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Revision as of 13:22, 22 February 2011 edit194.53.253.51 (talk) at neutral pH, the acid is predominantly protonated.← Previous edit		Latest revision as of 22:00, 24 May 2024 edit undoZefr (talk | contribs)Extended confirmed users, Pending changes reviewers69,493 edits Reverted 1 edit by 2A01:4B00:C012:5600:6DAF:466C:78C3:3412 (talk): Fine beforeTags: Twinkle Undo
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	{{chembox		{{Chembox
			|Verifiedfields = changed
	| verifiedrevid = 400006162
			|Watchedfields = changed
	|Reference=<ref>'']'', 12th Edition, '''7128'''.</ref>
			|verifiedrevid = 415315408
	| ImageFile_Ref = {{chemboximage|correct|??}}
			|Reference = <ref>'']'', 12th Edition, '''7128'''.</ref>
	| ImageFile=Palmitic acid.svg
			|ImageFile_Ref = {{chemboximage|correct|??}}
	|ImageSize=350px
			|ImageFile = Palmitic acid.svg
			|ImageSize = 250px
	|ImageFile2 = Palmitic-acid-3D-balls.png		|ImageFile2 = Palmitic-acid-3D-balls.png
	|ImageSize2 = 350px		|ImageSize2 = 250px
			|ImageFile3 = Kyselina palmitová.jpg
	|IUPACName=hexadecanoic acid
			|PIN = Hexadecanoic acid<!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) -->
	|OtherNames=C16:0 (])
			|OtherNames = Palmitic acid<br />C16:0 (])
	|Section1= {{Chembox Identifiers
			|Section1 = {{Chembox Identifiers
	| CASNo_Ref = {{cascite|correct|CAS}}
			|CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo=57-10-3
			|CASNo = 57-10-3
	| PubChem=985
			|UNII_Ref = {{fdacite|correct|FDA}}
	| IUPHAR_ligand = 1055
			|UNII = 2V16EO95H1
	| SMILES=CCCCCCCCCCCCCCCC(=O)O
			|PubChem = 985
	}}
			|ChEMBL_Ref = {{ebicite|changed|EBI}}
	|Section2= {{Chembox Properties
			|ChEMBL = 82293
	| Formula=C<sub>16</sub>H<sub>32</sub>O<sub>2</sub>
			|IUPHAR_ligand = 1055
	| MolarMass=256.42 g/mol
			|ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
	| Appearance=White crystals
			|ChemSpiderID = 960
	| Density=0.853 g/cm<sup>3</sup> at 62 °C
			|SMILES = CCCCCCCCCCCCCCCC(=O)O
	| MeltingPt=62.9 °C<ref name="lexicon">{{cite journal |year=2001 |title=Lexicon of lipid nutrition (IUPAC Technical Report) |journal=Pure and Applied Chemistry |volume=73 |issue=4 |pages=685–744 |url=http://iupac.org/publications/pac/73/4/0685/ |doi=10.1351/pac200173040685 |last1=Beare-Rogers |first1=J. |last2=Dieffenbacher |first2=A. |last3=Holm |first3=J.V. }}</ref>
			|InChI = 1/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18)
	| BoilingPt=351-352 °C<ref> at Inchem.org</ref><br>215 °C at 15 mmHg
			|InChIKey = IPCSVZSSVZVIGE-UHFFFAOYAJ
	| Solubility=Insoluble
			|StdInChI_Ref = {{stdinchicite|changed|chemspider}}
	}}
			|StdInChI = 1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18)
	|Section3= {{Chembox Hazards
			|StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
	| MainHazards=
			|StdInChIKey = IPCSVZSSVZVIGE-UHFFFAOYSA-N
	| FlashPt=
			}}
	| Autoignition=
			|Section2 = {{Chembox Properties
	}}
			|C=16 | H=32 | O=2
			|MolarMassUnit = g/mol
			|pKa = 4.75 <ref name=pubchem>{{PubChemLink|985}}</ref>
			|Appearance = White crystals
			|Density = 0.852 g/cm<sup>3</sup> (25 °C)<ref name="sigma" /><br/> 0.8527 g/cm<sup>3</sup> (62 °C)<ref name=pubchem />
			|MeltingPtC = 62.9
			|MeltingPt_ref = <ref name="lexicon">{{cite journal |year=2001 |title=Lexicon of lipid nutrition (IUPAC Technical Report) |journal=Pure and Applied Chemistry |volume=73 |issue=4 |pages=685–744 |doi=10.1351/pac200173040685 |doi-access=free |last1=Beare-Rogers |first1=J. |last2=Dieffenbacher |first2=A. |last3=Holm |first3=J.V. |s2cid=84492006 }}</ref>
			|BoilingPtC = 351-352
			|BoilingPt_ref = <ref> at Inchem.org</ref><br/>{{convert|271.5|C|F K}}, 100{{nbsp}}mmHg<ref name="sigma" /> <br/>{{convert|215|C|F K}}, 15{{nbsp}}mmHg
			|Solubility = 4.6 mg/L (0 °C)<br/> 7.2 mg/L (20 °C)<br/> 8.3 mg/L (30 °C)<br/> 10 mg/L (45 °C)<br/> 12 mg/L (60 °C)<ref name=chemister />
			|SolubleOther = Soluble in ], ], ],<ref name=chemister>{{cite web | url=http://chemister.ru/Database/properties-en.php?dbid=1&id=6488 | title=Palmitic acid}}</ref> ] <br/>Very soluble in ]<ref name=pubchem />
			|Solubility1 = 2 g/100 mL (0 °C)<br/> 2.8 g/100 mL (10 °C)<br/> 9.2 g/100 mL (20 °C)<br/> 31.9 g/100 mL (40 °C)<ref name=sioc>{{cite book|last1 = Seidell|first1 = Atherton|last2 = Linke|first2 = William F.|year = 1952|title = Solubilities of Inorganic and Organic Compounds|publisher = Van Nostrand|url = https://books.google.com/books?id=k2e5AAAAIAAJ|access-date = 2014-06-02}}</ref>
			|Solvent1 = ethanol
			|Solubility2 = 7.81 g/100 g<ref name=chemister />
			|Solvent2 = methyl acetate
			|Solubility3 = 10.7 g/100 g<ref name=chemister />
			|Solvent3 = ethyl acetate
			|VaporPressure = 0.051 mPa (25 °C)<ref name=pubchem>{{PubChemLink|985}}</ref><br/> 1.08 kPa (200 °C)<br/> 28.06 kPa (300 °C)<ref name=nist>{{nist|name=n-Hexadecanoic acid|id=C57103|accessdate=2014-05-11|mask=FFFF|units=SI}}</ref>
			|Viscosity = 7.8 cP (70 °C)<ref name=pubchem />
			|RefractIndex = 1.43 (70 °C)<ref name=pubchem />
			|MagSus = −198.6·10<sup>−6</sup> cm<sup>3</sup>/mol
			}}
			|Section3 = {{Chembox Thermochemistry
			|DeltaHf = −892 kJ/mol<ref name=nist />
			|DeltaHc = 10030.6 kJ/mol<ref name=pubchem />
			|HeatCapacity = 463.36 J/(mol·K)<ref name=nist />
			|Entropy = 452.37 J/(mol·K)<ref name=nist />
			}}
			|Section4 = {{Chembox Hazards
			|GHSPictograms = {{GHS07}}<ref name="sigma">{{Sigma-Aldrich|id=258725|name=Palmitic acid|accessdate=2014-06-02}}</ref>
			|GHSSignalWord = Warning
			|HPhrases = {{H-phrases|319}}<ref name="sigma" />
			|PPhrases = {{P-phrases|305+351+338}}<ref name="sigma" />
			|FlashPtC = 206
			|FlashPt_ref = <ref name="sigma" />
			| NFPA-H = 1
			| NFPA-F = 1
			| NFPA-R = 0
			}}
	}}		}}
	'''Palmitic acid''', or '''hexadecanoic acid''' in ], is one of the most common saturated ]s found in animals and plants.<ref name="lexicon" /> Its molecular formula is CH<sub>3</sub>(CH<sub>2</sub>)<sub>14</sub>COOH. As its name indicates, it is a major component of the oil from ]s (], ] oil and ]). The word palmitic is from the French "palmitique", the ] of the palm tree. Palmitic acid was discovered by ] in 1840, in ] 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> ], ], ] and ] also contain this fatty acid.<ref name="lexicon" /><ref> 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> ] is a term for the salts or ]s of palmitic acid. The palmitate anion is the observed form of palmitic acid at basic pH.
			'''Palmitic acid''' ('''hexadecanoic acid''' in ]) is a ] with a 16-carbon chain. It is the most common ] found in animals, plants and microorganisms.<ref name=lipidhb>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}}</ref><ref>The most common fatty acid is the monounsaturated oleic acid. See: https://pubchem.ncbi.nlm.nih.gov/compound/965#section=Top</ref> Its ] is {{chem2|CH3(CH2)14COOH}}, and its C:D ratio (the total number of carbon atoms to the number of carbon-carbon double bonds) is 16:0. It is a major component of ] from the fruit of '']'' (]s), making up to 44% of total fats. Meats, cheeses, butter, and other dairy products also contain palmitic acid, amounting to 50–60% of total fats.<ref>{{cite Q|Q46799280|doi-access=free}}</ref>
	] of palmitic acid yields ].
			'''Palmitates''' are the ] and ]s of palmitic acid. The palmitate anion is the observed form of palmitic acid at physiologic pH (7.4). Major sources of C16:0 are palm oil, palm kernel oil, coconut oil, and milk fat.<ref>{{Cite journal |last1=Loften |first1=J.R. |last2=Linn |first2=J.G. |last3=Drackley |first3=J.K. |last4=Jenkins |first4=T.C. |last5=Soderholm |first5=C.G. |last6=Kertz |first6=A.F. |date=August 2014 |title=Invited review: Palmitic and stearic acid metabolism in lactating dairy cows |journal=Journal of Dairy Science |volume=97 |issue=8 |pages=4661–4674 |doi=10.3168/jds.2014-7919 |pmid=24913651 |issn=0022-0302|doi-access=free}}</ref>
			==Occurrence and production==
			Palmitic acid was discovered by ] (in 1840) in the ] of palm oil, which process remains today the primary industrial route for producing the acid.<ref>{{cite journal |first=E. |last=Frémy |title=Memoire sur les produits de la saponification de l'huile de palme |journal=Journal de Pharmacie et de Chimie |volume=XII |year=1842 |pages=757 }}</ref> ]s (fats) in ] are ] by high-temperature water and the resulting mixture is ].<ref name=Ullmann>{{cite book |first1=David J. |last1=Anneken |first2=Sabine |last2=Both |first3=Ralf |last3=Christoph |first4=Georg |last4=Fieg |first5=Udo |last5=Steinberner |first6=Alfred |last6=Westfechtel |chapter=Fatty Acids |title=Ullmann's Encyclopedia of Industrial Chemistry |year=2006 |publisher=Wiley-VCH |location=Weinheim |doi=10.1002/14356007.a10_245.pub2 |isbn=978-3527306732 }}</ref>
			===Dietary sources===
			Palmitic acid is produced by a wide range of plants and organisms, typically at low levels. Among common foods it is present in ], ], ], and some ]s, as well as ], ], ], and ], (see table).<ref>{{cite web |url=http://www.oliveoilsource.com/page/chemical-characteristics |title=Chemical Characteristics |website=Olive Oil Source |accessdate=November 11, 2021}}{{dead link|date=March 2023}}</ref> ]s contain 44.90% palmitic acid.<ref name="Purwanto">{{cite journal |last1=Purwanto |first1=Y. |last2=Munawaroh |first2=Esti |title=Etnobotani Jenis-Jenis Pandanaceae Sebagai Bahan Pangan di Indonesia |journal=Berkala Penelitian Hayati |date=2010 |volume=5A |pages=97–108 |url=https://berkalahayati.org/files/journals/1/articles/265/submission/265-838-1-SM.pdf |access-date=10 November 2021 |trans-title=Ethnobotany Types of Pandanaceae as Foodstuffs in Indonesia |language=id |issn=2337-389X |oclc=981032990 }}</ref> The ] ester of palmitic acid, ], occurs in ].
			{|class="wikitable"
			|+ Palmitic acid content of common foods
			! scope="col" | Food
			! scope="col" | % of total calories
			|-
			|]
			|45.1%
			|-
			|]
			|26.5%
			|-
			|]
			|26.2%
			|-
			|]
			|25.8%
			|-
			|]
			|24.8%
			|-
			|]
			|24.7%
			|-
			|]
			|23.2%
			|-
			|]
			|12.2%
			|-
			|]
			|11.6%
			|-
			|]
			|11%
			|-
			|]
			|8.4%
			|-
			|]
			|8%
			|-
			|]
			|3.6%
			|-
			|colspan=2 style="text-align:center;"|<small>Source:<ref name="Nelson 1991">Nelson, Gary J. (1991). ''Health Effects of Dietary Fatty Acids''. American Oil Chemists' Society. pp. 84-86. {{ISBN|978-0935315318}}</ref></small>
			|}
	==Biochemistry==		==Biochemistry==
	Palmitic acid is the first fatty acid produced during ] (fatty acid synthesis) and from which longer fatty acids can be produced. Palmitate negatively feeds back on ] (ACC), which is responsible for converting acetyl-CoA to malonyl-CoA, which in turn is used to add to the growing acyl chain, thus preventing further palmitate generation.<ref></ref> In biology, some proteins are modified by the addition of a palmitoyl group in a process known as ]. Palmitoylation is important for membrane localisation of many proteins.		Palmitic acid is the first fatty acid produced during ] 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 ],<ref>{{cite journal |first1=K. J. |last1=Kingsbury |first2=S. |last2=Paul |first3=A. |last3=Crossley |first4=D. M. |last4=Morgan |title=The fatty acid composition of human depot fat |journal=] |year=1961 |volume=78 |issue= 3|pages=541–550 |pmc=1205373 |pmid=13756126|doi=10.1042/bj0780541 }}</ref> and it is a major, but highly variable, lipid component of ].<ref>{{cite journal | pmid = 352132 | volume=31 | issue=6 | title=Lipids of human milk and infant formulas: a review | date=June 1978 | journal=Am. J. Clin. Nutr. | pages=990–1016 | last1 = Jensen | first1 = RG | last2 = Hagerty | first2 = MM | last3 = McMahon | first3 = KE | doi=10.1093/ajcn/31.6.990 | doi-access=free }}</ref> Palmitate negatively feeds back on ] (ACC), which is responsible for converting ] to ], which in turn is used to add to the growing ], thus preventing further palmitate generation.<ref>{{cite web |website=] |title=Fatty acid biosynthesis - Reference pathway |url=http://www.genome.jp/pathway/map00061}} Pathway Map 00061</ref>
			Some proteins are modified by the addition of a palmitoyl group in a process known as ]. Palmitoylation is important for localisation of many ]s.
	==Uses and occurrence==
	The ] claims that dietary intake of palmitic acid increases risk of developing cardiovascular diseases.<ref>, WHO Technical Report Series 916, Report of a Joint WHO/FAO Expert Consultation, ], Geneva, 2003, p. 88 (Table)</ref>However, another study showed that palmitic acid has no hypercholesterolaemic effect if intake of ] 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=10.1046/j.1440-6047.11.s.7.3.x}}</ref>
			==Applications==
	Cetyl palmitate occurs in ]. ] is an ] and a source of ] 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, ], to make vitamin A stable in milk. Palmitate esters are also the major component of ]. The word palmitate is from the French "palmitique", the pith of the palm tree.
			=== Surfactant ===
			Palmitic acid is used to produce ]s, ], and industrial mold ]s. These applications use '''sodium palmitate''', which is commonly obtained by ] of palm oil. To this end, palm oil, rendered from palm trees (species '']''), is treated with ] (in the form of caustic soda or lye), which causes ] of the ] groups, yielding ] and sodium palmitate.
			=== Foods ===
	Recently, a long-acting antipsychotic medication, ] palmitate (marketed as INVEGA Sustenna), used in the treatment of ], has been synthesized using the oily palmitate ester as a long-acting release carrier medium when injected intramuscularly. The underlying method of drug delivery is similar to that used with ] to deliver long-acting depot medication, in particular, neuroleptics such as ] decanoate.
			Because it is inexpensive and adds texture and "]" to processed foods (]), palmitic acid and its sodium salt find wide use in foodstuffs. Sodium palmitate is permitted as a natural additive in ] products.<ref>US Soil Association standard 50.5.3</ref>
	===Napalm===		=== Military ===
			Aluminium ] of palmitic acid and ] were the ]s used with volatile petrochemicals during ] to produce ]. The word "napalm" is derived from the words naphthenic acid and palmitic acid.<ref>{{Cite journal|url=https://pubs.acs.org/doi/pdf/10.1021/ie50475a033|doi=10.1021/ie50475a033|title=Napalm. Mixture of Aluminum Disoaps|year=1949|last1=Mysels|first1=Karol J.|journal=Industrial & Engineering Chemistry|volume=41|issue=7|pages=1435–1438}}</ref>
	Derivatives of palmitic acid were used in combination with ] during ] to produce ] (aluminum '''''na'''''phthenate and aluminum '''''palm'''''itate).<ref name="GS Napalm"></ref>
	==See also==		==Research==
			It is well accepted in the medical community that palmitic acid from dietary sources raises ] (LDL) and total cholesterol.<ref name="Nelson 1991"/><ref>{{cite journal|vauthors=Mensink RP, Zock PL, Kester AD, Katan MB|year=2003|title=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|journal=Am J Clin Nutr|volume=77|issue=5|pages=1146–1155|doi=10.1093/ajcn/77.5.1146|pmid=12716665|doi-access=free}}</ref><ref>Mensink, Ronald P. (2016). . World Health Organization. Retrieved 14 March 2023.</ref><ref>Rao, Gundu HR. (2020). ''Clinical Handbook of Coronary Artery Disease''. Jaypee Brothers Medical Publishers. pp. 186-187. {{ISBN|978-9389188301}}</ref> The ] have stated there is convincing evidence that palmitic acid increases ] risk.<ref>. World Health Organization. p. 82. Retrieved 16 March 2023.</ref>
			A 2021 review indicated that replacing dietary palmitic acid and other saturated fatty acids with ]s, such as ], could reduce several ]s of cardiovascular and ] diseases.<ref name="Sellem">{{cite journal | last1=Sellem | first1=Laury | last2=Flourakis | first2=Matthieu | last3=Jackson | first3=Kim G | last4=Joris | first4=Peter J | last5=Lumley | first5=James | last6=Lohner | first6=Szimonetta | last7=Mensink | first7=Ronald P | last8=Soedamah-Muthu | first8=Sabita S | last9=Lovegrove | first9=Julie A | title=Impact of Replacement of Individual Dietary SFAs on Circulating Lipids and Other Biomarkers of Cardiometabolic Health: A Systematic Review and Meta-Analysis of Randomized Controlled Trials in Humans | journal=Advances in Nutrition | date=2021-11-25 | volume=13 | issue=4 | pages=1200–1225 | issn=2161-8313 | doi=10.1093/advances/nmab143 | pmid=34849532| pmc=9340975 | doi-access=free }}</ref>
			== See also ==
	* ]		* ]
	* ]		* ]
			* ]
			* ] (16-hydroxypalmitic acid)
	==References==		==References==
	{{Reflist}}		{{Reflist}}
			==External links==
			*{{Commons category-inline|Palmitic acid}}
			*{{Cite EB1911|wstitle=Palmitic Acid|short=x}}
	{{Fatty acids}}		{{Fatty acids}}
			{{Palm oil}}
			{{Authority control}}
			]
	{{DEFAULTSORT:Palmitic Acid}}
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