Palmitic acid

Palmitic acid^[1]
Names
	Preferred IUPAC name Hexadecanoic acid
	Other names Palmitic acid; C16:0 (Lipid numbers)
Identifiers
CAS Number	57-10-3 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL82293 ;
ChemSpider	960 ;
ECHA InfoCard	100.000.284
IUPHAR/BPS	1055;
PubChem CID	985;
UNII	2V16EO95H1 ;
CompTox Dashboard (EPA)	DTXSID2021602 ;
	InChI InChI=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) Key: IPCSVZSSVZVIGE-UHFFFAOYSA-N ; 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) Key: IPCSVZSSVZVIGE-UHFFFAOYAJ;
	SMILES CCCCCCCCCCCCCCCC(=O)O;
Properties
Chemical formula	C16H32O2
Molar mass	256.430 g/mol
Appearance	White crystals
Density	0.852 g/cm3 (25 °C); 0.8527 g/cm3 (62 °C)
Melting point	62.9 °C (145.2 °F; 336.0 K)
Boiling point	351–352 °C (664–666 °F; 624–625 K); 271.5 °C (520.7 °F; 544.6 K), 100 mmHg ; 215 °C (419 °F; 488 K), 15 mmHg
Solubility in water	4.6 mg/L (0 °C); 7.2 mg/L (20 °C); 8.3 mg/L (30 °C); 10 mg/L (45 °C); 12 mg/L (60 °C)
Solubility	Soluble in amyl acetate, alcohol, CCl4, C6H6 ; Very soluble in CHCl3
Solubility in ethanol	2 g/100 mL (0 °C); 2.8 g/100 mL (10 °C); 9.2 g/100 mL (20 °C); 31.9 g/100 mL (40 °C)
Solubility in methyl acetate	7.81 g/100 g
Solubility in ethyl acetate	10.7 g/100 g
Vapor pressure	0.051 mPa (25 °C); 1.08 kPa (200 °C); 28.06 kPa (300 °C)
Acidity (pKa)	4.75
Magnetic susceptibility (χ)	−198.6·10−6 cm3/mol
Refractive index (nD)	1.43 (70 °C)
Viscosity	7.8 cP (70 °C)
Thermochemistry
Heat capacity (C)	463.36 J/(mol·K)
Std molar; entropy (S⦵298)	452.37 J/(mol·K)
Std enthalpy of; formation (ΔfH⦵298)	−892 kJ/mol
Std enthalpy of; combustion (ΔcH⦵298)	10030.6 kJ/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H319
Precautionary statements	P305+P351+P338
NFPA 704 (fire diamond)	1 1 0
Flash point	206 °C (403 °F; 479 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Palmitic acid (hexadecanoic acid in IUPAC nomenclature) is a fatty acid with a 16-carbon chain. It is the most common saturated fatty acid found in animals, plants and microorganisms.^[9]^[10] Its chemical formula is 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 palm oil from the fruit of Elaeis guineensis (oil palms), 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.^[11]

Palmitates are the salts and esters 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.^[12]

Dietary palmitic acid intake is associated with an increased cardiovascular disease risk through raising low-density lipoprotein.^[13]

^ Merck Index, 12th Edition, 7128.
^ ^a ^b ^c ^d ^e ^f Sigma-Aldrich Co., Palmitic acid. Retrieved on 2014-06-02.
^ ^a ^b ^c ^d ^e ^f ^g CID 985 from PubChem
^ ^a ^b ^c ^d "Palmitic acid".
^ Seidell, Atherton; Linke, William F. (1952). Solubilities of Inorganic and Organic Compounds. Van Nostrand. Retrieved 2014-06-02.
^ ^a ^b ^c ^d n-Hexadecanoic acid in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2014-05-11)
^ Beare-Rogers, J.; Dieffenbacher, A.; Holm, J.V. (2001). "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry. 73 (4): 685–744. doi:10.1351/pac200173040685. S2CID 84492006.
^ Palmitic acid at Inchem.org
^ 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
^ The most common fatty acid is the monounsaturated oleic acid. See: https://pubchem.ncbi.nlm.nih.gov/compound/965#section=Top
^ 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.
^ 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.
^ Annevelink CE, Sapp PA, Petersen KS, Shearer GC, Kris-Etherton PM (2023). "Diet-derived and diet-related endogenously produced palmitic acid: Effects on metabolic regulation and cardiovascular disease risk". J Clin Lipidol. 17 (5): 577–586. doi:10.1016/j.jacl.2023.07.005. PMC 10822025. PMID 37666689.

[1] Merck Index, 12th Edition, 7128.

[sigma-2] ^ ^a ^b ^c ^d ^e ^f Sigma-Aldrich Co., Palmitic acid. Retrieved on 2014-06-02.

[pubchem-3] ^ ^a ^b ^c ^d ^e ^f ^g CID 985 from PubChem

[chemister-4] "Palmitic acid".

[sioc-5] Seidell, Atherton; Linke, William F. (1952). Solubilities of Inorganic and Organic Compounds. Van Nostrand. Retrieved 2014-06-02.

[nist-6] -Hexadecanoic acid in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2014-05-11)

[lexicon-7] Beare-Rogers, J.; Dieffenbacher, A.; Holm, J.V. (2001). "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry. 73 (4): 685–744. doi:10.1351/pac200173040685. S2CID 84492006.

[8] Palmitic acid at Inchem.org

[lipidhb-9] 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

[10] The most common fatty acid is the monounsaturated oleic acid. See: https://pubchem.ncbi.nlm.nih.gov/compound/965#section=Top

[11] 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.

[12] 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.

[13] Annevelink CE, Sapp PA, Petersen KS, Shearer GC, Kris-Etherton PM (2023). "Diet-derived and diet-related endogenously produced palmitic acid: Effects on metabolic regulation and cardiovascular disease risk". J Clin Lipidol. 17 (5): 577–586. doi:10.1016/j.jacl.2023.07.005. PMC 10822025. PMID 37666689.

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