Basic information
- CAS
506-32-1- Standard SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O- InChIKey
YZXBAPSDXZZRGB-DOFZRALJSA-N- Molecular formula
- C20H32O2
- Average molar mass
- 304.5 g/mol
- Monoisotopic mass
- 304.24023026
Names & identifiers
- Preferred name
- Arachidonic Acid
- IUPAC
- (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid
- English name
- Arachidonic acid
- Molecular formula
- C20H32O2
- Molecular weight
- 304.47
Names & synonyms
Show more names
Database identifiers
- CAS
506-32-1、93444-49-6- PubChem CID
- 444899
- DTXSID
DTXSID4040420- ChEMBL
CHEMBL15594- ChEBI
CHEBI:15843- UNII
- 27YG812J1I
- EC Number
- 208-033-4
- Nikkaji
- J12.228I
Properties
Computed structural properties
- XLogP
- 6.3
- Topological polar surface area
- 37.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 14
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 362
Experimental & physicochemical properties
LogP
6.98
6.98
Physical Description
Liquid; [Merck Index]
Liquid
Collision Cross Section
182.1 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Sample Type: Human bronchoalveolar lavage fluid (BALF); Dataset: Unambiguous Lipids]
178.94 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
182.21 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
183.66 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
179.8 Ų [M+Na]+;181.6 Ų [M-H]-;183 Ų [M-H]-
Physicochemical properties
- Melting point
- -49 °C · -49 °C (lit.)
- Boiling point
- 169 · 169-171 °C/0.15 mmHg (lit.)
- Density
- 0.922 g/mL · 0.922 g/mL at 25 °C (lit.)
- refractive index
- 20 · n20/D 1.4872(lit.)
- Flash point
- 230 °F · >230 °F
- storage temp.
- 2 · 2-8°C
- solubility
- 10 mg/mL · ethanol: ≥10 mg/mL
- form
- oil
- pka
- 4.75 · 4.75±0.10(Predicted)
- color
- colorless to light yellow
- biological source
- synthetic
- Water Solubility
- PRACTICALLY INSOLUBLE
- Merck
- 14 · 14,765
- BRN
- 1713889 · 1713889
- Concentration
- 1 mCi/ml · 1 mCi/ml
- Solvent
- Ethanol under argon
- Specific Activity
- 200 · 200-240 Ci/mmol
- Stability
- Light Sensitive, Temperature Sensitive
- Major Application
- 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
- 6.99 · 6.99
- CAS DataBase Reference
- 506 · 506-32-1(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 27 YG812J1I · 27YG812J1I
- NIST Chemistry Reference
- Arachidonic acid(506-32-1)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Danger
- Hazard statements
- 225 · H225-H319
- Precautionary statements
- 210 · P210-P233-P240-P241-P242-P305+P351+P338
- Risk Statements
- 19 · 19
- Safety Statements
- 24 · 24/25-19
- RIDADR
- 1170 · UN1170 - class 3 - PG 2 - Ethanol
- WGK Germany
- 3 · 3
- RTECS
- 6675000 · CE6675000
- F
- 8 · 8-10-23
- HS Code
- 29161900 · 29161900
- Storage Class
- 10 · 10 - Combustible liquids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2
- Toxicity
- 10 mg/L · dns-mus:mmr 10 mg/L CRNGDP 5,1123,84
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 10.3% (4 of 39) of reports.
Warning
H302 (84.6%): Harmful if swallowed [Warning Acute toxicity, oral];H312 (82.1%): Harmful in contact with skin [Warning Acute toxicity, dermal];H315 (89.7%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (89.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H332 (79.5%): Harmful if inhaled [Warning Acute toxicity, inhalation];H335 (84.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 4 of 39 reports by companies.;There are 5 notifications provided by 35 of 39 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Regulatory Information
Chemical: 5,8,11,14-Eicosatetraenoic acid, (all-Z)-
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.
Toxicology
Toxicity Summary
The safety of this ingredient has not been documented and substantiated for cosmetic product use. The CIR Expert Panel cannot conclude whether Arachidonic Acid is safe for use in cosmetic products until such time that the appropriate safety data have been obtained and evaluated.
Ingredients for which the data are insufficient and their use in cosmetics is not supported
Regulatory information
Regulatory Information
Chemical: 5,8,11,14-Eicosatetraenoic acid, (all-Z)-
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.
Safety data
- F
- 8-10-23
- wgk
- 3
- rtecs
- CE6675000
- ridadr
- UN1170 - class 3 - PG 2 - Ethanol
- hs_code
- 29161900
- Toxicity
- dns-mus:mmr 10 mg/L CRNGDP 5,1123,84
- risk_code
- 19
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07
- safety_code
- 24/25-19
- Storage Class
- 10 - Combustible liquids
- Hazard statements
- H225-H319
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2
- Precautionary statements
- P210-P233-P240-P241-P242-P305+P351+P338
Chemistry & industry
Pharmacology
Metabolite Pathways
Acetaminophen Action Pathway;Acetylsalicylic Acid Action Pathway;alpha-Linolenic acid metabolism;Antipyrine Action Pathway;Antrafenine Action Pathway;Arachidonic Acid Metabolism;Bromfenac Action Pathway;Carprofen Action Pathway;Celecoxib Action Pathway;Diclofenac Action Pathway;Total 43 pathways, visit the HMDB page for details
Uses & manufacturing
Uses
CIR ingredient: Arachidonic Acid
Essential fatty acid for animals and humans; Used as a nutrient and for the treatment of eczema in dogs and swine; [Merck Index]
Applications
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.
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.).
UsesAn unsaturated omega-6 fatty acid constituent of the phospholipids of cell membranes
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.
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.
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Additional notes
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.
Related reactions
Compound notes
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