Description
Palmitic acid is a kind of common saturated fatty acid of a 16-carbon backbone, which is contained in fats and waxes. It naturally exists in palm oil and palm kernel oil, and can also be found in butter, cheese, milk, meat, cocoa butter, soybean oil and sunflower oil. It can be produced by many kinds of plants and organisms. It can be used for the production of soap, cosmetics, and industrial mold release agents. It is also a food processing aid. It can also be used to produce cetyl alocohol which is useful in the production of detergents and cosmetics. Recently, it has been also used for the manufacture of a long-acting antipsychotic medication, paliperidone palmitate.
Chemical Properties
Palmitic acid is virtually odorless. It is also reported as having a slight characteristic odor and taste. It is a mixture of
solid organic acids obtained from fats consisting chiefly of palmitic acid (C16H35O2) with varying amounts of stearic acid (C16H36O2).
Chemical Properties
Palmitic acid occurs as white crystalline scales with a slight
characteristic odor and taste.
Chemical Properties
white chips, crystals or powder
Occurrence
Reported found in apple, beef fat, preferments of bread, celery, cheddar cheese, blue cheese, roquefort cheese,
other cheeses, roasted cocoa bean, cognac, country cured ham, essential oil of lemon, heated milk, essential oil of sweet orange, pork
fat, potato, black tea, tomato, banana, grapefruit juice, cranberry, guava, grapes, melon, papaya, pear, raspberry, strawberry, cinnamon,
ginger, saffron, milk powder, fatty fish, chicken, lamb, hop oil, beer, rum, whiskies, grape wines, peanut oil, popcorn, soybean,
coconut meat, avocado, cloudberry, plums, beans, mushroom, starfruit, marjoram, fenugreek, mango, tamarind, fig, kelp, cardamom,rice, prickly pear, dill, licorice, sake, buckwheat, corn oil, malt, wort, roasted chicory root, lemon balm, shrimp, crab, clam, scallop,
Chinese quince, pawpaw and sweet grass oil.
Application
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.
Hydrogenation of palmitic acid yields cetyl alcohol, which is used to produce detergents and cosmetics.
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.
Definition
ChEBI: A straight-chain, sixteen-carbon, saturated long-chain fatty acid.
Preparation
Palmitic acid is prepared from Palm kernel oil, Olive oil, Japan wax or Chinese vegetable tallow by saponification of the natural glycerylesters.
Production Methods
Palmitic acid occurs naturally in all animal fats as the glyceride,
palmitin, and in palm oil partly as the glyceride and partly
uncombined. Palmitic acid is most conveniently obtained from
olive oil after removal of oleic acid, or from Japanese beeswax.
Synthetically, palmitic acid may be prepared by heating cetyl
alcohol with soda lime to 270°C or by fusing oleic acid with
potassium hydrate.
General Description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO 17034. This CRM is traceable to primary material from an NMI, e.g. NIST or NMIJ.
Certified content by quantitative NMR incl. uncertainty and expiry date are given on the certificate.
Download your certificate at: http://www.sigma-aldrich.com.
Pharmaceutical Applications
Palmitic acid is used in oral and topical pharmaceutical formulations.
Palmitic acid has been used in implants for sustained release
of insulin in rats.
Biochem/physiol Actions
Palmitic acid (PA) is a component of membrane phospholipids (PL) and adipose triacylglycerols (TAG). Elevated levels of palmitic acid contributes to the pathophysiology of atherosclerosis, type 2 diabetes mellitus, neurodegenerative diseases, obesity and cancer. PA promotes apoptosis in the endothelial cell by modulating the p38 mitogen-activated protein kinase (MAPK) pathway and favors expression of TNF-α and reactive oxygen species accumulation. PA promotes interleukin 8 (IL-8) synthesis in hepatocytes contributing to hepatic inflammation. PA by interacting with toll-like receptor 4 (TLR4) induces inflammatory injury in cardiomyoctes.
Biotechnological Applications
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. 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.
Safety
Palmitic acid is used in oral and topical pharmaceutical formulations
and is generally regarded as nontoxic and nonirritant at the
levels employed as an excipient. However, palmitic acid is reported
to be an eye and skin irritant at high levels and is poisonous by
intravenous administration.
LD50 (mouse, IV): 57 mg/kg
storage
The bulk material should be stored in a well-closed container in a
cool, dry, place.
Purification Methods
Purify palmitic acid by slow (overnight) recrystallisation from hexane. Some samples are also crystallised from acetone, EtOH or EtOAc. The crystals are kept in air to lose solvent, or are pumped dry of solvent on a vacuum line. [Iwahashi et al. J Chem Soc, Faraday Trans 1 81 973 1985, pK: White J Am Chem Soc 72 1858 1950, Beilstein 2 IV 1157.]
Incompatibilities
Palmitic acid is incompatible with strong oxidizing agents and
bases.
Regulatory Status
GRAS listed. Included in the FDA Inactive Ingredients Database
(oral tablets). Included in nonparenteral medicines licensed in the
UK.
