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Palmitic acid
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<h2 id="occurrence-and-production">Occurrence and production</h2> <p>Palmitic acid was discovered by <a href="/facts/Saponification/xaH52S3q">saponification</a> of palm oil, which process remains today the primary industrial route for producing the acid.<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a> <a href="/facts/Triglyceride/BQmjv4A0">Triglycerides</a> (fats) in <a href="/facts/Palm_oil/n8zHXqoG">palm oil</a> are <a href="/facts/Hydrolysed/JTvwIHPs">hydrolysed</a> by high-temperature water and the resulting mixture is <a href="/facts/Fractional_distillation/DdNf0k8I"> fractionally distilled</a>.<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a> </p> <h3>Dietary sources</h3> <p>Palmitic acid is produced by a wide range of plants and organisms, typically at low levels. Among common foods it is present in <a href="/facts/Milk/wDJBUHvy">milk</a>, <a href="/facts/Butter/FqydR0dC">butter</a>, <a href="/facts/Cheese/JrG8nGCm">cheese</a>, and some <a href="/facts/Meat/DUHTTM1d">meats</a>, as well as <a href="/facts/Cocoa_butter/QYplogvG">cocoa butter</a>, <a href="/facts/Olive_oil/ae1Qnt2I">olive oil</a>, <a href="/facts/Soybean_oil/I9NzorzT">soybean oil</a>, and <a href="/facts/Sunflower_oil/WIxPvWz8">sunflower oil</a>, (see table).<a class="footnote-ref" id="fnref:7" href="#fn:7"><sup>7</sup></a> <a href="/facts/Karuka/admCLyX9">Karukas</a> contain 44.90% palmitic acid.<a class="footnote-ref" id="fnref:8" href="#fn:8"><sup>8</sup></a> The <a href="/facts/Cetyl_alcohol/sXr3PrSQ">cetyl</a> ester of palmitic acid, <a href="/facts/Cetyl_palmitate/217jLQRG">cetyl palmitate</a>, occurs in <a href="/facts/Spermaceti/827zadvU">spermaceti</a>. </p> Palmitic acid content of common foods<table><tbody><tr><th scope="col">Food</th><th scope="col">% of total calories</th></tr><tr><td><a href="/facts/Palm_oil/n8zHXqoG">Palm oil</a></td><td>45.1%</td></tr><tr><td><a href="/facts/Beef_tallow/JNWsebPc">Beef tallow</a></td><td>26.5%</td></tr><tr><td><a href="/facts/Butter_fat/enmcgMcH">Butter fat</a></td><td>26.2%</td></tr><tr><td><a href="/facts/Cocoa_butter/QYplogvG">Cocoa butter</a></td><td>25.8%</td></tr><tr><td><a href="/facts/Lard/nzueElhV">Lard</a></td><td>24.8%</td></tr><tr><td><a href="/facts/Cottonseed_oil/m1TpX35L">Cottonseed oil</a></td><td>24.7%</td></tr><tr><td><a href="/facts/Chicken_as_food/JCpSXfJV">Chicken</a></td><td>23.2%</td></tr><tr><td><a href="/facts/Corn_oil/eebVEq2J">Corn oil</a></td><td>12.2%</td></tr><tr><td><a href="/facts/Peanut_oil/TJoTgDfN">Peanut oil</a></td><td>11.6%</td></tr><tr><td><a href="/facts/Soybean_oil/I9NzorzT">Soybean oil</a></td><td>11%</td></tr><tr><td><a href="/facts/Coconut_oil/mULGkRTS">Coconut oil</a></td><td>8.4%</td></tr><tr><td><a href="/facts/Palm_kernel_oil/sCaLNndQ">Palm kernel oil</a></td><td>8%</td></tr><tr><td><a href="/facts/Rapeseed_oil/6KgzlLuc">Rapeseed oil</a></td><td>3.6%</td></tr><tr><td colspan="2">Source:<a class="footnote-ref" id="fnref:9" href="#fn:9"><sup>9</sup></a></td></tr></tbody></table> <h2 id="biochemistry">Biochemistry</h2> <p>Palmitic acid is the first fatty acid produced during <a href="/facts/Fatty_acid_synthesis/Cl17j9xE">fatty acid synthesis</a> and is the precursor to longer fatty acids. As a consequence, palmitic acid is a major body component of animals. In humans, one analysis found it to make up 21–30% (molar) of human <a href="/facts/Adipose_tissue/PxxedB6e">depot fat</a>,<a class="footnote-ref" id="fnref:10" href="#fn:10"><sup>10</sup></a> and it is a major, but highly variable, lipid component of <a href="/facts/Breast_milk/wVfKCjyw">human breast milk</a>.<a class="footnote-ref" id="fnref:11" href="#fn:11"><sup>11</sup></a> Palmitate negatively feeds back on <a href="/facts/Acetyl-CoA_carboxylase/9Lh10Lrs">acetyl-CoA carboxylase</a> (ACC), which is responsible for converting <a href="/facts/Acetyl-CoA/XyxFfC84">acetyl-CoA</a> to <a href="/facts/Malonyl-CoA/n1eNlSYs">malonyl-CoA</a>, which in turn is used to add to the growing <a href="/facts/Acyl_group/1vRPrmUX">acyl chain</a>, thus preventing further palmitate generation.<a class="footnote-ref" id="fnref:12" href="#fn:12"><sup>12</sup></a> </p><p>Some proteins are modified by the addition of a palmitoyl group in a process known as <a href="/facts/Palmitoylation/soDel1Xt">palmitoylation</a>. Palmitoylation is important for localisation of many <a href="/facts/Membrane_protein/FboTeM8Q">membrane proteins</a>. </p> <h2 id="applications">Applications</h2> <h3>Surfactant</h3> <p>Palmitic acid is used to produce <a href="/facts/Soap/S3nJa1oY">soaps</a>, <a href="/facts/Cosmetics/rb1x6P8c">cosmetics</a>, and industrial mold <a href="/facts/Release_agent/tuhXHNll">release agents</a>. These applications use sodium palmitate, which is commonly obtained by <a href="/facts/Saponification/xaH52S3q">saponification</a> of palm oil. To this end, palm oil, rendered from palm trees (species <i><a href="/facts/Elaeis_guineensis/SFLvBaLn">Elaeis guineensis</a></i>), is treated with <a href="/facts/Sodium_hydroxide/xjtdYtq7">sodium hydroxide</a> (in the form of caustic soda or lye), which causes <a href="/facts/Hydrolysis/JTvwIHPs">hydrolysis</a> of the <a href="/facts/Ester/FoUAIIw4">ester</a> groups, yielding <a href="/facts/Glycerol/sRQ6NBQQ">glycerol</a> and sodium palmitate. </p> <h3>Foods</h3> <p>Because it is inexpensive and adds texture and "<a href="/facts/Mouthfeel/rBy2P0Sg">mouthfeel</a>" to processed foods (<a href="/facts/Convenience_food/ayJbRMIt">convenience food</a>), palmitic acid and its sodium salt find wide use in foodstuffs. Sodium palmitate is permitted as a natural additive in <a href="/facts/Organic_certification/eE8t9jNl">organic</a> products.<a class="footnote-ref" id="fnref:13" href="#fn:13"><sup>13</sup></a> </p> <h3>Military</h3> <p>Aluminium <a href="/facts/Salt_(chemistry)/lsSKwGpn">salts</a> of palmitic acid and <a href="/facts/Naphthenic_acid/6QbBpU0q">naphthenic acid</a> were the <a href="/facts/Gelling_agent/lNPqbaWy">gelling agents</a> used with volatile petrochemicals during <a href="/facts/World_War_II/2efV5L1U">World War II</a> to produce <a href="/facts/Napalm/KbCMBjWe">napalm</a>. The word "napalm" is derived from the words naphthenic acid and palmitic acid.<a class="footnote-ref" id="fnref:14" href="#fn:14"><sup>14</sup></a> </p> <h2 id="research">Research</h2> <p>It is well accepted in the medical community that palmitic acid from dietary sources raises <a href="/facts/Low-density_lipoprotein/R5VLPxAg">low-density lipoprotein</a> (LDL) and total cholesterol.<a class="footnote-ref" id="fnref:15" href="#fn:15"><sup>15</sup></a><a class="footnote-ref" id="fnref:16" href="#fn:16"><sup>16</sup></a><a class="footnote-ref" id="fnref:17" href="#fn:17"><sup>17</sup></a><a class="footnote-ref" id="fnref:18" href="#fn:18"><sup>18</sup></a> The <a href="/facts/World_Health_Organization/YNN3bgug">World Health Organization</a> have stated there is convincing evidence that palmitic acid increases <a href="/facts/Cardiovascular_disease/HD420nMv">cardiovascular disease</a> risk.<a class="footnote-ref" id="fnref:19" href="#fn:19"><sup>19</sup></a> </p><p>A 2021 review indicated that replacing dietary palmitic acid and other saturated fatty acids with <a href="/facts/Unsaturated_fatty_acid/87HcP11s">unsaturated fatty acids</a>, such as <a href="/facts/Oleic_acid/NeVuHTbe">oleic acid</a>, could reduce several <a href="/facts/Biomarker/nk2LgXtq">biomarkers</a> of cardiovascular and <a href="/facts/Metabolic_syndrome/jI70tRBv">metabolic</a> diseases.<a class="footnote-ref" id="fnref:20" href="#fn:20"><sup>20</sup></a> </p> <h2 id="see-also">See also</h2> <ul><li><a href="/facts/Retinyl_palmitate/Lo4ebazz">Retinyl palmitate</a></li> <li><a href="/facts/Ascorbyl_palmitate/jYYVxawM">Ascorbyl palmitate</a></li> <li><a href="/facts/SN2_Palmitate/C29ckXPc">SN2 Palmitate</a></li> <li><a href="/facts/Juniperic_acid/hmdxMl0v">Juniperic acid</a> (16-hydroxypalmitic acid)</li></ul> <h2 id="external-links">External links</h2> <ul><li> Media related to Palmitic acid at Wikimedia Commons</li> <li><a href="https://en.wikisource.org/wiki/1911_Encyclop%C3%A6dia_Britannica/Palmitic_Acid">"Palmitic Acid" </a>. <i><a href="/facts/Encyclop%C3%A6dia_Britannica_Eleventh_Edition/mPElbCRY">Encyclopædia Britannica</a></i> (11th ed.). 1911.</li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Gunstone, F. D., John L. Harwood, and Albert J. Dijkstra. The Lipid Handbook, 3rd ed. Boca Raton: CRC Press, 2007. ISBN 0849396883 | ISBN 978-0849396885 <a href="/wiki/ISBN_(identifier)" target="_blank">/wiki/ISBN_(identifier)</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>The most common fatty acid is the monounsaturated oleic acid. See: https://pubchem.ncbi.nlm.nih.gov/compound/965#section=Top <a href="https://pubchem.ncbi.nlm.nih.gov/compound/965#section=Top" target="_blank">https://pubchem.ncbi.nlm.nih.gov/compound/965#section=Top</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Gianfranca Carta; Elisabetta Murru; Sebastiano Banni; Claudia Manca (8 November 2017). "Palmitic Acid: Physiological Role, Metabolism and Nutritional Implications". Frontiers in Physiology. 8: 902. doi:10.3389/FPHYS.2017.00902. ISSN 1664-042X. PMC 5682332. PMID 29167646. Wikidata Q46799280. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5682332" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5682332</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Loften, J.R.; Linn, J.G.; Drackley, J.K.; Jenkins, T.C.; Soderholm, C.G.; Kertz, A.F. (August 2014). "Invited review: Palmitic and stearic acid metabolism in lactating dairy cows". Journal of Dairy Science. 97 (8): 4661–4674. doi:10.3168/jds.2014-7919. ISSN 0022-0302. PMID 24913651. <a href="https://doi.org/10.3168%2Fjds.2014-7919" target="_blank">https://doi.org/10.3168%2Fjds.2014-7919</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Frémy, E. (1842). "Memoire sur les produits de la saponification de l'huile de palme". Journal de Pharmacie et de Chimie. XII: 757. <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>Anneken, David J.; Both, Sabine; Christoph, Ralf; Fieg, Georg; Steinberner, Udo; Westfechtel, Alfred (2006). "Fatty Acids". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_245.pub2. ISBN 978-3527306732. <a href="978-3527306732" target="_blank">978-3527306732</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>"Chemical Characteristics". Olive Oil Source. Archived from the original on February 18, 2010. Retrieved November 11, 2021. <a href="https://web.archive.org/web/20100218174052/http://www.oliveoilsource.com/page/chemical-characteristics" target="_blank">https://web.archive.org/web/20100218174052/http://www.oliveoilsource.com/page/chemical-characteristics</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li> <li id="fn:8"><p>Purwanto, Y.; Munawaroh, Esti (2010). "Etnobotani Jenis-Jenis Pandanaceae Sebagai Bahan Pangan di Indonesia" [Ethnobotany Types of Pandanaceae as Foodstuffs in Indonesia] (PDF). Berkala Penelitian Hayati (in Indonesian). 5A: 97–108. ISSN 2337-389X. OCLC 981032990. Retrieved 10 November 2021. <a href="https://berkalahayati.org/files/journals/1/articles/265/submission/265-838-1-SM.pdf" target="_blank">https://berkalahayati.org/files/journals/1/articles/265/submission/265-838-1-SM.pdf</a> <a href="#fnref:8" class="footnote-back-ref">↩</a></p></li> <li id="fn:9"><p>Nelson, Gary J. (1991). Health Effects of Dietary Fatty Acids. American Oil Chemists' Society. pp. 84-86. ISBN 978-0935315318 <a href="/wiki/ISBN_(identifier)" target="_blank">/wiki/ISBN_(identifier)</a> <a href="#fnref:9" class="footnote-back-ref">↩</a></p></li> <li id="fn:10"><p>Kingsbury, K. J.; Paul, S.; Crossley, A.; Morgan, D. M. (1961). "The fatty acid composition of human depot fat". Biochemical Journal. 78 (3): 541–550. doi:10.1042/bj0780541. PMC 1205373. PMID 13756126. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1205373" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1205373</a> <a href="#fnref:10" class="footnote-back-ref">↩</a></p></li> <li id="fn:11"><p>Jensen, RG; Hagerty, MM; McMahon, KE (June 1978). "Lipids of human milk and infant formulas: a review". Am. J. Clin. Nutr. 31 (6): 990–1016. doi:10.1093/ajcn/31.6.990. PMID 352132. <a href="https://doi.org/10.1093%2Fajcn%2F31.6.990" target="_blank">https://doi.org/10.1093%2Fajcn%2F31.6.990</a> <a href="#fnref:11" class="footnote-back-ref">↩</a></p></li> <li id="fn:12"><p>"Fatty acid biosynthesis - Reference pathway". KEGG. Pathway Map 00061 <a href="http://www.genome.jp/pathway/map00061" target="_blank">http://www.genome.jp/pathway/map00061</a> <a href="#fnref:12" class="footnote-back-ref">↩</a></p></li> <li id="fn:13"><p>US Soil Association standard 50.5.3 <a href="#fnref:13" class="footnote-back-ref">↩</a></p></li> <li id="fn:14"><p>Mysels, Karol J. (1949). "Napalm. Mixture of Aluminum Disoaps". Industrial & Engineering Chemistry. 41 (7): 1435–1438. doi:10.1021/ie50475a033. <a href="https://pubs.acs.org/doi/pdf/10.1021/ie50475a033" target="_blank">https://pubs.acs.org/doi/pdf/10.1021/ie50475a033</a> <a href="#fnref:14" class="footnote-back-ref">↩</a></p></li> <li id="fn:15"><p>Nelson, Gary J. (1991). Health Effects of Dietary Fatty Acids. American Oil Chemists' Society. pp. 84-86. ISBN 978-0935315318 <a href="/wiki/ISBN_(identifier)" target="_blank">/wiki/ISBN_(identifier)</a> <a href="#fnref:15" class="footnote-back-ref">↩</a></p></li> <li id="fn:16"><p>Mensink RP, Zock PL, Kester AD, Katan MB (2003). "Effects of dietary fatty acids and carbohydrates on the ratio of serum total to HDL cholesterol and on serum lipids and apolipoproteins: a meta-analysis of 60 controlled trials". Am J Clin Nutr. 77 (5): 1146–1155. doi:10.1093/ajcn/77.5.1146. 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