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Arachidonic acid belongs to a kind of polyunsaturated omega-6 fatty acid, which is highly biologically relevant.
Arachidonic acid is abundantly distributed in brain, muscles and liver.
Arachidonic acid is the precursor for all prostaglandins, thromboxanes, and leukotrienes.
CAS: 506-32-1
MF: C20H32O2
MW: 304.47
EINECS: 208-033-4
Synonyms
(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoic acid;(all-Z)-5,8,11,14-Eicosatetraenoic acid;(all-z)-5,8,11,14-eicosatetraenoicacid;5,8,11,14-Eicosatetraenoic acid, (all-Z)-;Arachidonate;5,8,11,14-ALL-CIS-EICOSATETRAENOIC ACID;5,8,11,14-EICOSATETRAENOIC ACID;5,8,11,14-EICOSATETRENOIC ACID
Most cellular Arachidonic acid is esterified in the membrane phospholipids.
Arachidonic acid is an important second messenger of cellular signalling participating in the regulation of signaling enzymes including PLC-γ, PLC-δ, and PKC-α, -β, and -γ isoforms.
In addition, Arachidonic acid acts as key inflammatory intermediate as well as avasodilator.
Generally, the body can synthesize the arachidonic acid through linoleic acid.
However, upon linoleic acid deficiency, Arachidonic acid is necessary to supplement arachidonic acid from the diets.
Food sources of Arachidonic acid include meat, eggs and some fishes.
Alternatively, we can also have arachidonic acid supplements.
Arachidonic acid is a polyunsaturated omega-6 fatty acid 20:4(ω-6).
Arachidonic acid is the counterpart to the saturated arachidic acid found in peanut oil.
A long-chain fatty acid that is a C20, polyunsaturated fatty acid having four (Z)-double bonds at positions 5, 8, 11 and 14.
A Certified Spiking Solution suitable for use in mass spectrometry-based fatty acid testing applications such as assessment of cardiovascular disease risk and fatty acid deficiency, and detection and quantification of arachidonic acid in nutraceuticals and dietary supplements.
Arachidonic acid, sometimes referred to as AA or ARA, is a polyunsaturated omega-6 fatty acid.
Studies suggests that Arachidonic acid as well as other fatty acids can serve as biomarkers for cardiovascular disease, and nutritional and metabolic disorders.
Arachidonic acid is a polyunsaturated omega−6 fatty acid 20:4(ω−6), or 20:4(5,8,11,14).
Arachidonic acid is a precursor in the formation of leukotrienes, prostaglandins, and thromboxanes.
Together with omega−3 fatty acids and other omega−6 fatty acids, Arachidonic acid provides energy for body functions, contributes to cell membrane structure, and participates in the synthesis of eicosanoids, which have numerous roles in physiology as signaling molecules.
Arachidonic acid was named after the similarly structured Arachidic acid, a constituent of peanut oil whose name in turn derives from the ancient Greek neologism arachis 'peanut'.
Peanut oil does not contain any arachidonic acid, itself.
Arachidonic acid is the name of the derived carboxylate anion (conjugate base of the acid), salts, and some esters.
Arachidonic acid is a polyunsaturated fatty acid that plays a crucial role in cellular signaling and is a key component of phospholipids in cell membranes.
Arachidonic acid is classified as an omega-6 fatty acid, characterized by a long carbon chain consisting of 20 carbon atoms and four double bonds, which are positioned at specific intervals along the chain.
This structure allows Arachidonic acid to be highly flexible and reactive, making it a precursor for various bioactive lipids, including prostaglandins, thromboxanes, and leukotrienes, which are involved in inflammatory responses and other physiological processes.
Arachidonic acid is primarily obtained from dietary sources, particularly animal products, and can also be synthesized in the body from linoleic acid.
Arachidonic acid's presence is vital for maintaining cellular integrity and function, and it is implicated in numerous health conditions, including cardiovascular diseases and inflammatory disorders.
Due to its biological significance, arachidonic acid is often studied in the context of nutrition, biochemistry, and pharmacology.
Arachidonic acid Chemical Properties
Melting point: -49 °C (lit.)
Boiling point: 169-171 °C/0.15 mmHg (lit.)
density: 0.922 g/mL at 25 °C (lit.)
refractive index: n20/D 1.4872(lit.)
Fp: >230 °F
storage temp.: 2-8°C
solubility ethanol: ≥10 mg/mL
form: oil
pka: 4.75±0.10(Predicted)
color: colorless to light yellow
biological source: synthetic
Water Solubility: PRACTICALLY INSOLUBLE
Merck: 14,765
BRN: 1713889
Concentration: 1 mCi/ml
Solvent Ethanol under argon
Specific Activity: 200-240 Ci/mmol
Stability: Light Sensitive, Temperature Sensitive
Major Application: food and beverages
Cosmetics Ingredients Functions: SKIN CONDITIONING
SKIN CONDITIONING - EMOLLIENT
Cosmetic Ingredient Review (CIR): Arachidonic acid (506-32-1)
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-
InChIKey: YZXBAPSDXZZRGB-DOFZRALJSA-N
LogP: 6.99
CAS DataBase Reference: 506-32-1(CAS DataBase Reference)
NIST Chemistry Reference: Arachidonic acid(506-32-1)
In chemical structure, Arachidonic acid is a carboxylic acid with a 20-carbon chain and four cis-double bonds; the first double bond is located at the sixth carbon from the omega end.
Some chemistry sources define 'arachidonic acid' to designate any of the eicosatetraenoic acids.
However, almost all writings in biology, medicine and nutrition limit the term to all-cis-5,8,11,14- eicosatetraenoic acid.
Chemistry
In chemical structure, Arachidonic acid is a carboxylic acid with a 20-carbon chain and four cis-double bonds; the first double bond is located at the sixth carbon from the omega end.
Some chemistry sources define 'arachidonic acid' to designate any of the eicosatetraenoic acids.
However, almost all writings in biology, medicine, and nutrition limit the term to all cis-5,8,11,14-eicosatetraenoic acid.
Biology
Arachidonic acid is a polyunsaturated fatty acid present in the phospholipids (especially phosphatidylethanolamine, phosphatidylcholine, and phosphatidylinositides) of membranes of the body's cells, and is abundant in the brain, muscles, and liver.
Skeletal muscle is an especially active site of arachidonic acid retention, accounting for roughly 10–20% of the phospholipid fatty acid content typically.
In addition to being involved in cellular signaling as a lipid second messenger involved in the regulation of signaling enzymes, such as PLC-γ, PLC-δ, and PKC-α, -β, and -γ isoforms, arachidonic acid is a key inflammatory intermediate and can also act as a vasodilator.
(Note separate synthetic pathways, as described in section below.)
Uses
An unsaturated omega-6 fatty acid constituent of the phospholipids of cell membranes.
arachidonic acid is an ingredient with skin-smoothing, emollient, and healing properties.
Arachidonic acid is an omega-6 essential fatty acid naturally occurring in the skin and considered critical for appropriate skin metabolism.
Arachidonic acid is a constituent of vitamin F.
Arachidonic Acid is an essential fatty acid and a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes.
Arachidonic Acid occurs in liver, brain, glandular organs, and depot fats of animals, in small amounts in human depot fats, and Arachidonic Acid is also a constituent of animal phosphatides.
