ADRENIC ACID
ADRENIC ACID
CAS Number: 28874-58-0
Molecular Formula: C22H36O2
Formula Weight: 332.5
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.
Adrenic acid is one of the abundant fatty acids in early human brain.
Adrenic acid is metabolized by cells into biologically active products such as dihomo-epoxyeicosatrienoic acids and dihomoprostaglandins.
Adrenic acid is a prostacyclin inhibitor which is a potential prothrombotic agent.
Adrenic acid is the first omega-6 fatty acid with proresolving functions.
Adrenic acid inhibits leukotriene B4 production, specifically in neutrophils.
Adrenic acid treatment alleviates leukotriene B4–mediated experimental arthritis.
Chemical Properties of Adrenic acid:
Docosa tetra enoic acid designates any straight chain 22:4 fatty acid.
Uses of Adrenic acid:
Adrenic acid is considered a sort of storage form of arachidnoic acid because Adrenic acid 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.
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.
Uses of Adrenic acid:
cis-7,10,13,16-Docosatetraenoic Acid has been identified as a protein kinase inhibitor, affecting serotonin levels in studies.
Adrenic acid, also known as adrenate, belongs to the class of organic compounds known as very long-chain fatty acids.
These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.
Based on a literature review a significant number of articles have been published on Adrenic acid.
Adrenic acid (ADA), which is an endogenously synthesized polyunsaturated free fatty acid, was significantly increased in nonalcoholic fatty liver disease (NAFLD) patients and NAFLD-model mice compared with the corresponding controls in our previous study.
To elucidate the involvement of ADA in NAFLD and nonalcoholic steatohepatitis (NASH), we examined ADA-induced lipotoxicity in human hepatocarcinoma HepG2 cells.
The ROS production in HepG2 cells was increased by exposure to ADA.
Adrenic acid was also shown that the treatment with ADA decreased cell viability in a dose-dependent manner.
Adrenic acid 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.
Adrenic acid 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.
The N-Acetyl-L-Cysteine pretreatment counteracted this ADA-induced ROS production and cell death.
Furthermore, ADA modulated the expressions of SOD2, HO-1 and Gpx1 as antioxidant enzymes.
These findings suggest that ADA could induce oxidative stress accompanied by cell death, providing new insights into lipotoxicity that is involved in the pathogenesis of NAFLD and NASH.
Chemical Formula: C22H36O2
Average Molecular Weight: 332.52
Monoisotopic Molecular Weight: 332.271530396
IUPAC Name: (7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoic acid
Traditional Name: docosatetraenoic acid
CAS Registry Number: 2091-25-0
SMILES: CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O
InChI Identifier: InChI=1S/C22H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21H2,1H3,(H,23,24)/b7-6-,10-9-,13-12-,16-15-
InChI Key: TWSWSIQAPQLDBP-DOFZRALJSA-N
Adrenic acid also called adrenate or 7, 10, 13, 16-docosatetraenoic acid is a member of class of compounds called very long chain fatty acids.
Very long chain fatty acids are fatty acids having aliphatic tail containing at least 22 carbon atoms.
Basically adrenic acid and weakly acidic compound.
Adrenic acid could be found in blood as well as in human myelin tissue.
Adrenic acid is located within cell located in cytoplasm, in the membrane and peroxisome.
Adrenic acid is present in extracellular space.
In humans, adrenic acid is involved in alpha-linolenic acid and linoleic acid metabolism.
Docosatetraenoic acid entitles any straight chain 22:4 fatty acid.
Adrenic acid is a naturally occurring polyunsaturated fatty acid composed through a 2 carbon chain elongation of arachidoic acid.
Formal Name: 7Z,10Z,13Z,16Z-docosatetraenoic acid
CAS Number: 28874-58-0
Molecular Formula: C22H36O2
Formula Weight: 332.5
Purity: ≥98%
Formulation: A solution in ethanol
Solubility: 0.15 M Tris-HCl pH 8.5: >1 mg/ml (from Oleic Acid)
DMF: >100 mg/ml (from Oleic Acid)
DMSO: >100 mg/ml (from Oleic Acid)
Ethanol: >100 mg/ml (from Oleic Acid)
PBS pH 7.2: <100 µg/ml (from Oleic Acid)
SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)O
InChi Code: InChI=1S/C22H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21H2,1H3,(H,23,24)/b7-6-,10-9-,13-12-,16-15-
InChi Key: TWSWSIQAPQLDBP-DOFZRALJSA-N
Adrenic acid (docosatetraenoic acid), an abundant fatty acid in the adrenal gland, is identical to arachidonic acid except for 2 additional carbons on the carboxyl end.
Adrenic acid is metabolized by cyclooxygenases, cytochrome P450s, and lipoxygenases; however, little is known regarding the role of adrenic acid and its metabolites in vascular tone.
Because of its abundance in the adrenal gland, we investigated the role of adrenic acid in vascular tone of bovine adrenal cortical arteries and its metabolism by bovine adrenal zona glomerulosa cells.
In adrenal cortical arteries, adrenic acid caused concentration-dependent relaxations, which were inhibited by the epoxyeicosatrienoic acid antagonist 14,15-epoxyeicosa-5(Z)-enoic acid and the cytochrome P450 inhibitor SKF-525A.
The large-conductance calcium-activated potassium channel blocker iberiotoxin or removal of the endothelium abolished these relaxations.
Reverse-phase high-pressure liquid chromatography and liquid chromatography/mass spectrometry isolated and identified numerous adrenic acid metabolites from zona glomerulosa cells, including dihomo-epoxyeicosatrienoic acids and dihomo-prostaglandins.
In denuded adrenal cortical arteries, adrenic acid caused concentration-dependent relaxations in the presence of zona glomerulosa cells but not in their absence.
These relaxations were inhibited by SKF-525A, 14,15-epoxyeicosa-5(Z)-enoic acid, and iberiotoxin.
Dihomo-16,17-epoxyeicosatrienoic acid caused concentration-dependent relaxations of adrenal cortical arteries, which were inhibited by 14,15-epoxyeicosa-5(Z)-enoic acid and high potassium.
Our results suggest that adrenic acid relaxations of bovine adrenal cortical arteries are mediated by endothelial and zona glomerulosa cell cytochrome P450 metabolites.
Thus, adrenic acid metabolites could function as endogenous endothelium-derived and zona glomerulosa-derived hyperpolarizing factors in the adrenal cortex and contribute to the regulation of adrenal blood flow.
(7Z,10Z,13Z,16Z)-7,10,13,16-Docosatetraenoic acid [ACD/IUPAC Name]
(7Z,10Z,13Z,16Z)-7,10,13,16-Docosatetraensäure [German] [ACD/IUPAC Name]
(All-Z)-7,10,13,16-docosatetraenoic acid
28874-58-0 [RN]
7,10,13,16-Docosatetraenoic acid, (7Z,10Z,13Z,16Z)- [ACD/Index Name]
7Z,10Z,13Z,16Z-docosatetraenoic acid
Acide (7Z,10Z,13Z,16Z)-7,10,13,16-docosatétraénoïque [French] [ACD/IUPAC Name]
adrenic acid
all-cis-7,10,13,16-Docosatetraenoic acid
all-cis-docosa-7,10,13,16-tetraenoic acid
cis-7,10,13,16-Docosatetraenoic acid
Docosatetraenoic acid [Wiki]
DTA
MFCD00673435
(7Z,10Z,13Z,16Z)-Docosa-7,10,13,16-tetraenoic acid
[28874-58-0]
1914611
2091-25-0; 28874-58-0
37743-18-3 [RN]
7,10,13,16-Docosatetraenoate [ACD/IUPAC Name]
7,10,13,16-Docosatetraenoic acid, (7Z,10Z,13Z,16Z)- (9CI)
7,10,13,16-Docosatetraenoic acid, (all-Z)-
7,10,13,16-Docosatetraenoic acid, (all-Z)- (8CI)
7C,10C,13C,16C-DOCOSATETRAENOIC ACID
7Z,10Z,13Z,16Z-Docosatetraenoate
7Z,10Z,13Z,16Z-Docosatetraenoic Acid|7Z,10Z,13Z,16Z-docosatetraenoic acid
Adrenate
Adrenic Acid (22:4, n-6)
ADRENICACID
CIS -7,10,13,16-DOCOSA- TETRAENOIC ACID
cis,cis,cis,cis-Docosa-7,10,13,16-tetraensaeure
δ7,10,13,16-Docosatetraenoic acid
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)
SCHEMBL19452
BSPBio_001499
BML3-C01
CHEMBL1491103
7,10,13,16-Docosatetraenoate
HMS1361K21
HMS1791K21
HMS1989K21
HMS3402K21
HMS3649J13
ZINC4543724
1602AH
LMFA01030178
MFCD00673435
7Z,10Z,13Z,16Z-Docosatetraenoate
ADRENIC ACID (22:4 n-6)
AKOS037646461
22:4n6
IDI1_033969
NCGC00161352-01
NCGC00161352-02
NCGC00161352-03
AS-68942
Delta7,10,13,16-Docosatetraenoic acid
SR-01000946666
7,10,13,16-Docosatetraenoic acid (VAN) Adrenate
cis,cis,cis,cis-Docosa-7,10,13,16-tetraensaeure
Q4351606
SR-01000946666-1
BRD-K17040651-001-02-0
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