PRODUCTS

EICOSADIENOIC ACID

CAS NUMBER: 5598-38-9

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-

MOLECULAR FORMULA: C20H36O2

MOLECULAR WEIGHT: 308.5

IUPAC NAME: (11Z,14Z)-icosa-11,14-dienoic acid

Eicosadienoic Acid is an omega-6 fatty acid found in human milk.
Eicosadienoic Acid is a family of unsaturated fatty acids which have in common a carbon-carbon double bond in the n−6 position; that is, the sixth bond from the end of the fatty acid.

The biological effects of the Eicosadienoic Acid is largely mediated by their conversion to n-6 eicosanoids that bind to diverse receptors found in every tissue of the body.
Eicosadienoic Acid has been identified in the human placenta.

Eicosadienoic Acid is a natural product found in Arbacia punctulata and Cannabis sativa with data available.
Eicosadienoic Acid is an icosadienoic acid with double bonds at positions 11 and 14 (both Z).

Eicosadienoic Acid has a role as a metabolite.
Eicosadienoic Acid is a conjugate acid of an (11Z,14Z)-icosadienoate.

Eicosadienoic Acid derives from a hydride of an icosanoic acid.
Eicosadienoic Acid is a diunsaturated fatty acid in the group of omega-6 fatty acids .

Biological Properties:
Cellular Locations; Extracellular, Membrane
Biospecimen Locations; Blood, Feces
Tissue Locations; Placenta

Alternative Classes:

-Unsaturated fatty acids
-Straight chain fatty acids
-Monocarboxylic acids and derivatives
-Carboxylic acids
-Organic oxides
-Organic compounds containing an oxide group.
-Hydrocarbon derivatives
-Carbonyl compounds

Isomers :
Eicosadienoic Acid has two double bonds that can be in cis or trans configuration.
The dienoic acid with two cis double bonds is an isomer of keteleeronic acid , (5 Z ,11 Z )-eicosadienoic acid

Occurrence:
Eicosadienoic Acid occurs esterified as a triacylglyceride in the seed oil of various conifer species in amounts of up to approx.
25%, as well as in other plants.
Eicosadienoic Acid occurs in:
-small amounts in black cumin oil ( Nigella )
-pine nut oil ( Pinus )
-camelina oil ( Camelina sativa )
-crambe ( Krambe )
-coriander oil ( Coriandrum sativum ) and in borage seed oil

This high purity Eicosadienoic Acid is ideal as a standard and for biological studies.
Eicosadienoic Acid is an omega-6 fatty acid that is found mainly in small amounts in animal tissues.

Eicosadienoic Acid is produced by a delta-9 elongase enzyme from linoleic acid and can be converted into dihomo-gamma-linolenic acid, arachidonic acid, sciadonic acid and other polyunsaturated fatty acids.
Eicosadienoic Acid has been found to be able to modulate the metabolism of polyunsaturated fatty acids and alter the responsiveness of macrophages to inflammatory stimulations.

Along with other mono and polyunsaturated fatty acids Eicosadienoic Acid can inhibit the binding of leukotriene B4 to pig neutrophil membranes, which may account in part for it’s anti-inflammatory activities.
The X-ray powder diffraction pattern of the sodium soap of Eicosadienoic Acid is typical of the crystalline lamellar phase.

Substituents:

*Long-chain fatty acid

*Unsaturated fatty acid

*Straight chain fatty acid

*Monocarboxylic acid or derivatives

*Carboxylic acid

*Carboxylic acid derivative

*Organic oxygen compound

*Organic oxide

*Hydrocarbon derivative

*Organooxygen compound

*Carbonyl group

*Aliphatic acyclic compound

Eicosadienoic Acid is fatty acids that contain more than one double bond in their backbone.
This class includes many important compounds, such as essential fatty acids and those that give drying oils their characteristic property.

Eicosadienoic Acid is an omega 6 fatty acid found in human milk.
Eicosadienoic Acid is a family of unsaturated fatty acids which have in common a carbon-carbon double bond in the n−6 position; that is, the sixth bond from the end of the fatty acid.
The biological effects of the Eicosadienoic Acid's are largely mediated by their conversion to n-6 eicosanoids that bind to diverse receptors found in every tissue of the body.

Eicosadienoic Acid belongs to the class of organic compounds known as long-chain fatty acids.
These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Eicosadienoic Acid is a novel ω-6 C20:2 fatty acid.
The more common Eicosadienoic Acid competitively inhibits inosine 5’-monophosphate dehydrogenase (Ki = 3.1 µM)1 and inhibits the binding of LTB4 to its receptor on neutrophils (Ki = 3.0 µM).

Also, serum levels of Eicosadienoic Acid's negatively correlate with degree of sleep disturbance.
Eicosadienoic Acids are converted by desaturases, in vivo, to eicosatrienoic acids, which are potent vasodilators.

The physiological effects of Eicosadienoic Acid is unstudied.
Eicosadienoic Acid is a fatty acid methyl ester resulting from the formal condensation of the carboxy group of (11Z,14Z)-icosadienoic acid with methanol.

Eicosadienoic Acid is a rare acid found mostly in animal tissues.
Eicosadienoic Acid is a naturally occurring n-6 polyunsaturated fatty acid.

PHYSICAL PROPERTIES:

-Molecular Weight: 308.5

-Exact Mass: 308.271530387

-Monoisotopic Mass: 308.271530387

-Topological Polar Surface Area: 37.3 Å²

-Water Solubility: 0.0015 mg/L

-LogP: 6.251

-Polar Surface Area: 37.3 Å²

-Rotatable Bond Count: 16

-Refractivity: 97.72 m³·mol⁻¹

-Polarizability: 39.94 Å³

-Water Solubility: 5.4e-05 g/L

-LogP: 6.251

-logS: 10(-6.8) g/L

-pKa (Strongest Acidic): 4.95

-Physical Description: Solid

-Boiling Point: 462.10°C

-Solubility: 0.001507 mg/L

-Collision Cross Section: 184.05 Å

Eicosadienoic Acid grows from linoleic acid (LA) and can also be metabolized to dihomo-y-linolenic acid (DGLA), arachidonic acid (AA), and siadonic acid (Δ5,11,14-20:3; SCA).
Although the metabolism of Eicosadienoic Acid has been extensively studied, there are few reports on how EDA affects inflammatory processes.

Eicosadienoic Acid is a novel omega-6 C20:2 fatty acid.
The more common Eicosadienoic Acid competitively inhibits inosine 5'-monophosphate dehydrogenase (Ki = 3.1 µM) and inhibits the binding of LTB4 to its receptor on neutrophils (Ki = 3.0 µM).

Eicosadienoic Acid is an omega 6 fatty acid.
Eicosadienoic Acid is the elongation product of Gamma linolenic acid (GLA) and the direct precursor of Dihomogamma Linolenic.

Levels of this fatty acid reflect levels of other polyunsaturated omega-6 fatty acids.
Plasma levels are significantly lower than those present in erythrocytes, which indicates that the conversion of linoleic to eicosadienoic acid occurs at a higher rate than the conversion of eicosadienoic acid to DGLA.

Eicosadienoic Acid is a rare, naturally occurring n-6 polyunsaturated fatty acid found mainly in animal tissues.
Eicosadienoic Acid is an ω-8 C20:2 fatty acid.

The presence of Eicosadienoic Acid has been detected in human milk at a level of 0.19% (weight % total fatty acids).
Eicosadienoic Acids are converted by desaturases, in vivo, to eicosatrienoic acids, which are potent vasodilators.

The physiological effects of Eicosadienoic Acid are unstudied.
Eicosadienoic Acid, is a polysaturated fatty acid.

CHEMICAL PROPERTIES:

-Heavy Atom Count: 22

-Formal Charge: 0

-Complexity: 292

-Isotope Atom Count: 0

-Defined Atom Stereocenter Count: 0

-Undefined Atom Stereocenter Count: 0

-Defined Bond Stereocenter Count: 2

-Undefined Bond Stereocenter Count: 0

-Covalently-Bonded Unit Count: 1

-Compound Is Canonicalized: Yes

-XLogP3: 7.9

-Hydrogen Bond Donor Count: 1

-Hydrogen Bond Acceptor Count: 2

-Rotatable Bond Count: 16

Eicosadienoic Acid has a role as a metabolite.
Eicosadienoic Acid is a conjugate acid of an (11Z,14Z)-icosadienoate.

Eicosadienoic Acid derives from a hydride of an icosanoic acid.
Eicosadienoic Acid is a diunsaturated fatty acid in the group of omega-6 fatty acids .

Eicosadienoic Acid has a role as a metabolite.
Eicosadienoic Acid is a conjugate acid of an (11Z,14Z)-icosadienoate.

Eicosadienoic Acid belongs to the class of organic compounds known as long-chain fatty acids.
These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
Eicosadienoic Acid is a novel ω-6 C20:2 fatty acid.
The more common Eicosadienoic Acid competitively inhibits inosine 5’-monophosphate dehydrogenase (Ki = 3.1 µM)1 and inhibits the binding of LTB4 to its receptor on neutrophils (Ki = 3.0 µM).

Also, serum levels of Eicosadienoic Acid's negatively correlate with degree of sleep disturbance.
Eicosadienoic Acid is converted by desaturases, in vivo, to eicosatrienoic acids, which are potent vasodilators.
The physiological effects of Eicosadienoic Acid are unstudied.
Eicosadienoic Acid is a fatty acid methyl ester resulting from the formal condensation of the carboxy group of (11Z,14Z)-icosadienoic acid with methanol.

Eicosadienoic Acid is a rare acid found mostly in animal tissues.
Eicosadienoic Acid is a naturally occurring n-6 polyunsaturated fatty acid.
Eicosadienoic Acid derives from a hydride of an icosanoic acid.
Eicosadienoic Acid is a diunsaturated fatty acid in the group of omega-6 fatty acids .

SYNONYMS:

Eicosadienoic acid
cis-11,14-Eicosadienoic acid
(11Z,14Z)-Icosa-11,14-dienoic acid
Icosadienoic acid
(11Z,14Z)-icosadienoic acid
11,14-Icosadienoic acid
11Z,14Z-eicosadienoic acid
cis-11,14-eicosadienoicacid
HOMO-GAMMA-LINOLEICACID
EICOSADIENOIC ACID (20:2 n-6)
(11Z,14Z)-Eicosa-11,14-dienoic acid
Homo-gamma-linoleic acid
11,14-Eicosadienoic acid, (Z,Z)-
11,14-Eicosadienoate
11, 14-icosadienoate
11C,14C-Eicosadienoic acid
(11Z,14Z)-eicosadienoic acid
cis,cis-11,14-eicosadienoic acid
Dihomolinoleic acid (20:2(n-6))
Eicosadienoic acid (cis-20:2n-6)
cis-11,14-Eicosadienoic acid, >=98%, liquid
(11Z,14Z)-Eicosa-11,14-dienoic acid
(11Z,14Z)-Eicosadienoic acid
(11Z,14Z)-Icosa-11,14-dienoic acid
11,14-Eicosadienoic acid
11,14-Icosadienoic acid
(11Z,14Z)-Eicosa-11,14-dienoate   Generator
(11Z,14Z)-Eicosadienoate   Generator
(11Z,14Z)-Icosa-11,14-dienoate   Generator
11,14-Eicosadienoate   Generator
11,14-Icosadienoate   Generator
Eicosadienoate   Generator
11, 14-Icosadienoate
11, 14-Icosadienoic acid
11,14-trans-Eicosadienoic acid
delta11,14-20:2
Eicosa-11,14-dienoic acid
Eicosa-11,14-dienoic acid, (Z,Z)-isomer
N-6 Eicosadienoic acid
Dihomolinoleate
(11Z,14Z)-Icosadienoate
(11Z,14Z)-11,14-Eicosadienate
(11Z,14Z)-11,14-Eicosadienic acid
(11Z,14Z)-11,14-Eicosadienoate
(11Z,14Z)-11,14-Eicosadienoic acid
11,14-all-cis-Eicosadienoate
11,14-all-cis-Eicosadienoic acid
11-cis,14-cis-Eicosadienoate
11-cis,14-cis-Eicosadienoic acid
Bishomolinoleate
Bishomolinoleic acid
Dihomo-linoleate (20:2n6)
Dihomo-linoleic acid (20:2n6)
FA(20:2(11Z,14Z))
Homo-gamma-linoleate
Homo-gamma-linoleic acid
Homo-γ-linoleate
Homo-γ-linoleic acid
all-cis-11,14-Eicosadienoate
all-cis-11,14-Eicosadienoic acid
cis,cis-Eicosa-11,14-dienoate
cis,cis-Eicosa-11,14-dienoic acid
cis,cis-delta11,14-Eicosadienoate
cis,cis-delta11,14-Eicosadienoic acid
cis,cis-Δ11,14-eicosadienoate
cis,cis-Δ11,14-eicosadienoic acid
cis-11,cis-14-Eicosadienoate
cis-11,cis-14-Eicosadienoic acid
delta11,14-Eicosadienoate
delta11,14-Eicosadienoic acid
Δ11,14-eicosadienoate
Δ11,14-eicosadienoic acid
FA(20:2n6)
Eicosadienoic acid