A8798
Arachidonic acid sodium salt
from Porcine liver, ≥99% (capillary GC), waxy solid
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Synonym(s):
5,8,11,14-Eicosatetraenoic acid, Eicosa-5Z,8Z,11Z,14Z-tetraenoic acid, Sodium arachidonate, cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid sodium salt, 20:4
Empirical Formula (Hill Notation):
C20H31O2Na
CAS Number:
Molecular Weight:
326.45
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
Recommended Products
biological source
Porcine liver
Assay
≥99% (capillary GC)
form
waxy solid
color
white to off-white
solubility
methanol: 50 mg/mL, clear, colorless to faintly yellow
shipped in
dry ice
storage temp.
−20°C
SMILES string
[Na+].CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC([O-])=O
InChI
1S/C20H32O2.Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22;/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22);/q;+1/p-1/b7-6-,10-9-,13-12-,16-15-;
InChI key
DDMGAAYEUNWXSI-XVSDJDOKSA-M
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General description
Arachidonic acid (AA) is a polyunsaturated ω6 fatty acid constituent of the phospholipids of cell membranes. Structurally, it is a 20-carbon chain that contains four cis double bonds, which allow the free acid form of AA to be an insoluble oil; this can be converted to the water-soluble sodium salt form within the normal physiological pH range. AA is metabolized by multiple enzymes to yield various metabolites; AA and its metabolites play important roles in a variety of biological processes, including signal transduction, smooth muscle contraction, chemotaxis, cell proliferation and differentiation and apoptosis.
Application
Arachidonic acid is used in assays to measure activity of oxidizing enzymes, such as cyclooxygenase, as well as in assays to determine platelet inhibition in whole blood. AA has been demonstrated to bind to the α subunit of G protein and inhibit the activity of Ras GTPase-activating proteins (GAPs), to have a role in the development and progression of prostate cancer, and to enhance formation of lipid bodies in human mast cells.
Biochem/physiol Actions
Released arachidonic acid (AA) reacts with molecular oxygen nonenzymatically, through oxidative stress, and enzymatically through the action of oxygenase enzymes. AA is oxidized to prostaglandins and thromboxanes by at least two cyclooxygenase (COX) isoforms, to leukotrienes and lipoxins by lipoxygenases, and to epoxyeicosatrienoic acids via cytochrome p450-catalyzed metabolism. Cellular uptake of AA is energy dependent and involves protein-facilitated transport across the plasma membrane.
Caution
The sodium salts of arachidonic acid are very sensitive to oxidation and will turn yellow and deteriorate rapidly in air. They are packaged under vacuum in sealed ampules. Once opened the product must be used quickly or transferred into an inert atmosphere (dry argon) as soon as possible.
WGK
WGK 3
Flash Point(F)
235.4 °F
Flash Point(C)
113 °C
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Tony L Walker et al.
Frontiers in behavioral neuroscience, 4 (2010-08-31)
Conditioned inhibition (CI) is a major category of associative learning that occurs when an organism learns that one stimulus predicts the absence of another. In addition to being important in its own right, CI is interesting because its occurrence implies
Joel S Cavallo et al.
Frontiers in behavioral neuroscience, 8, 354-354 (2014-11-07)
Extinction of a conditioned association is typically viewed as the establishment of new learning rather than the erasure of the original memory. However, recent research in the nudibranch, Hermissenda crassicornis (H.c.) demonstrated that extinction training (using repeated light-alone presentations) given
Arachidonic acid as a bioactive molecule.
A R Brash
The Journal of clinical investigation, 107(11), 1339-1345 (2001-06-08)
Andrea Dichlberger et al.
Journal of lipid research, 52(12), 2198-2208 (2011-10-06)
Lipid droplets, also called lipid bodies (LB) in inflammatory cells, are important cytoplasmic organelles. However, little is known about the molecular characteristics and functions of LBs in human mast cells (MC). Here, we have analyzed the genesis and components of
Ambre M Bertholet et al.
Frontiers in physiology, 11, 326-326 (2020-05-01)
Mitochondria convert the chemical energy of metabolic substrates into adenosine triphosphate (ATP) and heat. Although ATP production has become a focal point of research in bioenergetics, mitochondrial thermogenesis is also crucial for energy metabolism. Mitochondria generate heat due to H+
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