Edmond Frémy in 1840, in saponified palm oil.3 Butter, cheese, milk and meat also contain this fatty acid. 4 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. 5 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.citation needed Derivatives of palmitic acid were used in combination with naphtha during World War II to produce napalm naphthenic and palmitic acids. 6 The WHO claims there is convincing evidence that dietary intake of palmitic acid increases risk of developing cardiovascular diseases. 7 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.8 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. 9 References ^ Merck Index, 12th ion, 7128. ^ Palmitic acid at Inchem.org ^ E. Frémy, Memoire sur les produits de la saponification de l'huile de palme, Journal de Pharmacie et de Chimie XII 1842, p. 757. ^ 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. ^ Fatty acid biosynthesis - Reference pathway ^ Napalm ^ 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 ^ Palm oil and blood cholesterol controversy, ^ 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. v d e Lipids: fatty acids Saturated Butyric Hexanoic Caprylic Decanoic Lauric Myristic Palmitic Stearic Arachidic Behenic Lignoceric n-3 Unsaturated α-Linolenic Stearidonic Eicosapentaenoic Docosahexaenoic n-6 Unsaturated Linoleic γ-Linolenic Dihomo-γ-linolenic Arachidonic n-9 Unsaturated Oleic Erucic Nervonic Retrieved from http://en..org/wiki/Palmitic_acid Categories: Fatty acids | PalmitatesHidden categories: All articles with statements | Articles with statements since July 2007 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages БългарÑ?ки Català Česky Deutsch Español Esperanto Français Bahasa Indonesia Italiano LatvieÅ¡u Nederlands 日本語 ‪Norsk bokmÃ¥l‬ Polski Português РуÑ?Ñ?кий SlovenÄ?ina Suomi Svenska Türkçe ä¸æ–‡ This page was last modified on 1 May 2008, at 13:07
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