PALMITIC ACID

Palmitic acid (hexadecanoic acid in the IUPAC nomenclature) is the most common saturated fatty acid found in animals and plants. It has 16 carbons, its base form is called palmitate. Its melting temperature is 63.1 ° C, its chemical formula is CH3 (CH2) 14COOH. As the name suggests, it is found in palm oil and palm kernel. It is also found in butter, cheese, milk and meat.
The first fatty acid synthesized in the formation of fatty acids (lipogenesis) in living things is palmitic acid, longer fatty acids are produced from it. Acetyl-CoA carboxylase enzyme converts acetyl-ACP to malonyl-ACP, palmitate provides negative feedback on this enzyme, preventing further palmitate production.
CAS number 57-10-3
PubChem CID: 985

Synonyms:
PALMITIC ACID; Palmitic acid; Acid, Hexadecanoic; Acid, Palmitic; Calcium Palmitate; Hexadecanoic Acid; Palmitate, Calcium; Palmitate, Sodium; Palmitic Acid; Sodium Palmitate; palmitic acid; Hexadecanoic acid; 57-10-3; Cetylic acid; palmitate; n-Hexadecanoic acid; Hexadecylic acid; Hydrofol; n-Hexadecoic acid; 1-Pentadecanecarboxylic acid; Palmitinic acid; Pentadecanecarboxylic acid; C16 fatty acid; hexaectylic acid; Industrene 4516; Emersol 140; Emersol 143; Hystrene 8016; Hystrene 9016; 1- Hexyldecanoic Acid; hexadecoic acid; Palmitinsaeure; Palmitic acid, pure; Palmitic acid 95%; Palmitic acid (natural); Prifac 2960; FEMA No. 2832; Pristerene 4934; Edenor C16; Kortacid 1698; Lunac P 95KC; C16:0; Loxiol EP 278; Lunac P 95; Lunac P 98; Hydrofol Acid 1690; palmic acid; HSDB 5001; Fatty acids, C14-18; AI3-01594; C16H32O2; NSC 5030; UNII-2V16EO95H1; CCRIS 5443; Palmitic acid (NF); Glycon P-45; CHEBI:15756; Calcium palmitate; NSC5030; EINECS 200-312-9; Hexadecanoic acid (9CI); BRN 0607489; Palmitic acid (7CI,8CI); CHEMBL82293; CH3-[CH2]14-COOH; IPCSVZSSVZVIGE-UHFFFAOYSA-N; 2V16EO95H1;; n-hexadecoate; LMFA01010001; PA 900; FA 1695; 1-hexyldecanoate; NCGC00164358-01; DSSTox_CID_1602; pentadecanecarboxylate; DSSTox_RID_76229; DSSTox_GSID_21602; FAT; PLM; Hexadecanoate (n-C16:0); CAS-57-10-3; SR-01000944716; Palmitic acid [USAN:NF];; palmitoatei; Hexadecoate; Palmitinate; palmitic-acid; palmitoic acid; Aethalic acid; Hexadecanoic acid Palmitic acid; (C14-C18)Alkylcarboxylic acid; 2hmb; 2hnx; (C14-C18) Alkylcarboxylic acid; Fatty acid pathway; Palmitic acid_jeyam; EINECS 266-926-4; Kortacid 1695; Palmitic acid_RaGuSa; Univol U332; Prifrac 2960; Hexadecanoic acid anion; 3v2q; ACMC-1ASQF; SDA 17-005-00i Palmitic acid, >=99%; bmse000590; D0KS1O; Epitope ID:141181; C16:0 (Lipid numbers); EC 200-312-9; AC1L1AH2; SCHEMBL6177; 4-02-00-01157 (Beilstein Handbook Reference); KSC270O2R; WLN: QV15; P5585_SIGMA; GTPL1055; QSPL 166; Palmitic acid, 95% 500g; DTXSID2021602; CTK1H0728; hexadecanoic acid (palmitic acid); 1b56; MolPort-001-780-241; HMS3649N08; Palmitic acid, analytical standard; Palmitic acid, BioXtra, >=99%; Palmitic acid, Grade II, ~95%; BB_SC-09400; NSC-5030; Palmitic acid, natural, 98%, FG; ZINC6072466; Tox21_112105; Tox21_201671; Tox21_302966; ANW-13574; BBL011563; BDBM50152850; SBB017229; STL146733; Palmitic acid, >=95%, FCC, FG; AKOS005720983; Light end (C14-C18) saturated fatty acid fraction from tallow fatty acids; Tox21_112105_1; DB03796; FA 16:0; LS-2331; MCULE-1361949901; Palmitic acid, for synthesis, 98.0%; RP29137; RTC-060456; SEL10404124; NCGC00164358-02; NCGC00164358-03; NCGC00256424-01; NCGC00259220-01; AN-23574; I728; Palmitic acid, purum, >=98.0% (GC); SC-81752; ST023798; AB1002597; TC-060456; CS-0009861; FT-0626965; N2456; P0002; P1145; Palmitic acid, SAJ first grade, >=95.0%; ST24025707; C00249; D05341; Palmitic acid, Vetec(TM) reagent grade, 98%; Palmitic acid, >=98% palmitic acid basis (GC); S04-0102; SR-01000944716-1; SR-01000944716-2; BA71C79B-C9B1-451A-A5BE-B480B5CC7D0C; F0001-1488;; Z955123552; Palmitic acid, certified reference; material, TraceCERT(R); UNII-13FB83DEYU component IPCSVZSSVZVIGE-UHFFFAOYSA-N; UNII-44NH37HHP9 component IPCSVZSSVZVIGE-UHFFFAOYSA-N; UNII-5U9XZ261ER component IPCSVZSSVZVIGE-UHFFFAOYSA-N; UNII-7N137Q0QYJ component IPCSVZSSVZVIGE-UHFFFAOYSA-N; UNII-96GS7P39SN component IPCSVZSSVZVIGE-UHFFFAOYSA-N; UNII-B6G0Y5Z616 component IPCSVZSSVZVIGE-UHFFFAOYSA-N; UNII-D1CZ545P7Z component IPCSVZSSVZVIGE-UHFFFAOYSA-N; UNII-HBA528N3PW component IPCSVZSSVZVIGE-UHFFFAOYSA-N; UNII-MO7HV04S9Y component IPCSVZSSVZVIGE-UHFFFAOYSA-N; UNII-ODL221H4AM component IPCSVZSSVZVIGE-UHFFFAOYSA-N; UNII-Q8Y7S3B85M component; IPCSVZSSVZVIGE-UHFFFAOYSA-N; UNII-V1PY73ZXPE component IPCSVZSSVZVIGE-UHFFFAOYSA-N; Palmitic acid, European Pharmacopoeia (EP) Reference Standard; UNII-79P21R4317 component IPCSVZSSVZVIGE-UHFFFAOYSA-N; Palmitic acid, United States Pharmacopeia (USP) Reference Standard; Palmitic acid, Pharmaceutical Secondary Standard; Certified Reference Material; 116860-99-2; 212625-86-0; 60605-23-4; 66321-94-6; 8045-38-3; Sodium Palmitate, Palmitic acid sodium salt, Sodium hexadecanoate, Sodium pentadecanecarboxylate, HSDB 759; palimitik asit; palimtik asit; palimitik asid; palimtik asid; palmıtıc asid; palmıtıc asit

PALMITIC ACID
Since palmitic acid is a carboxylic acid, it can be esterified with various organic alcohols. In the production of low-fat milk, retinyl palmitate, which is the esterified form of retinol and palmitate, is added back to replace the vitamin A (retinol) lost along with the fat from milk. In the cosmetics industry, creams containing vitamin A also contain retinyl palmitate. In the pharmaceutical industry, some drugs esterified with palmitate, such as chloramphenicol palmitate, are ineffective and become active after hydrolysis in the small intestine. Ascorbyl palmitate, which is used to prevent the spoilage of oils in the food industry, combines the antioxidant properties of ascorbic acid with the oil solubility of palmitate.
In the cysteine ​​groups of some proteins in the cell membrane, palmitate is bound, thus the protein remains attached to the membrane.
Palmitic acid derivatives II. They were used in napalm production during World War II.
Palmityl alcohol is formed as a result of the reduction of palmitic acid.
PALMITIC ACID CH3 (CH2) 14COOH PALMITIC ACID CH3 (CH2) 14COOH PALMITIC ACID CH3 (CH2) 14COOH
CH3 (CH2) 14COOH
Description: White crystalline solid.
Packaging unit: 25 kg.
CAS No: 57-10-3
Chemical name: Hexadecanoic acid; hexadecilic acid.
Specifications
Acid value: 219 mg KOH / g
Iodine value, I2: 0.2%
Titer: 61,7 oC
Color, Lovibond 5 ¼: 0.1 R, 0.7 Y
Color, APHA: 30
Molecular weight: 256.22 g / mol
Chain dispersion C14: 0.7%
Saponification value: 217-223 mgKOH / g
C16: 98.9%
Water content: <0.2%
C18: 0.5%

Properties: It is a 16-carbon member of the saturated fatty acid group found in plants and animals. It was first obtained from palm oil. Despite its wide distribution, it is not found in very large proportions in oils. Usually it makes up 5% of total fatty acid, is found in common vegetable oils (peanut oil, soy, corn, coconut oil) as much as 10% and in marine animals. Lard, tallow, cocoa, butter, palm oil contain 25-40% of this component. It has good color and oxidation stability. Salts with alkalis dissolve more in water than salts of stearic acid.
Usage Areas: It finds wide use in cosmetics, wax formulations and waxes. It is used in the production of emulsifiers, anionic and non-ionic surfactants, textile chemicals and soap-detergent production. It is also used as an anti-caking agent in foods and has an anti-bacterial effect.
Storage: It is stable for approximately 2 years below 60 oC.
One of the unsaturated fatty acids found in animal fats is palmitoleic acid, which has 16 carbon atoms and 1 unsaturated bond.
Palmitoleic acid is a monounsaturated fatty acid with a closed formula C16H30O2, a molar mass of 254.408 kg / mol, a density of 0.894 g / cm3 and a melting point of -0.1 ° C. The geometric isomer of palmitoleic acid, which is shaped according to the configuration of hydrogen atoms attached to the carbon atoms at the end of double bonds; It has two isomers, cis and trans. If hydrogen atoms are on the same side of the carbon chain, cis and trans isomers appear in the opposite directions (Figure 1), and the position isomerism is formed by the displacement of double bonds in the molecule (Mensink and Katan, 1990).

PALMITIC ACID
SELF
Palmitic acid (PA) has long been negatively portrayed for its putative detrimental effects, overshadowing a number of important physiological activities. PA is the most common saturated fatty acid that makes up 20-30% of the total fatty acids in the human body and can be supplied in the diet or synthesized endogenously through de novo lipogenesis (DNL). PA tissue content appears to be controlled around a well-defined concentration, and changes in uptake do not significantly affect tissue concentration because the exogenous source is balanced by PA endogenous biosynthesis. Certain physiopathological conditions and nutritional factors may potently induce DNL, ​​resulting in increased tissue content of PA and impaired homeostatic control of tissue concentration. Strict homeostatic control of PA tissue concentration relates to its fundamental physiological role in ensuring the physical properties of the membrane, as well as protein palmitoylation, palmitoylethanolamide (PEA) biosynthesis and an effective surfactant activity in the lung. In order to maintain the balance of membrane phospholipids (PL), optimal intake of PA at a certain ratio with unsaturated fatty acids, particularly PUFAs of both the n-6 and n-3 families, can be crucial. However, in the presence of other factors, such as positive energy balance, excessive carbohydrate intake (especially mono and disaccharides), and a sedentary lifestyle, the mechanisms of maintaining a stable PA concentration state may be impaired, resulting in excessive tissue accumulation. PA resulting in dyslipidemia, hyperglycemia, increased ectopic fat deposition and increased inflammatory tone via toll-like receptor 4, therefore, controversial data on the relationship between dietary PA and harmful health effects are likely to be associated with excessive dietary imbalance in certain pathophysiological conditions and in the presence of an increased DNL. The PA / PUFA ratio can further accelerate these deleterious effects.

Palmitic acid (16: 0, PA) is the most common saturated fatty acid found in the human body and can be supplied in the diet or synthesized endogenously from other fatty acids, carbohydrates and amino acids. PA represents 20--30% of total fatty acids (FA) in membrane phospholipids (PL) and adipose triacylglycerols (TAG) (Carta et al., 2015). On average, a 70 kg man consists of 3.5 Kg PA. As the name suggests, PA is an important component of palm oil (44% of total fats), but significant amounts of PA can also be found in meat and dairy products (50-60% of total fats) and cocoa butter. (26%) and olive oil (8-20%). Also, PA is present in breast milk at 20-30% of total fats (Innis, 2016). Average PA intake is about 20-30 g / day, representing about 8-10% width (Sette et al., 2011). Since changes in uptake do not significantly affect tissue concentration (Innis and Dyer, 1997; Song et al., 2017), PA tissue content appears to be controlled around a well-defined concentration, as uptake is balanced by PA endogenous biosynthesis. by de novo lipogenesis (DNL). Certain physiopathological conditions and nutritional factors can potently induce DNL, ​​resulting in increased tissue content of PA and impaired homeostatic control of tissue concentration (Wilke et al., 2009). However, under normal physiological conditions, PA accumulation is prevented by increased delta 9 desaturation to palmitoleic acid (16: 1n - 7, POA) and / or elongation to stearic acid (SA) and greater delta 9 desaturation to oleic acid (18: 1). . , OA) (Strable and Ntambi, 2010; Silbernagel et al., 2012). Strict homeostatic control of PA tissue concentration is probably related to its fundamental physiological role in various biological functions. PA seems to play a very important role, especially in infants, as it was recently extensively revised by Innis (Innis, 2016). Disturbance of PA homeostatic balance, which occurs in different physiopathological conditions such as atherosclerosis, neurodegenerative diseases, and cancer, is usually related to an uncontrolled PA endogenous biosynthesis independent of dietary supplements.

Chemical structural formula of palmitic acid.
Palmitic acid (hexadecanoic acid in the IUPAC nomenclature) is the most common saturated fatty acid found in animals and plants. It has 16 carbons, its base form is called palmitate. Its melting temperature is 63.1 ° C, its chemical formula is CH3 (CH2) 14COOH. As the name suggests, it is found in palm oil and palm kernel. It is also found in butter, cheese, milk and meat.
The first fatty acid synthesized in the formation of fatty acids (lipogenesis) in living things is palmitic acid, longer fatty acids are produced from it. Acetyl-CoA carboxylase enzyme converts acetyl-ACP to malonyl-ACP, palmitate provides negative feedback on this enzyme, preventing further palmitate production.
Since palmitic acid is a carboxylic acid, it can be esterified with various organic alcohols. In the production of low-fat milk, retinyl palmitate, which is the esterified form of retinol and palmitate, is added back to replace the vitamin A (retinol) lost along with the fat from milk. In the cosmetics industry, creams containing vitamin A also contain retinyl palmitate. In the pharmaceutical industry, some drugs esterified with palmitate, such as chloramphenicol palmitate, are ineffective, they become active after hydrolysis in the small intestine. Fat deterioration in the food industry Ascorbyl palmitate combines the antioxidant properties of ascorbic acid with the oil solubility of palmitate.
In the cysteine ​​groups of some proteins in the cell membrane, palmitate is bound, so the protein remains attached to the membrane.
Palmitic acid derivatives II. They were used in napalm production during World War II.
Palmityl alcohol is formed as a result of the reduction of palmitic acid.
Palmitic Acid
Palmitic acid Long chain and very important saturated fatty acid. In nature, it is found in practically all vegetable and animal oils, often together with stearic acid. It is found in 10% in many fish oil, 20% in cotton oil and 40% in palm oil. Like other fatty acids, palmitic acid is not found free in nature. However, like others, it is found in oils esterified with glycerin, which are called glycerides. Palmitic acid is found in oils as glycerine tripalmitate. Palmi
2nd
Palmitic acid Long chain and very important saturated fatty acid. In nature, it is found in practically all vegetable and animal oils, often together with stearic acid. It is found in 10% in many fish oil, 20% in cotton oil and 40% in palm oil. Like other fatty acids, palmitic acid is not found free in nature. However, like others, it is found in oils esterified with glycerin, which are called glycerides. Palmitic acid is found in oils as glycerin tripalmitate. The formula of palmitic acid is CH3 (CH2) 14CO2H, it is a colorless solid and has various crystal forms, the most stable of which has a melting point of 62.9 ° C. Since palmitic acid is a monocarboxylic acid, it shows the general chemical properties of this class. E.g; they form esters with alcohols.
C15H31COOH + ROH ® C15H31COOR + H2O

It forms phosphorus pentachloride (PCl5) and acid chloride (C15H31COCl). The most important compound of palmitic acid is the compounds it makes with sodium or potassium. Sodium palmitate (C15H31COONa) is white solid soap, potassium palmitate (C15H31COOK) is brown liquor (liquid) soap. In the soap industry, glycerine esters are often used to produce soap, not palmitic acid or other acids themselves. Palmitic acid, containing sixteen carbon atoms, consists of the biosynthesis of two-carbon acetic acid.
Hexadecanoic acid, in palmitic acid or IUPAC designation, is the most common saturated fatty acid found in animals, plants and microorganisms. Its chemical formula is CH3 (CH2) 14COOH and C: D 16: 0. As the name suggests, palm oil (palm oil) is an essential component of the oil extracted from its fruit. Palmitic acid can also be found in meats, cheeses, butter, and other dairy products. Palmitates are salts and esters of palmitic acid. Palmitate anion is the form of palmitic acid observed at physiological pH (7.4).
Aluminum salts of palmitic acid and naphthenic acid were gelling agents that were used in conjunction with volatile petrochemicals to produce napalm during World War II. The word "napalm" is derived from the words naphthenic acid and palmitic acid.

Formation and production
Palmitic acid was discovered in saponified palm oil by Edmond Frémy in 1840. By hydrolyzing the triglycerides (oils) in palm oil with high temperature water (above 200 ° C or 390 ° F) and fractionally distilling the resulting mixture to yield the pure product, this remains the primary industrial route for its production.
Palmitic acid is produced naturally by a wide variety of other plants and organisms, typically at low levels. It occurs naturally in butter, cheese, milk and meat, as well as cocoa butter, soybean oil, and sunflower oil. Karukas contains 44.90% palmitic acid. Cetyl ester of palmitic acid (cetyl palmitate) occurs in spermacets.
biochemistry
Excess carbohydrate in the body is converted into palmitic acid. Palmitic acid is the first fatty acid produced during fatty acid synthesis and is the precursor to longer fatty acids. As a result, palmitic acid is an important body component of animals. In humans, an analysis found it to make up 21-30% (molar) of human storage fat and is an important but highly variable lipid component of breast milk. Palmitate negatively feeds acetyl-CoA carboxylase (ACC), which is responsible for converting acetyl-CoA to malonyl-CoA, which is used to attach to the growing acyl chain and thus prevents further palmitate formation. In biology, some proteins are modified by the addition of a palmitoyl group in a process known as palmitoylation. Palmitoylation is important for the membrane localization of many proteins.

Applications
Surfactant
Palmitic acid is used to produce soaps, cosmetics and industrial mold release agents. In these applications, sodium palmitate, which is usually obtained by saponification of palm oil, is used. For this purpose, palm oil obtained from palm tree (Elaeis guineensis species) is processed with sodium hydroxide (in the form of caustic soda or lye), which produces glycerol and sodium palmitate by causing hydrolysis of ester groups.
Hydrogenation of palmitic acid yields cetyl alcohol used in detergent and cosmetics production.