E3127

cis-11,14-Eicosadienoic acid

Name: <I>cis</I>-11,14-Eicosadienoic acid
Brand: SIGMA

≥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

Key Documents

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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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This Item	68277
Sigma-Aldrich E3127 cis-11,14-Eicosadienoic acid	Supelco 68277 Palmitic-d₃₁ acid
biological source plant	biological source -
assay ≥98%	assay ≥98.5% (GC)
form liquid	form -
bp 198 °C/0.08 mmHg (lit.)	bp -
application(s) food and beverages	application(s) food and beverages
functional group carboxylic acid	functional group carboxylic acid

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

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Activation of the neutrophil NADPH-oxidase by free fatty acids requires the ionized carboxyl group and partitioning into membrane lipid.

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

Eicosadienoic acid differentially modulates production of pro-inflammatory modulators in murine macrophages.

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

Inhibition studies of soybean and human 15-lipoxygenases with long-chain alkenyl sulfate substrates.

R Mogul et al.

Biochemistry, 40(14), 4391-4397 (2001-04-04)

Lipoxygenases are currently potential targets for therapies against asthma, artherosceloris, and cancer. Recently, inhibition studies on both soybean (SLO) and human lipoxygenase (15-HLO) revealed the presence of an allosteric site that binds both substrate, linoleic acid, and inhibitors; oleic acid

Dietary linoleic acid has no effect on arachidonic acid, but increases n-6 eicosadienoic acid, and lowers dihomo-gamma-linolenic and eicosapentaenoic acid in plasma of adult men.

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

Samia Selmi-Ruby et al.

Environmental health perspectives, 128(12), 127006-127006 (2020-12-10)

Aryl phosphate esters (APEs) are widely used and commonly present in the environment. Health hazards associated with these compounds remain largely unknown and the effects of diphenyl phosphate (DPhP), one of their most frequent derivatives, are poorly characterized. Our aim

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