Arachidonic acid
Arachidonic acid
  • CAS No.:506-32-1
Other grades of this product :

Arachidonic acid Basic information
Description References
Product Name:Arachidonic acid
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
CAS:506-32-1
MF:C20H32O2
MW:304.47
EINECS:208-033-4
Product Categories:Mixed Fatty Acids;Higher Fatty Acids & Higher Alcohols;Unsaturated Higher Fatty Acids;Biochemistry;Polyunsaturated Fatty Acids (PUFAs) and Omega-3 Fatty Acids;AN-AZ;Bioactive Small Molecules;Biochemicals and Reagents;Building Blocks;C13 to C42+;Carbonyl Compounds;Carboxylic Acids;Cell Biology;Cell Signaling and Neuroscience;Industrial/Fine Chemicals;Fatty & Aliphatic Acids, Esters, Alcohols & Derivatives;Arachidonic Acid;Lipids in Cell Signaling;Omega 6 fatty acids and derivatives;Chemical Synthesis;Fatty Acids and conjugates;Fatty Acyls;Lipids;Metabolic Pathways;Metabolomics;Nutrition Research;Organic Building Blocks;Polyunsaturated;Unsaturated Fatty Acids and Derivatives;API intermediate;Fatty Acid Derivatives & Lipids;Glycerols;Arachidonic Acid Cascade;Fatty Acid Metabolism;Functional Foods
Mol File:506-32-1.mol
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/D1.4872(lit.)
Fp >230 °F
storage temp. 2-8°C
solubility ethanol: ≥10 mg/mL
form oil
pka4.75±0.10(Predicted)
color colorless to light yellow
Water Solubility PRACTICALLY INSOLUBLE
Merck 14,765
BRN 1713889
Concentration1 mCi/ml
SolventEthanol under argon
Specific Activity200-240 Ci/mmol
Stability:Light Sensitive, Temperature Sensitive
InChIKeyYZXBAPSDXZZRGB-DOFZRALJSA-N
CAS DataBase Reference506-32-1(CAS DataBase Reference)
NIST Chemistry ReferenceArachidonic acid(506-32-1)
Safety Information
Risk Statements 19
Safety Statements 24/25-19
RIDADR UN1170 - class 3 - PG 2 - Ethanol
WGK Germany 3
RTECS CE6675000
8-10-23
HS Code 29161900
Toxicitydns-mus:mmr 10 mg/L CRNGDP 5,1123,84
MSDS Information
ProviderLanguage
Icosa-5,8,11,14-tetraenoic acidEnglish
SigmaAldrichEnglish
ACROSEnglish
Arachidonic acid Usage And Synthesis
DescriptionArachidonic acid belongs to a kind of polyunsaturated omega-6 fatty acid, which is highly biologically relevant. It is abundantly distributed in brain, muscles and liver. It is the precursor for all prostaglandins, thromboxanes, and leukotrienes. Most cellular arachidonic acid is esterified in the membrane phospholipids. It 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, it 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.
Referenceshttp://www.fitday.com/fitness-articles/nutrition/healthy-eating/what-is-arachidonic-acid.html https://en.wikipedia.org/wiki/Arachidonic_acid https://www.caymanchem.com/product/90010
DescriptionArachidonic acid (AA, sometimes ARA) is a polyunsaturated omega-6 fatty acid 20:4(ω-6). It is the counterpart to the saturated arachidic acid found in peanut oil, (L. arachis – peanut.).
Chemical PropertiesIn 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.
Chemical Propertiesliquid
UsesAn unsaturated omega-6 fatty acid constituent of the phospholipids of cell membranes
UsesArachidonic 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.
Usesarachidonic 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. It is a constituent of vitamin F.
DefinitionChEBI: A long-chain fatty acid that is a C20, polyunsaturated fatty acid having four (Z)-double bonds at positions 5, 8, 11 and 14.
General DescriptionA 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 (cis-5,8,11,14), sometimes referred to as AA or ARA, is a polyunsaturated omega-6 fatty acid. Studies suggests that ARA as well as other fatty acids can serve as biomarkers for cardiovascular disease, and nutritional and metabolic disorders.
Biological ActivityEndogenous free fatty acid released from phospholipids by phospholipase A 2 . Important cellular signaling mediator and precursor of eicosanoids. Metabolized by lipoxygenases, cyclooxygenases and cytochrome P450 monooxygenases.
Biochem/physiol ActionsArachidonic acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .
Safety ProfilePoison by intravenous route.Experimental reproductive effects. Mutation datareported. When heated to decomposition it emits acridsmoke and irritating fumes.
CarcinogenicityIn vitro and in vivo studies indicate that inhibition of arachidonic acid metabolism inhibits the growth of malignant cells, including head and neck squamous cell carcinoma, and implicates arachadonic acid in facilitating the metastasis of these tumor cells. Arachidonic acid reaction with cyclooxygenase and lipoxygenases yield eicosanoids that can mediate prostate cancer proliferation and enhance both tumor vascularization and metastasis. Cytochrome P450 arachidonic acid epoxygenases promote cell proliferation and inhibit apoptosis in endothelial cells.
Arachidonic acid Preparation Products And Raw materials
Raw materialsEthanol-->Hydrochloric acid-->Potassium hydroxide-->ZINC-->Bromide-->METHYL ARACHIDONATE-->ETHANOL-1,1,2,2-D4-AMINE
Preparation ProductsProstaglandin E1-->Prostaglandin E2-->EPA-->2-AG-->trans,trans-2,4-Decadien-1-al

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