ChemicalBook CAS DataBase List 6610-25-9

6610-25-9

Name	ARACHIDONIC ACID SODIUM SALT
CAS	6610-25-9
Molecular Formula	C20H31NaO2
MDL Number	MFCD00065458
Molecular Weight	326.45
MOL File	6610-25-9.mol

Synonyms

SODIUM ARACHIDONATE Arachidonicacidsodiumsal ARACHIDONIC ACID SODIUM SALT 5Z,8Z,11Z,14Z-EICOSATETRAENOIC 5,8,11,14-EICOSATETRAENOIC ACID Arachidonic acid sodium salt from EICOSA-5Z,8Z,11Z,14Z-TETRAENOIC ACID ARACHIDONIC ACID SODIUM FROM PORCINELIVE R 5,8,11,14-EICOSATETRAENOIC ACID SODIUM SALT ARACHIDONIC ACID, PORCINE LIVER, SODIUM SALT 11,14-eicosatetraenoicacid,sodiumsalt,(all-z)-8 5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID, SODIUM SALT ARACHIDONIC ACID SODIUM SALT, FROM PORCINE LIVER sodium:(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate Arachidonic acid sodium salt from Mortierella alpina CIS,CIS,CIS,CIS-5,8,11, 14-EICOSATETRAENOIC ACID, NA (5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoic acid sodium salt CIS,CIS,CIS,CIS-5,8,11,14-EICOSATETRAENOIC ACID SODIUM SALT Arachidonic acid sodium salt from Mortierella alpina >=98.5% (GC) Arachidonic acid sodium salt,5,8,11,14-Eicosatetraenoic acid, Eicosa-5Z,8Z,11Z,14Z-tetraenoic acid, Sodium arachidonate, cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid sodium salt, 20:4

Chemical Properties

Fp	113℃
storage temp.	-20°C
solubility	methanol: 50 mg/mL, clear, colorless to faintly yellow
form	waxy solid
color	white to off-white
biological source	Mortierella alpina
Water Solubility	water: 5mg/mL
InChIKey	DDMGAAYEUNWXSI-XVSDJDOKSA-M
SMILES	C(/C/C=C\CCCC([O-])=O)=C/C/C=C\C/C=C\CCCCC.[Na+]

Safety Data

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H315-H319-H335
Precautionary statements	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501
Risk Statements	19 less more
WGK Germany	3
RTECS	JX3874000

Hazard Information

Uses

Arachidonic acid is used in assays to measure activity of oxidizing enzymes, such as cyclooxygenase, as well as in assays to determine platelet inhibition in whole blood. Arachidonic acid has been demonstrated to bind to the a subunit of G protein and inhibit the activity of Ras GTPase-activating proteins (GAPs), to have a role in the development and progression of prostate cancer, and to enhance formation of lipid bodies in human mast cells.

General Description

Arachidonic acid (AA) is a polyunsaturated ? fatty acid constituent of the phospholipids of cell membranes. Structurally, it is a 20-carbon chain that contains four cis double bonds, which allow the free acid form of AA to be an insoluble oil; this can be converted to the water-soluble sodium salt form within the normal physiological pH range. Arachidonic acid is metabolized by multiple enzymes to yield various metabolites; 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.

Biochem/physiol Actions

Released arachidonic acid (AA) reacts with molecular oxygen nonenzymatically, through oxidative stress, and enzymatically through the action of oxygenase enzymes. AA is oxidized 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. Cellular uptake of arachidonic acid is energy dependent and involves protein-facilitated transport across the plasma membrane.

in vivo

Arachidonic acid sodium salt can be used to induce paw edema models^[2].

Induction of Paw Edema Model^[2]

Background

Principle: Injecting arachidonic acid into the hind paws of rats can induce rapid and sustained inflammatory responses.

Specific Modeling Methods

Rat: Lewis ? male ?
Administration: 0.5% ? s.c. ? single dose

Note

A single subcutaneous injection of 0.10 mL of arachidonic acid (dissolved in 0.2 M carbonate buffer with a pH value of 8.43-8.56) was administered into the right hind paw of male Lewis rats weighing 144-241 grams.

Modeling Indicators

Appearance Monitoring: Significant edema became apparent within 5 minutes, and the reaction reached its peak at 1 hour after injection.

Correlated Product(s): /

Opposite Product(s): phenidone (HY-W010144); SK&F86002 (HY-12511)

Animal Model:	Male Lew rats (4-week-old) induced arthritis^[1]
Dosage:	0.07%, 0.15% or 0.32% in diet (w/w)
Administration:	4 weeks
Result:	The Arachidonic acid content of phospholipids in the paw was significantly elevated in a dose-dependent manner.

IC 50

Human Endogenous Metabolite

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