MilliporeSigma
All Photos(1)

10931

Sigma-Aldrich

Arachidonic acid

>95.0% (GC)

Synonym(s):
Immunocytophyte, Eicosa-5Z,8Z,11Z,14Z-tetraenoic acid, cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid
Linear Formula:
CH3(CH2)4(CH=CHCH2)4CH2CH2CO2H
CAS Number:
Molecular Weight:
304.47
Beilstein:
1713889
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25

biological source

fungus

assay

>95.0% (GC)

form

liquid

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.)

functional group

carboxylic acid

shipped in

dry ice

storage temp.

−20°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

Looking for similar products? Visit Product Comparison Guide

Application

Arachidonic acid has been used:
  • in calibration curve generation in Raman spectroscopy and atomic force microscopy (AFM) in normal and breast cancer samples
  • as a polyunsaturated fatty acid supplement to the reconstituted synthetic bile (RSB) in drug resistance analysis
  • for the activation of mechanistic target of rapamycin 1 (mTOR1) and mTOR2

Packaging

1 g in glass bottle
250 mg in glass bottle

Biochem/physiol Actions

Arachidonic acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .
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.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Lipid sensing by mTOR via de novo synthesis of phosphatidic acid
Menon D, et al.
The Journal of Biological Chemistry, jbc-M116 (2017)
Lipid components of bile increase the protective effect of conjugated bile salts against antifungal drugs
Hsieh SH and Brock M
Fungal Biology, 121(11), 929-938 (2017)
Angiogenesis-a crucial step in breast cancer growth, progression and dissemination by Raman imaging
Kopec M and Abramczyk H
Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 198, 338-345 (2018)
Shih-Hung Hsieh et al.
Fungal biology, 121(11), 929-938 (2017-10-17)
Fungi and bacteria can persist in the human gall bladder. Previous studies have shown that bile protects Candida albicans in this cryptic host niche from antifungals, providing a reservoir for intestinal re-colonization after discontinuation of antifungal therapy. Bile and conjugated
Yanhong Hao et al.
iScience, 24(9), 102974-102974 (2021-08-17)
Asymptomatic infection is a big challenge in curbing the spread of COVID-19. However, its identification and pathogenesis elucidation remain issues. Here, by performing comprehensive lipidomic characterization of serum samples from 89 asymptomatic COVID-19 patients and 178 healthy controls, we screened

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service