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Adrenic acid, also known as 7,10,13,16-docosatetraenoic acid or adrenate, is a member of the class of compounds known as very long-chain fatty acids.
Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.
CAS Number: 28874-58-0
IUPAC Name: (7Z,10Z,13Z,16Z)-Docosa-7,10,13,16-tetraenoic acid
Chemical Formula: C22H36O2
Other names: adrenic acid, 28874-58-0, (7Z,10Z,13Z,16Z)-Docosa-7,10,13,16-tetraenoic acid, 7Z,10Z,13Z,16Z-Docosatetraenoic acid, cis-7,10,13,16-Docosatetraenoic acid, all-cis-docosa-7,10,13,16-tetraenoic acid, CHEBI:53487, 7,10,13,16-Docosatetraenoic acid, all-cis-7,10,13,16-Docosatetraenoic acid, 7,10,13,16-docosatetraenoic acid, (7Z,10Z,13Z,16Z)-, 7,10,13,16-Docosatetraenoic acid, (all-Z)-, C22:4n-6,9,12,15, Adrenic Acid (22:4, n-6), 7,10,13,16-Docosatetraenoate, 7Z,10Z,13Z,16Z-Docosatetraenoate, ADRENIC ACID (22:4 n-6), Delta7,10,13,16-Docosatetraenoic acid, 7,10,13,16-Docosatetraenoic acid (VAN) Adrenate, cis,cis,cis,cis-Docosa-7,10,13,16-tetraensaeure, 7,10,13,16-Docosatetraenoic acid (VAN) Adrenic acid, 7,10,13,16-Docosatetraenoic acid, (all-Z)- (8CI), cis-7,10,13,16-Docosatetraenoic acid, >=98% (GC), 7,10,13,16-Docosatetraenoic acid, (7Z,10Z,13Z,16Z)- (9CI), cis-7,10,13,16-Docosatetraenoic acidcis-7,10,13,16-Docosatetraenoic acid, CIS-7,10,13,16,19-DOCOSA-TETRAENOIC ACID, CIS-7,10,13,16-DOCOSA-TETRAENOIC ACID, DOCOSATETRAENOIC ACID, DOCOSA-7Z,10Z,13Z,16Z-PENTAENOIC ACID, DOCOSA-7Z,10Z,13Z,16Z-TETRAENOIC ACID, cis-7,10,13,16-Docosatetraenoic acid, C22:4n6, 7Z,10Z,13Z,16Z-DOCOSATETRAENOIC ACID, ADRENIC ACID, (All-Z)-7,10,13,16-docosatetraenoic acid, 7,10,13,16-Docosatetraenoic acid, (all-Z)-, 7,10,13,16-Docosatetraenoic acid (all-cis), (7Z,10Z,13Z,16Z)-Docosa-7,10,13,16-tetraenoic acid, Adrenic Acid (Solution in ethanol), Adrenic Acid (22:4, n-6), 7,10,13,16-Docosatetraenoic acid, (7Z,10Z,13Z,16Z)-
Adrenic acid designates any straight chain 22:4 fatty acid.
One isomer is of particular interest:
all-cis-7,10,13,16-docosatetraenoic acid is an ω-6 fatty acid with the common name adrenic acid (AdA).
This is a naturally occurring polyunsaturated fatty acid formed through a 2-carbon chain elongation of arachidonic acid.
Adrenic acid is one of the most abundant fatty acids in the early human brain.
This unsaturated fatty acid is also metabolized by cells to biologically active products viz., dihomoprostaglandins, and epoxydocosatrienoic acids (EDTs, also known as dihomo-EETs).
In addition to being endothelium-derived hyperpolarizing factors, EDTs have demonstrated anti-endoplasmic reticulum stress and anti-nociceptive activities.
They are hydrolyzed by the soluble epoxide hydrolase (sEH) to dihydroxydocosatrienoic acids (DHDTs) and hence might play a role in the efficacy of sEH inhibitors.
Adrenic acid is practically insoluble in water and a weakly acidic compound (based on its pKa).
Adrenic acid can be found in blood and in human myelin tissue.
Within the cell, adrenic acid is primarily located in the cytoplasm, in the membrane (predicted from logP), and in the peroxisome.
Adrenic acid can also be found in the extracellular space. In humans, adrenic acid is involved in alpha-linolenic acid and linoleic acid metabolism. Docosatetraenoic acid designates any straight chain 22:4 fatty acid.
In particular, all-cis-7,10,13,16-docosatetraenoic acid is an ω-6 fatty acid with the trivial name adrenic acid (AdA).
This is a naturally occurring polyunsaturated fatty acid formed through a 2-carbon chain elongation of arachidonic acid.
Adrenic acid is one of the most abundant fatty acids in the early human brain.
This unsaturated fatty acid is also metabolized by cells into biologically active products, such as dihomoprostaglandins and dihomo-epoxyeicosatrienoic acids (dihomo-EETs) (Wikipedia ).
Adrenic acid, which is a prostacyclin inhibitor, appears to be a potential prothrombotic agent (PMID: 1642692 ).
Description
Adrenic acid is a naturally occurring polyunsaturated fatty acid (PUFA) formed through a 2-carbon chain elongation of arachidonic acid.
Adrenic acid is present in the adrenal glands, brain, testis, and kidney.
Although there is trace metabolism of adrenic acid in the forebrain, the renal medulla is the only tissue which readily metabolizes the acid through cyclooxygenase activity.
The primary metabolite of adrenic acid in the rabbit kidney is 1a,1b-dihomo prostaglandin E2.
Chemical Properties
Docosa tetra enoic acid designates any straight chain 22:4 fatty acid.
One isomer is of particular interest :
all-cis-7,10,13,16-docosa tetra enoic acid is an ω-6 fatty acid with the trivial name adrenic acid.
This is a naturally occurring polyunsaturated fatty acid formed through a 2-carbon chain elongation of arachidonic acid.
Adrenic acid is one of the most abundant fatty acids in the early human brain.
Uses:
Adrenic acid is considered a sort of storage form of arachidnoic acid because it can be retro-converted into arachidonic acid by enzymes.
Arachidonic acid is relatively abundant especially in the phospholipids that are found in cellular membranes, and it is precursor for many hormone-like signaling molecules, e.g. prostaglandins and leukotrienes.
Adrenic acid shall be liberated from the phospholipids by phospholipase enzymes before it can be converted into these signaling molecules.
Omnivorous humans also consume small amounts of arachidonic acid with the diet, since arachidonic acid is found in small amounts in all animal products.
Adrenic acid is not found in higher plants.
Adrenic acid serves many important functions in the body, e.g. as a structural element in membrane phospholipids, and as precursor for signalling.
Adrenic acid has been identified as a protein kinase inhibitor, affecting serotonin levels in studies.
Adrenic acid is a naturally occurring polyunsaturated fatty acid (PUFA) formed through a 2-carbon chain elongation of arachidonic acid.
Adrenic acid is present in the adrenal glands, brain, testis, and kidney.
Although there is trace metabolism of adrenic acid in the forebrain, the renal medulla is the only tissue which readily metabolizes the acid through cyclooxygenase activity.
The primary metabolite of adrenic acid in the rabbit kidney is 1a,1b-dihomo prostaglandin.
Adrenic Acid (22-4,n-6), also known as 7,10,13,16-Docosatetraenoic acid, is a polyunsaturated fatty acid.
Peroximal β-oxidation of 7,10,13,16-docosatetraenoic acid has been shown to form arachidonic acid.
Endothelial cells have been shown to convert arachidonic acid to docosatetraenoic acid and releasing docosatetraenoic acid when exposed to ionophore A23187 (sc-3591).
Additionally, endothelial cell studies have demonstrated that adrenic acid reduces prostaglandin.
Adrenic acid is a member of the class of compounds known as very-long-chain fatty acids.
Adrenic acid can be found in blood and in human myelin tissue.
All-cis-docosa-7,10,13,16-tetraenoic acid is the all-cis-isomer of a C22 polyunsaturated fatty acid having four double bonds in the 7-, 10-, 13- and 16-positions. One of the most abundant fatty acids in the early human brain. It has a role as a human metabolite and an algal metabolite. It is a docosatetraenoic acid and an omega-6 fatty acid. It is a conjugate acid of an all-cis-docosa-7,10,13,16-tetraenoate.
Adrenic acid, also known as 7,10,13,16-docosatetraenoic acid or adrenate, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.
Adrenic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Adrenic acid can be found in blood and in human myelin tissue. Within the cell, adrenic acid is primarily located in the cytoplasm, in the membrane (predicted from logP), and in the peroxisome. It can also be found in the extracellular space.
In humans, adrenic acid is involved in alpha-linolenic acid and linoleic acid metabolism. Docosatetraenoic acid designates any straight chain 22:4 fatty acid.
In particular, all-cis-7,10,13,16-docosatetraenoic acid is an ω-6 fatty acid with the trivial name adrenic acid (AdA).
This is a naturally occurring polyunsaturated fatty acid formed through a 2-carbon chain elongation of arachidonic acid.
Adrenic acid is one of the most abundant fatty acids in the early human brain.
This unsaturated fatty acid is also metabolized by cells into biologically active products, such as dihomoprostaglandins and dihomo-epoxyeicosatrienoic acids (dihomo-EETs).
Adrenic acid, which is a prostacyclin inhibitor, appears to be a potential prothrombotic agent.
