|Jmol-3D images||Image 1|
|Molar mass||256.42 g/mol|
|Density||0.853 g/cm3 at 62 °C|
|Melting point||62.9 °C|
|Boiling point||351-352 °C
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 (77 °F), 100 kPa)|
|(what is: / ?)|
Palmitic acid, or hexadecanoic acid in IUPAC nomenclature, is the most common fatty acid (saturated) found in animals, plants and microorganisms. Its molecular formula is CH3(CH2)14CO2H. As its name indicates, it is a major component of the oil from palm trees (palm oil, palm kernel, and palm kernel oil), but can also be found in meats, cheeses, butter, and dairy products. Palmitate is a term for the salts and esters of palmitic acid. The palmitate anion is the observed form of palmitic acid at basic pH.
Occurrence and production
Palmitic acid mainly occurs as its ester in triglycerides (fats), especially palm oil but also tallow. The cetyl ester of palmitic acid (cetyl palmitate) occurs in spermaceti. It was discovered by Edmond Frémy in 1840, in saponified palm oil. Butter, cheese, milk and meat also contain this fatty acid.
Palmitic acid is prepared by treating fats and oils with water at a high pressure and temperature (above 200 °C or 390 °F), leading to the hydrolysis of triglycerides. The resulting mixture is then distilled.
Excess carbohydrates in the body are converted to palmitic acid. Palmitic acid is the first fatty acid produced during fatty acid synthesis and 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 comprise 21–30% (molar) of human depot fat, and it is a major, but highly variable, lipid component of human breast milk. Palmitate negatively feeds back on acetyl-CoA carboxylase (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. In biology, some proteins are modified by the addition of a palmitoyl group in a process known as palmitoylation. Palmitoylation is important for membrane localisation of many proteins.
Palmitic acid is mainly used to produce soaps, cosmetics, and release agents. These applications utilize sodium palmitate, which is commonly obtained by saponification of palm oil. To this end, palm oil, rendered from the coconut palm nut, is treated with sodium hydroxide (in the form of caustic soda or lye), which causes hydrolysis of the ester groups. This procedure affords glycerol and sodium palmitate.
Because it is inexpensive and adds texture to processed foods (convenience food), palmitic acid and its sodium salt find wide use including foodstuffs. Sodium palmitate is permitted as a natural additive in organic products.
Recently, a long-acting antipsychotic medication, paliperidone palmitate (marketed as INVEGA Sustenna), used in the treatment of schizophrenia, 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 decanoic acid to deliver long-acting depot medication, in particular, neuroleptics such as haloperidol decanoate.
According to the World Health Organization, evidence is "convincing" that consumption of palmitic acid increases risk of developing cardiovascular diseases, placing it in the same evidence category as trans fatty acids. Retinyl palmitate is an antioxidant and a source of vitamin A 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, to make vitamin A stable in milk.
Rats fed a diet of 20% palmitic acid and 80% carbohydrate for extended periods showed alterations in central nervous system control of insulin secretion, and suppression of the body's natural appetite-suppressing signals from leptin and insulin (the key hormones involved in weight regulation).
And according to "Dietary intake of palmitate and oleate has broad impact on systemic and tissue lipid profiles in humans" palmitate does raise the bad cholesterol known as LDL, ie, low density lipoprotein.
- Merck Index, 12th Edition, 7128.
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- Palmitic acid at Inchem.org
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- US Soil Association standard 50.5.3
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