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E3127

Sigma-Aldrich

cis-11,14-Eicosadienoic acid

≥98%, liquid

Synonym(s):

11,14-Eicosadienoic acid

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About This Item

Linear Formula:
CH3(CH2)4(CH=CHCH2)2(CH2)8CO2H
CAS Number:
2091-39-6
Molecular Weight:
308.50
MDL number:
MFCD00673431
UNSPSC Code:
12352106
PubChem Substance ID:
24894497
NACRES:
NA.25

biological source

plant

Quality Level

200

Assay

≥98%

form

liquid

bp

198 °C/0.08 mmHg (lit.)

application(s)

food and beverages

functional group

carboxylic acid

lipid type

omega FAs

shipped in

ambient

storage temp.

−20°C

SMILES string

CCCCC\C=C/C\C=C/CCCCCCCCCC(O)=O

InChI

1S/C20H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10H,2-5,8,11-19H2,1H3,(H,21,22)/b7-6-,10-9-

InChI key

XSXIVVZCUAHUJO-HZJYTTRNSA-N

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Packaging

Sealed ampule.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

143.6 °F - closed cup

Flash Point(C)

62 °C - closed cup

Certificates of Analysis (COA)

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M J Steinbeck et al.
Journal of leukocyte biology, 49(4), 360-368 (1991-04-01)
To investigate NADPH-oxidase activation, we studied the effects of free fatty acid (FFA), their uncharged derivatives, and calcium on membrane lipid structure and superoxide anion (O2-) release from intact neutrophils and in cell-free O2(-)-generating systems. This study determined that in
Y Angela Liou et al.
Prostaglandins, leukotrienes, and essential fatty acids, 80(4), 201-206 (2009-04-10)
High intakes of linoleic acid (LA,18:2n-6) have raised concern due to possible increase in arachidonic acid (ARA, 20:4n-6) synthesis, and inhibition of alpha linolenic acid (ALA, 18:3n-3) desaturation to eicosapentaenoic (EPA, 20:5n-3) and docosahexaenoic acid (DHA, 22:6n-3). In healthy men
V Koshkin et al.
The Journal of biological chemistry, 273(11), 6046-6049 (1998-04-16)
The pre-steady-state phase of the oxygenase reaction of prostaglandin endoperoxide synthase with cis,cis-eicosa-11, 14-dienoic acid has been studied using stopped flow techniques. Because some intermediate forms of prostaglandin endoperoxide synthase are spectrally indistinguishable, the enzyme and substrate transformations were monitored
M Bakovic et al.
Prostaglandins, leukotrienes, and essential fatty acids, 53(6), 423-431 (1995-12-01)
The stoichiometry of the oxygenation reaction of cis,cis-eicosa-11,14-dienoic acid catalyzed by prostaglandin endoperoxide synthase and soybean lipoxygenase has been investigated by using steady-state initial rate measurements. The rate of product formation (conjugated diene hydroperoxy and hydroxy derivatives) was followed spectrophotometrically
Yung-Sheng Huang et al.
Molecular and cellular biochemistry, 358(1-2), 85-94 (2011-06-21)
Eicosadienoic acid (Δ11,14-20:2; EDA) is a rare, naturally occurring n-6 polyunsaturated fatty acid (PUFA) found mainly in animal tissues. EDA is elongated from linoleic acid (LA), and can also be metabolized to dihomo-γ-linolenic acid (DGLA), arachidonic acid (AA), and sciadonic
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