PRODUCTS

EICOSATETRAENOIC ACID

CAS NUMBER: 236743-58-1

MOLECULAR FORMULA: C20H32O2

MOLECULAR WEIGHT: 304.5

IUPAC NAME: (2E,4E,6E,8E)-icosa-2,4,6,8-tetraenoic Acid

Eicosatetraenoic Acid (ETA) designates any straight chain 20:4 fatty Acid.
Eicosatetraenoic Acid belongs to the family of eicosanoids, molecules synthesized from oxidized polyunsaturated fatty Acids (PUFAs) to mediate cell-cell communication.
The eicosanoids, working in tandem, contribute to a lipid signaling complex widely responsible for inducing an inflammatory immune response.

Eicosatetraenoic Acid (AA, sometimes ETA) is a polyunsaturated omega-6 fatty Acid 20:4(ω-6), or 20:4(5,8,11,14).
Eicosatetraenoic Acid is structurally related to the saturated arachidic Acid found in cupuaçu butter.
Eicosatetraenoic Acid's name derives from the New Latin word arachis (peanut), but it is important to note that peanut oil does not contain any Eicosatetraenoic Acid

Eicosatetraenoic Acid is an unsaturated, essential fatty Acid.
Eicosatetraenoic Acid is found in animal and human fat as well as in the liver, brain, and glandular organs, and is a constituent of animal phosphatides.
Eicosatetraenoic Acid is formed by the synthesis from dietary linoleic Acid and is a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes.

Eicosatetraenoic Acid is a long-chain fatty Acid that is a C20, polyunsaturated fatty Acid having four (Z)-double bonds at positions 5, 8, 11 and 14.
Eicosatetraenoic Acid has a role as a human metabolite, an EC 3.1.1.1 (carboxylesterase) inhibitor, a Daphnia galeata metabolite and a mouse metabolite.

Eicosatetraenoic Acid is an icosa-5,8,11,14-tetraenoic Acid, an omega-6 fatty Acid and a long-chain fatty Acid.
Eicosatetraenoic Acid is a conjugate Acid of an arachidonate.

Common signs of inflammation are both internal and external, with effects like visible redness, pain in the surrounding area, swelling, and the sensation of heat—many of these an effect of varying eicosanoid species.
These effects are associated with and have been observed in patients suffering from cancers and various neurological/metabolic disorders.

Two isomers, both of them essential fatty Acids, are of particular interest:
-all-cis-5,8,11,14-eicosatetraenoic Acid is an ω-6 fatty Acid with the trivial name Eicosatetraenoic Acid.
Eicosatetraenoic Acid is formed by a desaturation of dihomo-gamma-linolenic Acid (DGLA, 20:3 ω-6).

-all-cis-8,11,14,17-eicosatetraenoic Acid is an ω-3 fatty Acid.
Eicosatetraenoic Acid is an intermediate between stearidonic Acid (18:4 ω-3) and eicosapentaenoic Acid (EPA, 20:5 ω-3)
Some chemistry sources define 'Eicosatetraenoic Acid' to designate any of the eicosatetraenoic Acids.
However, almost all writings in biology, medicine and nutrition limit the use of the term 'Eicosatetraenoic Acid' to all-cis-5,8,11,14-eicosatetraenoic Acid (ω-6).

Recent Studies:
Eicosatetraenoic Acid is found in green-lipped mussel and appears to act as dual inhibitor of Eicosatetraenoic Acid oxygenation by both the cyclooxygenase (COX) and lipoxygenase pathway.
According to the journal of nutrition, feeding green-lipped mussel to arthritic dogs leads to an improved response.
In addition to their inflammatory nature, eicosanoid molecules such as ETA can also contribute to an anti-inflammatory response.

Many ω-3-PUFAs are abundantly produced in nature and can be extracted and studied.
These molecules have exhibited anti-inflammatory properties and have led scientists to believe that they may serve as relief to patients with rheumatoid arthritis, asthma, and heart disease, afflictions associated with an overly active inflammatory response.
Eicosatetraenoic Acid , which is much less abundant in nature, has been the subject of significantly less studies.
As a member of the eicosanoid family, it is expected that ETA should have a similar positive effect in the human body however there is a lack in its production and therefore a lack in its scientific investigation and understanding.

Eicosatetraenoic Acid is a fungus employed in the biological production of Eicosatetraenoic Acid, and so biotechnology has allowed for the biosynthesis of a mutant strain of this fungus.
Mortierella alpina typically only produces Eicosatetraenoic Acid in trace amounts at low temperatures, making it difficult to isolate and examine.
This developed mutant strain is capable of producing larger amounts of ETA due to the expression of an ω-3-desaturase gene, typically responsible for the significant production of the more abundant PUFAs.
The development of a mutant strain was considered in the context of the over-expression of the endogenous ω-3-desaturase gene versus the heterologous Saprolegnia diclina Δ17 (sdd17m) desaturase gene.

The endogenous ω-3-desaturase gene transformed fungi had Eicosatetraenoic Acid at 42.1% in total lipid concentration, 84.2-fold and 3.2-fold more than two wild-type strain fungi when contrasted at a temperature of 12 degrees Celsius.
While no Eicosatetraenoic Acid accumulation is documented at 28 degrees Celsius, the mutant strain of the fungus transformed with the heterologous sdd17mgene exhibited 24.9% of the total lipid content at the same temperature, indicating success in the genetic alteration and abundance of ETA provided for the study, at a variety of different temperatures and conditions.
This allows for a more inclusive analysis of the effects of Eicosatetraenoic Acid on the human body and provides new insight for medical treatments to inflammatory conditions, given the newfound methods for producing and collecting these molecules for isolation and analysis.
This study provides insight as to how many molecules may have multiple functions, some of which are unknown and are still being determined by scientists.
The duality of molecules like eicosatetraenoic Acid and other eicosanoids, both as inflammatory and anti-inflammatory molecules, is a point of compelling research

Eicosatetraenoic Acid is an omega-3 fatty Acid.
Eicosatetraenoic Acid, an omega-6 fatty Acid, is an essential fatty Acid for most mammals and has many important biological functions in signaling, inflammation, nervous system functions and other processes.
Eicosatetraenoic Acid is usually most abundant as a membrane lipid where it is esterified mainly at the sn2 position of phospholipids.

Eicosatetraenoic Acid mediates numerous actions that range from induction of cell death to promotion of cell survival and enhancement of neurite extension.
Some of Eicosatetraenoic Acids functions include modulation of the activities of protein kinases and ion channels, inhibition of neurotransmitter uptake, enhancement of synaptic transmission, and induction of cellular adhesion.

Eicosatetraenoic Acid has been suggested to be a critical mediator in amyloid-beta induced pathogenesis, leading to learning, memory, and behavioral impairments in Alzheimer's disease.
In the CNS it plays a fast messenger role in synaptic modulation.

An imbalance in n-6 fatty Acid and n-3 fatty Acid dietary intake has been suggested as the reason for several diseases, including inflammatory and autoimmune diseases, and has recently been blamed predominantly on Eicosatetraenoic Acid because it is a precursor for eicosanoids which have proinflammatory and immuno-regulatory activity.
Eicosatetraenoic Acid is also a precursor for autacoids and prostaglandins in mammals.

Eicosatetraenoic Acid has been shown to trigger calcium signals in endothelial cells derived from human breast carcinoma but not from healthy cells.
This has caused it to be considered a component of the tumor microenvironment although some results suggest that release of Eicosatetraenoic Acid from membrane lipids my help to prevent tumors.

Eicosatetraenoic Acid is structurally related to the saturated arachidic Acid found in cupuaçu butter.
Eicosatetraenoic Acid's name derives from the New Latin word arachis (peanut), but it is important to note that peanut oil does not contain any Eicosatetraenoic Acid.

Eicosatetraenoic Acid is not one of the essential fatty Acids.
However, Eicosatetraenoic Acid does become essential if a deficiency in linoleic Acid exists or if an inability to convert linoleic Acid to Eicosatetraenoic Acid occurs.

Some mammals lack the ability or have a very limited capacity to convert linoleic Acid to Eicosatetraenoic Acid, making it an essential part of their diets.
Since linoleic Acid consumption does not seem to affect levels of Eicosatetraenoic Acid in plasma/serum or erythrocytes, it is uncertain if humans can in fact convert linoleic Acid to Eicosatetraenoic Acid.

Since little or no Eicosatetraenoic Acid is found in common plants, such animals are obligate carnivores; the cat is a common example of having the inability to desaturate essential fatty Acids.
Eicosatetraenoic Acid is a commercial source of Eicosatetraenoic Acid has been derived, however, from the fungus Mortierella alpina

Eicosatetraenoic Acid is important because the human body uses it as a starting material in the synthesis of two kinds of essential substances, the prostaglandins and the leukotrienes, both of which are also unsaturated carboxylic Acids.
Eicosatetraenoic Acid is a liquid unsaturated fatty Acid C20H32O2 that occurs in most animal fats, is a precursor of prostaglandins, and is considered essential in animal nutrition.

Eicosatetraenoic Acid (ETA) is a 20-carbon chain fatty Acid with four methylene-interrupted cis double bonds, the first with respect to the methyl end (omega, ω or n) is located between carbon 6 and 7.
Hence, Eicosatetraenoic Acid belongs to the omega-6 (n-6) polyunsaturated fatty Acids (PUFA), is designated as 20:4ω-6, with a biochemical nomenclature of all-cis-5,8,11,14-eicosatetraenoic Acid, and usually assumes a hairpin configuration

Eicosatetraenoic Acid is obtained from food such as:
-poultry

-animal organs

-meat

-fish

-seafood

-eggs

Eicosatetraenoic Acid is an essential fatty Acid, which is consumed in small amounts in our regular diets. It is considered an "essential" fatty Acid because it is an absolute requirement for the proper functioning for the human body.
Eicosatetraenoic Acid can be found mainly in the fatty parts of meats and fish (largely red meat), so vegetarians usually have lower levels of Eicosatetraenoic Acid in the body than those with omnivorous diets.
Eicosatetraenoic Acid is important because the human body uses it as a starting material in the synthesis of two kinds of essential substances, the prostaglandins and the leukotrienes, both of which are also unsaturated carboxylic Acids.

Eicosatetraenoic Acid mediates inflammation and the functioning of several organs and systems either directly or upon its conversion into eicosanoids.
Eicosatetraenoic Acid in cell membrane phospholipids is the substrate for the synthesis of a range of biologically active compounds (eicosanoids) including prostaglandins, thromboxanes, and leukotrienes.
These compounds can act as mediators in their own right and can also act as regulators of other processes, such as platelet aggregation, blood clotting, smooth muscle contraction, leukocyte chemotaxis, inflammatory cytokine production, and immune function.

Alternative Classes:
-Unsaturated fatty Acids
-Straight chain fatty Acids
-Monocarboxylic Acids and derivatives
-Carboxylic Acids
-Organic oxides
-Hydrocarbon derivatives
-Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.
-Carbonyl compounds

Substituents:
-Long-chain fatty Acid
-Unsaturated fatty Acid
-Straight chain fatty Acid
-Monocarboxylic Acid or derivatives
-Carboxylic Acid
-Carboxylic Acid derivative
-Organic oxygen compound
-Organic oxide
-Hydrocarbon derivative
-Organooxygen compound
-Carbonyl group
-Aliphatic acyclic compound

Eicosatetraenoic Acid is a natural fatty Acid that plays an essential role in physiological homeostases, such as repair and growth of cells.
Eicosatetraenoic Acid is found in animal and human fat as well as in the liver, brain, and glandular organs, and is a constituent of animal phosphatides.
Eicosatetraenoic Acid is formed by the synthesis from dietary linoleic Acid and is a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes.

Eicosatetraenoic Acid belongs to a kind of polyunsaturated omega-6 fatty Acid, which is highly biologically relevant.
Eicosatetraenoic Acid is abundantly distributed in brain, muscles and liver.
Eicosatetraenoic Acid is the precursor for all prostaglandins, thromboxanes, and leukotrienes.

Eicosatetraenoic Acid (AA, sometimes ETA) is a polyunsaturated omega-6 fatty Acid 20:4(ω-6). It is the counterpart to the saturated arachidic Acid found in peanut oil
Eicosatetraenoic Acid is an unsaturated omega-6 fatty Acid constituent of the phospholipids of cell membranes

Eicosatetraenoic Acid is an essential fatty Acid and a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes.
Eicosatetraenoic Acid occurs in liver, brain, glandular organs, and depot fats of animals, in small amounts in human depot fats
Eicosatetraenoic Acid is also a constituent of animal phosphatides.

Eicosatetraenoic Acid is an ingredient with skin-smoothing, emollient, and healing properties.
Eicosatetraenoic Acid is an omega-6 essential fatty Acid naturally occurring in the skin and considered critical for appropriate skin metabolism.

Eicosatetraenoic Acid is a constituent of vitamin F.
Eicosatetraenoic Acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules

PHYSICAL PROPERTIES OF Eicosatetraenoic Acid:

-Molecular Weight: 304.5

-XLogP3-AA: 6.3

-Exact Mass: 304.240230259

-Monoisotopic Mass: 304.240230259

-Topological Polar Surface Area: 37.3 Å²

-Physical Description: Liquid

-Boiling Point: 170 °C

-Melting Point: -49.5 °C

-LogP: 6.98

-Collision Cross Section: 178.94 Å²

-Acidity (pKa): 4.752

-Refractivity: 99.95 m³·mol⁻¹

-Polarizability: 37.2 Å³

-logS: 10(-6.3) g/L

Eicosatetraenoic Acid is found in animal and human fat as well as in the liver, brain, and glandular organs, and is a constituent of animal phosphatides.
Eicosatetraenoic Acid is formed by the synthesis from dietary linoleic Acid and is a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes.

Eicosatetraenoic Acid is an icosa-5,8,11,14-tetraenoic Acid, an omega-6 fatty Acid and a long-chain fatty Acid.
Eicosatetraenoic Acid is a conjugate Acid of an arachidonate.

CHEMICAL PROPERTIES OF Eicosatetraenoic Acid:

-Heavy Atom Count: 22

-Formal Charge: 0

-Complexity: 362

-Isotope Atom Count: 0

-Defined Atom Stereocenter Count: 0

-Undefined Atom Stereocenter Count: 0

-Defined Bond Stereocenter Count: 4

-Undefined Bond Stereocenter Count: 0

-Covalently-Bonded Unit Count: 1

-Compound Is Canonicalized: Yes

-Hydrogen Bond Donor Count: 1

-Hydrogen Bond Acceptor Count: 2

-Rotatable Bond Count: 14

Eicosatetraenoic Acid is important because the human body uses it as a starting material in the synthesis of two kinds of essential substances, the prostaglandins and the leukotrienes, both of which are also unsaturated carboxylic Acids.
Eicosatetraenoic Acid mediates inflammation and the functioning of several organs and systems either directly or upon its conversion into eicosanoids.

Eicosatetraenoic Acid in cell membrane phospholipids is the substrate for the synthesis of a range of biologically active compounds (eicosanoids) including prostaglandins, thromboxanes, and leukotrienes.
These compounds can act as mediators in their own right and can also act as regulators of other processes, such as platelet aggregation, blood clotting, smooth muscle contraction, leukocyte chemotaxis, inflammatory cytokine production, and immune function.

STORAGE OF EICOSATETRAENOIC ACID:

Eicosatetraenoic Acid should be stored at –20 °C.
Eicosatetraenoic Acid should be stored in a dry environment.
Eicosatetraenoic Acid should be stored in moisture-free containers.

Eicosatetraenoic Acid should be kept in a well ventilated place.
Eicosatetraenoic Acid should be stored under an inert atmosphere.

Eicosatetraenoic Acid should be kept in clean containers.
Eicosatetraenoic Acid should not be kept in the same place as very strong bases.
Eicosatetraenoic Acid should be stored in an environment that does not reach high temperatures.

SYNONYMS:

(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic Acid
Immunocytophyte
arachidonate
(all-Z)-5,8,11,14-Eicosatetraenoic Acid
cis-5,8,11,14-Eicosatetraenoic Acid
5,8,11,14-Eicosatetraenoic Acid, (all-Z)-
5Z,8Z,11Z,14Z-eicosatetraenoic Acid
all-cis-5,8,11,14-eicosatetraenoic Acid
5,8,11,14-Eicosatetraenoic Acid
Icosa-5,8,11,14-tetraenoic Acid
cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic Acid
5Z,8Z,11Z,14Z-icosatetraenoic Acid
[1-14C]Eicosatetraenoic Acid
5,8,11,14-Icosatetraenoic Acid
(14C)Eicosatetraenoic Acid
Eicosatetraenoic Acid, 99%
EicosatetraenoicAcid
Arachidonsaeure
Immunocytophyt
Vevodar
(5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraenoic Acid
(14C)-Eicosatetraenoic Acid
(5Z,8Z,11Z,14Z)-5,8,11,14-Eikosatetraensaeure
5,8,11,14-Eicosatetraenoate
5Z,8Z,11Z,14Z-Eicosatetraenoate
5,8,11,14-Eicosatetraenoic Acid, labeled with carbon-14, (all-Z)-
cis-D5,8,11,14-Eicosatetraenoate
5,8,11,14-all-cis-Eicosatetraenoate
all-cis-5,8,11,14-Eicosatetraenoate
cis-D5,8,11,14-Eicosatetraenoic Acid
(5Z,8Z,11Z,14Z)-Icosatetraenoic Acid
(all-Z)-5,8,11,14-Eicosatetraenoate
Eicosa-5Z,8Z,11Z,14Z-tetraenoic Acid
all-cis-eicosa-5,8,11,14-tetraenoic Acid
cis-Delta(5,8,11,14)-eicosatetraenoic Acid
5-cis,8-cis,11-cis,14-cis-Eicosatetraenoate