506-32-1

Name	Arachidonic acid
CAS	506-32-1
EINECS(EC#)	208-033-4
Molecular Formula	C20H32O2
MDL Number	MFCD00004417
Molecular Weight	304.47
MOL File	506-32-1.mol

Synonyms

20:4, CIS,CIS,CIS-CIS-5,8,11,14-EICOSATETRAENOIC ACID 5,8,11,14-ALL-CIS-EICOSATETRAENOIC ACID 5,8,11,14-EICOSATETRAENOIC ACID 5,8,11,14-EICOSATETRENOIC ACID 5,8,11,14-EICOSATETRENOIC ACID (5 CIS, 8 CIS, 11 CIS, 14 CIS) 5,8,11,14-ICOSATETRAENOIC ACID 5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID ALL CIS-5,8,11,14-EICOSATETRAENOIC ACID ARACHIDONIC ACID ARACHIDONIC ACID, PORCINE LIVER C20:4 (ALL CIS-5,8,11,14) ACID CIS-5,8,11,14-EICOSATETRAENOIC ACID CIS,CIS,CIS,CIS-5,8,11,14-EICOSATETRAENOIC ACID DELTA 5 CIS 8 CIS 11 CIS 14 CIS EICOSATETRAENOIC ACID EICOSA-5Z,8Z,11Z,14Z-TETRAENOIC ACID icosa-5,8,11,14-tetraenoic acid (5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoic acid (all-Z)-5,8,11,14-Eicosatetraenoic acid (all-z)-5,8,11,14-eicosatetraenoicacid 5,8,11,14-Eicosatetraenoic acid, (all-Z)-

Chemical Properties

Appearance	liquid
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.)
Fp	>230 °F
storage temp.	−20°C
solubility	ethanol: ≥10 mg/mL
form	oil
pka	4.75±0.10(Predicted)
color	colorless to light yellow
Water Solubility	PRACTICALLY INSOLUBLE
Usage	An unsaturated omega-6 fatty acid constituent of the phospholipids of cell membranes
Merck	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
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. less more
CAS DataBase Reference	506-32-1(CAS DataBase Reference)
NIST Chemistry Reference	Arachidonic acid(506-32-1)

Safety Data

Risk Statements	R19:May form explosive peroxides. less more
Safety Statements	S24/25:Avoid contact with skin and eyes . less more
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 less more

Raw materials And Preparation Products

Hazard Information

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

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.

Material Safety Data Sheet(MSDS)

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506-32-1

Chemical Properties

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Raw materials And Preparation Products

Raw materials

Preparation Products

Hazard Information

Chemical Properties

Chemical Properties

Definition

General Description

Biological Activity

Biochem/physiol Actions

Safety Profile

Carcinogenicity

Material Safety Data Sheet(MSDS)

Questions And Answer

Description

References

Spectrum Detail

Well-known Reagent Company Product Information

Supplier

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