57-10-3 Usage
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
Different sources of media describe the Uses of 57-10-3 differently. You can refer to the following data:
1. 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.
2. 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.
3. 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.
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.
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.
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/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.
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
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.
Check Digit Verification of cas no
The CAS Registry Mumber 57-10-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 7 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 57-10:
(4*5)+(3*7)+(2*1)+(1*0)=43
43 % 10 = 3
So 57-10-3 is a valid CAS Registry Number.
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)
57-10-3Relevant articles and documents
A fluorometric assay for lysosomal phospholipase A2 activity using fluorescence-labeled truncated oxidized phospholipid
Abe, Akira,Hiraoka, Miki,Shayman, James A.,Ohguro, Hiroshi
, p. 164 - 170 (2018)
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
Buckman,VanBrocklin,Dence,Bergmann,Welch,Katzenellenbogen
, p. 2481 - 2485 (1994)
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
Saepou, Siriporn,Pohmakotr, Manat,Reutrakul, Vichai,Yoosook, Chalobon,Kasisit, Jitra,Napaswad, Chanita,Tuchinda, Patoomratana
, p. 721 - 725 (2010)
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)
Salinas, Roberta,Arellano-Garcia, Jesus,Perea-Arango, Irene,Alvarez, Laura,Garduno-Ramirez, Maria Luisa,Marquina, Silvia,Zamilpa, Alejandro,Castillo-Espana, Patricia
, p. 8679 - 8690 (2014)
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.
Biochemical and biophysical characterisation of a small purified lipase from Rhizopus oryzae ZAC3
Ayinla, Zainab A.,Ademakinwa, Adedeji N.,Gross, Richard A.,Agboola, Femi K.
, (2021/02/16)
The characteristics of a purified lipase from Rhizopus oryzae ZAC3 (RoL-ZAC3) were investigated. RoL-ZAC3, a 15.8 kDa protein, which was optimally active at pH 8 and 55 °C had a half-life of 126 min at 60 °C. The kinetic parameters using p-nitrophenylbuty
Fabrication of dual catalytic microcapsules by mesoporous graphitic carbon nitride (mpg-C3N4) nanoparticle-enzyme conjugate stabilized emulsions
Varshney, Rohit,Kumar, Sushil,Ghosh, Kaushik,Patra, Debabrata
, p. 3097 - 3102 (2020/03/03)
Emulsionlated microcapsules (MCs) were fabricated by simultaneous self-assembly and crosslinking of mpg-C3N4 nanoparticles (NPs) and lipase conjugates at an oil-water interface. The presence of both enzymes and mpg-C3Nsub
