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Palmitic acid
Palmitic acid
Palmitic acid
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Palmitic acid[1]
Names
Preferred IUPAC name
Hexadecanoic acid
Other names
Palmitic acid
C16:0 (Lipid numbers)
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.284 Edit this at Wikidata
UNII
  • InChI=1S/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) ☒N
    Key: IPCSVZSSVZVIGE-UHFFFAOYSA-N ☒N
  • 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)
    Key: IPCSVZSSVZVIGE-UHFFFAOYAJ
  • CCCCCCCCCCCCCCCC(=O)O
Properties
C16H32O2
Molar mass 256.430 g/mol
Appearance White crystals
Density 0.852 g/cm3 (25 °C)[2]
0.8527 g/cm3 (62 °C)[3]
Melting point 62.9 °C (145.2 °F; 336.0 K)[7]
Boiling point 351–352 °C (664–666 °F; 624–625 K)[8]
271.5 °C (520.7 °F; 544.6 K), 100 mmHg[2]
215 °C (419 °F; 488 K), 15 mmHg
4.6 mg/L (0 °C)
7.2 mg/L (20 °C)
8.3 mg/L (30 °C)
10 mg/L (45 °C)
12 mg/L (60 °C)[4]
Solubility Soluble in amyl acetate, alcohol, CCl4,[4] C6H6
Very soluble in CHCl3[3]
Solubility in ethanol 2 g/100 mL (0 °C)
2.8 g/100 mL (10 °C)
9.2 g/100 mL (20 °C)
31.9 g/100 mL (40 °C)[5]
Solubility in methyl acetate 7.81 g/100 g[4]
Solubility in ethyl acetate 10.7 g/100 g[4]
Vapor pressure 0.051 mPa (25 °C)[3]
1.08 kPa (200 °C)
28.06 kPa (300 °C)[6]
Acidity (pKa) 4.75 [3]
−198.6·10−6 cm3/mol
1.43 (70 °C)[3]
Viscosity 7.8 cP (70 °C)[3]
Thermochemistry
463.36 J/(mol·K)[6]
452.37 J/(mol·K)[6]
−892 kJ/mol[6]
10030.6 kJ/mol[3]
Hazards
GHS labelling:
GHS07: Exclamation mark[2]
Warning
H319[2]
P305+P351+P338[2]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Flash point 206 °C (403 °F; 479 K)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Palmitic acid (hexadecanoic acid in IUPAC nomenclature) is a fatty acid with a 16-carbon chain. It is the most common saturated fatty acid found in animals, plants and microorganisms.[9][10] Its 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. It 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 palmitic acid, amounting to 50–60% of total fats.[11]

Palmitates are the salts and esters of palmitic acid. The palmitate anion is the observed form of palmitic acid at physiologic pH (7.4). Major sources of C16:0 are palm oil, palm kernel oil, coconut oil, and milk fat.[12]

Dietary palmitic acid intake is associated with an increased cardiovascular disease risk through raising low-density lipoprotein.[13]

Occurrence and production

[edit]

Palmitic acid was discovered by saponification of palm oil, which process remains today the primary industrial route for producing the acid.[14] Triglycerides (fats) in palm oil are hydrolysed by high-temperature water and the resulting mixture is fractionally distilled.[15]

Dietary sources

[edit]

Palmitic acid is produced by a wide range of plants and organisms, typically at low levels. Among common foods it is present in milk, butter, cheese, and some meats, as well as cocoa butter, olive oil, soybean oil, and sunflower oil, (see table).[16] Karukas contain 44.90% palmitic acid.[17] The cetyl ester of palmitic acid, cetyl palmitate, occurs in spermaceti.

Palmitic acid content of common foods
Food % of total calories
Palm oil 45.1%
Beef tallow 26.5%
Butter fat 26.2%
Cocoa butter 25.8%
Lard 24.8%
Cottonseed oil 24.7%
Chicken 23.2%
Corn oil 12.2%
Peanut oil 11.6%
Soybean oil 11%
Coconut oil 8.4%
Palm kernel oil 8%
Rapeseed oil 3.6%
Source:[18]

Biochemistry

[edit]

Palmitic acid is the first fatty acid produced during fatty acid synthesis and is the precursor to longer fatty acids. As a consequence, palmitic acid is a major body component of animals. In humans, one analysis found it to make up 21–30% (molar) of human depot fat,[19] and it is a major, but highly variable, lipid component of human breast milk.[20] Palmitic acid comprises nearly half of total human brain saturated fatty acids.[21]

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.[22] 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.

Applications

[edit]

Surfactant

[edit]

Palmitic 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

[edit]

Because it is inexpensive and adds texture and "mouthfeel" to processed foods (convenience food), palmitic acid and its sodium salt find wide use in foodstuffs. Sodium palmitate is permitted as a natural additive in organic products.[23]

Military

[edit]

Aluminium salts of palmitic 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 palmitic acid.[24]

Research

[edit]

It is well accepted in the medical community that palmitic acid from dietary sources raises low-density lipoprotein (LDL) and total cholesterol.[18][25][26][27] The World Health Organization have stated there is convincing evidence that palmitic acid increases cardiovascular disease risk.[28] Palmitic acid intake is associated with an increased cancer risk, including prostate cancer.[29][30]

A 2021 review indicated that replacing dietary palmitic acid and other saturated fatty acids with unsaturated fatty acids, such as oleic acid, could reduce several biomarkers of cardiovascular and metabolic diseases.[31]

See also

[edit]

References

[edit]
[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

Palmitic acid

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from Grokipedia
Palmitic acid, also known as hexadecanoic acid, is a straight-chain saturated with the molecular formula C16H32O2 and a molecular weight of 256.42 g/mol. It is the most common saturated fatty acid in , occurring widely in and , and serves as a key building block in biological membranes and . In the , palmitic acid accounts for 20–30% of total fatty acids, where it can be endogenously synthesized via or obtained from dietary sources such as (which contains about 44% palmitic acid), , cheese, , and fatty fish. Biologically, it plays essential roles in cellular processes, including the palmitoylation of proteins to anchor them to cell membranes, β-oxidation for energy production, and as a major component of phospholipids and triglycerides in cell membranes. Its chemical structure consists of a 16-carbon chain with a group at one end, rendering it solid at room temperature with a of approximately 63°C and poor in but good in organic solvents. Industrially, palmitic acid is produced primarily through the of or and is widely used in the manufacture of soaps, , detergents, and emulsifiers due to its emulsifying and stabilizing properties. In research, it is studied for its metabolic effects, including its role as a for (TLR4), which can influence and metabolic health, though its overall nutritional impact depends on dietary context and positioning.

Chemical properties

Structure and formula

Palmitic acid, whose systematic IUPAC name is hexadecanoic acid, has the molecular formula C₁₆H₃₂O₂. The common name "palmitic acid" originates from its initial isolation through of in the . As a , it features a straight chain of 16 carbon atoms with no carbon-carbon double bonds, terminating in a (-COOH) that imparts its acidic properties. The condensed structural formula of palmitic acid is CH₃(CH₂)₁₄COOH, illustrating the unbranched chain of 14 methylene (-CH₂-) groups between a terminal methyl (-CH₃) group and the carboxyl (-COOH) group. In visual representations, the molecule is depicted as a linear zigzag chain to reflect the tetrahedral around each carbon atom, with the carboxyl group often shown in expanded form as -C(=O)OH to highlight the carbonyl and hydroxyl components. In biological contexts, palmitic acid refers specifically to the n- (straight-chain) , which predominates in natural . Although branched-chain C16 fatty acids, such as iso- and anteiso-hexadecanoic acids, occur naturally in microbial membranes and tissues, these variants differ chemically from the straight-chain palmitic acid and are classified separately.

Physical characteristics

Palmitic acid appears as a , waxy at . This form is characteristic of its saturated chain, which contributes to its solidity under standard conditions. It melts at 62.9 °C and boils at 351 °C. The molecular weight is 256.42 g/mol, and the of the phase is 0.848 g/cm³. In its pure form, palmitic acid is odorless and tasteless. Palmitic acid has very low solubility in water (0.05 mg/L at 20 °C), reflecting its hydrophobic nature. However, it is readily soluble in various organic solvents, including , , and .

Reactivity

Palmitic acid, a saturated , displays characteristic acidic behavior with a pKa value of 4.95, enabling it to readily donate its carboxyl proton in aqueous solutions and form corresponding salts, such as sodium palmitate, upon reaction with bases like . This salt formation is a neutralization reaction where the anion pairs with the metal cation, producing soaps used in various applications. A prominent reactivity of palmitic acid is esterification, typically achieved through acid-catalyzed reactions with alcohols, as exemplified by the esterification with to yield methyl palmitate. The balanced equation for this reversible process is: \ceCH3(CH2)14COOH+CH3OH⇌[H+]CH3(CH2)14COOCH3+H2O\ce{CH3(CH2)14COOH + CH3OH ⇌[H+] CH3(CH2)14COOCH3 + H2O} This reaction proceeds via a nucleophilic acyl substitution mechanism, where the alcohol attacks the protonated carbonyl carbon, and is influenced by factors such as catalyst loading, temperature, and reactant ratios to achieve high conversions, often exceeding 80% under optimized conditions. The reverse of esterification, , involves the alkaline of palmitic acid-derived s, cleaving the linkage to regenerate the salt and release the alcohol component, such as from s. This base-promoted reaction, commonly using , follows a mechanism involving nucleophilic attack by on the carbonyl, leading to tetrahedral intermediate formation and subsequent expulsion of the . Owing to its saturated aliphatic chain devoid of double bonds, palmitic acid exhibits high resistance to auto-oxidation and peroxidation, contrasting with unsaturated fatty acids that are vulnerable at sites. Chemically, this stability arises from the absence of reactive sites for radical in oxidative processes. In analogy to beta-oxidation, palmitic acid can undergo stepwise degradation by cleaving two-carbon acetyl units through dehydrogenation and hydration steps, though this is primarily enzymatic in nature. Furthermore, being fully saturated, palmitic acid remains unchanged under standard conditions, as no carbon-carbon multiple bonds are present to accept hydrogen.

Sources and occurrence

Natural distribution

Palmitic acid is the most common saturated found in , accounting for approximately 20–30% of total fatty acids in many organisms across biological kingdoms. This prevalence stems from its role as a fundamental building block in structures, enabling efficient and membrane formation in diverse . In , palmitic acid is highly concentrated in tropical oils, where it comprises about 44% of the fatty acids in and 8–10% in , alongside presence in other tropical oils. It also occurs in seeds and leaves of various species, contributing to cuticular waxes and structural that protect against environmental stress. Animal sources feature palmitic acid prominently in such as (25–30%), beef tallow (around 26%), and (25–30%), as well as in mammalian , where it often represents 20–30% of total fatty acids. In microbial and algal systems, it is a key component of produced by and ; for instance, it can constitute up to 45% of total fatty acids in species like , supporting applications in microbial production for biofuels. Environmentally, palmitic acid is detected in soils and aquatic sediments as a of , and it forms part of natural waxes on surfaces and in products.

Dietary sources

Palmitic acid is a prevalent in many everyday foods, particularly those rich in fats and tropical oils. It constitutes a significant portion of the total fat content in these sources, contributing to overall dietary intake. Major dietary contributors include palm oil-based products, such as , baked goods, and shortenings, where typically contains 41–44% palmitic acid by weight of total fatty acids. products like , cheese, and are also key sources; for instance, unsalted provides about 24 g of palmitic acid per 100 g serving. Meats, especially beef fat (), contain approximately 19–25% palmitic acid, making a notable contributor in omnivorous diets. derives its content primarily from , which is composed of roughly 25–26% palmitic acid. In processed foods, palmitic acid is commonly incorporated through s, emulsifiers, and frying oils derived from or fats; for example, vegetable can contain up to 26 g per 100 g. The following table summarizes palmitic acid levels in select common (per 100 g portion, based on USDA-derived data):
Food ItemPalmitic Acid (g/100 g)
41.0
(unsalted)24.0
fat ()24.0
26.0
9.0
Vegetable 26.0
Average daily intake of palmitic acid in Western diets ranges from 15–20 g, representing about 6–7% of total energy . levels are notably higher in Southeast Asian diets, often exceeding 25–30 g per day due to widespread use of in cooking and processed foods. Variations occur based on dietary patterns, with higher consumption in saturated fat-rich diets and more limited vegan sources primarily from plant oils like palm and .

Production

Biosynthesis

Palmitic acid is produced endogenously in living organisms through de novo , a cytosolic anabolic pathway that assembles saturated fatty acids from simpler precursors. This process is essential for and occurs primarily in , , and other eukaryotes, enabling the formation of palmitate as the primary product before further elongation or desaturation. The pathway begins with the carboxylation of to , catalyzed by the enzyme (ACC), which represents the committed step. The then serves as the two-carbon donor in a series of iterative reactions performed by the (FAS) complex. In mammals, FAS is a Type I multifunctional enzyme complex that facilitates condensation of the acyl chain with , followed by reduction, dehydration, and a second reduction, requiring NADPH as the reductant. Seven such cycles extend the chain to 16 carbons, releasing free palmitate upon completion. In , a similar process occurs in plastids via a Type II FAS system of discrete enzymes, also yielding palmitate as the end product. The overall stoichiometry of palmitate synthesis from eight acetyl-CoA molecules is given by the equation: 8 acetyl-CoA+7 \ceATP+14 \ceNADPH+14 \ceH+→ palmitate+7 \ceADP+7 \cePi+14 \ceNADP++8 \ceCoA+6 \ceH2O8 \ acetyl\text{-CoA} + 7 \ \ce{ATP} + 14 \ \ce{NADPH} + 14 \ \ce{H+} \rightarrow \ palmitate + 7 \ \ce{ADP} + 7 \ \ce{P_i} + 14 \ \ce{NADP+} + 8 \ \ce{CoA} + 6 \ \ce{H2O} This reaction highlights the energy investment, with ATP used for malonyl-CoA formation and NADPH for reductions. De novo fatty acid synthesis is tightly regulated, primarily through transcriptional control by insulin, which activates the sterol regulatory element-binding protein-1 (SREBP-1), a key that induces expression of ACC and FAS genes. This upregulation occurs in response to high availability, promoting in fed states. The pathway is most active in lipogenic tissues including the liver, , and mammary glands, where it supports and milk fat production. Evolutionarily, the core mechanism of is highly conserved across kingdoms. employ a Type II FAS system with individual soluble enzymes, whereas eukaryotes, including mammals and fungi, utilize a Type I FAS as a large, integrated polypeptide to enhance in compartmentalized environments. This reflects adaptations to cellular while maintaining the fundamental iterative elongation process.

Industrial methods

Palmitic acid was first isolated commercially in the through the of , a method developed by French chemist Edmond Frémy in 1840, marking the beginning of its large-scale production from natural lipid sources. This process evolved into modern industrial techniques focused on efficient extraction and synthesis to meet growing demand for oleochemicals. The primary industrial method for producing palmitic acid involves extraction from natural sources such as and through fat splitting, a high-pressure process. In this technique, triglycerides in the oil or fat are reacted with water at temperatures of 200-260°C and pressures of 30-60 bar in a continuous countercurrent column, yielding free s including palmitic acid (typically 40-45% in palm oil) and as a byproduct. Alternative approaches include acid or base-catalyzed followed by acidification, though the latter is more commonly associated with production rather than direct fatty acid isolation. The resulting crude fatty acid mixture from or is then subjected to , often via solvent extraction or dry fractionation, to enrich the palmitic acid content before further processing. Synthetic routes to palmitic acid exist but are rarely employed commercially due to high costs compared to extraction methods. These include partial of unsaturated fatty acids like (C16:1) or (C18:1, followed by chain shortening), using catalysts such as or under controlled hydrogen pressure. synthesis from smaller carboxylic acids via carbon chain elongation is also possible but uneconomical for bulk production, limiting its use to specialty applications. Purification of the extracted or synthesized palmitic acid is achieved primarily through , which operates at reduced pressures (1-10 mmHg) to lower s and prevent , achieving purities exceeding 99% for food-grade or technical-grade products. This step separates palmitic acid based on its (around 351°C at , reduced to 150-200°C under ) from other fatty acids like oleic and stearic acids in the mixture. Global production of plant-derived palmitic acid reached approximately 1.65 million tons in 2024, with the majority sourced from , primarily in and , which together account for over 80% of the world's output. This scale of production has raised significant environmental concerns, including and loss in tropical regions. For instance, a 2016 study found that 45% of oil palm plantations in were established on land that was forested as of 1989. To address these concerns, initiatives like the (RSPO) promote certified sustainable production, with over 20% of global volume certified as of 2024.

Biochemistry

Metabolic pathways

Palmitic acid, a long-chain saturated fatty acid, undergoes activation in the cytosol or endoplasmic reticulum before entering metabolic pathways. This process involves conversion to palmitoyl-CoA by the enzyme acyl-CoA synthetase (ACS), which catalyzes the reaction using ATP and coenzyme A, forming a high-energy thioester bond essential for subsequent transport and oxidation. The activation occurs primarily in the outer mitochondrial membrane or endoplasmic reticulum, preparing the fatty acid for entry into the mitochondria via the carnitine shuttle system. The primary catabolic pathway for palmitoyl-CoA is mitochondrial beta-oxidation, a repetitive four-step process that sequentially removes two-carbon units as . Long-chain , such as palmitoyl-CoA, is transported into the by the carnitine palmitoyltransferase (CPT) system, involving CPT1 on the outer membrane, carnitine-acylcarnitine translocase, and CPT2 on the inner membrane. Inside , beta-oxidation proceeds through dehydrogenation (by ), hydration (by enoyl-CoA hydratase), a second dehydrogenation (by 3-hydroxyacyl-CoA dehydrogenase), and thiolysis (by beta-ketothiolase), yielding one per cycle. For palmitoyl-CoA (16 carbons), seven cycles occur, producing eight molecules. The general equation for each beta-oxidation cycle is: Palmitoyl-CoA+CoA+FAD+NAD++H2O→Myristoyl-CoA+Acetyl-CoA+FADH2+NADH+H+\text{Palmitoyl-CoA} + \text{CoA} + \text{FAD} + \text{NAD}^+ + \text{H}_2\text{O} \rightarrow \text{Myristoyl-CoA} + \text{Acetyl-CoA} + \text{FADH}_2 + \text{NADH} + \text{H}^+ These reducing equivalents (FADH₂ and NADH) feed into the electron transport chain, while acetyl-CoA enters the citric acid cycle for further oxidation. Complete oxidation of one palmitate molecule, after subtracting the 2 ATP cost of activation, yields 106 ATP: 7 FADH₂ (each ~1.5 ATP), 7 NADH (each ~2.5 ATP), and 8 acetyl-CoA (each ~10 ATP via the citric acid cycle and oxidative phosphorylation)./24%3A_Lipid_Metabolism/24.05%3A_Oxidation_of_Fatty_Acids) In addition to beta-oxidation, palmitic acid can follow alternative metabolic fates, including elongation to longer-chain fatty acids by elongases in the or desaturation to monounsaturated (16:1n-7) via stearoyl-CoA desaturase-1 (SCD1). Peroxisomal oxidation serves as an alternative route, particularly for very-long-chain fatty acids derived from palmitate elongation, shortening them before mitochondrial processing, though it generates rather than ATP. Defects in the carnitine shuttle, such as carnitine palmitoyltransferase deficiencies, impair long-chain transport into mitochondria, reducing palmitate oxidation and leading to energy deficits during . Similarly, medium-chain (MCAD) deficiency, the most common oxidation disorder, compromises the dehydrogenation step, indirectly affecting palmitate metabolism by causing accumulation of intermediates and reduced overall beta-oxidation efficiency, resulting in hypoketotic hypoglycemia and metabolic crises.

Biological functions

Palmitic acid serves as a major structural component of cell membranes, where it is incorporated into phospholipids and triglycerides, comprising 20–30% of total fatty acids in human tissues. Palmitic acid influences the packing of lipid bilayers, contributing to membrane rigidity and maintaining appropriate physical properties essential for cellular integrity and function. In protein modification, palmitic acid undergoes post-translational S-acylation, known as palmitoylation, which covalently attaches it to residues on proteins, thereby anchoring them to cellular membranes. This dynamic and reversible process is crucial for the localization and activity of signaling proteins, such as Ras , which require palmitoylation for plasma membrane association and downstream in pathways like MAPK/ERK. Similarly, Src family kinases, including Src itself, depend on palmitoylation for membrane recruitment and regulation of activity in immune and oncogenic signaling. As a key precursor in , palmitic acid is esterified with to form triglycerides, serving as the primary molecule for in adipocytes. This supports long-term reserves by facilitating the deposition of neutral in droplets. Palmitic acid participates in through its role in ceramide biosynthesis, where it acts as a substrate for de novo synthesis of that modulate by activating pathways such as cascades in various cell types. Additionally, palmitic acid functions as a ligand for (TLR4), triggering inflammatory responses via activation and production in immune cells like macrophages. Although palmitic acid cannot be classified as an due to its endogenous production via de novo from , it remains critical for cellular growth and proliferation, as disruptions in its synthesis impair membrane formation and developmental processes.

Applications

Food and nutrition

Palmitic acid is utilized in the as a under the designation E570, functioning primarily as an emulsifier to blend oil and water-based ingredients, a stabilizer in products to maintain consistency and prevent separation, and a flavor enhancer in processed meats by contributing to the fatty and richness. In various food formulations, palmitic acid, often derived from shortenings, enhances texture in baked goods by providing tenderness and flakiness through its solid content at room temperature. It is incorporated into mixes to promote partial coalescence of globules, which helps prevent large formation and improves smoothness during storage. Additionally, in production, palm-based fats rich in palmitic acid are blended with to increase bloom resistance by stabilizing the and delaying fat migration to the surface. Nutritionally, palmitic acid is classified as a , providing 9 kcal per gram like other dietary fats, with no specific recommended daily allowance established for it individually. Dietary guidelines, such as those from the , recommend limiting total saturated fat intake to less than 10% of daily calories to support cardiovascular health. Palmitic acid is commonly added to infant formulas at levels approximating 20-25% of total fats to replicate the fatty acid profile of human , where it supports provision and absorption in newborns. In food labeling, palmitic acid must be declared as "palmitic acid" if added directly as an ingredient, or it contributes to the total "" value in the nutrition facts panel under regulatory requirements like those from the FDA.

Industrial and cosmetic uses

Palmitic acid serves as a primary in the production of and detergents, where it is saponified to form sodium palmitate, a key ingredient used for its cleansing properties in bar soaps and liquid formulations. This salt contributes to foaming action in shampoos and lotions, enhancing their lathering and emulsifying capabilities during personal care routines. In cosmetics, palmitic acid functions as an emollient in creams, lotions, and lipsticks, providing moisturizing effects by mimicking the 's natural and improving product texture. It also stabilizes emulsions, preventing ingredient separation, and is typically incorporated at concentrations of 1-5% in formulations for optimal performance without greasiness. Additionally, it appears in makeup products to help conceal imperfections by forming a smooth barrier. For industrial applications, palmitic acid is utilized in lubricants and fluids due to its high of approximately 63°C, which imparts resistance and wear protection in greases and cutting oils. Its derivatives enhance in these formulations, making it suitable for automotive and sectors. In pharmaceuticals, palmitic acid acts as an in topical ointments, aiding in drug absorption and formulation stability, and serves as a precursor for palmitate esters employed in sustained-release systems. For instance, it has been incorporated into insulin implants to control release rates in experimental models. Palmitic acid is a of the oleochemical industry, with global market value exceeding USD 300 million annually and derivatives like widely used as solvents in cosmetic and industrial solvents. These esters, produced via esterification of palmitic acid with isopropanol, provide non-oily emolliency and are to high-volume processes.

Other uses

Palmitic acid derivatives, particularly aluminum salts combined with , were historically used in the production of , an incendiary gelled fuel mixture deployed by military forces during for operations. This formulation thickened into a sticky, slow-burning substance that adhered to targets, enhancing its effectiveness in aerial incendiary attacks. In modern military applications, palmitic acid is combined with to create anti-clumping agents for fibers, which are deployed during adversary air training exercises to simulate countermeasures and improve tactical simulations. Palmitic acid contributes to biodiesel production through the transesterification of , where triglycerides containing palmitic acid are reacted with or in the presence of a catalyst to yield methyl esters (FAME) or ethyl esters, with the palmitate fraction comprising a significant portion—often around 40-45%—of the final composition. This process converts the saturated palmitic acid content into stable components that enhance the and oxidative stability of the diesel substitute, making it suitable for applications derived from palm feedstocks. Enzymatic methods further optimize yields from , reducing energy inputs while preserving the palmitic acid-derived esters' in fuels. In , palmitic acid and its esters serve as carriers and co-formulants in formulations, improving the and of active ingredients to plant surfaces, thereby enhancing efficacy against pests while minimizing environmental runoff. Palm-based methyl esters, rich in palmitate, act as eco-friendly solvents in these mixtures, replacing petroleum-based carriers and supporting practices. Additionally, fatty acids including palmitic acid are incorporated into formulations to promote uptake, with applications in foliar sprays that facilitate targeted delivery of micronutrients like to crops such as palms, preventing deficiencies and boosting growth. These uses leverage palmitic acid's properties to ensure even distribution and absorption in spray applications. Palmitic acid is applied in coatings for medical implants to enhance and reduce complications such as or rejection. For instance, palmitic acid coatings on allogeneic cancellous bone grafts enable sustained local release of antibiotics like , achieving high concentrations at implant sites while maintaining structural integrity and promoting . Composite coatings combining and palmitic acid on implants provide superhydrophobic surfaces that inhibit bacterial adhesion and corrosion, improving long-term performance in orthopedic applications. These modifications exploit palmitic acid's hydrophobic nature to create barriers that support tissue compatibility without eliciting adverse immune responses. Emerging applications of palmitic acid include its use in nanomaterial synthesis for drug targeting, where it caps or functionalizes nanoparticles to improve stability, bioavailability, and site-specific delivery. Palmitic acid-capped metal-organic framework nanoparticles, such as MIL-101-Al, serve as nano-adjuvants in , enhancing immune responses by facilitating and targeted uptake in dendritic cells. In drug delivery systems, biomimetic palmitic acid-functionalized polydopamine nanoparticles enable targeted transport of therapeutics like across the blood-brain barrier, achieving higher encapsulation efficiency and controlled release in neuronal cells. Conjugation of palmitic acid to peptides or siRNA further amplifies potency in therapies, extending circulation time and cellular penetration for precise therapeutic interventions.

Health effects and research

Nutritional role

Palmitic acid is efficiently absorbed in the following the of dietary triglycerides by pancreatic into free fatty acids and 2-monoacylglycerols, which form mixed micelles with salts to facilitate uptake by enterocytes, with typically around 95% for long-chain fatty acids including palmitic acid. Within enterocytes, it is re-esterified into triglycerides and assembled into chylomicrons, which enter the before reaching the bloodstream for distribution to tissues. This process ensures high utilization of dietary palmitic acid, though its absorption can be influenced by the positional distribution in triglycerides, with sn-2 positioning enhancing efficiency as seen in human milk fats. As a non-essential fatty acid, palmitic acid is synthesized endogenously via de novo lipogenesis from excess carbohydrates or proteins in the liver and , reducing the strict dietary requirement but allowing dietary intake to supplement endogenous production. In typical Western diets, dietary palmitic acid provides 20–30 g per day, representing approximately 8–10% of total energy intake and comprising a significant portion of consumption. Common sources include , , and dairy products, where it contributes to overall fat-derived energy. Within the broader dietary fat profile, palmitic acid should be balanced as part of total intake, with the recommending that saturated fatty acids, including palmitic acid, be limited to less than 10% of total energy intake to minimize risks associated with excessive consumption. This guideline emphasizes replacing saturated fats with unsaturated alternatives where possible to optimize nutritional balance. In special populations like infants, palmitic acid meets higher relative needs, constituting 20–25% of total fatty acids in human to support rapid and body growth through efficient provision and formation. During recovery, particularly in children, palmitic acid-rich promote intestinal mucosal repair and enhance , aiding rehabilitation when provided in balanced therapeutic formulas. Palmitic acid interacts with other dietary fats during absorption, competing with unsaturated fatty acids for intestinal enzymes such as those involved in esterification and micelle incorporation, which can result in slightly lower absorption efficiency for saturated versus unsaturated fatty acids.

Physiological impacts

Palmitic acid, the most abundant saturated fatty acid in human diets and tissues, exerts both beneficial and adverse effects on human physiology depending on intake levels and dietary context. At high intakes exceeding 10% of total caloric energy from saturated fats, palmitic acid contributes to elevated low-density lipoprotein (LDL) cholesterol concentrations, which is a key risk factor for atherosclerosis and cardiovascular disease (CVD). Replacement of palmitic acid with unsaturated fatty acids in diets has been shown to reduce LDL cholesterol by approximately 0.36 mmol/L, underscoring its hypercholesterolemic potential in isolation. However, recent meta-analyses of observational and interventional studies indicate that palmitic acid's cardiovascular effects are neutral or less pronounced in mixed diets where it is consumed alongside polyunsaturated fats and fiber, challenging earlier concerns about saturated fats broadly. For instance, the 2014 Chowdhury meta-analysis of 32 prospective studies found no significant association between circulating or dietary saturated fatty acids, including palmitic acid, and coronary risk. In metabolic physiology, excess palmitic acid promotes components of metabolic syndrome, including insulin resistance and hepatic steatosis, primarily through its conversion to ceramides. Palmitic acid induces ceramide accumulation in hepatocytes and adipocytes, which disrupts insulin signaling pathways and impairs glucose uptake, with effects becoming evident at intakes above 20 g per day in high-fat diets. This ceramide-mediated lipotoxicity also drives ectopic fat deposition in the liver, exacerbating non-alcoholic fatty liver disease (NAFLD) by increasing de novo lipogenesis and oxidative stress. Additionally, palmitic acid activates the nuclear factor kappa B (NF-κB) pathway in macrophages and endothelial cells, leading to upregulated production of pro-inflammatory cytokines such as tumor necrosis factor-alpha (TNF-α), which amplifies systemic inflammation and endothelial dysfunction. Despite these risks, palmitic acid plays essential positive roles in at moderate levels. As a primary component of phospholipids, it maintains integrity and fluidity, supporting cellular signaling and structural stability across tissues. During fetal development, palmitic acid is critical for embryonic growth, providing energy substrates and precursors for synthesis; fetal tissues actively metabolize it, with maternal supply ensuring adequate levels for . Studies from the 2020s highlight the context-dependent nature of palmitic acid's impacts, with less adverse outcomes when derived from whole foods compared to isolated or excessive supplemental forms. A review in Frontiers in Nutrition emphasized that tissue accumulation of palmitic acid often stems from dysregulated endogenous synthesis rather than dietary intake alone, resulting in milder effects in balanced diets rich in whole foods like and versus purified palmitic acid in processed items. This nuance suggests that overall dietary patterns modulate palmitic acid's physiological burden, promoting a more individualized approach to intake.

Current studies

Recent research has illuminated the role of protein S-palmitoylation in neurodegenerative diseases, particularly (AD). A 2024 study demonstrated that inhibition of zDHHC7, a palmitoyltransferase , significantly reduces protein S-palmitoylation in the hippocampus of AD mouse models and human post-mortem brain tissue, preventing cognitive deficits and amyloid-beta plaque formation by modulating synaptic function. Similarly, bioinformatics analyses in 2025 identified the palmitoylation-related gene ZDHHC22 as a potential diagnostic and immunomodulatory target in AD, with elevated expression linked to and disease progression through and weighted gene co-expression network analysis (WGCNA). These findings suggest that targeting palmitoylation pathways could offer novel therapeutic strategies for AD, addressing synaptic dysfunction central to neurodegeneration. In metabolic research, palmitic acid has been shown to influence gut microbiota composition and host metabolism. A 2023 study revealed that diets enriched in long-chain saturated fatty acids like palmitic acid alter gut microbiota profiles independently of fiber intake, leading to dysbiosis that promotes hepatic lipid accumulation and insulin resistance in mice. High-fat diets increase circulating palmitic acid levels via production by dominant gut bacteria such as Bacteroides thetaiotaomicron, exacerbating systemic inflammation and metabolic syndrome, as observed in 2025 rodent models. Regarding cancer, palmitate-induced lipotoxicity contributes to tumor cell death or survival depending on context; a 2023 investigation found that CD36-mediated uptake of monounsaturated fatty acids protects breast cancer cells from palmitate-induced lipotoxicity by maintaining lipid homeostasis, highlighting palmitoylation's role in cancer progression. Lysosomal calcium release mediates palmitate's lipotoxic effects in non-cancerous cells, but similar mechanisms in cancer suggest potential for targeted therapies to exploit this vulnerability. Nutritional studies post-2020 have reevaluated the impacts of palmitic acid within s, challenging blanket restrictions. A 2024 review emphasized that palmitic acid's position in triacylglycerols affects absorption and ; sn-2 positioning, common in human milk and some vegetable oils, enhances palmitate without elevating postprandial lipemia as much as sn-1/sn-3 forms, supporting nuanced dietary guidelines over total limits. Emerging 2025 evidence from interesterified fat trials indicates that palmitic acid-rich processed fats do not adversely affect short-term cardiovascular markers like LDL-cholesterol or when consumed in moderation, suggesting no direct causation of (CVD) in isolation and calling for context-specific recommendations. A 2024 analysis further noted that endogenously produced palmitic acid from may contribute more to CVD risk via synthesis than dietary sources alone. For low-palmitate diets in , a 2024 review of interventions highlighted that reducing saturated fats like palmitic acid improves glucose metabolism and insulin sensitivity in patients, though direct clinical trials on isolated low-palmitate regimens remain limited. In emerging applications, efforts aim to develop crops with reduced palmitic acid content for healthier oils; 2023 multi-gene editing in increased seed oil content while altering profiles to lower saturates, paving the way for low-palmitate oilseeds like . In biofuels, 2025 studies on palm distillate conversion to green diesel reported high efficiency, with yields up to 90% via catalytic hydrodeoxygenation, offering a sustainable alternative to fossil fuels with lower . These advancements address previous biases toward palmitic acid's harms by emphasizing balanced, context-dependent roles in health and industry.

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