5,8,11,14-Eicosatetraenoic acid, (5Z,8Z,11Z,14Z)-
ARA · Arachidonate · Arachidonic · 5,8,11,14-EICOSATETRAENOIC ACID · icosa-5,8,11,14-tetraenoic acid · Arachidonic Acid (peroxide free) · (5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid · 20:4n-6
Identifiers & Physical Properties
| CAS No. | 506-32-1 |
|---|---|
| Molecular formula | C20H32O2 |
| Average molar mass | 304.5 g/mol |
| Monoisotopic mass | 304.24023026 g/mol |
| SMILES | CCCCCC=CCC=CCC=CCC=CCCCC(=O)O |
| InChIKey | YZXBAPSDXZZRGB-UHFFFAOYSA-N |
| PubChem CID | 231 |
| DTXSID | DTXSID50859424 |
Chemical & Physical Properties
| XLogP | 6.3 |
|---|---|
| Topological polar surface area | 37.3 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 14 |
| Heavy atoms | 22 |
| Formal charge | 0 |
| Complexity | 362 |
| 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.) |
| Flash point | >230 °F |
| Storage conditions | 2-8°C |
| Solubility | ethanol: ≥10 mg/mLPRACTICALLY INSOLUBLE |
| Physical state | oil |
| pKa (acidity coefficient) | 4.75±0.10(Predicted) |
| Color | colorless to light yellow |
| Biological source | synthetic |
| 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 applications | food and beverages |
| Cosmetics Ingredients Functions | SKIN CONDITIONINGSKIN 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 |
| SMILES | OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O |
| LogP (partition coefficient) | 6.99 |
| CAS DataBase Reference | 506-32-1(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | 27YG812J1I |
| NIST Chemistry Reference | Arachidonic acid(506-32-1) |
| UNSPSC Code | 85151701 |
| NACRES | NA.77 |
| GHS pictogram | GHS02,GHS07 |
| Signal word | Danger |
| GHS hazard statements | H225-H319 |
| GHS precautionary statements | P210-P233-P240-P241-P242-P305+P351+P338 |
| Risk statements (R) | 19 |
| Safety statements (S) | 24/25-19 |
| UN transport number | UN1170 - class 3 - PG 2 - Ethanol |
| Water hazard class (WGK) | 3 |
| RTECS number | CE6675000 |
| F | 8-10-23 |
| Customs code | 29161900 |
| Storage class | 10 - Combustible liquids |
| Hazard class | Eye Irrit. 2Skin Irrit. 2 |
| Toxicity | dns-mus:mmr 10 mg/L CRNGDP 5,1123,84 |
Safety & Regulations
| Regulatory information | 5,8,11,14-Eicosatetraenoic acid, (5Z,8Z,11Z,14Z)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
|---|---|
| F | 8-10-23 |
| Water hazard class (WGK) | 3 |
| RTECS number | CE6675000 |
| UN transport number | UN1170 - class 3 - PG 2 - Ethanol |
| Customs code | 29161900 |
| Toxicity | dns-mus:mmr 10 mg/L CRNGDP 5,1123,84 |
| Risk statements (R) | 19 |
| Signal word | Danger |
| GHS pictogram | GHS02,GHS07 |
| Safety statements (S) | 24/25-19 |
| Storage class | 10 - Combustible liquids |
| GHS hazard statements | H225-H319 |
| Hazard class | Eye Irrit. 2Skin Irrit. 2 |
| GHS precautionary statements | P210-P233-P240-P241-P242-P305+P351+P338 |
Applications & Uses
Description
Arachidonic 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.
Description
Arachidonic 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.).
Uses
An unsaturated omega-6 fatty acid constituent of the phospholipids of cell membranes
Uses
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. It is a constituent of vitamin F.
Uses
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.
General Description
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 (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.