57-10-3

Basic information

• Product Name: Palmitic acid
• Synonyms: acidehexadecylique;acidepalmitique;Cetylsαure;Emersol 140;Emersol 143;emersol140;emersol143;Glycon P-45
• CAS NO: 57-10-3
• Molecular Formula: C₁₆H₃₂O₂
• Molecular Weight: 256.42
• EINECS: 200-312-9
• Product Categories: Fatty & Aliphatic Acids, Esters, Alcohols & Derivatives;Saturated Fatty Acids 13C & 2H;Alkylcarboxylic Acids;Color Former & Related Compounds;Functional Materials;Monofunctional & alpha,omega-Bifunctional Alkanes;Monofunctional Alkanes;Sensitizer;Biochemistry;Higher Fatty Acids & Higher Alcohols;Saturated Higher Fatty Acids;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors
• Mol File: 57-10-3.mol
• Article Data: 142

Chemical Properties

• Melting Point: 61-62.5 °C(lit.)
• Boiling Point: 351.5 °C
• Flash Point: >230 °F
• Appearance: White or almost white/Flakes
• Density: 0.852 g/mL at 25 °C(lit.)
• Vapor Pressure: 10 mm Hg ( 210 °C)
• Refractive Index: 1.4273
• Storage Temp.: +15C to +30C
• Solubility: chloroform: 0.5 M, clear, colorless
• PKA: 4.78±0.10(Predicted)
• Water Solubility: insoluble
• Stability: Stable. Combustible. Incompatible with bases, oxidizing agents, reducing agents.
• Merck: 14,6996
• BRN: 607489
• CAS DataBase Reference: Palmitic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Palmitic acid(57-10-3)
• EPA Substance Registry System: Palmitic acid(57-10-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36-36/38-36/37/38
• Safety Statements: 26-37/39-36
• RTECS: RT4550000
• TSCA: Yes
• Hazardous Substances Data: 57-10-3(Hazardous Substances Data)

Usage

Description

Palmitic acid is a common saturated fatty acid with a 16-carbon backbone, found in plants and animals. It is the first fatty acid produced during fatty acid synthesis and serves as a precursor for longer fatty acids. Palmitic acid naturally exists in palm oil, palm kernel oil, butter, cheese, milk, meat, cocoa butter, soybean oil, and sunflower oil. It is used in the production of soap, cosmetics, industrial mold release agents, and as a food processing aid. Additionally, it is used to produce cetyl alcohol, which is useful in the production of detergents and cosmetics. Recently, it has been utilized in the manufacture of a long-acting antipsychotic medication, paliperidone palmitate.

Uses

1. Used in Cosmetic Preparations:
Palmitic acid is used as a formula texturizer for its natural occurrence in various plant oils and its role as one of the skin's major fatty acids produced by the sebaceous glands.
2. Used in Soap, Cosmetic, and Release Agent Production:
Palmitic acid is used to produce soaps, cosmetics, and release agents, utilizing sodium palmitate, which is obtained by saponification of palm oil.
3. Used in Food Processing:
Palmitic acid and its sodium salt are used in the food industry due to their inexpensive nature and ability to add texture to processed foods. Sodium palmitate is permitted as a natural additive in organic products.
4. Used in Detergent and Cosmetic Production:
Cetyl alcohol, derived from the hydrogenation of palmitic acid, is used in the production of detergents and cosmetics.
5. Used in Pharmaceutical Industry:
Palmitic acid is used in the synthesis of paliperidone palmitate, a long-acting antipsychotic medication used in the treatment of schizophrenia. The oily palmitate ester serves as a long-acting release carrier medium when injected intramuscularly.
6. Found in Various Natural Sources:
Palmitic acid is reported to be found in apple, beef fat, bread preferments, celery, various cheeses, roasted cocoa bean, cognac, country cured ham, essential oils of lemon and 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.

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.

Synthesis Reference(s)

The Journal of Organic Chemistry, 27, p. 2950, 1962 DOI: 10.1021/jo01055a527Tetrahedron 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.

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

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.

InChI:InChI=1/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18)

Upstream product

• 143-07-7 lauric acid 
• 626-86-8 adipinic acid monoethyl ester 
• 7373-13-9 octadecan-2-one 
• 629-80-1 n-hexadecylaldehyde 
• 1060652-72-3 hexadeca-2,4,6,8,10,12,14-heptaenoic acid 
• 4444-12-6 hexadeca-6,10,14-trienoic acid 
• 2388-81-0 11-oxo-hexadecanoic acid 
• 70444-63-2 5-oxohexadecanoic acid 
• 107-21-1 ethylene glycol 
• 103-40-2 succinic acid monobenzyl ester 
• 544-63-8 n-tetradecanoic acid 
• 112-62-9 Methyl oleate 
• 544-76-3 Hexadecane 
• 110-34-9 hexadecanoic acid 2-methylpropyl ester 

Downstream Products

• 10443-62-6 2-pentadecyl-4,5-dihydro-1H-imidazole 
• 623-65-4 palmitic anhydride 
• 74058-77-8 N-1-(4-hydroxyphenyl) hexadecanamide 
• 79352-13-9 N-(1-naphthalenyl)hexadecanamide 
• 6876-53-5 palmitic acid p-toluidide 
• 54535-83-0 1-(3,4-dihydroxy-phenyl)-hexadecan-1-one 
• 102898-91-9 palmitic acid p-anisidide 
• 112-39-0 hexadecanoic acid methyl ester 
• 708261-28-3 N-(3,4-dimethoxy-β-phenylethyl)hexadecanamide 
• 16108-99-9 N,N'-hexadecanoyl-4,4'-diaminodiphenylmethane 
• 629-54-9 Palmitamide 
• 18261-92-2 octadecan-3-one 
• 102898-55-5 1-(4-methoxyphenyl)hexadecan-1-one 
• 2157-84-8 N-methyl-palmitanilide 

Relevant articles and documents

A fluorometric assay for lysosomal phospholipase A2 activity using fluorescence-labeled truncated oxidized phospholipid

Lysosomal phospholipase A2 (LPLA2) is a key enzyme involved in the homeostasis of cellular phospholipids. Recently, LPLA2 was reported to preferentially degrade some truncated oxidized phospholipids at the sn-1 position. A commercially available, truncated oxidized phospholipid conjugated with a fluorescent dye, 1-palmitoyl-2-glutaroyl-sn-glycero-3-phosphoethanolamine-N-[4-(dipyrrometheneboron difluoride) butanoyl] (PGPE-BODIPY), was used to develop a specific assay for this enzyme. When recombinant mouse LPLA2 was incubated with liposomes consisting of 1,2-O-octadecyl-sn-glycero-3-phosphocholine/PGPE-BODIPY under acidic conditions, PGPE-BODIPY was converted to palmitic acid and a polar BODIPY-product. After phase partitioning by chloroform/methanol, the polar BODIPY-product was recovered in the aqueous phase and identified as 1-lyso-PGPE-BODIPY. The formation of 1-lyso-PGPE-BODIPY was quantitatively determined by fluorescent measurements. The Km and Vmax values of the recombinant LPLA2 for PGPE-BODIPY were 5.64 μM and 20.7 μmol/min/mg protein, respectively. Detectable activity against PGPE-BODIPY was present in LPLA2 deficient mouse sera, but the deacylase activity was completely suppressed by treatment with 4-(2-aminoethyl)benzenesulfonyl fluoride (AEBSF). AEBSF had no effect on LPLA2 activity. The LPLA2 activity of mouse serum pre-treated with AEBSF was specifically and quantitatively determined by this assay method. The PGPE-BODIPY and AEBSF based LPLA2 assay is convenient and can be used to measure LPLA2 activity in a variety of biological specimens.

Synthesis and tissue biodistribution of [ω-11C]palmitic acid. A novel PET imaging agent for cardiac fatty acid metabolism

In order to diagnose patients with medium-chain acyl-CoA dehydrogenase deficiency with a noninvasive diagnostic technique such as positron emission tomography, we have developed a synthesis of [ω-11C]palmitic acid. The radiochemical synthesis was achieved by coupling an alkylfuran Grignard reagent (7) with [11C]methyl iodide, followed by rapid oxidative cleavage of the furan ring to the carboxylate using ruthenium tetraoxide. Tissue biodistribution studies in rats comparing [ω-11C]palmitic acid and [1- 11C]palmitic acid show that the %ID/g and %ID/organ in the heart tissue after administration of [ω-11C]palmitic acid is approximately 50% greater than after administration of [1-11C]palmitic acid, due to the diminished metabolism of the [ω-11C]palmitic acid. These studies show as well, low uptake in nontarget tissues (blood, lung, kidney, and muscle). PET images of a dog heart obtained after administration of [ω-11C] and [1- 11C]palmitic acid show virtually identical uptake and distribution in the myocardium. The differing cardiac washout of labeled palmitates measured by dynamic PET studies may allow diagnosis of disorders in cardiac fatty acid metabolism.

Anti-HIV1 Diterpenoids from Leaves and Twigs of Polyalthia sclerophylla

Bioassay-guided fractionation and purification of the anti-HIV-1-active MeOH extract from the leaves and twigs of Polyalthia sclerophylla led to the isolation of two new compounds, ent-kaur-sclerodimer (1) and cyclotucanol 3-palmitate (2), along with the known ent-kaur-16-en-19-oic acid (3), 15-hydroxy-ent-kaur-16-en-19-oic acid (4), 15-acetoxy-ent-kaur-16-en-19-oic acid (5), 15-oxo-ent-kaur-16-en-19-oic acid (6), 16,17-dihydroxy-ent-kauran-19-oic acid (7), 16-hydroxy-ent-kauran-19-oic acid (xylopic acid) (8), a pseudodimer (15-hydroxy-ent-kaur-16-en-19-oic acid/17-hydroxy-ent-kaur-15-en-19-oic acid) (9), ermanin, nicotiflorin, and allantoin. Among these isolates, compound 3 was the most active in both anti-syncytium (EC50 13.7μg/mL and selectivity index 3.1) and HIV-1 reverse transcriptase (IC50 34.1μg/mL) assays. Georg Thieme Verlag KG Stuttgart.

Production of the anti-inflammatory compound 6-o-palmitoyl-3-O-β-D- glucopyranosylcampesterol by callus cultures of lopezia racemosa cav. (onagraceae)

Lopezia racemosa Cav. is a plant used in Mexican traditional medicine to heal inflammatory diseases. From this plant we isolated the novel compound 6-O-palmitoyl- 3-O-β-D-glucopyranosylcampesterol (1) and 6-O-palmitoyl-3-O-β-D-glucopyranosyl-β- sitosterol (2), previously reported to have cytotoxic activity on several cancer cell lines. We evaluated the anti-inflammatory activity of 1 in vivo by mouse ear edema induced with 12-O-tetradecanoylphorbol-13-acetate (TPA) and 57.14% inhibition was observed. The aim of our study was to obtain callus cultures derived from this plant species with the ability to produce the compounds of interest. Callus cultures were initiated on MS basal medium amended with variable amounts of naphthaleneacetic acid (NAA), or 2,4-dichlorophenoxyacetic acid (2,4-D), combined or not with 6-benzylaminopurine (BAP). Ten treatments with these growth regulators were carried out, using in vitro germinated seedlings as source of three different explants: hypocotyl, stem node, and leaf. Highest yield of 1 was observed on callus derived from leaf explants growing in medium containing 1.0 mg/L 2,4-D and 0.5 mg/L BAP. Selected callus lines produced less 1 than wild plants but the in vitro cultured seedlings showed higher production. So we conclude that it could be attractive to further investigate their metabolic potential.

Lipase mimetic cyclodextrins

Glycerophospholipids (GPLs) perform numerous essential functions in biology, including forming key structural components of cellular membranes and acting as secondary messengers in signaling pathways. Developing biomimetic molecular devices that can detect specific GPLs would enable modulation of GPL-related processes. However, the compositional diversity of GPLs, combined with their hydrophobic nature, has made it challenging to develop synthetic scaffolds that can react with specific lipid species. By taking advantage of the host-guest chemistry of cyclodextrins, we have engineered a molecular device that can selectively hydrolyze GPLs under physiologically relevant conditions. A chemically modified α-cyclodextrin bearing amine functional groups was shown to hydrolyze lyso-GPLs, generating free fatty acids. Lyso-GPLs are preferentially hydrolyzed when part of a mixture of GPL lipid species, and reaction efficiency was dependent on lyso-GPL chemical structure. These findings lay the groundwork for the development of molecular devices capable of specifically manipulating lipid-related processes in living systems.

Acceptorless dehydrogenative oxidation of primary alcohols to carboxylic acids and reduction of nitroarenes via hydrogen borrowing catalyzed by a novel nanomagnetic silver catalyst

A novel silver nano magnetic catalyst was devised for dehydrogenative oxidation of aromatic and aliphatic alcohols to the corresponding acid with water as the sole oxygen source and hydrogen gas as the only by-product. The designed catalytic system advantages from easy recovery of magnetic materials i.e. magnetic decantation, being economically viable and environmentally friendly. Furthermore, the catalytic reaction is able to reduce aryl nitro compounds in the absence of any reducing agent.