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EICOSATRIENOIC ACID

CAS NUMBER: 17046-59-2

MOLECULAR FORMULA: C20H34O2

MOLECULAR WEIGHT: 306.5

IUPAC NAME: (11Z,14Z,17Z)-icosa-11,14,17-trienoic acid


Eicosatrienoic Acid is a natural product found in Elaeis guineensis with data available.
Eicosatrienoic Acid is an icosatrienoic acid having three cis- double bonds at positions 11, 14 and 17. 

Eicosatrienoic Acid is a fatty acid 20:3 and an omega-3 fatty acid. 
Eicosatrienoic Acid is a conjugate acid of an (11Z,14Z,17Z)-icosatrienoate.

Eicosatrienoic Acid is a 20-carbon ω−6 fatty acid. 
In physiological literature, Eicosatrienoic Acid is given the name 20:3 (ω−6). 

Eicosatrienoic Acid is a carboxylic acid with a 20-carbon chain and three cis double bonds; the first double bond is located at the sixth carbon from the omega end. 
Eicosatrienoic Acid is the elongation product of γ-linolenic acid (GLA; 18:3, ω−6). 

Eicosatrienoic Acid is a long-chain fatty acid.
Eicosatrienoic Acid is an omega-3 fatty acid, supplied through diet as it cannot be synthesized by humans. 

Eicosatrienoic Acid has an important role in human health. 
Eicosatrienoic Acid is converted to long chain more unsaturated n-3 fatty acids by a series of alternating desaturation and elongation reactions.

Eicosatrienoic Acid, in turn, is a desaturation product (Delta 6 desaturase) of linoleic acid (18:2, ω−6). DGLA is made in the body by the elongation of GLA, by an efficient enzyme which does not appear to suffer any form of (dietary) inhibition. 
Eicosatrienoic Acid is an extremely uncommon fatty acid, found only in trace amounts in animal products.

Eicosatrienoic Acid is a long-chain, polyunsaturated fatty acid in the group of omega-3 fatty acids . 
The three double bonds have a cis configuration, they are each separated by a methylene group . 

The trienoic acid is therefore one of the isolenic acids .
Eicosatrienoic Acid occurs esterified as a triacylglyceride in small amounts in various conifer species, but also in other plant species and in microalgae 

Eicosatrienoic Acid (20:3ω-3) is a rare polyunsaturated fatty acid of the ω-3 series. 
In normal humans, Eicosatrienoic Acid represents less than 0.25% of serum phospholipid fatty acids. 

However, Eicosatrienoic Acid is one of the most active essential fatty acids when assayed for the inhibition of fatty acid elongation/desaturation reactions which convert dietary C-18 fatty acids to C-20 eicosanoid precursors.
Eicosatrienoic Acid (Mead acid) is a carboxylic acid with a 20-carbon chain and three methylene-interrupted cis double bonds. 
The first double bond is located at the ninth carbon from the omega end. 

Alternative Classes:    
-Unsaturated fatty acids 

-Straight chain fatty acids 

-Monocarboxylic acids and derivatives 

-Carboxylic acids 

-Compounds containing a carboxylic acid group with the formula -C(=O)OH.

-Organic oxides 

-Hydrocarbon derivatives 

-Carbonyl compounds 

In physiological literature, Eicosatrienoic Acid is given the name 20:3(n-9). 
In the presence of lipoxygenase, Eicosatrienoic Acid can form various hydroxy products (HETE). 

Eicosatrienoic Acid is the only polyunsaturated fatty acid that the body can make de novo. 
Eicosatrienoic Acid's elevated presence in the blood is an indication of essential fatty acid (EFA)deficiency. 

During dietary Eicosatrienoic Acid insufficiency, especially arachidonic acid deficiency, the body will make Mead acid by the elongation and desaturation of oleic acid. 
Eicosatrienoic 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.


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

Eicosatrienoic Acid is one of the most active essential fatty acids for the inhibition of fatty acid elongation/desaturation reactions
Eicosatrienoic Acid is the (n-9) homologue of (n-6) arachidonic acid (AA) and (n-3) eicosapentaenoic acid (EPA).

Eicosatrienoic Acid is a 20-carbon-chain omega-6 fatty acid, unsaturated at positions 8, 11, and 14. 
Eicosatrienoic Acid differs from arachidonic acid (5,8,11,14-eicosatetraenoic acid) only at position 5. 

Eicosatrienoic Acid is also known as Dihomo-gamma-linolenic acid (DGLA). 
In physiological literature, Eicosatrienoic Acid is given the name 20:3(n-6). 


PHYSICAL PROPERTIES: 

-Molecular Weight: 306.5

-Exact Mass: 306.255880323

-Monoisotopic Mass: 306.255880323

-Topological Polar Surface Area: 37.3 Ų

-Heavy Atom Count: 22

-Formal Charge: 0

-Complexity: 327

-Isotope Atom Count: 0    

-Compound Is Canonicalized: Yes

-Water Solubility: 7.3e-05 g/L    

-logP: 10(7.35) g/L

-Polar Surface Area: 37.3 Ų

-Rotatable Bond Count: 15

-Refractivity: 98.84 m³·mol⁻¹

-Polarizability: 39.08 ų


Eicosatrienoic Acid is the elongation product of the 18 carbon gamma-linolenic acid (GLA). 
Eicosatrienoic Acid can be converted into prostaglandin E1 (PGE1). 

Eicosatrienoic Acid inhibits platelet aggregation and also exerts a vasodilatory effect. 
Eicosatrienoic Acid competes with arachadonic acid for COX and lipoxygenase, inhibiting the production of arachadonic acid's eicosanoids.
Eicosatrienoic Acid is a rare naturally occurring n-3 polyunsaturated fatty acid 

Eicosatrienoic Acid is a polyunsaturated long-chain fatty acid with a 20-carbon backbone and 3 double bonds, originating from the 6th, 9th and 12th positions from the methyl end, with all bonds in the cis- configuration.
Eicosatrienoic Acid is a natural product found in Grimmia pilifera, Plagiothecium euryphyllum, and other organisms with data available.


CHEMICAL PROPERTIES:

-XLogP3: 6.9

-Hydrogen Bond Donor Count: 1

-Hydrogen Bond Acceptor Count: 2

-Rotatable Bond Count: 15

-Defined Atom Stereocenter Count: 0

-Undefined Atom Stereocenter Count: 0

-Defined Bond Stereocenter Count: 3    

-Undefined Bond Stereocenter Count: 0    

-Covalently-Bonded Unit Count: 1


Eicosatrienoic Acid is an icosatrienoic acid having three cis double bonds at positions 8, 11 and 14. 
Eicosatrienoic Acid has a role as a nutraceutical, a human metabolite and a fungal metabolite. 

Eicosatrienoic Acid is a fatty acid 20:3 and a long-chain fatty acid.
Eicosatrienoic Acid is a conjugate acid of an all-cis-icosa-8,11,14-trienoate.
Eicosatrienoic Acid or dihomo-γ-linolenic acid or DGLA (18 carbon atoms) is a polyunsaturated fatty acid (PUFA) with three cis (Z) double bounds (the first one from the methyl end is in omega-6 (ω-6) or n-6, so in shorthand 20:3n-6) member of sub-group called very long chain fatty acids (VLCFA), from 20 carbon atoms onwards.

Eicosatrienoic Acid is a natural product found in Elaeis guineensis with data available.
Eicosatrienoic Acid is an icosatrienoic acid having three cis- double bonds at positions 11, 14 and 17. 

Eicosatrienoic Acid is a fatty acid 20:3 and an omega-3 fatty acid. 
Eicosatrienoic Acid is a conjugate acid of an (11Z,14Z,17Z)-icosatrienoate.

Eicosatrienoic Acid is one of the most active essential fatty acids for the inhibition of fatty acid elongation/desaturation reactions
Eicosatrienoic Acid is the (n-9) homologue of (n-6) arachidonic acid (AA) and (n-3) eicosapentaenoic acid (EPA).

Eicosatrienoic Acid is a 20-carbon-chain omega-6 fatty acid, unsaturated at positions 8, 11, and 14. 
Eicosatrienoic Acid differs from arachidonic acid (5,8,11,14-eicosatetraenoic acid) only at position 5. 

In physiological literature, Eicosatrienoic Acid is given the name 20:3(n-9). 
In the presence of lipoxygenase, Eicosatrienoic Acid can form various hydroxy products (HETE). 

Eicosatrienoic Acid is the only polyunsaturated fatty acid that the body can make de novo. 
Eicosatrienoic Acid's elevated presence in the blood is an indication of essential fatty acid (EFA)deficiency. 


SYNONYM:

Eicosatrienoic acid
Dihomolinolenic acid
(11Z,14Z,17Z)-Icosa-11,14,17-trienoic acid
11,14,17-Eicosatrienoic acid
(Z,Z,Z)-11,14,17-Eicosatrienoic acid
11,14,17-Icosatrienoic acid
all-cis-icosa-11,14,17-trienoic acid
Icosatrienoic acid
Bishomo-alpha-linolenic acid
11Z,14Z,17Z-Eicosatrienoic acid
eicosa-11Z,14Z,17Z-trienoic acid
(11Z,14Z,17Z)-Eicosa-11,14,17-trienoic acid
cis,cis,cis-11,14,17-Eicosatrienoic acid
11,14,17-Eicosatrienoic acid, (Z,Z,Z)-
11c,14c,17c-Eicosatriensaeure
11c,14c,17c-eicosatrienoic acid
11,14,17-Eicosatrienoicacid, (11Z,14Z,17Z)-
11,14,17-eicosatrienoic acid, (11Z,14Z,17Z)-
ETrE(11Z, 14Z, 17Z)
all-cis-11,14,17-eicosatrienoic acid
all-cis-Eicosa-11,14,17-triensaeure
all-cis-eicosa-11,14,17-trienoic acid
EICOSATRIENOIC ACID (20:3 n-3)
C20:3n-3,6,9
Cis-11,14,17-Eicosatrienoicacid
Homo-alpha-linolenic acid
Dihomo-alpha-linolenic acid
Eicosatrienoic Acid (11Z,14Z,17Z)
(all-cis)-11,14,17-Eicosatrienoic acid
11-cis,14-cis,17-cis-Eicosatrienoic acid
Dihomo-alpha-linolenic acid (20:3(n-3))
(all-cis)-Delta11,14,17-Eicosatrienoic acid
(11z,14z,17z)-11,14,17-icosatrienoic acid
11,14,17-Eicosatrienoic acid, (Z,Z,Z)- (8CI)
11,14,17-Eicosatrienoic acid, (11Z,14Z,17Z)- (9CI)
 

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