Palmitic acid Chemical Properties

Melting point:

61-62.5 °C(lit.)

Boiling point:

351.5 °C

Density 

0.852 g/mL at 25 °C(lit.)

vapor pressure 

10 mm Hg ( 210 °C)

refractive index 

1.4273

FEMA 

2832 | PALMITIC ACID

Flash point:

>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

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

Palmitic acid (57-10-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36-36/38-36/37/38

Safety Statements 

26-37/39-36

WGK Germany 

-

RTECS 

RT4550000

TSCA 

Yes

HS Code 

29157015

Hazardous Substances Data

57-10-3(Hazardous Substances Data)

Toxicity

LD50 i.v. in mice: 57±3.4 mg/kg (Or, Wretlind)

MSDS

• Language:English Provider:Hexadecanoic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Palmitic acid Usage And Synthesis

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 occurs as white crystalline scales with a slight characteristic odor and taste. It is one of the most common saturated fatty acids found in animals and plants. It 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, it is found in palm oil but also in butter, cheese, milk and meat.

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.

Uses

palmitic acid is one of the skin’s major fatty acids produced by the sebaceous glands. In cosmetic preparations, it is used as a formula texturizer. This acid is naturally occurring in allspice, anise, calamus oil, cascarilla bark, celery seed, coffee, tea, and many animal fats and plant oils. It is obtained from palm oil, Japan wax, or Chinese vegetable tallow.

Uses

Palmitic Acid is a common fatty acid found in plants and animals. The body converts excess carbohydrates into Palmitic Acid, thus Palmitic Acid is the first fatty acid produced during fatty acid synt hesis as well as a precursor for longer fatty acids.

Uses

Palmitic 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. it functions as a lubricant, binder, and defoaming agent.

Definition

ChEBI: Palmitic acid is a saturated long-chain fatty acid with a 16-carbon backbone. It is a metabolite found in the aging mouse brain. It is found naturally in palm oil and palm kernel oil, as well as in butter, cheese, milk and meat.

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.

Preparation

Palmitic acid is prepared from Palm kernel oil, Olive oil, Japan wax or Chinese vegetable tallow by saponification of the natural glycerylesters.

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.

Synthesis Reference(s)

The Journal of Organic Chemistry, 27, p. 2950, 1962 DOI: 10.1021/jo01055a527
Tetrahedron Letters, 17, p. 4697, 1976 DOI: 10.1016/S0040-4039(00)92999-X

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 Profile

A poison by intravenous route. A human skin irritant. Questionable carcinogen with experimental neoplastigenic data. When heated to decomposition it emits acrid smoke and irritating fumes

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.

Palmitic acid(57-10-3)Related Product Information

• Hyaluronic acid
• 2,2,4,4,6,8,8-HEPTAMETHYLNONANE
• N-HEXADECANE-D34
• 1-Hexadecanol
• Folic acid
• Citric acid
• Clindamycin palmitate hydrochloride
• N-HEXADECANE-D34
• Isopropyl palmitate
• Methyl palmitate
• Cetearyl alcohol
• Ethyl 2-(Chlorosulfonyl)acetate
• Hexadecanoic acid ethyl
• GREASES
• FATTY ACID KIT
• HEXADECANOIC ACID-1-13C
• HEXADECANOIC-D31 ACID
• HEXADECANOIC-2,2-D2 ACID