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About This Item

Empirical Formula (Hill Notation):
C20H31O2 · Na
CAS Number:
6610-25-9
Molecular Weight:
326.45
MDL number:
MFCD00065458
UNSPSC Code:
12352200
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Assay

≥99% (TLC and GC)

Quality Level

100

form

crystalline solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

white

solubility

water: 5 mg/mL

storage temp.

−20°C

InChI

1S/C20H32O2.Na/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);/q;+1/p-1/b7-6-,10-9-,13-12-,16-15-;

InChI key

DDMGAAYEUNWXSI-XVSDJDOKSA-M

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.

Biochem/physiol Actions

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

Packaging

Packaged under inert gas

Warning

Toxicity: Harmful (C)

Reconstitution

Unstable in solution; reconstitute just prior to use.

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.

Legal Information

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

Storage Class Code

11 - Combustible Solids

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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