ADRENIC ACID

ADRENIC ACID Basic information
Product Name:ADRENIC ACID
Synonyms: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
CAS:28874-58-0
MF:C22H36O2
MW:332.52
EINECS:
Product Categories:Unsaturated fatty acids and derivatives;DJ - DZUnsaturated fatty acids and derivatives;Omega 6 fatty acids and derivatives;Polyunsaturated;Alphabetic;D
Mol File:28874-58-0.mol
ADRENIC ACID Structure
ADRENIC ACID Chemical Properties
Boiling point 161-164.5 °C(Press: 0.07 Torr)
density 0.9220 g/cm3
storage temp. −20°C
solubility Chloroform (Sparingly), Methanol (Slightly)
form Oil
pka4.76±0.10(Predicted)
color Colourless
Stability:Light Sensitive
Safety Information
WGK Germany 3
MSDS Information
ProviderLanguage
SigmaAldrich English
ADRENIC ACID Usage And Synthesis
DescriptionAdrenic acid is a naturally occurring polyunsaturated fatty acid (PUFA) formed through a 2-carbon chain elongation of arachidonic acid. It 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 PropertiesDocosa 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. It is one of the most abundant fatty acids in the early human brain.

UsesAdrenic 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. It 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. Arachidonic acid is not found in higher plants. Arachidonic acid serves many important functions in the body, e.g. as a structural element in membrane phospholipids, and as precursor for signalling.
Usescis-7,10,13,16-Docosatetraenoic Acid has been identified as a protein kinase inhibitor, affecting serotonin levels in studies.
DefinitionChEBI: 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.
Enzyme inhibitorThis long-chain, unsaturated fatty acid (FWfree-acid = 332.53 g/mol; CAS 28874-58-0), also known as adrenic acid and (7Z,10Z,13Z,16Z)- docosatetraenoic acid, inhibits arachidonyl-CoA synthetase, orarachidonate:CoA ligase and prostaglandin biosynthesis.
ADRENIC ACID Preparation Products And Raw materials
Eicosapentaenoic acid ethyl ester Nervonic acid Vitamin B12 CIS-6,9,12,15-OCTADECATETRAENOIC ACID*SO DIUM cis-11-Eicosenoic acid 3(R,S)-HYDROXY-7(Z),10(Z),13(Z),16(Z)-DOCOSATETRAENOIC ACID ADRENIC ACID DELTA 7 CIS, 10 CIS,13 CIS, 16 CIS DOCOSATETRAENOIC ACID METHYL ESTER 3(R,S)-HYDROXY-7(Z),10(Z),13(Z),16(Z)-DOCOSATETRAENOIC ACID METHYL ESTER DELTA 7 CIS, 10 CIS,13 CIS, 16 CIS DOCOSATETRAENOIC ACID ETHYL ESTER

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