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Eicosadienoic acid is used in biochemical research as a reference compound for studying polyunsaturated fatty acid metabolism.
Eicosadienoic acid is applied in enzymology studies to examine the activity and specificity of desaturase and elongase enzymes.
Eicosadienoic Acid is also used in industrial and laboratory standards for quality control in fatty acid analysis and lipid profiling.
CAS Number: 2091-39-6 (for the common omega-6 isomer)
EC / EINECS Number: Not widely listed in major chemical inventories for this specific fatty acid isomer; can be absent due to its niche biochemical role.
Molecular Formula: C₂₀H₃₆O₂
Molecular Weight: ~308.50 g/mol
SYNONYMS:
Eicosadienoic acid, Icosadienoic acid, 11,14-Icosadienoic acid, (11Z,14Z)-Eicosa-11,14-dienoic acid, fatty acid 20:2, RefChem:1084059, CHEBI:72850, (11Z,14Z)-Icosa-11,14-dienoic acid, 5598-38-9, cis-11,14-Eicosadienoic acid, HOMO-GAMMA-LINOLEICACID, FA 20:2, 11Z,14Z-eicosadienoic acid, CHEMBL464983, (11Z,14Z)-icosadienoic acid, (z,z)-11,14-eicosadienoic acid, 2091-39-6, EICOSADIENOIC ACID (20:2 n-6), 11(Z),14(Z)-Eicosadienoic Acid, 11,14-Eicosadienoate, Homo-gamma-linoleic acid, eicosa-11z,14z-dienoic acid, (11Z,14Z)-eicosadienoic acid, MFCD00673431, 11,14-Eicosadienoic acid, (Z,Z)-, 11, 14-icosadienoate, cis-11,14-eicosenoic acid, BSPBio_001326, cis-11,14-eicosadienoicacid, SCHEMBL416181, BML3-B08, orb2283599, CHEBI:73731, DTXSID20912353, XSXIVVZCUAHUJO-HZJYTTRNSA-N, HMS1361C08, HMS1791C08, HMS1989C08, HMS3402C08, HMS3649J19, 11(Z)14(Z)-Eicosadienoic Acid, cis,cis-11,14-eicosadienoic acid, BDBM50269533, LMFA01031043, AKOS027326225, IDI1_033796, NCGC00161348-01, NCGC00161348-02, NCGC00161348-03, BP-40900, PD020533, SY314031, HY-149589, CS-0897467, FA(20:2(11Z,14Z)), NS00074153, G61912, cis-11,14-Eicosadienoic acid, >=98%, liquid, SR-01000946668, SR-01000946668-1, BRD-K80325895-001-02-3, Q25402866, (11Z,14Z)-icosa-11,14-dienoic acid, Eicosadienoic acid, icsoa-11,14-dienoic acid, (11Z,14Z)-eicosa-11,14-dienoic acid, 20:2(n-6) fatty acid, cis-11,14-eicosadienoic acid, 11,14-Eicosadienoic acid, 11,13-eicosadienoic acid, SCHEMBL3201530, LMFA01031095, 5,11-Eicosadienoic acid, C20:2n-9,15, RefChem:100920, LMFA01030374, (5E,11E)-icosa-5,11-dienoic acid, CHEBI:165473, Eicosadienoic acid, HOMO-GAMMA-LINOLEICACID, Homo-gamma-linoleic acid, Icosadienoic acid, SCHEMBL416181, cis-11,14-Eicosadienoic acid, cis-11,14-eicosadienoicacid, (11Z,14Z)-Eicosa-11,14-dienoic acid, (11Z,14Z)-Icosa-11,14-dienoic acid, (11Z,14Z)-icosadienoic acid, 11, 14-icosadienoate, 11, 14-icosadienoic acid, 11,14-Eicosadienoate, 11,14-Eicosadienoic acid, (Z,Z)-, 11,14-Icosadienoic acid, 11C,14C-Eicosadienoic acid, 11Z,14Z-eicosadienoic acid, 2091-39-6, 5598-38-9, AC1O5SJA, BSPBio_001326, CHEBI:73731, CHEMBL464983, FA 20:2
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 (DGLA).
Levels of Eicosadienoic 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 an omega 6 fatty acid.
Eicosadienoic acid is the elongation product of Gamma linolenic acid (GLA) and the direct precursor of Dihomogamma Linolenic (DGLA).
Levels of Eicosadienoic 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.
High blood omega-6 PUFAs specifically arachidonic acid and eicosadienoic acid, oleic acid (a MUFA) and SFA levels increased the odds ratio of having neovascular age-related macular degeneration (AMD).
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.
cis-11,14-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.
cis-11,14-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 cis-11,14-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 cis-11,14-eicosadienoic acid is typical of the crystalline lamellar phase.
Eicosadienoic Acid (5Z,14Z) inhibits inosine 5′-monophosphate.
Eicosadienoic Acid (5Z,14Z), with the CAS number 122055-58-7, is a polyunsaturated fatty acid that is notable for its structure consisting of 20 carbon atoms and two cis-configured double bonds located at the 5th and 14th positions.
This specific spatial arrangement imparts distinct physical and chemical properties to the molecule, making it an interesting subject for various research studies.
In scientific investigations, Eicosadienoic Acid (5Z,14Z) is often utilized to explore the effects of fatty acid unsaturation on membrane fluidity and integrity.
Due to Eicosadienoic Acid's unsaturated nature, this fatty acid can influence membrane dynamics by altering the packing of lipids within the bilayer, thus affecting the overall membrane properties such as permeability, phase transitions, and interactions with other molecules.
This makes Eicosadienoic Acid a valuable tool for studying lipid-lipid interactions and the role of fatty acids in modulating the structure and function of cellular membranes.
Additionally, research involving Eicosadienoic Acid (5Z,14Z) extends to studying its role in lipid signaling pathways and its interaction with enzymes involved in lipid metabolism.
Understanding these interactions helps explain the complex regulatory mechanisms controlling cellular lipid levels and their implications in various biological processes and systems.
Eicosadienoic acid (Standard) is the analytical standard of Eicosadienoic acid.
Eicosadienoic Acid is intended for research and analytical applications.
Eicosadienoic acid is a rare, naturally occurring n-6 polyunsaturated fatty acid found mainly in animal tissues.
Eicosadienoic acid is a 20-carbon polyunsaturated fatty acid (C₂₀H₃₆O₂) with two cis double bonds, most commonly found as the omega-6 (11,14) isomer.
Eicosadienoic Acid is a liquid hydrophobic molecule that resembles other long chain fatty acids in physical and chemical behavior, distinguished by its polyunsaturation and biological presence.
Eicosadienoic Acid participates in lipid metabolism, is used primarily in biochemical research to probe fatty acid effects on cells, and occurs in modest quantities in some food oils and human milk.
Eicosadienoic Acid is safe in typical dietary contexts and should be stored under conditions that minimize oxidation.
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 rare, naturally occurring n-6 polyunsaturated fatty acid found mainly in animal tissues.
Eicosadienoic Acid (8Z,14Z), cataloged under the CAS number 135498-07-6, is an unsaturated fatty acid characterized by having 20 carbon atoms and two double bonds located at the 8th and 14th positions in the cis configuration.
This specific structure classifies Eicosadienoic Acid within the family of polyunsaturated fatty acids (PUFAs), which are crucial components in cellular lipid metabolism and membrane architecture.
The double bonds in eicosadienoic acid influence its fluidity and integration into cell membranes, affecting the membrane′s properties such as fluidity, flexibility, and the function of embedded proteins and signaling pathways.
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 has been reported in Salvia hispanica, Arbacia punctulata, and other organisms with data available.
Eicosadienoic Acid is a polyunsaturated long-chain fatty acid with a 20-carbon backbone and exactly 2 double bonds.
At least 5 different isomers can be called by this name.
Eicosadienoic acid (EDA) is a polyunsaturated omega-6 fatty acid with the chemical formula C20H36O2.
Eicosadienoic Acid is classified as a 20-carbon fatty acid with two double bonds, specifically at the 11th and 14th positions (denoted as 20:2(ω-6)).
Eicosadienoic Acid is a minor fatty acid found in certain animal and plant sources and plays a role in lipid metabolism.
Like other polyunsaturated fatty acids (PUFAs), Eicosadienoic Acid is hydrophobic and insoluble in water but soluble in organic solvents.
Eicosadienoic Acid is a precursor for longer-chain omega-6 fatty acids, such as dihomo-gamma-linolenic acid (DGLA) and arachidonic acid (AA).
Several isomers are common, all with bonds in the cis-configuration.
The omega-6 isomer with bonds in the positions 11 and 14, also known as di-homo-linoleic acid, can be detected in modest concentrations, generally not exceeding 2%, in the seed oils of hundreds of plants, particularly Cruciferae, Ranunculaceae, and Pinaceae, as well as in human breast milk.
The omega-9 isomer with bonds in the positions 5 and 11, also known as keteleeronic acid, can be detected in modest concentrations, generally not exceeding 2%, in the seed oils of Pinaceae and Cupressaceae.
Rarer in the plant world are the isomers with bonds in the positions 6 and 9, or 7 and 11, known as di-homotaxoleic acid.
Eicosadienoic acid is an omega-6 fatty acid found in human milk.
Omega-6 fatty acids are 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 omega−6 fatty acids are 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 polyunsaturated long-chain fatty acid belonging to the family of fatty acids found in certain plant and animal lipids.
Eicosadienoic Acid typically has 20 carbon atoms and two carbon-carbon double bonds, which place it in the broader category of polyunsaturated fatty acids (PUFAs).
The most commonly discussed form in biochemical and nutritional contexts is cis-11,14-eicosadienoic acid, an omega-6 (n-6) fatty acid that can act as a metabolic precursor to other longer chain fatty acids and participates in lipid metabolism and membrane structure.
Eicosadienoic Acid is naturally occurring in modest concentrations in seed oils, human tissues such as breast milk, and some animal fats.
USES and APPLICATIONS of EICOSADIENOIC ACID:
Metabolism uses of Eicosadienoic Acid: In vivo it may be metabolized further to stearidonic acid (a longer chain PUFA) in certain biological systems, reflecting participation in fatty acid metabolic pathways.
In research, eicosadienoic acid has been utilized to understand the role of fatty acids in modulating membrane dynamics and in the production of signaling molecules that govern various cellular processes.
Eicosadienoic Acid's involvement in the synthesis of lipid mediators and its potential impact on the regulation of gene expression are areas of particular interest.
By studying eicosadienoic acid, researchers aim to explain the broader physiological roles of unsaturated fatty acids in maintaining cellular homeostasis, influence on metabolic pathways, and their overall impact on the biophysical properties of cell membranes.
This research contributes to a deeper understanding of lipid biochemistry and the complex network of lipid-mediated cellular regulation.
Eicosadienoic acid is used in biochemical research as a reference compound for studying polyunsaturated fatty acid metabolism.
Eicosadienoic Acid is applied in lipidomics and analytical chemistry to help identify and quantify fatty acids in biological samples.
Eicosadienoic acid is utilized in cell culture studies to investigate the effects of specific fatty acids on cell membranes and signaling pathways.
Eicosadienoic Acid serves as a model molecule in research on inflammation and eicosanoid biosynthesis due to its structural similarity to other bioactive fatty acids.
In nutritional science, eicosadienoic acid is studied to better understand the role of minor dietary fatty acids in human health.
Eicosadienoic Acid is used in pharmaceutical research as a precursor or comparative compound when developing drugs that target fatty acid–related pathways.
Eicosadienoic acid is applied in enzymology studies to examine the activity and specificity of desaturase and elongase enzymes.
Eicosadienoic Acid is also used in industrial and laboratory standards for quality control in fatty acid analysis and lipid profiling.
-Biochemical Research uses of Eicosadienoic Acid:
Eicosadienoic acid is used experimentally to study changes in cellular fatty acid composition and effects on membrane fluidity and function.
Research includes in vitro studies on immune cells (e.g., macrophages) to understand pro- and anti-inflammatory modulations of signaling pathways.
-Nutrition & Food Science uses of Eicosadienoic Acid:
Eicosadienoic Acid is present in seed oils and in low amounts in some plant and animal tissues, contributing modestly to dietary PUFA intake.
Eicosadienoic Acid's presence in human breast milk and some seed oils reflects its role in natural lipid pools.
FUNCTIONAL CHARACTERISTICS of EICOSADIENOIC ACID:
As an omega-6 type PUFA, eicosadienoic acid is incorporated into lipid bilayers of cell membranes, contributing to their fluidity, flexibility, and signaling properties.
It is a structural analogue to other long-chain fatty acids and can be elongated and desaturated by enzymes in metabolic pathways that produce other omega-6 fatty acids.
In biochemical research, it has been examined for roles in modulating membrane fatty acid composition, effects on inflammatory mediators, and participation in lipid metabolism.
ALTERNATIVE PARENTS of EICOSADIENOIC ACID:
*Unsaturated fatty acids
*Straight chain fatty acids
*Monocarboxylic acids and derivatives
*Carboxylic acids
*Organic oxides
*Hydrocarbon derivatives
*Carbonyl compounds
SUBSTITUENTS of EICOSADIENOIC ACID:
*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
BENEFITS & BIOLOGICAL ROLES of EICOSADIENOIC ACID:
Although less extensively studied than other omega-3 and omega-6 fatty acids, eicosadienoic acid contributes to several biological features:
*Membrane structure:
Eicosadienoic Acid helps maintain appropriate membrane fluidity in cells.
*Biosynthetic intermediate:
In certain tissues, Eicosadienoic Acid can act as a precursor to other long-chain fatty acids such as stearidonic acid, which may then participate in subsequent lipid signaling roles.
*Inflammation modulation:
Experimental data suggest that Eicosadienoic Acid can affect inflammatory mediator expression in immune cells, although these effects are context-dependent and not widely characterized in humans.
WHAT DOES IT MEAN IF YOUR EICOSADIENOIC ACID RESULT IS TOO HIGH?
High blood omega-6 PUFAs specifically arachidonic acid and eicosadienoic acid, oleic acid (a MUFA) and SFA levels increased the odds ratio of having neovascular age-related macular degeneration (AMD).
PHYSICAL and CHEMICAL PROPERTIES of EICOSADIENOIC ACID:
Molecular Weight: 308.5 g/mol
XLogP3: 7.9
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 16
Exact Mass: 308.271530387 Da
Monoisotopic Mass: 308.271530387 Da
Topological Polar Surface Area: 37.3 Ų
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
Chemical Formula: C20H36O2
Molar Mass: 308.506 g·mol−1
Appearance: colorless liquid
Density: 0.9 g/cm³
Melting Point: 148.9 °C
Boiling Point: 198 °C
Solubility in Water: insoluble
Flash Point: 297.4 °C
Preferred Name: Eicosadienoic acid
Common Isomer: cis-11,14-eicosadienoic acid
IUPAC Name: (11Z,14Z)-icosa-11,14-dienoic acid
Molecular Formula: C20H36O2
Molecular Weight: 308.50 g/mol
CAS Number: 2091-39-6
EC / EINECS Number: Not widely listed
Chemical Structure: Long linear chain with carboxylic acid at one end and two double bonds in cis configuration
Appearance: Clear colorless to light yellow liquid
State: Liquid fatty acid
Boiling Point: 198 °C
Density: 0.905 g/cm³
Flash Point: 62 °C
Solubility: Insoluble in water; hydrophobic. Soluble in organic solvents such as ethanol, chloroform and hexane
pKa: 4.78
Chemical Behavior: As a fatty acid, it will undergo typical acid reactions (esterification, salt formation) and is subject to oxidation of its double bonds under appropriate conditions, especially in the presence of heat, light, or oxygen
Chemical Formula: C20H36O2
Average Molecular Weight: 308.4986
Monoisotopic Molecular Weight: 308.271530396
IUPAC Name: (11Z,14Z)-icosa-11,14-dienoic acid
Traditional Name: eicosadienoic acid
CAS Registry Number: 5598-38-9
SMILES: CCCCCC=C/CC=C/CCCCCCCCCC(O)=O
InChI Identifier: 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
CAS Number: 2091-39-6
Purity: >99%
Molecular Weight: 308.5 Da
Molecular Formula: C20H36O2
PubChem: 5282805
Nature: Synthetic
Biochemical Name: 11,14-Eicosadienoic acid
Canonical SMILES: CCCCCC=CCC=CCCCCCCCCCC(=O)O
Isomeric SMILES: CCCCC/C=C/C/C=C/CCCCCCCCCC(=O)O
InChi: 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+
IUPAC Name: (11E,14E)-icosa-11,14-dienoic acid
Formulation: A solution in ethanol
Physical State: Liquid
Storage: Store at -20° C
Boiling Point: 78 °C
Linear Formula: CH3(CH2)4(CH=CHCH2)2(CH2)8CO2H
CAS Number: 2091-39-6
Molecular Weight: 308.50
Synonyms: 11(Z),14(Z)-Eicosadienoic Acid
IUPAC Name: (11E,14E)-icosa-11,14-dienoic acid
InChI Key: XSXIVVZCUAHUJO-AVQMFFATSA-N
Boiling Point: 198 °C at 0.08 mm Hg
Flash Point: 326.3 °C
Density: 0.905 g/cm³
Appearance: Colorless Liquid
Storage: -20 °C
Bond Position: Cis 11 cis 14 cis
CNo Chain: C20:2
Compound Derivative: Acid
Exact Mass: 308.27200
Fatty Acid: 11-14 Eicosadienoic
H-Bond Acceptor: 2
H-Bond Donor: 1
Physical State: Colorless Liquid
Type: N6, OMEGA 6
Physical state: liquid
Color: No data available
Odor: No data available
Melting point/freezing point: No data available
Boiling point: 198 °C at 0.1 hPa
Flammability: No data available
Upper/lower flammability or explosive limits: No data available
Flash point: 62 °C - closed cup
Autoignition temperature: No data available
Decomposition temperature: No data available
pH: No data available
Viscosity: No data available
Water solubility: No data available
Partition coefficient: No data available
Vapor pressure: No data available
Density: No data available
Relative density: No data available
Relative vapor density: No data available
Particle characteristics: No data available
Explosive properties: No data available
Oxidizing properties: No data available
Other safety information: No data available
FIRST AID MEASURES of EICOSADIENOIC ACID:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation:
Fresh air.
*In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.
*If swallowed:
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available
ACCIDENTAL RELEASE MEASURES of EICOSADIENOIC ACID:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up dry.
Dispose of properly.
Clean up affected area.
FIRE FIGHTING MEASURES of EICOSADIENOIC ACID:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2)
Foam
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.
EXPOSURE CONTROLS/PERSONAL PROTECTION of EICOSADIENOIC ACID:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection.
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A
-Control of environmental exposure:
Do not let product enter drains.
HANDLING and STORAGE of EICOSADIENOIC ACID:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed.
Dry.
STABILITY and REACTIVITY of EICOSADIENOIC ACID:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available
