Arachidonic Acid

HCID 444899

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

arachidonic acid506-32-1(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid(all-Z)-5,8,11,14-Eicosatetraenoic acidcis-5,8,11,14-Eicosatetraenoic acid5Z,8Z,11Z,14Z-eicosatetraenoic acid5,8,11,14-Eicosatetraenoic acid, (all-Z)-all-cis-5,8,11,14-eicosatetraenoic acid27YG812J1I(5Z,8Z,11Z,14Z)-Icosatetraenoic acidC20:4DTXSID4040420
Show more names
ARAArachidonateArachidonic5,8,11,14-EICOSATETRAENOIC ACIDicosa-5,8,11,14-tetraenoic acidArachidonic Acid (peroxide free)20:4n-6Single-Use Arachidonic Acid (peroxide free)
CHEBI:15843Arachidonate, SodiumRefChem:5560Fatty Acid 20:4 n-6DTXCID2020420All-cis-icosa-5,8,11,14-tetraenoic acid208-033-4Immunocytophyte

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

Experimental & physicochemical properties

LogP · 2 items

6.98

6.98

Boiling Point170
Melting Point-49.5
Vapor Pressure0.00000015 [mmHg]
Physical Description · 2 items

Liquid; [Merck Index]

Liquid

Kovats Retention Index2324.3

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

Safety & regulation

GHS classification

GHS Classification · 6 items

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 · 2 items

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.

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards SummaryMay form explosive peroxides; May cause irritation; Targets the female reproductive system; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (84.6%);Acute Tox. 4 (82.1%);Skin Irrit. 2 (89.7%);Eye Irrit. 2 (89.7%);Acute Tox. 4 (79.5%);STOT SE 3 (84.6%)

Toxicology

Toxicity Summary · 2 items

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 · 2 items

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

Chemistry & industry

Pharmacology

Metabolism/MetabolitesArachidonic acid has known human metabolites that include 5,6-EET, 15-HETE, 8,9-EET, 14,15-EET, 11,12-EET, 13-HETE, 20-HETE, 11-HETE, 10-HETE, 18-HETE, 9-HETE, 8-HETE, 16-HETE, 19-HETE, 7-HETE, 12-HETE, 5-HETE, and 17-HETE.
Tissue LocationsAdipose Tissue;Epidermis;Fibroblasts;Intestine;Kidney;Liver;Lung;Neuron;Pancreas;Placenta;Platelet;Prostate;Skeletal Muscle;Spleen;Testis;Thyroid Gland
Cellular LocationsCytoplasm;Endoplasmic reticulum;Extracellular;Membrane
Metabolite Pathways · 1 item

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 · 2 items

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]

Use ClassificationCosmetics -> Emollient
Applications · 6 items

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.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
爱斯特(成都)生物制药股份有限公司+86-28-85122536 85324413 · [email protected]

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

42 records

Compound notes

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