ChemicalBook > Product Catalog > Organic Chemistry > Carboxylic acids and derivatives > Acyclic carboxylic acid > Palmitic acid
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)
- FEMA 2832 | PALMITIC ACID
- refractive index 1.4273
- Flash point:>230 °F
- storage temp. +15C to +30C
- solubility chloroform: 0.5 M, clear, colorless
- form Flakes
- color White or almost white
- Water Solubility insoluble
- JECFA Number115
- Merck 14,6996
- BRN 607489
- Stability:Stable. Combustible. Incompatible with bases, oxidizing agents, reducing agents.
- CAS DataBase Reference57-10-3(CAS DataBase Reference)
- NIST Chemistry ReferenceHexadecanoic acid(57-10-3)
- EPA Substance Registry SystemPalmitic acid (57-10-3)
Palmitic acid Usage And Synthesis
- DescriptionPalmitic 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 Propertieswhite chips, crystals or powder
- Chemical PropertiesPalmitic acid occurs as white crystalline scales with a slight characteristic odor and taste.
- Chemical PropertiesPalmitic 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).
- OccurrenceReported 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.
- UsesPalmitic 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.
- Usespalmitic 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.
- UsesPalmitic 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.
- DefinitionChEBI: A straight-chain, sixteen-carbon, saturated long-chain fatty acid.
- Production MethodsPalmitic 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.
- ApplicationPalmitic 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 ApplicationsPalmitic acid is used in oral and topical pharmaceutical formulations. Palmitic acid has been used in implants for sustained release of insulin in rats.
- Biotechnological ApplicationsExcess 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 ProfileA 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
- SafetyPalmitic 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
LD50 (mouse, IV): 57 mg/kg
- storageThe bulk material should be stored in a well-closed container in a cool, dry, place.
- Purification MethodsPurify 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.]
- IncompatibilitiesPalmitic acid is incompatible with strong oxidizing agents and bases.
- Regulatory StatusGRAS listed. Included in the FDA Inactive Ingredients Database (oral tablets). Included in nonparenteral medicines licensed in the UK.
Palmitic acid Preparation Products And Raw materials
- Preparation Productscis-9-Octadecenoic acid1,2-HEXADECANEDIOLLinoleic acid1-TriacontanolCIVETONE1,11-Undecanedicarboxylic acidTween seriesChloramphenicol palmitatePolyoxyethylene fatty acidSorbitan monopalmitatePolyoxyethylene sorbitan monopalmitateL-Ascorbyl 6-palmitatePALMITIC ACID VINYL ESTERPalmitoyl chlorideETHOXYLATEDMONO-ANDDI-GLYCERIDESAMBRETTOLIDEtrimethyl α-hexadecyl betaineIsopropyl palmitateMethyl hexadecanoateamphoteric fatliquor agent DLF-5Sizing paste
- Raw materialsCoconut oilRAPESEED OILFATTY ACID MIXTURERICE BRAN OILPALM KERNEL OIL
- GREASES FATTY ACID KIT Hexadecanoic acid-16-13C,Palmitic acid-16-13C Hexadecanoic acid-1,2,3,4-13C4,Palmitic acid-1,2,3,4-13C4 Hexadecanoic acid-1-13C potassium salt, Palmitic acid-1-13C potassium salt, Potassium hexadecanoate-1-13C,Hexadecanoic acid-1-13C potassium salt, Palmitic acid-1-13C potassium salt, Potassium hexadecanoate-1-13C HEXADECANOIC ACID-1-13C HEXADECANOIC-D31 ACID HEXADECANOIC-2,2-D2 ACID HEXADECANOIC ACID-13C16 (ALGAL SOURCE) ( HEXADECANOIC ACID-1,2-13C2 HEXADECANOIC-16,16,16-D3 ACID Methyl palmitate Hexadecanoic acid ethyl Palmitoyl chloride OCTADECANOIC ACID-1-13C HEXADECANEDIOIC ACID HENEICOSANOIC ACID AGARIC ACID
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