Merck
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A3611

Sigma-Aldrich

Arachidonic acid

from non-animal source, ≥98.5% (GC)

Sinónimos:
Immunocytophyte, Eicosa-5Z,8Z,11Z,14Z-tetraenoic acid, cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid
Fórmula lineal:
CH3(CH2)4(CH=CHCH2)4CH2CH2CO2H
Número de CAS:
Peso molecular:
304.47
Beilstein:
1713889
Número de EC:
Número MDL:
ID de la sustancia en PubChem:
NACRES:
NA.25

Nivel de calidad

300

origen biológico

non-animal source

ensayo

≥98.5% (GC)

formulario

liquid

índice de refracción

n20/D 1.4872 (lit.)

bp

169-171 °C/0.15 mmHg (lit.)

mp

−49 °C (lit.)

densidad

0.922 g/mL at 25 °C (lit.)

grupo funcional

carboxylic acid

enviado en

dry ice

temp. de almacenamiento

−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

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Categorías relacionadas

Envase

10, 100 mg in ampule
1 g in ampule
Sealed ampule

Acciones bioquímicas o fisiológicas

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.

Código de clase de almacenamiento

10 - Combustible liquids

WGK

WGK 3

Punto de inflamabilidad F

235.4 °F - closed cup

Punto de inflamabilidad C

113 °C - closed cup

Certificado de Análisis

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Certificado de origen

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Abdulaziz M S Alsaad et al.
Drug metabolism reviews, 45(2), 173-195 (2013-04-23)
A plethora of studies have demonstrated the expression of cytochrome P450 (CYP) and soluble epoxide hydrolase (sEH) enzymes in the heart and other cardiovascular tissues. In addition, the expression of these enzymes is altered during several cardiovascular diseases (CVDs), including
Alma M Astudillo et al.
Biochimica et biophysica acta, 1821(2), 249-256 (2011-12-14)
The development of mass spectrometry-based techniques is opening new insights into the understanding of arachidonic acid (AA) metabolism. AA incorporation, remodeling and release are collectively controlled by acyltransferases, phospholipases and transacylases that exquisitely regulate the distribution of AA between the
Tamás Decsi et al.
The American journal of clinical nutrition, 98(2), 543S-548S (2013-07-05)
We summarize data on the potential interaction of trans isomeric fatty acids [trans fatty acids (TFAs)] with the availability of long-chain polyunsaturated fatty acids (LC-PUFAs) in the perinatal period. Today, TFA intakes in pregnant and lactating women can be estimated
Peter Willatts et al.
The American journal of clinical nutrition, 98(2), 536S-542S (2013-06-21)
Evidence is accumulating that a dietary supply of long-chain polyunsaturated fatty acids (LC-PUFAs) enhances the development of attention and efficient information processing in infants. However, it is uncertain whether LC-PUFAs in infancy influence cognitive development in later childhood. The objective
Jesmond Dalli et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 27(7), 2573-2583 (2013-03-19)
Maresins are produced by macrophages from docosahexaenoic acid (DHA) and exert potent proresolving and tissue homeostatic actions. Maresin 1 (MaR1; 7R,14S-dihydroxy-docosa-4Z,8E,10E,12Z,16Z,19Z-hexaenoic acid) is the first identified maresin. Here, we investigate formation, stereochemistry, and precursor role of 13,14-epoxy-docosahexaenoic acid, an intermediate

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