TS Final Answer: This product is a neat or pure liquid that has a melting point of −49 °C. This material is soluble in ethanol, DMSO, or dimethyl formamide at 100 mg/ml, and in chloroform or methanol at 50 mg/ml. Additional information may be accessed in the product datasheet for item A3555, available at the link below. This product is an identical compound but is tested for use in cell culture.
https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/239/399/a3555pis.pdf
10931
Arachidonic acid
>95.0% (GC)
Synonym(s):
cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid, Eicosa-5Z,8Z,11Z,14Z-tetraenoic acid, Immunocytophyte
Sign Into View Organizational & Contract Pricing
Select a Size
250 MG
$190.00
1 G
$476.00
All Photos(1)
Select a Size
Change View
250 MG
$190.00
1 G
$476.00
About This Item
Linear Formula:
CH3(CH2)4(CH=CHCH2)4CH2CH2CO2H
CAS Number:
Molecular Weight:
304.47
Beilstein/REAXYS Number:
1713889
EC Number:
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.25
Recommended Products
biological source
fungus
Quality Level
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
lipid type
omega FAs
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[1]
- as a polyunsaturated fatty acid supplement to the reconstituted synthetic bile (RSB) in drug resistance analysis[2]
- for the activation of mechanistic target of rapamycin 1 (mTOR1) and mTOR2[3]
Biochem/physiol Actions
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.
Arachidonic acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2
Storage Class
10 - Combustible liquids
wgk_germany
WGK 3
flash_point_f
235.4 °F - closed cup
flash_point_c
113 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, multi-purpose combination respirator cartridge (US)
Choose from one of the most recent versions:
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
Customers Also Viewed
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)
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
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)
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
-
IS THIS IN A SOLID FORM? HOW CAN THIS BE DILUTED
1 answer-
Helpful?
-
-
What is the solubility of item 10931, Arachidonic acid?
1 answer-
Arachidonic acid is almost insoluble in water; it is soluble in ethanol, ether, acetone. The exact concentrations at which the material can be solubilized has not been determined.
Helpful?
-
-
Is this supplied in a bottle with a septa such that the headspace can be flushed with Nitrogen?
1 answer-
This material is packaged in a glass bottle with a screw-type cap. It does not include a septa.
Helpful?
-
Active Filters
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
