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.)

Flash point:

>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

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

InChIKey

YZXBAPSDXZZRGB-DOFZRALJSA-N

LogP

6.99

CAS DataBase Reference

506-32-1(CAS DataBase Reference)

NIST Chemistry Reference

Arachidonic 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

F 

8-10-23

HS Code 

29161900

Toxicity

dns-mus:mmr 10 mg/L CRNGDP 5,1123,84

MSDS

• Language:English Provider:Icosa-5,8,11,14-tetraenoic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Arachidonic acid Usage And Synthesis

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.

References

http://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

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.).

Chemical Properties

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.

Chemical Properties

liquid

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.

Definition

ChEBI: 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 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.

Biological Activity

Endogenous 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 Actions

Arachidonic acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .

Safety Profile

Poison by intravenous route.Experimental reproductive effects. Mutation datareported. When heated to decomposition it emits acridsmoke and irritating fumes.

Carcinogenicity

In 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.

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