PRODUCTS

ARACHIDONIC ACID

CAS NUMBER: 506-32-1

EC NUMBER: 208-033-4

MOLECULAR FORMULA: C20H32O2

MOLECULAR WEIGHT: 304.5

IUPAC NAME: (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid

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

Arachidonic Acid is an unsaturated, essential fatty acid.
Arachidonic 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.
Arachidonic Acid is formed by the synthesis from dietary linoleic acid and is a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes.

Arachidonic 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.
Arachidonic Acid has a role as a human metabolite, an EC 3.1.1.1 (carboxylesterase) inhibitor, a Daphnia galeata metabolite and a mouse metabolite.
Arachidonic Acid is an icosa-5,8,11,14-tetraenoic acid, an omega-6 fatty acid and a long-chain fatty acid.
Arachidonic Acid is a conjugate acid of an arachidonate.
Arachidonic Acid derives from a hydride of a (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraene.

Chemistry of Arachidonic Acid:
In chemical structure, Arachidonic Acid is a carboxylic acid with a 20-carbon chain and four cis-double bonds; the first double bond is located at the sixth carbon from the omega end.
Some chemistry sources define 'Arachidonic Acid' to designate any of the eicosatetraenoic acids.
However, almost all writings in biology, medicine, and nutrition limit the term to all cis-5,8,11,14-eicosatetraenoic acid.

Biology of Arachidonic Acid:
Arachidonic acid is a polyunsaturated fatty acid present in the phospholipids (especially phosphatidylethanolamine, phosphatidylcholine, and phosphatidylinositides) of membranes of the body's cells, and is abundant in the brain, muscles, and liver.
Skeletal muscle is an especially active site of arachidonic acid retention, accounting for roughly 10-20% of the phospholipid fatty acid content typically.
In addition to being involved in cellular signaling as a lipid second messenger involved in the regulation of signaling enzymes, such as PLC-γ, PLC-δ, and PKC-α, -β, and -γ isoforms, arachidonic acid is a key inflammatory intermediate and can also act as a vasodilator

Conditionally essential fatty acid:
Arachidonic Acid is not one of the essential fatty acids.
However, it does become essential if a deficiency in linoleic acid exists or if an inability to convert linoleic acid to arachidonic acid occurs.
Some mammals lack the ability or have a very limited capacity to convert linoleic acid to arachidonic acid, making it an essential part of their diets.
Since linoleic acid consumption does not seem to affect levels of arachidonic acid in plasma/serum or erythrocytes, it is uncertain if humans can in fact convert linoleic acid to arachidonic acid.
Since little or no arachidonic 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.
A commercial source of arachidonic acid has been derived, however, from the fungus Mortierella alpina

Biosynthesis and Cascade in Humans:
Arachidonic Acid is freed from phospholipid by hydrolysis, catalyzed by the phospholipase A2 (PLA2).
Arachidonic Acid for signaling purposes appears to be derived by the action of group IVA cytosolic phospholipase A2 (cPLA2, 85 kDa), whereas inflammatory arachidonic acid is generated by the action of a low-molecular-weight secretory PLA2

Arachidonic Acid is a precursor to a wide range of eicosanoids:
-The enzymes cyclooxygenase-1 and -2 (i.e. prostaglandin G/H synthase 1 and 2 {PTGS1 and PTGS2}) convert arachidonic acid to prostaglandin G2 and prostaglandin H2, which in turn may be converted to various prostaglandins, to prostacyclin, to thromboxanes, and to the 17-carbon product of thromboxane metabolism of prostaglandin G2/H2, 12-Hydroxyheptadecatrienoic acid (12-HHT).
-The enzyme 5-lipoxygenase catalyzes the oxidation of arachidonic acid to 5-hydroperoxyeicosatetraenoic acid (5-HPETE), which in turn converts to various leukotrienes (i.e., leukotriene B4, leukotriene C4, leukotriene D4, and leukotriene E4 as well as to 5-hydroxyeicosatetraenoic acid (5-HETE) which may then be further metabolized to 5-HETE's more potent 5-keto analog, 5-oxo-eicosatetraenoic acid (5-oxo-ETE) (also see 5-Hydroxyeicosatetraenoic acid.
-The enzymes 15-lipoxygenase-1 (ALOX15 and 15-lipoxygenase-2 (ALOX15B catalyzes the oxidation of arachidonic acid to 15-hydroperoxyeicosatetraenoic acid (15-HPETE), which may then be further converted to 15-hydroxyeicosatetraenoic acid (15-HETE) and lipoxins;15-Lipoxygenase-1 may also further metabolize 15-HPETE to eoxins in a pathway analogous to (and presumably using the same enzymes as used in) the pathway which metabolizes 5-HPETE to leukotrienes.
-The enzyme 12-lipoxygenase (ALOX12) catalyzes oxidation of arachidonic acid to 12-hydroperoxyeicosatetraenoic acid (12-HPETE), which may then be metabolized to 12-hydroxyeicosatetraenoic acid (12-HETE) and to hepoxilins.
-Arachidonic Acid is also a precursor to anandamide.
-Some Arachidonic Acid is converted into hydroxyeicosatetraenoic acids (HETEs) and epoxyeicosatrienoic acids (EETs) by epoxygenase.

Arachidonic Acid (ARA) 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, Arachidonic 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
Arachidonic Acid is obtained from food such as:
-poultry
-animal organs
-meat
-fish
-seafood
-eggs

Arachidonic 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.
Arachidonic Acid can be found mainly in the fatty parts of meats and fish (largely red meat), so vegetarians usually have lower levels of arachidonic acid in the body than those with omnivorous diets.
Arachidonic 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.

Arachidonic Acid is a polyunsaturated fatty acid consisting of a chain of 20 carbon atoms with 4 cis (Z) double bonds at positions 5, 8, 11 and 14. Since the first double bond, with respect to the methyl end, is located at carbon 6, the molecule belongs to the group of omega-6 polyunsaturated fatty acids or omega-6 fatty acids.
Arachidonic acid is a long-chain polyunsaturated fatty acid or LC-PUFA.
Arachidonic Acid is found mainly in cell membranes, esterified in phospholipids; hence, again like EPA and DHA, it is a structural components of cellular membranes. The highest content, expressed as a percentage of phospholipid fatty acids, is found in platelets.

Tissue Locations:
-Adipose Tissue
-Epidermis
-Fibroblasts
-Intestine
-Kidney
-Liver
-Lung
-Neuron
-Pancreas
-Placenta
-Platelet
-Prostate
-Skeletal Muscle
-Spleen
-Testis
-Thyroid Gland

Animals can synthesize Arachidonic Acid from linoleic acid or LA or 18:2n-6, the precursor to omega-6 polyunsaturated fatty acids, and, with alpha-linolenic acid or ALA or 18:3n-3, one of the two essential fatty acids for animals.
In the absence of dietary linoleic acid, the other omega-6 polyunsaturated fatty acids, including ARA, become essential, too. For this reason, they are defined as conditionally essential fatty acids.
Arachidonic 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.

Arachidonic Acid is available in high amounts in foods of animal origin: meats, fish, dairy products and eggs
In humans, Arachidonic Acid can be synthesized by elongation and saturation of linoleic acid (C18:2), an essential fatty acid.
This means that a lack of linoleic acid can hinder processes requiring arachidonic acid. However, the degradation of phospholipids by phospholipases such as PLA2 can also be a source of arachidonic acid from endogenous metabolism.

Arachidonic Acid and Cellular Membranes:
The role of lipids in cellular organization and signalling is gaining momentum, putting fatty acids and complex lipids at the forefront of modern biomedical research.
As a fatty acid present in phospholipids, arachidonic acid plays an important role in cellular structure.
Thanks to its four cis double bonds, it contributes to the flexibility of cellular membranes which is essential for cell function, particularly in the nervous system, skeletal muscle and immune system

Arachidonic Acid is a slippery molecule that owes its mobility to its four cis double bonds.
These are the source of its flexibility, keeping the pure fatty acid liquid, even at subzero temperatures, and helping to give mammalian cell membranes their correct fluidity at physiological temperatures.
The double bonds are also the key to the propensity of arachidonic acid to react with molecular oxygen.
This can happen nonenzymatically, contributing to oxidative stress, or through the actions of three types of oxygenase: cyclooxygenase (COX), lipoxygenase (LOX), and cytochrome P450.
While the products of these enzymes and of the nonenzymatic transformations have well-substantiated bioactivities, unchanged arachidonic acid itself has biological activity.

The most important protaglandin precursor is arachidonic acid.
Arachidonic Acid is an essential fatty acid and is also synthesized from dietarily essential linoleic acid.

Arachidonic Acid (ARA), used in conjunction with Docosahexaenoic acid (DHA), represent a nutrient combination that is important for infant development.
Arachidonic Acid is an omega-6 polyunsaturated fatty acid [C20:4 (n-6)], naturally present in human mother’s milk.
Adults can easily convert dietary fatty acids to ARA and DHA but that ability is incompletely developed in infants, leaving breast milk as their only natural source of ARA and DHA.

Arachidonic Acid is a polyunsaturated, essential fatty acid that has a 20-carbon chain as a backbone and four cis-double bonds at the C5, C8, C11, and C14 positions.
Arachidonic 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.
Arachidonic Acid is synthesized from dietary linoleic acid.

Arachidonic Acid mediates inflammation and the functioning of several organs and systems either directly or upon its conversion into eicosanoids.
Arachidonic 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

Arachidonic Acid can be metabolized by cytochrome p450 (CYP450) enzymes into 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acids (EETs), their corresponding dihydroxyeicosatrienoic acids (DHETs), and 20-hydroxyeicosatetraenoic acid (20-HETE).
The production of kidney CYP450 arachidonic acid metabolites is altered in diabetes, pregnancy, hepatorenal syndrome, and in various models of hypertension
Arachidonic Acid is likely that changes in this system contribute to the abnormalities in renal function that are associated with many of these conditions.
Phospholipase A2 (PLA2) catalyzes the hydrolysis of the sn-2 position of membrane glycerophospholipids to liberate arachidonic acid

The beneficial effects of omega-3 fatty acids are believed to be due in part to selective alteration of arachidonate metabolism that involves cyclooxygenase (COX) enzymes
Oxononanoic acid (9-ONA), one of the major products of peroxidized fatty acids, was found to stimulate the activity of phospholipase A2 (PLA2), the key enzyme to initiate the arachidonate cascade and eicosanoid production
Arachidonate lipoxygenase (ALOX) enzymes metabolize arachidonic acid to generate potent inflammatory mediators and play an important role in inflammation-associated diseases
It 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.

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

Arachidonic Acid is a natural fatty acid that plays an essential role in physiological homeostases, such as repair and growth of cells.
Arachidonic 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.
Arachidonic Acid is formed by the synthesis from dietary linoleic acid and is a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes.
arachidonic acid is commonly used in arachidonic acid release assays and fatty acid metabolism studies.

Arachidonic Acid is an essential fatty acid and a precursor for all prostaglandins, thromboxanes, and leukotrienes.
Virtually all cellular arachidonic acid is esterified in membrane phospholipids where its presence is tightly regulated through multiple interconnected pathways.
Free arachidonic acid is a transient, critical substrate for the biosynthesis of eicosanoid second messengers.
Receptor-stimulated release, metabolism, and re-uptake of free arachidonate are all important aspects of cell signaling and inflammation.

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

Most cellular arachidonic acid is esterified in the membrane phospholipids.
Arachidonic Acid is an important second messenger of cellular signalling participating in the regulation of signaling enzymes including PLC-γ, PLC-δ, and PKC-α, -β, and -γ isoforms.
In addition, arachidonic acid acts as key inflammatory intermediate as well as avasodilator.

Generally, the body can synthesize the arachidonic acid through linoleic acid.
However, upon linoleic acid deficiency, it is necessary to supplement arachidonic acid from the diets.
Food sources of arachidonic acid include meat, eggs and some fishes.

Arachidonic Acid (AA, sometimes ARA) is a polyunsaturated omega-6 fatty acid 20:4(ω-6). It is the counterpart to the saturated arachidic acid found in peanut oil
Arachidonic Acid is an unsaturated omega-6 fatty acid constituent of the phospholipids of cell membranes
Arachidonic Acid is an essential fatty acid and a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes.
Arachidonic Acid occurs in liver, brain, glandular organs, and depot fats of animals, in small amounts in human depot fats
Arachidonic Acid is also a constituent of animal phosphatides.

Arachidonic Acid is an ingredient with skin-smoothing, emollient, and healing properties.
Arachidonic Acid is an omega-6 essential fatty acid naturally occurring in the skin and considered critical for appropriate skin metabolism.
Arachidonic Acid is a constituent of vitamin F.
Arachidonic Acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules

PHYSICAL PROPERTIES OF ARACHIDONIC 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

Arachidonic 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.
Arachidonic Acid is formed by the synthesis from dietary linoleic acid and is a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes.
Arachidonic Acid is structurally related to the saturated arachidic acid found in cupuaçu butter.
Arachidonic Acid's name derives from the New Latin word arachis (peanut), but it is important to note that peanut oil does not contain any arachidonic acid

Arachidonic 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.
Arachidonic Acid is available in high amounts in foods of animal origin: meats, fish, dairy products and eggs
In humans, arachidonic acid can be synthesized by elongation and saturation of linoleic acid (C18:2), an essential fatty acid.
This means that a lack of linoleic acid can hinder processes requiring arachidonic acid. However, the degradation of phospholipids by phospholipases such as PLA2 can also be a source of arachidonic acid from endogenous metabolism.
Arachidonic Acid (AA, sometimes ARA) is a polyunsaturated omega-6 fatty acid 20:4(ω-6), or 20:4(5,8,11,14).

Arachidonic Acid has a role as a human metabolite, an EC 3.1.1.1 (carboxylesterase) inhibitor, a Daphnia galeata metabolite and a mouse metabolite.
Arachidonic Acid is an icosa-5,8,11,14-tetraenoic acid, an omega-6 fatty acid and a long-chain fatty acid.
Arachidonic Acid is a conjugate acid of an arachidonate.

CHEMICAL PROPERTIES OF ARACHIDONIC 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

STORAGE OF ARACHIDONIC ACID:

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

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

Arachidonic Acid should be kept in clean containers.
Arachidonic Acid should not be kept in the same place as very strong bases.
Arachidonic 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]Arachidonic acid
5,8,11,14-Icosatetraenoic Acid
(14C)Arachidonic acid
Arachidonic Acid, 99%
Arachidonicacid
Arachidonsaeure
Immunocytophyt
Vevodar
(5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraenoic Acid
(14C)-arachidonic 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