HEXADECANOIC ACID

Hexadecanoic Acid is a straight-chain, sixteen-carbon, saturated long-chain fatty acid. 
Hexadecanoic Acid has a role as an EC 1.1. 1.189 (prostaglandin-E2 9-reductase) inhibitor, a plant metabolite, a Daphnia magna metabolite and an algal metabolite. 
Hexadecanoic Acid is a long-chain fatty acid and a straight-chain saturated fatty acid.

CAS:    57-10-3
MF:    C16H32O2
MW:    256.42
EINECS:    200-312-9

Synonyms
industrene4516;Kortacid1698;LoxiolEP278;LunacP95;LunacP95KC;NAA160;Neo-Fat16;pentadecanecarboxylicacid

Hexadecanoic Acid is a kind of common saturated fatty acid of a 16-carbon backbone, which is contained in fats and waxes. 
Hexadecanoic Acid 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. 
Hexadecanoic Acid can be produced by many kinds of plants and organisms. 
Hexadecanoic Acid can be used for the production of soap, cosmetics, and industrial mold release agents. 
Hexadecanoic Acid is also a food processing aid. 
Hexadecanoic Acid can also be used to produce cetyl alocohol which is useful in the production of detergents and cosmetics. 
Recently, Hexadecanoic Acid has been also used for the manufacture of a long-acting antipsychotic medication, paliperidone palmitate.
Hexadecanoic Acid is a saturated long-chain fatty acid with a 16-carbon backbone. 
Hexadecanoic Acid is a metabolite found in the aging mouse brain. 
Hexadecanoic Acid is found naturally in palm oil and palm kernel oil, as well as in butter, cheese, milk and meat.

Hexadecanoic Acid is prepared from Palm kernel oil, Olive oil, Japan wax or Chinese vegetable tallow by saponification of the natural glycerylesters.
Hexadecanoic Acid is a saturated fatty acid that is found in many animal and vegetable fats. 
Hexadecanoic Acid has been used as a model system for studying the effects of salt on enzyme activity, specifically in the murine sarcoma virus. 
Hexadecanoic Acid has also been shown to have significant cytotoxicity at low concentrations due to its ability to inhibit protein synthesis, which may be due to receptor activity or phase transition temperature. 
Hexadecanoic Acid has been shown to have bioactive properties that include anti-inflammatory and antioxidant effects, as well as the ability to protect against reactive oxygen species and apoptosis.
Hexadecanoic Acid is a fatty acid with a 16-carbon chain. 

Hexadecanoic Acid is the most common saturated fatty acid found in animals, plants and microorganisms. 
Hexadecanoic Acid's 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. 
Hexadecanoic Acid 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 Hexadecanoic Acid, amounting to 50–60% of total fats.
Palmitates are the salts and esters of palmitic acid. 
The palmitate anion is the observed form of Hexadecanoic Acid at physiologic pH (7.4). 
Major sources of C16:0 are palm oil, palm kernel oil, coconut oil, and milk fat.

Hexadecanoic Acid Chemical Properties
Melting point: 61-62.5 °C(lit.)
Boiling point: 351.5 °C
Density: 0.852 g/mL at 25 °C(lit.)
Bulk density: 415kg/m3
Vapor pressure: 10 mm Hg ( 210 °C)
Refractive index: 1.4273
FEMA: 2832 | PALMITIC ACID
Fp: >230 °F
Storage temp.: room temp
Solubility: chloroform: 0.5 M, clear, colorless
Form: Flakes
Pka: 4.78±0.10(Predicted)
Color: White or almost white
Odor: at 100.00 %. slightly waxy fatty
Odor Type: waxy
Biological source: plant (vegetable)
Water Solubility: insoluble
Merck: 14,6996
JECFA Number: 115
BRN: 607489
Dielectric constant: 2.3（71℃）
Stability: Stable. Combustible. Incompatible with bases, oxidizing agents, reducing agents.
InChIKey: IPCSVZSSVZVIGE-UHFFFAOYSA-N
LogP: 7.170
CAS DataBase Reference: 57-10-3(CAS DataBase Reference)
NIST Chemistry Reference: Hexadecanoic acid(57-10-3)
EPA Substance Registry System: Hexadecanoic Acid (57-10-3)

Hexadecanoic Acid occurs as white crystalline scales with a slight characteristic odor and taste. 
Hexadecanoic Acid is one of the most common saturated fatty acids found in animals and plants. 
Hexadecanoic Acid is a mixture of solid organic acids obtained from fats consisting chiefly of palmitic acid (C16H35O2) with varying amounts of stearic acid (C16H36O2). 
As its name tells us, Hexadecanoic Acid is found in palm oil but also in butter, cheese, milk and meat.

Biochemistry
Hexadecanoic Acid is the first fatty acid produced during fatty acid synthesis and is the precursor to longer fatty acids. 
As a consequence, Hexadecanoic Acid is a major body component of animals. 
In humans, one analysis found it to make up 21–30% (molar) of human depot fat, and Hexadecanoic Acid 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.
Some proteins are modified by the addition of a palmitoyl group in a process known as palmitoylation. 
Palmitoylation is important for localisation of many membrane proteins.

Uses    
Hexadecanoic Acid is one of the skin’s major fatty acids produced by the sebaceous glands. 
In cosmetic preparations, Hexadecanoic Acid is used as a formula texturizer. 
Hexadecanoic Acid is naturally occurring in allspice, anise, calamus oil, cascarilla bark, celery seed, coffee, tea, and many animal fats and plant oils. 
Hexadecanoic Acid is obtained from palm oil, Japan wax, or Chinese vegetable tallow.
Hexadecanoic Acid is a common fatty acid found in plants and animals. 
The body converts excess carbohydrates into Hexadecanoic Acid, thus Palmitic Acid is the first fatty acid produced during fatty acid synt hesis as well as a precursor for longer fatty acids.
Hexadecanoic Acid is a fatty acid which is a mixture of solid organic acids from fats consisting principally of palmitic acid with varying amounts of stearic acid. 
Hexadecanoic Acid functions as a lubricant, binder, and defoaming agent.

Hexadecanoic 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 Hexadecanoic Acid 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 Hexadecanoic 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.
Hexadecanoic Acid is used in oral and topical pharmaceutical formulations. 
Hexadecanoic Acid has been used in implants for sustained release of insulin in rats.

Surfactant
Hexadecanoic Acid is used to produce soaps, cosmetics, and industrial mold release agents. 
These applications use sodium palmitate, which is commonly obtained by saponification of palm oil. 
To this end, palm oil, rendered from palm trees (species Elaeis guineensis), is treated with sodium hydroxide (in the form of caustic soda or lye), which causes hydrolysis of the ester groups, yielding glycerol and sodium palmitate.

Foods
Because Hexadecanoic Acid is inexpensive and adds texture and "mouthfeel" to processed foods (convenience food), Hexadecanoic Acid and its sodium salt find wide use in foodstuffs. 
Hexadecanoic Acid is permitted as a natural additive in organic products.

Military
Aluminium salts of Hexadecanoic Acid and naphthenic acid were the gelling agents used with volatile petrochemicals during World War II to produce napalm. 
The word "napalm" is derived from the words naphthenic acid and Hexadecanoic Acid.

Production Methods    
Hexadecanoic Acid occurs naturally in all animal fats as the glyceride, palmitin, and in palm oil partly as the glyceride and partly uncombined. 
Hexadecanoic Acid is most conveniently obtained from olive oil after removal of oleic acid, or from Japanese beeswax. 
Synthetically, Hexadecanoic Acid may be prepared by heating cetyl alcohol with soda lime to 270°C or by fusing oleic acid with potassium hydrate.

Biochem/physiol Actions    
Hexadecanoic Acid 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. 
Hexadecanoic Acid 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. 
Hexadecanoic Acid promotes interleukin 8 (IL-8) synthesis in hepatocytes contributing to hepatic inflammation. 
Hexadecanoic Acid by interacting with toll-like receptor 4 (TLR4) induces inflammatory injury in cardiomyoctes.

Biotechnological Applications    
Excess carbohydrates in the body are converted to Hexadecanoic Acid. 
Hexadecanoic 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.