10931
Arachidonic acid
>95.0% (GC)
동의어(들):
cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid, Eicosa-5Z,8Z,11Z,14Z-tetraenoic acid, Immunocytophyte
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제품정보 (DICE 배송 시 비용 별도)
Linear Formula:
CH3(CH2)4(CH=CHCH2)4CH2CH2CO2H
CAS 번호:
Molecular Weight:
304.47
UNSPSC Code:
12352211
NACRES:
NA.25
PubChem Substance ID:
EC Number:
208-033-4
Beilstein/REAXYS Number:
1713889
MDL number:
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
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
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 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.
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
저장 등급
10 - Combustible liquids
wgk
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)
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)
Lipid sensing by mTOR via de novo synthesis of phosphatidic acid
Menon D, et al.
The Journal of Biological Chemistry, jbc-M116 (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