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23401

Arachidonic acid

analytical standard

Synonym(s):

cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid, Eicosa-5Z,8Z,11Z,14Z-tetraenoic acid, Immunocytophyte

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Size/SKUAvailabilityPrice
50 mg

Available to ship TODAYfromMILWAUKEE

$250.00

About This Item

Linear Formula:
CH3(CH2)4(CH=CHCH2)4CH2CH2CO2H
CAS Number:
Molecular Weight:
304.47
UNSPSC Code:
85151701
NACRES:
NA.24
PubChem Substance ID:
EC Number:
208-033-4
Beilstein/REAXYS Number:
1713889
MDL number:

$250.00


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biological source

synthetic

Quality Segment

grade

analytical standard

assay

≥97.0% (GC)

form

liquid

shelf life

limited shelf life, expiry date on the label

refractive index

n20/D 1.4872 (lit.)

bp

169-171 °C/0.15 mmHg (lit.)

mp

−49 °C (lit.)

density

0.922 g/mL at 25 °C (lit.)

application(s)

food and beverages

format

neat

functional group

carboxylic acid

storage temp.

2-8°C

SMILES string

OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O

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-

InChI key

YZXBAPSDXZZRGB-DOFZRALJSA-N

Biochem/physiol Actions

Arachidonic acid (AA) is an unsaturated ω6 fatty acid constituent of the phospholipids of cell membranes. Phospholipase A2 releases AA from the membrane phospholipids in response to inflammation. AA is subsequently metabolized to prostaglandins and thromboxanes by at least two cyclooxygenase (COX) isoforms, to leukotrienes and lipoxins by lipoxygenases, and to epoxyeicosatrienoic acids via cytochrome p450-catalyzed metabolism. AA and its metabolites play important roles in a variety of biological processes, including signal transduction, smooth muscle contraction, chemotaxis, cell proliferation and differentiation, and apoptosis. AA has been demonstrated to bind to the a subunit of G protein and inhibit the activity of Ras GTPase-activating proteins (GAPs). Cellular uptake of AA is energy dependent and involves protein-facilitated transport across the plasma membrane.
Arachidonic acid and its metabolites play important roles in a variety of biological processes, including signal transduction, smooth muscle contraction, chemotaxis, cell proliferation and differentiation, and apoptosis.
Arachidonic acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .

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This Item
10931A3611181198
description

analytical standard

description

>95.0% (GC)

description

from non-animal source, ≥98.5% (GC)

description

Precursor for prostaglandins, prostacyclin, and thromboxane.

grade

analytical standard

grade

-

grade

-

grade

-

format

neat

format

-

format

-

format

-

density

0.922 g/mL at 25 °C (lit.)

density

0.922 g/mL at 25 °C (lit.)

density

0.922 g/mL at 25 °C (lit.)

density

-

mp

−49 °C (lit.)

mp

−49 °C (lit.)

mp

−49 °C (lit.)

mp

-

shelf life

limited shelf life, expiry date on the label

shelf life

-

shelf life

-

shelf life

-

assay

≥97.0% (GC)

assay

>95.0% (GC)

assay

≥98.5% (GC)

assay

≥99% (TLC and GC)


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Pictograms

Exclamation mark

Signal Word

Warning

Hazard Codes

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

10 - Combustible liquids

WGK

WGK 3

Flash Point (°F)

235.4 °F - closed cup

Flash Point (°C)

113 °C - closed cup



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