A3611
Arachidonic acid
from non-animal source, ≥98.5% (GC)
Synonym(s):
cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid, Eicosa-5Z,8Z,11Z,14Z-tetraenoic acid, Immunocytophyte
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All Photos(2)
About This Item
Linear Formula:
CH3(CH2)4(CH=CHCH2)4CH2CH2CO2H
CAS Number:
Molecular Weight:
304.47
Beilstein:
1713889
EC Number:
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.25
Recommended Products
biological source
non-animal source
Quality Level
Assay
≥98.5% (GC)
form
liquid
refractive index
n20/D 1.4872 (lit.)
bp
169-171 °C/0.15 mmHg (lit.)
mp
−49 °C (lit.)
density
0.922 g/mL at 25 °C (lit.)
functional group
carboxylic acid
lipid type
omega FAs
shipped in
dry ice
storage temp.
−20°C
SMILES string
OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O
InChI
1S/C20H32O2/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)/b7-6-,10-9-,13-12-,16-15-
InChI key
YZXBAPSDXZZRGB-DOFZRALJSA-N
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Application
<ul>
<li><strong>Molecular Mechanisms Associated with the Inhibitory Role of Long Chain n-3 PUFA in Colorectal Cancer:</strong> This study discusses the effects of long-chain polyunsaturated fatty acids, like arachidonic acid, on colorectal cancer mechanisms. The research focuses on the anti-inflammatory and cancer inhibitory roles through the modulation of lipid metabolism and signal transduction pathways (Jayathilake et al., 2024).</li>
<li><strong>Zhilining Formula alleviates DSS-induced colitis through suppressing inflammation and gut barrier dysfunction via the AHR/NF-Bp65 axis:</strong> This article presents arachidonic acid′s role in the suppression of inflammation and restoration of gut barrier function, crucial for understanding inflammatory diseases and developing therapeutic strategies (Zhou et al., 2024).</li>
<li><strong>5,6-diHETE lactone (EPA-L) mediates hypertensive microvascular dilation by activating the endothelial GPR-PLC-IP(3) signaling pathway:</strong> Explores the cardiovascular implications of arachidonic acid metabolites, specifically their role in microvascular responses, which could influence hypertension treatment strategies (Asulin et al., 2024).</li>
</ul>
<li><strong>Molecular Mechanisms Associated with the Inhibitory Role of Long Chain n-3 PUFA in Colorectal Cancer:</strong> This study discusses the effects of long-chain polyunsaturated fatty acids, like arachidonic acid, on colorectal cancer mechanisms. The research focuses on the anti-inflammatory and cancer inhibitory roles through the modulation of lipid metabolism and signal transduction pathways (Jayathilake et al., 2024).</li>
<li><strong>Zhilining Formula alleviates DSS-induced colitis through suppressing inflammation and gut barrier dysfunction via the AHR/NF-Bp65 axis:</strong> This article presents arachidonic acid′s role in the suppression of inflammation and restoration of gut barrier function, crucial for understanding inflammatory diseases and developing therapeutic strategies (Zhou et al., 2024).</li>
<li><strong>5,6-diHETE lactone (EPA-L) mediates hypertensive microvascular dilation by activating the endothelial GPR-PLC-IP(3) signaling pathway:</strong> Explores the cardiovascular implications of arachidonic acid metabolites, specifically their role in microvascular responses, which could influence hypertension treatment strategies (Asulin et al., 2024).</li>
</ul>
Biochem/physiol Actions
Arachidonic acid (AA) is an unsaturated ω6 fatty acid constituent of the phospholipids of cell membranes. Phospholipase A2 releases AA from the membrane phospholipids in response to inflammation. AA is subsequently metabolized 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. 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. AA has been demonstrated to bind to the a subunit of G protein and inhibit the activity of Ras GTPase-activating proteins (GAPs). Cellular uptake of AA is energy dependent and involves protein-facilitated transport across the plasma membrane.
Arachidonic acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .
Packaging
Sealed ampule
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2
Storage Class Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
235.4 °F - closed cup
Flash Point(C)
113 °C - closed cup
Certificates of Analysis (COA)
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Abdulaziz M S Alsaad et al.
Drug metabolism reviews, 45(2), 173-195 (2013-04-23)
A plethora of studies have demonstrated the expression of cytochrome P450 (CYP) and soluble epoxide hydrolase (sEH) enzymes in the heart and other cardiovascular tissues. In addition, the expression of these enzymes is altered during several cardiovascular diseases (CVDs), including
Alma M Astudillo et al.
Biochimica et biophysica acta, 1821(2), 249-256 (2011-12-14)
The development of mass spectrometry-based techniques is opening new insights into the understanding of arachidonic acid (AA) metabolism. AA incorporation, remodeling and release are collectively controlled by acyltransferases, phospholipases and transacylases that exquisitely regulate the distribution of AA between the
Tamás Decsi et al.
The American journal of clinical nutrition, 98(2), 543S-548S (2013-07-05)
We summarize data on the potential interaction of trans isomeric fatty acids [trans fatty acids (TFAs)] with the availability of long-chain polyunsaturated fatty acids (LC-PUFAs) in the perinatal period. Today, TFA intakes in pregnant and lactating women can be estimated
Peter Willatts et al.
The American journal of clinical nutrition, 98(2), 536S-542S (2013-06-21)
Evidence is accumulating that a dietary supply of long-chain polyunsaturated fatty acids (LC-PUFAs) enhances the development of attention and efficient information processing in infants. However, it is uncertain whether LC-PUFAs in infancy influence cognitive development in later childhood. The objective
Jesmond Dalli et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 27(7), 2573-2583 (2013-03-19)
Maresins are produced by macrophages from docosahexaenoic acid (DHA) and exert potent proresolving and tissue homeostatic actions. Maresin 1 (MaR1; 7R,14S-dihydroxy-docosa-4Z,8E,10E,12Z,16Z,19Z-hexaenoic acid) is the first identified maresin. Here, we investigate formation, stereochemistry, and precursor role of 13,14-epoxy-docosahexaenoic acid, an intermediate
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