PALMITIC ACID
PALMITIC ACID
Palmitic Acid is a saturated long-chain fatty acid with a 16-carbon backbone.
Palmitic acid is found naturally in palm oil and palm kernel oil, as well as in butter, cheese, milk and meat.
Hexadecanoic acid is a straight-chain, sixteen-carbon, saturated long-chain fatty acid.
It has a role as an EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor, a plant metabolite, a Daphnia magna metabolite and an algal metabolite. It is a long-chain fatty acid and a straight-chain saturated fatty acid. It is a conjugate acid of a hexadecanoate.
Preferred IUPAC name: Hexadecanoic acid
Other names: Palmitic acid
C16:0 (Lipid numbers)
CAS Number: 57-10-3
EC/List no.: 200-312-9
Mol. formula: C16H32O2
PALMITIC ACID
Hexadecanoic acid
1-Pentadecanecarboxylic acid
Cetylic acid
Hexadecanoic acid;
Hexadecanoate;
Hexadecylic acid;
Palmitic acid;
Palmitate;
Cetylic acid
Palmitic acid is one of the most prevalent fatty acids occurring in the oils and fats of animals; it also occurs naturally in palm oil.
It is generated through the addition of an acetyl group to multiple malonyl groups connected by single bonds between carbons.
This structure forms a saturated acid—a major component of solid glycerides.
Palmitic Acid is widely used as a raw material for production of various esters, fatty alcohols, fatty acid isethionates, metallic soaps, fatty acid sarcosinates, imidazolines, fatty amines, oxazolines, surfactants in personal care products, liquid and transparent soaps, corrosion/rust inhibitor for antifreeze; Used in agricultural chemicals, food, adhesive, crayon, candles, cements, coatings, inks, leather waxes, lubricants, metal workings, mining, pencils, capsules and ointments, plastics, rubber, textiles etc.
Palmitic acid is one of the most common saturated fatty acids and one of the most common in body lipids: it accounts for 21 to 30% of human fat tissue (fat). It is found in both animals and plants, mainly from palm oil (hence its name). Palmitic acid is used for many functions in cosmetic products: surfactant (detergent), emulsifier (allows mixing oil and water), opacifying agent or emollient (softens the skin). It is authorized in Bio.
Palmitic acid is a fatty acid that can be found naturally in the skin. In fact, it’s the most common saturated fatty acid found in animals and plants.
As for skincare, it can make the skin feel nice and smooth in moisturizers (emollient) or it can act as a foam building cleansing agent in cleansers. It’s also a very popular ingredient in shaving foams.
Palmitic acid is one of several fatty acids used in skin care as an emollient or moisturiser.
Fatty acids are oily molecules that combine with glycerol to make the many fats found in nature.
Palmitic acid is most commonly produced from palm oil, although it is found in smaller amounts in other vegetable oils as well as dairy and meat.
To produce pure palmitic acid, the oil is boiled to break the fatty acids off of the glycerol and then the different acids are separated out based on their boiling point.
In skin care products it is commonly used in the form of an alkali salt, where the fatty acid has been reacted with an alkali like sodium hydroxide to produce sodium palmitate.
As a fatty acid, palmitic acid can act as an emollient. When applied to the skin by lotions, creams or bath oils, emollients can soften the skin and help it retain moisture by forming an oily, water blocking layer that slows the loss of water through the skin. This can improve dry and flaky skin as well as conditions like psoriasis and eczema.
One of the main functions of palmitic acid alkali salts is that they acts as emulsifiers and surfactants, allowing oil based, hydrophobic molecules to interact with water where normally they would repel each other. This works by the fatty acid end of the salt interacting with the oil while the salt end interacts with the water creating an adapter between oil and water. In some products this increases the stability of the product as oil and water would naturally separate without it. In soaps and cleansing oils, the fatty end grabs oil and water-resistant make up on your skin while the salt end then lets water wash everything off.
Palmitic acid is also sometimes used in skin care products to make a clear product more opaque.
Palmitic acid (also known as hexadecanoic acid) is a fatty acid that is found naturally in animals and plants and also can be created in laboratory settings.
Palmitic acid is widely used in a variety of applications, including personal care products and cosmetics.
Palmitic acid, also known as C16 or hexadecanoate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Palmitic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Palmitic acid is a potentially toxic compound.
Palmitic acid is a saturated fat. It’s naturally found in some animal products like meat and dairy, as well as in palm and coconut oils.
Because these two oils are frequently used in processed foods, you might be getting palmitic acid in your diet without even realizing it.
One of the main uses of palmitic acid is in soaps because of its ability to help keep skin smooth. Palmitic acid is found in beeswax, which is a popular ingredient in personal care products. In cosmetics, palmitic acid is used in skin make-up to hide blemishes. It is also used in certain surfactants as a cleaning agent.
Palmitic acid shows an opposite effect upon our ΔTotal:HDL cholesterol ratio compared to lauric and stearic acid and increases the ratio substantially.
Cosmetics and Pharmaceuticals use: Oil base for creams, lotions, lipsticks, powders, skin ointments, face cleaners, body shampoos, soaps etc,.
Use: Cosmetics and Personal Care, Cleaning and Detergents, Industrial, Pharmaceutical and Veterinary
Palmitic acid, or hexadecanoic acid in IUPAC nomenclature, is the most common saturated fatty acid found in animals, plants and microorganisms.
Its chemical formula is CH3(CH2)14COOH, and its C:D is 16:0.
As its name indicates, it is a major component of the oil from the fruit of oil palms (palm oil).
Palmitic acid can also be found in meats, cheeses, butter, and other dairy products. Palmitates are the salts and esters of palmitic acid.
The palmitate anion is the observed form of palmitic acid at physiologic pH (7.4).
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.
Occurrence and production
Palmitic acid was discovered by Edmond Frémy in 1840, in saponified palm oil.
This remains the primary industrial route for its production, with the triglycerides (fats) in palm oil being hydrolysed by high temperature water (above 200 °C or 390 °F), and the resulting mixture fractionally distilled to give the pure product.
Palmitic acid is naturally produced by a wide range of other plants and organisms, typically at low levels.
It is naturally present in butter, cheese, milk, and meat, as well as cocoa butter, soybean oil, and sunflower oil. Karukas contain 44.90% palmitic acid.
The cetyl ester of palmitic acid (cetyl palmitate) occurs in spermaceti.
Biochemistry
Excess carbohydrates in the body are converted to palmitic acid. 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, and it is a major, but highly variable, lipid component of human breast milk.
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.
Applications
Surfactant
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 tree (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.
Hydrogenation of palmitic acid yields cetyl alcohol, which is used to produce detergents and cosmetics.[citation needed]
Foods
Because it is inexpensive and adds texture and “mouth feel” 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.
Military
The aluminium salt is used as a thickening agent of napalm used in military actions.
Schizophrenia
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.
Health effects
According to the World Health Organization, evidence is “convincing” that consumption of palmitic acid increases the risk of developing cardiovascular disease, based on studies indicating that it may increase LDL levels in the blood.
Retinyl palmitate is a source of vitamin A added to low-fat milk to replace the vitamin content lost through the removal of milk fat.
Palmitate is attached to the alcohol form of vitamin A, retinol, to make vitamin A stable in milk.
Other names: Hexadecanoic acid; n-Hexadecoic acid; Palmitic acid; Pentadecanecarboxylic acid; 1-Pentadecanecarboxylic acid; Cetylic acid; Emersol 140; Emersol 143; Hexadecylic acid; Hydrofol; Hystrene 8016; Hystrene 9016; Industrene 4516; Glycon P-45; Prifac 2960; NSC 5030; Palmitinic acid; Kortacid 1695; 60605-23-4; 116860-99-2; 212625-86-0; Hexadecanoic acid (palmitic acid); Hexadecanoic (palmitic) acid; Palmitic acid (hexadecanoic acid)
Preferred IUPAC name: Hexadecanoic acid
Other names: Palmitic acid
C16:0 (Lipid numbers)
Identifiers
CAS Number: 57-10-3
Properties
Chemical formula: C16H32O2
Molar mass: 256.430 g·mol−1
Appearance: white crystals
Density: 0.852 g/cm3 (25 °C)
0.8527 g/cm3 (62 °C)
Melting point: 62.9 °C (145.2 °F; 336.0 K)
Boiling point: 351–352 °C (664–666 °F; 624–625 K)
271.5 °C (520.7 °F; 544.6 K) at 100 mmHg
215 °C (419 °F; 488 K) at 15 mmHg
Solubility in water: 0.46 mg/L (0 °C)
0.719 mg/L (20 °C)
0.826 mg/L (30 °C)
0.99 mg/L (45 °C)
1.18 mg/L (60 °C)[5]
Solubility: soluble in amyl acetate, alcohol, CCl4, C6H6 very soluble in CHCl3
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)
Solubility in methyl acetate: 7.81 g/100 g
Solubility in ethyl acetate: 10.7 g/100 g
Vapor pressure: 0.051 mPa (25 °C)
1.08 kPa (200 °C)
28.06 kPa (300 °C)
Acidity (pKa) 4.75
Magnetic susceptibility (χ): -198.6·10−6 cm3/mol
Refractive index (nD): 1.43 (70 °C)
Viscosity: 7.8 cP (70 °C)
Thermochemistry
Heat capacity (C): 463.36 J/mol·K
Std molar entropy (So298): 452.37 J/mol·K
Std enthalpy of formation (ΔfH⦵298): -892 kJ/mol
Std enthalpy of combustion (ΔcH⦵298): 10030.6 kJ/mol
1-Pentadecanecarboxylic acid
C16 fatty acid
Cetylic acid
Emersol 140
Emersol 143
Hexadecylic acid
Hydrofol
Hystrene 8016
Hystrene 9016
Industrene 4516
n-Hexadecanoic acid
n-Hexadecoic acid
Palmitate
palmitic acid
Pentadecanecarboxylic acid
CAS names
Hexadecanoic acid
IUPAC names
Hexadecanoic acid
hexadecanoic acid
hexadecanoic acid
PALMITIC ACID
Palmitic Acid
Trade names
CREMERAC
KORTACID 1698/1695/1690
MASCID 1680
MASCID 1698
PALMAC 80-16, Palmitic Acid 80% Min.
PALMAC 95-16, Palmitic Acid 95% Min.
PALMAC 98-16, Palmitic Acid 98% Min.
Palmata 1698
PALMERA A8016
PALMERA A9216
PALMERA A9516
PALMERA A9816
Palmitic Acid
RADIACID 0656
RADIACID 0657
RADIACID 0658
Tefacid Palmitic 92
Tefacid Palmitic 98
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
1-Hexyldecanoic Acid
Industrene 4516
Emersol 140
Emersol 143
Hystrene 8016
Hystrene 9016
hexadecoic acid
Palmitic acid, pure
Palmitinsaeure
Palmitic acid 95%
Palmitic acid (natural)
Fatty acids, C14-18
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
HSDB 5001
AI3-01594
C16H32O2
NSC 5030
MFCD00002747
UNII-2V16EO95H1
Palmitic acid (NF)
Glycon P-45
CHEBI:15756
NSC5030
Hexadecanoic acid (9CI)
Palmitic acid (7CI,8CI)
CHEMBL82293
67701-02-4
CH3-[CH2]14-COOH
2V16EO95H1
n-hexadecoate
LMFA01010001
PA 900
FA 1695
1-hexyldecanoate
Palmitic acid, 98%
NCGC00164358-01
DSSTox_CID_1602
pentadecanecarboxylate
DSSTox_RID_76229
DSSTox_GSID_21602
PLM
palmitic-acid
palmic acid
Hexadecanoate (n-C16:0)
CAS-57-10-3
CCRIS 5443
SR-01000944716
EINECS 200-312-9
Palmitic acid [USAN:NF]
BRN 0607489
palmitoate
Hexadecoate
Palmitinate
palmitoic acid
Aethalic acid
Hexadecanoic acid Palmitic acid
(C14-C18)Alkylcarboxylic acid
2hmb
2hnx
(C14-C18) Alkylcarboxylic acid
Fatty acid pathway
palmitic acid group
Palmitic acid_jeyam
EINECS 266-926-4
Palmitic Acid, FCC
Kortacid 1695
Palmitic acid_RaGuSa
Univol U332
Prifrac 2960
Palmitic acid (NMR)
Hexadecanoic acid anion
3v2q
ACMC-1ASQF
SDA 17-005-00
Palmitic acid, >=99%
bmse000590
Epitope ID:141181
EC 200-312-9
SCHEMBL6177
4-02-00-01157 (Beilstein Handbook Reference)
FAT
WLN: QV15
P5585_SIGMA
GTPL1055
Palmitic acid (PA) has been for long time negatively depicted for its putative detrimental health effects, shadowing its multiple crucial physiological activities.
Palmitic acid is the most common saturated fatty acid accounting for 20–30% of total fatty acids in the human body and can be provided in the diet or synthesized endogenously via de novo lipogenesis (DNL).
Palmitic acid tissue content seems to be controlled around a well-defined concentration, and changes in its intake do not influence significantly its tissue concentration because the exogenous source is counterbalanced by Palmitic acid endogenous biosynthesis.
Particular physiopathological conditions and nutritional factors may strongly induce DNL, resulting in increased tissue content of PA and disrupted homeostatic control of its tissue concentration. The tight homeostatic control of Palmitic acid tissue concentration is likely related to its fundamental physiological role to guarantee membrane physical properties but also to consent protein palmitoylation, palmitoylethanolamide (PEA) biosynthesis, and in the lung an efficient surfactant activity.
In order to maintain membrane phospholipids (PL) balance may be crucial an optimal intake of PA in a certain ratio with unsaturated fatty acids, especially PUFAs of both n-6 and n-3 families.
However, in presence of other factors such as positive energy balance, excessive intake of carbohydrates (in particular mono and disaccharides), and a sedentary lifestyle, the mechanisms to maintain a steady state of PA concentration may be disrupted leading to an over accumulation of tissue PA resulting in dyslipidemia, hyperglycemia, increased ectopic fat accumulation and increased inflammatory tone via toll-like receptor.
It is therefore likely that the controversial data on the association of dietary PA with detrimental health effects, may be related to an excessive imbalance of dietary PA/PUFA ratio which, in certain physiopathological conditions, and in presence of an enhanced DNL, may further accelerate these deleterious effects.
Introduction
Palmitic acid (16:0, PA) is the most common saturated fatty acid found in the human body and can be provided in the diet or synthesized endogenously from other fatty acids, carbohydrates and amino acids.
Palmitic acid 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 is made up of 3.5 Kg of PA. As the name suggests,
Palmitic acid is a major component of palm oil (44% of total fats), but significant amounts of Palmitic acid can also be found in meat and dairy products (50–60% of total fats), as well as cocoa butter (26%) and olive oil (8–20%).
Furthermore, Palmitic acid is present in breast milk with 20–30% of total fats (Innis, 2016).
The average intake of Palmitic acid is around 20–30 g/d representing about 8–10 en% (Sette et al., 2011).
Palmitic acid tissue content seems to be controlled around a well-defined concentration, since changes in its intake do not influence significantly its tissue concentration (Innis and Dyer, 1997; Song et al., 2017), because the intake is counterbalanced by Palmitic acid endogenous biosynthesis via de novo lipogenesis (DNL).
Particular physiopathological conditions and nutritional factors may strongly induce DNL, resulting in increased tissue content of PA and disrupted homeostatic control of its tissue concentration (Wilke et al., 2009). However, under normal physiological conditions, Palmitic acid accumulation is prevented by enhanced delta 9 desaturation to palmitoleic acid (16:1n−7, POA) and/or elongation to stearic acid (SA) and further delta 9 desaturation to oleic acid (18:1, OA) (Strable and Ntambi, 2010; Silbernagel et al., 2012).
The tight homeostatic control of Palmitic acid tissue concentration is likely related to its fundamental physiological role in several biological functions.
Particularly in infants PA seems to play a crucial role as recently thoroughly revised by Innis (Innis, 2016).
The disruption of PA homeostatic balance, implicated in different physiopathological conditions such as atherosclerosis, neurodegenerative diseases and cancer, is often related to an uncontrolled PA endogenous biosynthesis, irrespective of its dietary contribution.
Palmitic acid forms a large proportion of total dietary SFA intake and can be found in palm oil, meat, and butter.
Palmitic acid can also be synthesized endogenously by elongation of C14:0, although this pathway is thought to be less active in the context of Western, high-fat diets (Hellerstein, 1999) and it is by far the largest component of circulating SFAs (Khaw et al., 2012; Wu et al., 2011). Various studies have investigated the association of circulating palmitic acid with CHD, with conflicting results.
One of these is the CHS, a community-based prospective study in the United States among men and women aged 65 years and older (Wu et al., 2011).
In this population, palmitic acid contributed 25.3% to the total fatty acids measured.
The authors reported no association of CHD risk between subjects with levels in the top versus bottom fifth of the distribution of palmitic acid, after adjusting for a range of potential confounding risk factors (Wu et al., 2011).
Similarly, no association was found in another US-based study, Atherosclerosis Risk in Communities (ARIC; Wang et al., 2003a), and in a Japanese study, Japan EPA Lipid Intervention Study (JELIS; Itakura et al., 2011).
A potential detrimental effect was reported in the subjects at high baseline cardiovascular risk enrolled in multiple risk factor intervention trial (MRFIT), although only when levels of palmitic acid were measured in cholesterol esters (CEs; Simon et al., 1995).
When measured in PLs, no significant association was observed.
However, the minimally adjusted association of CE levels of palmitic acid with CHD, like that of PL levels, was not significant.
Instead, the association of palmitic acid CEs only became significant after adjusting for various factors, including smoking, a potential strong confounder, and cholesterol levels, which may be a potential mediating factor rather than confounder.
Similar adjustments were not conducted for PL levels of palmitic acid.
Although differences in adjustment levels may account for some of the difference in association between CE and PL levels in this study, mean concentrations of palmitic acid in PLs (27.86%) were more than two times higher than concentrations in CEs (11.8%) (Simon et al., 1995), which is consistent with other studies reporting on fatty acid levels measured in CEs and PLs (Wang et al., 2003a).
This highlights the importance of metabolic pathways in determining fatty acid levels in different blood fractions, and this should be considered when comparing results from different studies. The EPIC-Norfolk study reported a strong detrimental association in which each SD increase in PL levels of palmitic acid was associated with a 37% higher risk of CHD (Khaw et al., 2012).
The association of CE levels of palmitic acid was also investigated in Finnish subjects enrolled in European Action on Secondary and Primary Prevention through Intervention to Reduce Events (EUROASPIRE), originally a pan-European secondary CAD prevention trial (Erkkila et al., 2003).
Among patients with established CAD, the authors reported that the middle tertile of palmitic acid was significantly associated with a lower risk of fatal CHD and nonfatal MI. However, there was no significant trend across tertiles (P=0.06), and as the authors rightfully noted, results from this study among CAD patients taking cardiovascular drugs should not directly be generalized to healthy populations.
Palmitic acid and the importance of its position on triglycerides
Palmitic acid is not an essential fatty acid as the infant is capable of de novo synthesis of palmitic acid via glucose.
Still, in human breast milk triglycerides, palmitic acid is very abundant (20–25% of total milk fatty acids).
Furthermore, the human mammary gland has evolved with unusual pathways for acylation of fatty acids into triglycerides for secretion in milk, with these pathways resulting in the preferential position of palmitic acid at the sn-2 position (70–75%), a different triglyceride structure observed in other human tissues and plasma, common dietary fats and oils (with the exception of lard) or in the fat blends used in the manufacture of infant formula (Bar-Yoseph, 2013; Bracco, 1994).
Studies over the last 2–3 decades have provided increasing evidence that this unusual positioning of C16:0 in human milk triglycerides promotes the absorption of both C16:0 and calcium in term and preterm infants (Carnielli et al., 1995a,b, 1996; Lucas et al., 1997; Kennedy et al., 1999), with potential long-term benefits linked to bone mineralization and bone strength (Litmanovitz et al., 2013).
Lipid absorption is essential for the energy requirements of the growing infant.
The rate of lipid absorption is influenced by both the type of fatty acid and the position of fatty acid on the triglyceride backbone.
When triglycerides are consumed, the fatty acids bound in the sn-1 and -3 positions are freed by digestive enzymes, leaving the fatty acid in the sn-2 position as a monoglyceride (Figure 12.6).
Palmitic acid is favorably absorbed in the sn-2 position as a monoglyceride rather than as free fatty acid because it tends to form insoluble calcium soaps that cannot be absorbed in the small intestine and are thus excreted in the feces (Scott, 2010).
The presence of fecal palmitic acid represents a needless loss of available dietary energy and calcium for the infant, especially preterm infants who, in view of their less-developed digestion system and lower weight compared to full-term infants, need to maximize feed efficiency.
Furthermore, palmitic acid calcium soaps can accumulate in the feces, resulting in harder stools, which may lead to constipation, obstruction, and overall discomfort in the infants.
Trials have indeed shown beneficial effects on stool softness and constipation (Carnielli et al. 1996; Kennedy et al. 1999; Bongers et al., 2007) and reduction in crying episodes (Bar-Yoseph et al., 2014; Litmanovitz et al., 2014) when infants were fed high β-palmitate IF.
Despite the very promising results, clear benefits of β-palmitate as expressed as bone strength and bone mass have still to be shown
Fatty acids longer than palmitic acid are produced by fatty acid chain elongation enzymes called elongases. These elongases lengthen palmitate to form many of the other fatty acids.
Palmitic acid is the first fatty acid produced during lipogenesis (fatty acid synthesis) and from which longer fatty acids can be produced. Palmitate negatively feeds back on acetyl-CoA carboxylase (ACC) which is responsible for converting acetyl-ACP to malonyl-ACP on the growing acyl chain, thus preventing further palmitate generation
Palmitic Acid in Cell Culture
Importance and uses of palmitic acid in serum-free eukaryotic, including hybridoma and Chinese Hamster Ovary (CHO) cell, cultures
Palmitic Acid, a Serum-Free Medium Supplement, Useful In Biomanufacturing; Tissue Engineering and Specialty Media:
Fatty acids of the n-3, n-6 and n-9 families are important supplements for cell culture systems. They are important in cell culture systems used to biomanufacture heterologous proteins, such as monoclonal antibodies. Fatty acids have been shown to be important for the growth and productivity of Chinese Hamster Ovary (CHO) cells.
The n-9 family of fatty acids, including oleic acid, can be synthesized by animal cells from the saturated precursors palmitic and stearic acids.
Historically, palmitic acid has been provided to cells in culture as a component of serum, albumin complex or esterified to molecules such as cholesterol.
Palmitic acid is poorly soluble in aqueous media, but it is non-susceptible to peroxidation.
For a more complete discussion of palmitic acid and other fatty acids as a cell culture additives go to our Media Expert.
Primary Functions of Palmitic Acid in Cell Culture Systems:
Long-term energy storage: energy derived from NADPH and ATP is stored in fatty acids.
Fatty acids are esterified to a glycerol backbone to form a group of compounds known as mono-, di- and tri- glycerides (neutral fats).
Energy is released when fatty acids are degraded.
Fatty acids are precursors of other molecules: prostaglandins, prostacyclins, thromboxanes, phospho-lipids, glycolipids, and vitamins.
Structural elements: fatty acids are important constituents of cell structures such as the membranes.
Chemical Attributes of Palmitic Acid that make it a Useful Serum-Free Medium Supplement:
Fatty acids (FA) are long-chain carboxylic acids that are insoluble in water.
These fatty acid chains can be from 4 to 30 carbons long, but physiologically the most important fatty acids are from 16 to 22 carbons long.
Since fatty acids are synthesized naturally by the addition of acetyl groups, they have an even numbers of carbon atoms-C2, C4, etc.
They can be saturated or unsaturated.
Natural fatty acids have their double bonds in the cis-configuration and are usually esterified to glycerol backbones to form complex lipids.
Fatty acids that contain more than one double bond are called polyunsaturated fatty acids (PUFAs).
In animals, most fatty acids with 16 or more carbons belong to one of three main fatty acid families.
All unsaturated members of a family are n-3, n-6, or n-9. Members of these FA families are not inter-convertible.
Palmitic acid family; palmitic acid is saturated, but unsaturated fatty acids derived from it are of the n-9 type.
Animal cells can de novo synthesize palmitic fatty acid and its n-9 derivatives. However, de novo synthesis requires the utilization of energy.
Palmitic acid (16:0) is a precursor of stearic acid (18:0). Palmitic acid can also be dehydrogenated to form palmitoleic acid (16:1, n-9).
A number of other important fatty acids are derived from palmitoleic acid.
In animal cells, oleic (18:1, n-9) acid is created by the dehydrogenation (desaturation) of stearic acid.
Oleic acid is further elongated and desaturated into a family of n-9 fatty acids.
If oleic acid is not provided in sufficient quantity, cells cannot produce other important fatty acids, and fatty acid derivatives.
Palmitic acid is a common 16-carbon saturated fat that represents 10-20% of human dietary fat intake and comprises approximately 25 and 65% of human total plasma lipids and saturated fatty acids, respectively.
Acylation of palmitic acid to proteins facilitates anchoring of membrane-bound proteins to the lipid bilayer and trafficking of intracellular proteins, promotes protein-vesicle interactions, and regulates various G protein-coupled receptor functions.
Palmitic acid (200 µM) increases NF-ĸB p65 levels, matrix metalloproteinase-9 (MMP-9) activity, and production of reactive oxygen species (ROS) in AsPC-1 pancreatic cancer cells, as well as increases migration of AsPC-1 cells.
It increases COX-2 levels in RAW 264.7 cells and increases LPS-induced IL-1β levels and caspase-1 activity in isolated mouse peritoneal macrophages.
Dietary administration of palmitic acid (2.2% w/w for 12 weeks) increases mouse hippocampal β-secretase 1 (BACE1) activity and amyloid β (1-42) (Aβ42; Item No. 20574) levels.
It also induces systolic contractile dysfunction in isolated mouse hearts.
Red blood cell palmitic acid levels are increased in patients with metabolic syndrome compared to patients without metabolic syndrome and are also increased in the plasma of patients with type 2 diabetes compared to individuals without diabetes.
hexadecanoic acid has role Daphnia magna metabolite
hexadecanoic acid has role algal metabolite
hexadecanoic acid has role EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor
hexadecanoic acid has role plant metabolite
hexadecanoic acid is a long-chain fatty acid
hexadecanoic acid is a straight-chain saturated fatty acid
hexadecanoic acid is conjugate acid of hexadecanoate
Incoming α-D-Gal-(1→4)-β-D-Gal-(1→4)-β-D-Glc-(1↔1′)-Cer(d18:1/16:0) has functional parent hexadecanoic acid
α-Neu5Ac-(2→3)-β-D-Gal-(1→4)-β-D-Glc-(1↔1′)-Cer(d18:1/16:0) (CHEBI:84674) has functional parent hexadecanoic acid
β-D-Gal-(1→3)-β-D-GalNAc-(1→4)-[α-Neu5Ac-(2→3)]-β-D-Gal-(1→4)-β-D-Glc-(1↔1′)-Cer(d18:1/16:0) (CHEBI:84670) has functional parent hexadecanoic acid
β-D-galactosyl-(1→4)-β-D-glucosyl-(1↔1)-N-hexadecanoylsphingosine has functional parent hexadecanoic acid
β-D-galactosyl-(1↔1ʼ)-N-hexadecanoylsphinganine has functional parent hexadecanoic acid
β-D-glucosyl-(1↔1ʼ)-N-hexadecanoylsphinganine has functional parent hexadecanoic acid
β-D-glucosyl-N-hexadecanoylsphingosine has functional parent hexadecanoic acid
β-GalNAc-(1→4)-[α-Neu5Ac-(2→8)-α-Neu5Ac-(2→8)-α-Neu5Ac-(2→3)]-β-Gal-(1→4)-β-Glc-(1→1′)-Cer(d18:1/16:0) (CHEBI:84653) has functional parent hexadecanoic acid
(15R)-15-hydroxypalmitic acid (CHEBI:78998) has functional parent hexadecanoic acid
(2S)-2-hydroxyphytanate (CHEBI:58398) has functional parent hexadecanoic acid
(2S)-2-hydroxyphytanic acid (Chas functional parent hexadecanoic acid
1,1ʼ,2-trilinoleoyl-2ʼ-palmitoyl cardiolipin has functional parent hexadecanoic acid
1,2-dihexadecanoyl-sn-glycero-3-phospho-(1ʼ-sn-glycerol-3ʼ-phosphate) has functional parent hexadecanoic acid
1,2-dihexadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol-3,4,5-trisphosphate) has functional parent hexadecanoic acid
1,2-dihexadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol-3,4-bisphosphate) has functional parent hexadecanoic acid
1,2-dihexadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol-4,5-bisphosphate) has functional parent hexadecanoic acid
1,2-dihexadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol-4-phosphate) has functional parent hexadecanoic acid
1,2-dihexadecanoyl-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine has functional parent hexadecanoic acid
1,2-dihexadecanoyl-sn-glycero-3-phosphoserine has functional parent hexadecanoic acid
1,2-dioleoyl-3-palmitoylglycerol has functional parent hexadecanoic acid
1,2-dipalmitoyl-3-palmitoleoyl-sn-glycerol has functional parent hexadecanoic acid
1,2-dipalmitoyl-sn-glycero-3-phospho-(1ʼD-myo-inositol-3ʼ,5ʼ-bisphosphate) (CHEBI:82954) has functional parent hexadecanoic acid
1,2-dipalmitoyl-sn-glycero-3-phospho-(1ʼD-myo-inositol-3ʼ-phosphate) (CHEBI:82963) has functional parent hexadecanoic acid
1,2-dipalmitoyl-sn-glycero-3-phospho-(1D-myo-inositol-5-phosphate) (CHEBI:85521) has functional parent hexadecanoic acid
1,2-dipalmitoyl-sn-glycero-3-phosphoethanol (CHEBI:85431) has functional parent hexadecanoic acid
1,2-dipalmitoylglycero-3-phospho-(1ʼ-D-myo-inositol-3ʼ-phosphate) (CHEBI:82948) has functional parent hexadecanoic acid
1,2-dipalmitoylglycerol (CHEBI:78090) has functional parent hexadecanoic acid
1,3-dioleoyl-2-palmitoylglycerol has functional parent hexadecanoic acid
1,3-dipalmitoyl-2-oleoylglycerol has functional parent hexadecanoic acid
1,3-dipalmitoylglycerol has functional parent hexadecanoic acid
1-α-linolenoyl-2-hexadecanoylphosphatidylglycerol has functional parent hexadecanoic acid
1-(1Z-hexadecenyl)-2-hexadecanoyl-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-(1Z-octadecenyl)-2-hexadecanoyl-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-(1Z-octadecenyl)-2-hexadecanoyl-sn-glycero-3-phosphoethanolamine has functional parent hexadecanoic acid
1-(1Z-octadecenyl)-sn-glycero-3-phospho-(N-hexadecanoyl)ethanolamine has functional parent hexadecanoic acid
1-(9Z,12Z,15Z-octadecatrienoyl)-2-hexadecanoyl-3-[α-D-galactosyl-(1→6)-β-D-galactosyl]-sn-glycerol has functional parent hexadecanoic acid
1-O-(alk-1-enyl)-2-palmitoyl-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-O-octadecyl-2-palmitoyl-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-O-palmitoyl-N-acetylsphingosine has functional parent hexadecanoic acid
1-[(10Z,13Z,16Z)-docosatrienoyl]-2-hexadecanoyl-sn-glycero-3-phospho-1D-myo-inositol has functional parent hexadecanoic acid
1-[(11Z)-octadecenoyl]-2-hexadecanoyl-sn-glycerol (CHEBI:86346) has functional parent hexadecanoic acid
1-[(13Z,16Z)-docosadienoyl]-2-hexadecanoyl-sn-glycero-3-phospho-1D-myo-inositol has functional parent hexadecanoic acid
1-[(1Z,11Z)-octadecadienyl]-2-palmitoyl-sn-glycero-3-phosphoethanolamine has functional parent hexadecanoic acid
1-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl]-2-hexadecanoyl-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-[(9Z)-octadecenyl]-2-hexadecanoyl-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-[(9Z,12Z)-octadecadienoyl]-2-hexadecanoyl-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-acyl-2-hexadecanoyl-sn-glycero-3-phosphate has functional parent hexadecanoic acid
1-acyl-2-hexadecanoyl-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-acyl-2-palmitoyl-sn-glycero-3-phospho-(1ʼ-sn-glycerol) has functional parent hexadecanoic acid
1-acyl-2-palmitoyl-sn-glycero-3-phosphoethanolamine zwitterion has functional parent hexadecanoic acid
1-arachidonoyl-2-palmitoyl-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-docosanoyl-2-hexadecanoyl-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-heptadecanoyl-2-palmitoyl-sn-glycero-3-phosphate has functional parent hexadecanoic acid
1-hexadecanoyl-2-(11Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine has functional parent hexadecanoic acid
1-hexadecanoyl-2-(13Z-docosenoyl)-sn-glycero-3-phosphoethanolamine has functional parent hexadecanoic acid
1-hexadecanoyl-2-(4E,7E,10E,13E,16E,19E-docosahexaenoyl)-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoethanolamine has functional parent hexadecanoic acid
1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoserine has functional parent hexadecanoic acid
1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-icosatetraenoyl)-sn-glycero-3-phosphoethanolamine has functional parent hexadecanoic acid
1-hexadecanoyl-2-(7-oxoheptanoyl)-sn-glycero-3-phosphocholinehas functional parent hexadecanoic acid
1-hexadecanoyl-2-(7Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine has functional parent hexadecanoic acid
1-hexadecanoyl-2-(8Z,11Z,14Z-icosatrienoyl)-sn-glycero-3-phosphoethanolamine has functional parent hexadecanoic acid
1-hexadecanoyl-2-(9,10-epoxyoctadecanoyl)-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-hexadecanoyl-2-(9-oxononanoyl)-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamine has functional parent hexadecanoic acid
1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine has functional parent hexadecanoic acid
1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-hexadecanoyl-2-[(11Z)-octadec-9-enoyl]-sn-glycero-3-phospho-(1′-sn-glycerol) has functional parent hexadecanoic acid
1-hexadecanoyl-2-[(11Z,14Z,17Z)-icosatrienoyl]-sn-glycero-3-phosphocholinehas functional parent hexadecanoic acid
1-hexadecanoyl-2-[(13Z)-docosenoyl]-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-hexadecanoyl-2-[(15Z)-tetracosenoyl]-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-hexadecanoyl-2-[(5S,6E,8Z,11Z,14Z)-5-hydroxyicosatetraenoyl]-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-hexadecanoyl-2-[(5Z,8Z,10E,12S,14Z)-12-hydroxyicosatetraenoyl]-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-hexadecanoyl-2-[(5Z,8Z,11Z)-icosatrienoyl]-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-hexadecanoyl-2-[(5Z,8Z,11Z,14Z,17Z)-icosapentaenoyl]-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-hexadecanoyl-2-[(5Z,9Z)-hexacosadienoyl]-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-hexadecanoyl-2-[(6Z,9Z,12Z,15Z)-octadecatetraenoyl]-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-hexadecanoyl-2-[(7Z,10Z,13Z,16Z)-docosatetraenoyl]-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-hexadecanoyl-2-[(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl]-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-hexadecanoyl-2-[(8Z,11Z,14Z)-eicosatrienoyl]-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-hexadecanoyl-2-docosanoyl-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-hexadecanoyl-2-docosanoyl-sn-glycerol has functional parent hexadecanoic acid
1-hexadecanoyl-2-hexadecyl-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-hexadecanoyl-2-icosanoyl-sn-glycero-3-phosphoethanolamine has functional parent hexadecanoic acid
1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-hexadecanoyl-2-octadecanoyl-sn-glycerol has functional parent hexadecanoic acid
1-hexadecanoyl-sn-glycero-3-phospho-(1ʼ-sn-glycerol) has functional parent hexadecanoic acid
1-icosanoyl-2-hexadecanoyl-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-methyl-2-hexadecanoyl-sn-glycero-3-phosphocholine (has functional parent hexadecanoic acid
1-monopalmitoylglycerol (CHEBI:69081) has functional parent hexadecanoic acid
1-myristoyl-2-palmitoyl-sn-glycerol (CHEBI:84385) has functional parent hexadecanoic acid
1-oleoyl-2-hexadecanoyl-sn-glycero-3-phospho-(1ʼ-sn-glycerol-3ʼ-phosphate) has functional parent hexadecanoic acid
1-oleoyl-2-palmitoyl-sn-glycero-3-phospho-L-serine has functional parent hexadecanoic acid
1-oleoyl-2-palmitoyl-sn-glycero-3-phosphoethanolamine has functional parent hexadecanoic acid
1-oleoyl-2-palmitoylglycerol (CHEBI:76065) has functional parent hexadecanoic acid
1-oleoyl-3-palmitoylglycerol (CHEBI:75869) has functional parent hexadecanoic acid
1-palmitoyl-2-(11Z,14Z-eicosadienoyl)-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-palmitoyl-2-(11Z,14Z-eicosadienoyl)-sn-glycerol has functional parent hexadecanoic acid
1-palmitoyl-2-(11Z-eicosenoyl)-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-palmitoyl-2-(11Z-octadecenoyl)-sn-glycero-3-phosphocholine (CHEBI:85037) has functional parent hexadecanoic acid
1-palmitoyl-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycero-3-phosphoethanolamine (CHEBI:84549) has functional parent hexadecanoic acid
1-palmitoyl-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycerol has functional parent hexadecanoic acid
1-palmitoyl-2-(8-epi-prostaglandin F2α)-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-palmitoyl-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycerol has functional parent hexadecanoic acid
1-palmitoyl-2-(9Z-heptadecenoyl)-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-palmitoyl-2-[(10E)-9-hydroperoxyoctadecenoyl]-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-palmitoyl-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl]-sn-glycero-3-phosphate has functional parent hexadecanoic acid
1-palmitoyl-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl]-sn-glycerol has functional parent hexadecanoic acid
1-palmitoyl-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-palmitoyl-2-[(9Z,12Z,15Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-palmitoyl-2-acetyl-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-palmitoyl-2-acyl-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-palmitoyl-2-arachidonoyl-sn-glycero-3-phospho-(1′-sn-glycerol) ( has functional parent hexadecanoic acid
1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-palmitoyl-2-arachidonoyl-sn-glycerol has functional parent hexadecanoic acid
1-palmitoyl-2-butanoyl-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-palmitoyl-2-capryloyl-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-palmitoyl-2-icosanoyl-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-palmitoyl-2-lauroyl-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-palmitoyl-2-linoleoyl-sn-glycerol has functional parent hexadecanoic acid
1-palmitoyl-2-oleoyl-3-stearoyl-sn-glycerol has functional parent hexadecanoic acid
1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoglycerol ( has functional parent hexadecanoic acid
1-palmitoyl-2-oleoylglycerol (CHEBI:75585) has functional parent hexadecanoic acid
1-palmitoyl-2-palmitoleoyl-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-palmitoyl-2-palmitoleoyl-sn-glycerol has functional parent hexadecanoic acid
1-palmitoyl-2-propionyl-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-palmitoyl-2-stearoyl-sn-glycero-3-phosphoserine has functional parent hexadecanoic acid
1-palmitoyl-2-valeroyl-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
1-palmitoyl-3-linoleoylglycerol has functional parent hexadecanoic acid
1-palmitoyl-3-stearoyl-sn-glycerol has functional parent hexadecanoic acid
1-palmitoyl-sn-glycero-3-phosphoglycerol has functional parent hexadecanoic acid
1-palmityl-2-acetyl-3-lauroyl-sn-glycerol has functional parent hexadecanoic acid
1-palmityl-2-acetyl-3-palmitoyl-sn-glycerolhas functional parent hexadecanoic acid
1-tetradecanoyl-2,3-dihexadecanoyl-sn-glycerol has functional parent hexadecanoic acid
1-tetradecyl-2-hexadecanoyl-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
10-PAHSA has functional parent hexadecanoic acid
11-PAHSA has functional parent hexadecanoic acid
12-PAHSA has functional parent hexadecanoic acid
13-PAHSA has functional parent hexadecanoic acid
14-hydroxypalmitic acid has functional parent hexadecanoic acid
14-methylhexadecanoic acid has functional parent hexadecanoic acid
15-hydroxypalmitic acid (CHEBI:83935) has functional parent hexadecanoic acid
16-hydroxyhexadecanoic acid (CHEBI:55328) has functional parent hexadecanoic acid
16-oxohexadecanoic acid (CHEBI:134195) has functional parent hexadecanoic acid
2,3-dipalmitoyl-α,α-trehalose (CHEBI:84042) has functional parent hexadecanoic acid
2,3-dipalmitoyl-S-glycerylcysteine (CHEBI:61842) has functional parent hexadecanoic acid
2,3-dipalmitoyl-sn-glycerol has functional parent hexadecanoic acid
2-O-palmitoyl-α,α-trehalose has functional parent hexadecanoic acid
2-bromohexadecanoic acid has functional parent hexadecanoic acid
2-hexadecanoyl-sn-glycero-3-phosphoethanolamine has functional parent hexadecanoic acid
2-hydroxy-3-methylhexadecanoic acid has functional parent hexadecanoic acid
2-methoxyhexadecanoic acid (CHEBI:34295) has functional parent hexadecanoic acid
2-methylhexadecanoic acid has functional parent hexadecanoic acid
2-oxopalmitic acid has functional parent hexadecanoic acid
2-oxophytanatehas functional parent hexadecanoic acid
2-palmitoyl-3-oleoyl-sn-glycerol has functional parent hexadecanoic acid
2-palmitoyl-sn-glycero-3-phosphocholine has functional parent hexadecanoic acid
2-palmitoylglycerol has functional parent hexadecanoic acid
2-palmitoyloxypalmityl palmitate has functional parent hexadecanoic acid
3,4-dihydroxy-4-methylhexadecanoic acid has functional parent hexadecanoic acid
3-hydroxypalmitic acid has functional parent hexadecanoic acid
3-oxopalmitic acid (CHEBI:37251) has functional parent hexadecanoic acid
5-PAHSA (CHEBI:84457) has functional parent hexadecanoic acid
7-PAHSA (CHEBI:84479) has functional parent hexadecanoic acid
8-PAHSA (CHEBI:84486) has functional parent hexadecanoic acid
9-PAHSA (CHEBI:84425) has functional parent hexadecanoic acid
N,1-dipalmitoyl-2-linoleoyl-sn-glycero-3-phosphoethanolamine has functional parent hexadecanoic acid
N,1-dipalmitoyl-sn-glycero-3-phosphoethanolamine has functional parent hexadecanoic acid
N-(hexadecanoyl)-β-D-galactosylsphingosine has functional parent hexadecanoic acid
N-(hexadecanoyl)hexadecasphingosine-1-phosphocholine has functional parent hexadecanoic acid
N-benzylhexadecanamide (CHEBI:140849) has functional parent hexadecanoic acid
N-butyryl-1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphoethanolamine has functional parent hexadecanoic acid
N-caproyl-1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphoethanolamine has functional parent hexadecanoic acid
N-capryl-1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphoethanolamine has functional parent hexadecanoic acid
N-capryloyl-1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphoethanolamine has functional parent hexadecanoic acid
N-hexadecanoyl-(2S)-hydroxyglycine has functional parent hexadecanoic acid
N-hexadecanoyl-1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine has functional parent hexadecanoic acid
N-hexadecanoyl-14-methylhexadecasphingosine has functional parent hexadecanoic acid
N-hexadecanoyl-15-methylhexadecasphingosine-1-phosphocholine has functional parent hexadecanoic acid
N-hexadecanoyl-sn-glycero-3-phosphoethanolamine has functional parent hexadecanoic acid
N-hexadecanoylglycine has functional parent hexadecanoic acid
N-hexadecanoylphosphatidylethanolamine has functional parent hexadecanoic acid
N-hexadecanoylphytosphingosine-1-phosphocholine has functional parent hexadecanoic acid
N-hexadecanoylphytosphingosine-1-phosphoethanolamine has functional parent hexadecanoic acid
N-hexadecanoylsphingadienine-1-phosphocholine has functional parent hexadecanoic acid
N-hexadecanoylsphinganine has functional parent hexadecanoic acid
N-hexadecanoylsphinganine-1-phosphocholine has functional parent hexadecanoic acid
N-hexadecanoylsphinganine-1-phosphoethanolamine has functional parent hexadecanoic acid
N-hexadecanoylsphingosine has functional parent hexadecanoic acid
N-hexadecanoylsphingosine 1-phosphate has functional parent hexadecanoic acid
N-hexadecanoylsphingosine-1-phosphocholine has functional parent hexadecanoic acid
N-hexadecanoyltaurine has functional parent hexadecanoic acid
N-palmitoyl dopamine has functional parent hexadecanoic acid
N-palmitoyl-1,2-dioleoyl-sn-glycero-3-phosphoethanolamine has functional parent hexadecanoic acid
N-palmitoyl-1-oleoyl-sn-glycero-3-phosphoethanolamine has functional parent hexadecanoic acid
N-palmitoylhexadecasphinganine has functional parent hexadecanoic acid
N-palmitoylserotonin has functional parent hexadecanoic acid
O-palmitoyl-L-carnitine has functional parent hexadecanoic acid
O-palmitoylcarnitine has functional parent hexadecanoic acid
S-hexadecanoyl-4ʼ-phosphopantetheine has functional parent hexadecanoic acid
ascorbyl dipalmitate has functional parent hexadecanoic acid
CDP-1-palmitoyl-2-arachidonoyl-sn-glycerol has functional parent hexadecanoic acid
CDP-dipalmitoyl-sn-glycerol has functional parent hexadecanoic acid
cholesteryl palmitate has functional parent hexadecanoic acid
dihexadecanoyl phosphatidic acid has functional parent hexadecanoic acid
dihexadecanoylglycerol has functional parent hexadecanoic acid
dipalmitoyl phosphatidylglycerol has functional parent hexadecanoic acid
glycosyl-N-hexadecanoylsphinganine has functional parent hexadecanoic acid
hexadecanamide has functional parent hexadecanoic acid
hexadecanoate ester has functional parent hexadecanoic acid
hexadecanoyl phosphate has functional parent hexadecanoic acid
hexadecanoyl-AMP has functional parent hexadecanoic acid
hexadecanoylcholine has functional parent hexadecanoic acid
hydroxypalmitic acid has functional parent hexadecanoic acid
isopropyl palmitate has functional parent hexadecanoic acid
kansuiphorin A has functional parent hexadecanoic acid
kansuiphorin B has functional parent hexadecanoic acid
klymollin G has functional parent hexadecanoic acid
lysophosphatidylcholine (16:1/0:0) has functional parent hexadecanoic acid
monoacylglycerol 16:0 has functional parent hexadecanoic acid
palmitoyl bioconjugate has functional parent hexadecanoic acid
palmitoyl ethanolamide has functional parent hexadecanoic acid
palmitoyl-CoA has functional parent hexadecanoic acid
phytanate has functional parent hexadecanoic acid
phytanic acid has functional parent hexadecanoic acid
PIM2 has functional parent hexadecanoic acid
sapacitabine has functional parent hexadecanoic acid
sitoindoside I has functional parent hexadecanoic acid
tetrahexadecanoyl cardiolipin has functional parent hexadecanoic acid
tripalmitin has functional parent hexadecanoic acid
soybean oil has part hexadecanoic acid
1-hexadecanoyl-2-methyl-sn-glycero-3-phosphocholine is a hexadecanoic acid
hexadecanoate is conjugate base of hexadecanoic acid
IUPAC Name: hexadecanoic acid
Synonyms
1-hexyldecanoic acid
1-Pentadecanecarboxylic acid
16:00 ChEBI
C16 ChEBI
C16 fatty acid HMDB
C16:0 LIPID MAPS
cetylic acid KEGG COMPOUND
CH3‒[CH2]14‒COOH IUPAC
FA 16:0 ChEBI
Hexadecanoate KEGG COMPOUND
hexadecoic acid ChEBI
Hexadecylic acid KEGG COMPOUND
Hexadecylic acid HMDB
Hexaectylic acid HMDB
n-hexadecanoic acid
n-hexadecoic acid
Palmitate KEGG COMPOUND
PALMITIC ACID PDBeChem
Palmitic acid KEGG COMPOUND
palmitic acid ChEBI
Palmitinic acid HMDB
Palmitinsäure Deutsch ChEBI
Pentadecanecarboxylic acid
1-hexyldecanoate
1-hexyldecanoic acid
1-Pentadecanecarboxylic acid
C16 fatty acid
Cetylic acid
Coconut oil fatty acids
Edenor C16
Hexadecanoate
Hexadecanoic (palmitic) acid
Hexadecanoic acid
Hexadecanoic acid (palmitic acid)
Hexadecanoic acid palmitic acid
Hexadecoate
Hexadecoic acid
Hexadecylic acid
Hexaectylic acid
Hydrofol
n-Hexadecanoate
n-Hexadecanoic acid
n-Hexadecoate
n-Hexadecoic acid
Palmitate
palmitic acid
Palmitinate
Palmitinic acid
Palmitinsaeure
palmitoate
palmitoic acid
PAM
Pentadecanecarboxylate
Pentadecanecarboxylic acid
PLM
16:00
C16
C16:0
CH3-[CH2]14-COOH
FA 16:0
1-Pentadecanecarboxylate
Cetylate
Hexadecylate
Hexaectylate
Emersol 140
Emersol 143
Glycon p-45
Hexadecanoate (N-C16:0)
Hydrofol acid 1690
Hystrene 8016
Hystrene 9016
Industrene 4516
Kortacid 1698
Loxiol ep 278
Lunac p 95
Lunac p 95KC
Lunac p 98
Prifac 2960
Prifrac 2960
Pristerene 4934
Univol u332
Acid, hexadecanoic
Acid, palmitic
FA(16:0)
1-hexadecanoic acid
1-Pentadecanecarboxylic acid
266-926-4 [EINECS]
57-10-3 [RN]
607489 [Beilstein]
Acide palmitique [French] [ACD/IUPAC Name]
Cetylic acid
Hexadecanoic acid [ACD/Index Name]
hexdecanoic acid
MFCD00002747 [MDL number]
Neo-Fat 16
n-hexadecanoic acid
Palmitic Acid [ACD/IUPAC Name] [Wiki]
Palmitic Acid MaxSpec® Standard
Palmitinsäure [German] [ACD/IUPAC Name]
Glycon P-45
1173022-49-5 [RN]
1219802-61-5 [RN]
1-hexyldecanoate
1-HEXYLDECANOIC ACID
272442-14-5 [RN]
285979-77-3 [RN]
30719-28-9 [RN]
3343-33-7 [RN]
358730-99-1 [RN]
39756-30-4 [RN]
62690-28-2 [RN]
75736-47-9 [RN]
75736-53-7 [RN]
75736-57-1 [RN]
81462-28-4 [RN]
83293-32-7 [RN]
CR-0047
Emersol 140 [Trade name]
Emersol 143 [Trade name]
Hexadecanoic acid 10 µg/mL in Acetonitrile
hexadecoic acid
HEXADECYLIC ACID
hexaectylic acid
http:////www.amadischem.com/proen/505746/
http://www.hmdb.ca/metabolites/HMDB0000220
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:15756
Hydrofol
Loxiol EP 278 [Trade name]
Lunac P 95 [Trade name]
Lunac P 95KC [Trade name]
Lunac P 98 [Trade name]
n-hexadecoic acid
Palmitic Acid – CAS 57-10-3 – Calbiochem
Palmitic Acid-d2
Palmitic Acid-d3
Palmitic Acid-d4
Palmitinic acid
Palmitinsaeure
Palmitoic acid
Palmitoleic acid [Wiki]
Pentadecanecarboxylic acid
QV15 [WLN]
Palmitic Acid in Early Human Development
Sheila M. Innis
Pages 1952-1959 | Accepted author version posted online: 12 Mar 2015, Published online:27 Jun 2016
Download citation https://doi.org/10.1080/10408398.2015.1018045 CrossMark LogoCrossMark
Abstract
Palmitic acid (16:0) is a saturated fatty acid present in the diet and synthesized endogenously.
Although often considered to have adverse effects on chronic disease in adults, 16:0 is an essential component of membrane, secretory, and transport lipids, with crucial roles in protein palmitoylation and signal molecules.
At birth, the term infant is 13–15% body fat, with 45–50% 16:0, much of which is derived from endogenous synthesis in the fetus.
After birth, the infant accumulates adipose tissue at high rates, reaching 25% body weight as fat by 4–5 months age.
Over this time, human milk provides 10% dietary energy as 16:0, but in unusual triglycerides with 16:0 on the glycerol center carbon.
This paper reviews the synthesis and oxidation of 16:0 and possible reasons why the infant is endowed with large amounts of fat and 16:0.
The marked deviations in tissues with displacement of 16:0 that can occur in infants fed vegetable oil formulas is introduced.
Assuming fetal fatty acid synthesis and the unusual delivery of 16:0 in human milk evolved to afford survival advantage to the neonate, it is timely to question if 16:0 is an essential component of tissue lipids whereby both deficiency and excess are detrimental.
Keywords: Palmitic acid human milk placental fatty acid transfer triglyceride structure adipose tissue infant development
Definition of palmitic acid: a waxy crystalline saturated fatty acid C16H32O2 occurring free or in the form of esters (such as glycerides) in most fats and fatty oils and in several essential oils and waxes
Palmitate: An antioxidant and a vitamin A compound that is added to low-fat and fat-free milk to replace the vitamin content lost through the removal of milk fat.
Palmitate (more formally known as retinyl palmitate) contains palmitic acid, a 16-carbon saturated fatty acid, which is the major fatty acid found in palm oil.
The palmitic acid is attached to the alcohol form of vitamin A, called retinol, to make vitamin A stable in milk.
The name “palmitate” comes from the French “palmitique” from palmite, the pith of the palm tree.
Palmitic acid is a saturated fatty acid occurring as combustible white crystals in many natural oils (such as spermaceti and palm oil) and fats.
Palmitic acid is most commonly produced from palm oil, although it is found in smaller amounts in other vegetable oils as well as dairy and meat.
To produce pure palmitic acid, the oil is boiled to break the fatty acids off of the glycerol and then the different acids are separated out based on their boiling point.
Its chemical formula: C16H32O2. It is used in making soaps.
Palmitic acid can also be found in meats, cheeses, butter, and dairy products.
Palmitate is the salts and esters of palmitic acid. The palmitate anion is the observed form of palmitic acid at physiologic pH (7.4).
In skin care products it is commonly used in the form of an alkali salt, where the fatty acid has been reacted with an alkali like sodium hydroxide to produce sodium palmitate.
Structure, Occurrences and Properties of Palmitic Acid
Palmitic acid is a saturated fatty acid (no double bond so in shorthand 16:0) member of the sub-group called long chain fatty acids (LCFA), from 14 to 18 carbon atoms.
It is the first fatty acid produced during fatty acid synthesis in humans and the fatty acid from which longer fatty acids can be produced.
Palmitic acid was discovered by Edmond Frémy in 1840, in saponified palm oil.
This remains the primary industrial route for its production, with the triglycerides (fats) in palm oil being hydrolysed by high temperature water (above 200 °C or 390 °F), and the resulting mixture fractionally distilled to give the pure product.
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, and it is a major, but highly variable, lipid component of human breast milk.
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
One of the main functions of palmitic acid alkali salts is that they acts as emulsifiers and surfactants, allowing oil based, hydrophobic molecules to interact with water where normally they would repel each other.
This works by the fatty acid end of the salt interacting with the oil while the salt end interacts with the water creating an adapter between oil and water.
In some products this increases the stability of the product as oil and water would naturally separate without it.
In soaps and cleansing oils, the fatty end grabs oil and water-resistant make up on your skin while the salt end then lets water wash everything off.
Applications and Effets of Palmitic Acid
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 tree (species Elaeis guineensis), is treated with sodium hydroxide, which causes hydrolysis of the ester groups, yielding glycerol and sodium palmitate.
Hydrogenation of palmitic acid yields cetyl alcohol, which is used to produce detergents and cosmetics
Topical palmitic acid is not known to cause side effects. A diet containing large amounts of palmitic acid can increase risk of heart disease but topical application doesn’t contribute to this.
Palmitic acid strongly boosts metastasis in mouse models of human oral cancer cells.
Among all fatty acids, it has the strongest effect in boosting the metastatic potential of CD36+ metastasis-initiating cells.
Palmitic AcidPalmitic acid is a saturated fatty acid commonly found in both animals and plants. It is a major component in the oils from palm trees, such as palm oil, palm kernel oil and coconut oil.
Palmitic acid, a kind of fatty acid, derived from palm oil. It is a major component in the oils from palm trees. Applications of palmitic acid include soap & detergent, cosmetics, grease & lubricant, etc. Among those applications, soap & detergent accounts for the largest market share, which was about 49.99% in 2016.
The palmitic acid industry production is mainly concentrated in Asian region, such as Malaysia, Indonesia, China and so on. The largest producing region is Southeast Asia, which produced 135373 MT in 2016. The follower is China, holding 18.50% production share. Global production of palmitic acid increased from 166874 MT in 2012 to 202753 MT in 2016.
As for consumption, Europe is the largest consumer with about 33.51% share in 2016. The second consumer is China, consuming 57456 MT in the same year.
The palmitic acid industry has close relationship with the palm oil industry. Due to its low profit, some companies engaged in the palm oil industry have given up the business. In China, there are just a few suppliers.
The Palmitic Acid Industry Report indicates that the global market size of Palmitic Acid was XX USD in 2020, and will grow at a XX% CAGR between 2021 and 2027.
A collective analysis on ’Palmitic Acid Industry’ offers an exhaustive study supported current trends influencing this vertical throughout assorted geographies.
Key information regarding market size, market share, statistics, application, and revenue is within the research to develop an ensemble prediction.
Additionally, this research offers an in-depth competitive analysis that specializes in business outlook emphasizing expansion strategies accepted by Palmitic Acid market majors.
Palmitic acid is a saturated fatty acid, the principal constituent of refined palm oil, present in the diet and synthesized endogenously.
Palmitic acid is able to activate the orphan G protein-coupled receptor GPR40. Palmitic acid was also a weak ligand of peroxisome proliferator-activated receptor gamma.
Palmitic acid is a ligand of lipid chaperones – the fatty acid-binding proteins (FABPs).
Dietary palm oil and palmitic acid may play a role in the development of obesity, type 2 diabetes mellitus, cardiovascular diseases and cancer
Palmitic acid is a saturated fatty acid that occurs in natural fats and oils, tall oil, and most commercial grade stearic acid. Palmitic acid is prepared by treating fats and oils with water at a high pressure and temperature, leading to the hydrolysis of triglycerides.
Palmitic acid is mainly usedin the manufacture of metallic palmitates, soaps, cosmetics, lubricating oils, waterproofing release agents, and in food-grade additives.
The solubility of palmitic acid has been measured in ethanol, 2-propanol, acetone, heptane, hexane, and trichloroethylene and in the azeotropic mixtures of the solvents (ethanol−heptane; hexane−ethanol; ethanol−trichloroethylene; acetone−heptane; heptane−2-propanol; acetone−hexane; hexane−2-propanol; 2-propanol−trichloroethylene), by a dynamic method, from (290 to 325) K. Solubility data in pure solvents were fitted by the Wilson, NRTL, and UNIQUAC equations and the solubility of palmitic acid in azeotropic mixtures with the NIBS/Redlich−Kister equation.
For all calculated results, the root-mean-square deviations of solubility temperatures vary from (0.2 to 0.82) K, depending on the equation used.
The solubility in pure solvents decreased in the order: trichloroethylene > 2-propanol > hexane > heptane > acetone > ethanol.
The solubility of the palmitic acid increased in azeotropic mixtures compared to the pure solvents, except for the ethanol−trichloroethylene mixture where the solubility was similar to the one in pure trichloroethylene.
Palmitic acid is a long-chain saturated fatty acid commonly found in both animals and plants.
Palmitic acid is a white, crystalline, water-insoluble solid, C16H32O2, obtained by hydrolysis from palm oil and natural fats, in which it occurs as the glyceride, and from spermaceti: used in the manufacture of soap.
Palmitic acid can induce the expression of glucose-regulated protein 78 (GRP78) and CCAAT/enhancer binding protein homologous protein (CHOP) in in mouse granulosa cells.