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Merck

181198

Arachidonic Acid

≥99% (TLC and GC), oil, membrane phospholipid component, Calbiochem®

Synonym(s):

Arachidonic Acid, cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic Acid, 20:4

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About This Item

Empirical Formula (Hill Notation):
C20H32O2
CAS Number:
506-32-1
Molecular Weight:
304.47
UNSPSC Code:
12352211
NACRES:
NA.77
MDL number:
MFCD00004417

Product Name

Arachidonic Acid, Precursor for prostaglandins, prostacyclin, and thromboxane.

SMILES string

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

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-CGRWFSSPSA-N

description

Merck USA index - 14, 765

assay

≥99% (TLC and GC)

form

oil

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

colorless

solubility

ethanol: 5 mg/mL

shipped in

dry ice

storage temp.

−70°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Cell permeable: no
Primary Target
Ras-GAP
Product does not compete with ATP.
Reversible: no

Disclaimer

Toxicity: Harmful (C)

General description

A cis-polyunsaturated fatty acid found in the plasma membrane. Major component of membrane phospholipids. Following its release by cellular phospholipases, it is enzymatically converted to a variety of inflammatory and vasoactive metabolites, such as prostaglandins (via the cyclooxygenase pathway), leukotrienes (via the lipoxygenase pathway), and epoxides (via the cytochrome P450 pathway). Binds to G-protein α-subunits in a covalent, posttranslational manner. Inhibits Ras-GAP. Stimulates the synthesis of nitric oxide by platelets.
Precursor for prostaglandins, prostacyclin, and thromboxane. Binds to G-protein α-subunits in a covalent, post-translational manner. Inhibits Ras-GAP. Stimulates the synthesis of nitric oxide by platelets. Modulates nitric oxide production by prostaglandin synthesis via the cyclooxygenase pathway.

Other Notes

Hallak, H., et al. 1994. J. Biol. Chem. 269, 4713.
Khurana, G., and Bennett, M.R. 1993. Br. J. Pharmacol. 109, 480.
Han, J.-W., et al. 1991. Science252, 576.
Radomski, M.W., et al. 1990. Br. J. Pharmacol. 101, 325.
Neddleman P., et al. 1986. Annu. Rev. Biochem.55, 69.

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 1 month at -20°C.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H315,H319

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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