Quick Search
Eicosenoic Acid is used as standards in lipid analysis and metabolic studies.
Eicosenoic Acid serves as a starting material or intermediate for synthesizing specialty esters and fatty acid derivatives.
Eicosenoic Acid is also applied in plant and agricultural studies to investigate seed oil composition and genetic regulation of fatty acid biosynthesis.
CAS Number (cis-9): 29204-02-2
CAS Number (cis-11): 5561-99-9
CAS Number (cis-13): 34316-64-8
EC number: Not unique / isomer-dependent
Molecular formula: C₂₀H₃₈O₂
Molecular weight: 310.51 g/mol
SYNONYMS:
eicos-enoic acid, icosenoic acid, C20:1 fatty acid, eicos-1-enoic acid (generic), monoenoic eicosanoic acid, (E)-icos-2-enoic acid;trans-2-icosenoic acid;Eicosenoic Acid (C20 Unsaturated Fatty Acid)
Depending on isomer:
cis-9-Eicosenoic acid:
gadoleic acid, (Z)-9-Eicosenoic acid, 9Z-Eicosenoic acid, cis-Δ(9)-Eicosenoic acid, Eicos-9C-enoic acid, 9C-eicosensaeure, (Z)-Eicos-9-enoic acid
gadoleic acid, (Z)-9-eicosenoic acid, cis-9-eicosenoic acid, 9Z-eicosenoic acid, eicos-9-enoic acid, Δ9-eicosenoic acid, omega-11 eicosenoic acid, 20:1(n-11)
cis-11-Eicosenoic acid:
gondoic acid, (11Z)-Eicosenoic acid, cis-11-Eicosenoic acid, (Z)-Eicos-11-enoic acid, 11Z-Icosenoic acid
(Z)-11-Eicosenic acid; (Z)-11-Eicosenoic acid; cis-11-eicosenoic acid (gondoic acid)
gondoic acid, (Z)-11-eicosenoic acid, cis-11-eicosenoic acid, 11Z-eicosenoic acid, eicos-11-enoic acid, Δ11-eicosenoic acid, omega-9 eicosenoic acid, 20:1(n-9)
cis-13-Eicosenoic acid (Paullinic acid)
paullinic acid, (Z)-13-eicosenoic acid, cis-13-eicosenoic acid, 13Z-eicosenoic acid, eicos-13-enoic acid, Δ13-eicosenoic acid, omega-7 eicosenoic acid, 20:1(n-7)
Other less common isomers
cis-5-eicosenoic acid, cis-7-eicosenoic acid, trans-9-eicosenoic acid, (E)-11-eicosenoic acid
Eicosenoic acid is a monounsaturated omega-9 fatty acid with a 20-carbon chain and a single double bond.
Eicosenoic Acid exists in two main isomeric forms:
*Gondoic acid (11-eicosenoic acid) – found primarily in jojoba oil.
*Paullinic acid (13-eicosenoic acid) – found in guarana seed oil and certain marine and plant oils.
While not as widely known as omega-3 or omega-6 fatty acids, eicosenoic acid contributes to membrane structure, lipid metabolism, and may play a role in skin and cardiovascular health.
Eicosenoic Acid is not considered essential—the body can synthesize it from oleic acid—but dietary sources may provide additional support for lipid balance and anti-inflammatory signaling.
From a safety and regulatory perspective, eicosenoic acid is generally regarded as a low-hazard organic acid.
Overall, eicosenoic acid represents a structurally simple yet chemically informative example of how chain length and degree of unsaturation shape fatty acid behavior.
With growing interest in personalized medicine and precision healthcare, the exploration of novel biomarkers such as 11-Eicosenoic Acid holds promise for enhancing diagnostic accuracy and therapeutic efficacy.
11-Eicosenoic Acid, also known as gondoic acid, is a monounsaturated omega-9 fatty acid with a chain length of 20 carbons and one double bond located at the 11th carbon from the methyl end.
11-Eicosenoic acid is found in various nuts and plant oils.
This type of fatty acid has an aliphatic tail that contains between 13 and 21 carbon atoms.
Eicosenoic acid is not soluble in water and exhibits weak acidity.
Eicosenoic acid is not synthesized by humans but must be obtained through diet.
Elevated levels of 11Z-Eicosenoic acid have been observed in the red blood cell membranes of children with regressive autism.
Otherwise, little research exists on the health benefits or toxicity of eicosenoic acid.
An icosenoic acid in which the double bond is at the 2-3 position and has E configuration.
Eicosenoic acid is a long-chain monounsaturated fatty acid characterized by a twenty-carbon backbone containing a single carbon–carbon double bond and a terminal carboxylic acid group.
This structural simplicity places eicosenoic acid between saturated fatty acids such as eicosanoic acid and more reactive polyunsaturated fatty acids in terms of chemical behavior, stability, and biological function.
The exact location of the double bond defines distinct isomers, which explains why eicosenoic acid is treated as a class rather than a single unique substance.
From a structural chemistry perspective, naturally occurring eicosenoic acids are predominantly found in the cis (Z) configuration, which introduces a bend in the hydrocarbon chain.
This bend reduces molecular packing efficiency, lowers the melting point compared with saturated C20 fatty acids, and enhances fluidity when incorporated into lipid matrices.
Trans isomers, which are far less common in nature, adopt a more linear shape and therefore exhibit higher melting points and different physical behavior.
In biological systems, eicosenoic acid is primarily present as an esterified fatty acyl chain within triglycerides and phospholipids rather than in free form.
Eicosenoic Acid contributes to membrane architecture and energy storage but does not play as direct a signaling role as polyunsaturated C20 fatty acids such as eicosatrienoic or eicosatetraenoic acids.
Nevertheless, its presence influences membrane fluidity, lipid phase behavior, and interactions between lipids and membrane proteins.
Metabolically, eicosenoic acid can be synthesized through elongation of oleic acid (C18:1) by fatty acid elongase enzymes.
Conversely, it can undergo β-oxidation for energy production or be incorporated into complex lipids.
Because Eicosenoic Acid contains only one double bond, it is less susceptible to enzymatic oxygenation and lipid mediator formation compared with polyunsaturated fatty acids.
This relative metabolic inertness contributes to Eicosenoic Acid's stability in biological tissues.
From a physicochemical standpoint, eicosenoic acid exhibits high hydrophobicity and low polarity, dominated by its long hydrocarbon chain.
The single carboxylic acid group confers weak acidity and enables salt formation with alkali metals as well as esterification reactions.
The monoenoic structure makes eicosenoic acid significantly more resistant to oxidative degradation than fatty acids with multiple double bonds, although prolonged exposure to heat, light, or oxygen can still lead to peroxidation at the unsaturated site.
Analytically, eicosenoic acid is commonly identified and quantified using gas chromatography, typically after conversion to its methyl ester.
Because only one double bond is present, chromatographic separation is relatively straightforward compared with polyunsaturated fatty acids, although positional isomers may still require specialized columns or silver-ion chromatography for clear differentiation.
Mass spectrometry provides characteristic fragmentation patterns, while nuclear magnetic resonance spectroscopy can unambiguously confirm double-bond position and geometry.
cis-11-Eicosenoic acid is an omega-9 monounsaturated fatty acid compound identified in many different biological systems.
Monounsaturated fatty acids are of interest due to their effects on metabolism.
In organic chemistry, the presence of a double bond in fatty acids like cis-11-Eicosenoic acid offers points of reactivity that can be exploited in the synthesis of complex molecules, including polymers, surfactants, and other chemically active compounds.
Such monounsaturated fatty acids are studied for their roles in the production of biologically active compounds or as intermediates in the synthesis of industrial materials.
cis-11-Eicosenoic acid is useful as a reference compound for the analysis of fatty acids derived from various biological sources.
Eicosenoic acid C20:1, a monounsaturated fatty acid that exists in three different forms: 9-eicosenoic acid (gadoleic acid), an omega-11 fatty acid common in fish oils, 11-eicosenoic acid (gondoic acid), an omega-9 fatty acid characteristic of jojoba oil, and 13-eicosenoic acid (paullinic acid), an omega-7 fatty acid.
Eicosenoic acid, also known as 11-eicosenoate, 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.
11-Eicosenoic acid is a weakly acidic compound (based on its pKa).
9Z-Eicosenoic acid, also known as gadoleic acid, is a member of the class of compounds known as long-chain fatty acids.
Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
9Z-Eicosenoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa).
9Z-Eicosenoic acid can be found in a number of food items such as lemon, sugar, garlic, and mung bean, which makes 9Z-eicosenoic acid a potential biomarker for the consumption of these food products.
9Z-Eicosenoic acid can be found in feces, blood, and urine.
Eicosenoic acid refers to a group of monounsaturated long-chain fatty acids with the general formula C₂₀H₃₈O₂.
These compounds consist of a 20-carbon backbone with a single carbon–carbon double bond (monoenoic) and a terminal carboxylic acid group.
The position of the double bond distinguishes the different isomers, and this positional difference also affects physical properties, biological roles, and sources.
Common eicosenoic acid isomers include 9-eicosenoic acid (gadoleic acid), 11-eicosenoic acid (gondoic acid), and 13-eicosenoic acid (paullinic acid).
Functional groups: One carboxylic acid (–COOH) and one carbon–carbon double bond (C=C).
Geometry: Can be cis (Z) or trans (E) configuration; natural fatty acids are predominantly cis.
The double bond confers mild unsaturation, making the molecule more reactive than saturated fatty acids but less so than polyunsaturated acids.
Undergoes typical fatty acid oxidation and hydrogenation reactions.
Esterification to form triglycerides or methyl esters is common in analytical and biological contexts.
Eicosenoic acid is generally not commodity chemicals but are important in biological, nutritional, and research contexts.
Biochemical research: Eicosenoic Acid is used as standards in lipid analysis and metabolic studies.
Biological role: Components of natural fats and oils; present in fish oils, plant seed oils, and animal fats in small to moderate quantities.
They are constituents of membranes and energy storage lipids.
Nutritional science: Studied as part of the spectrum of fatty acids in diet and metabolism.
Industrial: Monoenoic fatty acids can be intermediates for surfactants, lubricants, and specialty chemicals when chemically modified (though C20 monounsaturates have limited large-scale industrial use compared with shorter-chain analogs).
Stability: Relatively stable compared to polyunsaturated fatty acids; however, double bond can undergo oxidative degradation if exposed to air and light over time.
Natural occurrence: Found in various plant oils and fish oils; specific isomers can predominate in different species’ lipid profiles.
Biochemical context: Eicosenoic acids integrate into triglycerides and phospholipids in biological membranes.
Eicosenoic acid may refer to one of three closely related chemical compounds: 9-Eicosenoic acid (gadoleic acid), an omega-11 fatty acid (20:1ω11).
11-Eicosenoic acid (gondoic acid), an omega-9 fatty acid (20:1ω9).
13-Eicosenoic acid (paullinic acid), an omega-7 fatty acid (20:1ω7).
11Z-Eicosenoic acid, also known as gondoic acid, is a member of the class of compounds known as long-chain fatty acids.
Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
11Z-Eicosenoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa).
More specifically, 11Z-Eicosenoic acid is a monounsaturated omega-9 fatty acid found in a variety of nuts and plant oils.
It is not produced by humans and comes from the diet.
It has been found in the red blood cell membrane with increased concentrations in children with regressive autism.
(11Z)-icos-11-enoic acid is an icosenoic acid having a cis- double bond at position 11.
It has a role as a plant metabolite and a human metabolite.
It is a conjugate acid of a gondoate.
cis-11-Eicosenoic acid has been reported in Salvia hispanica, Pringlea antiscorbutica, and other organisms with data available.
Eicosenoic Acid is a monounsaturated long-chain fatty acid with a 20-carbon backbone and the sole double bond originating from the 5th, 6th, 7th, 9th, 11th 12th or 15th positions from the methyl end.
USES and APPLICATIONS of EICOSENOIC ACID:
In industrial and applied contexts, eicosenoic acid is not a high-volume commodity chemical but is relevant as a component of natural oils, particularly in certain plant seeds and marine sources.
Eicosenoic Acid can serve as a precursor or intermediate in the synthesis of specialty lipids, surfactants, lubricants, and esters used in cosmetic or technical formulations.
Its moderate oxidative stability makes Eicosenoic Acid more suitable for such applications than highly polyunsaturated fatty acids.
Its balance of stability, hydrophobicity, and biological compatibility explains why Eicosenoic Acid is commonly encountered as a natural lipid component and a reference compound in lipid chemistry, rather than as a highly bioactive or industrially reactive substance.
Eicosenoic Acid is used as standards in lipid analysis and metabolic studies.
Eicosenoic acid is used in biochemical and nutritional research as a reference compound for studying long-chain monounsaturated fatty acids and their metabolic pathways.
Eicosenoic Acid is applied in lipid metabolism studies to understand fatty acid elongation, desaturation, and oxidation processes in animals and plants.
Eicosenoic acid is utilized in the formulation of experimental diets for laboratory animals to evaluate the physiological effects of specific fatty acid profiles.
In the food science field, Eicosenoic Acid is used for analytical calibration and quality control when characterizing oils and fats by chromatographic methods.
Eicosenoic Acid has applications in cosmetic and personal care research, where long-chain fatty acids are evaluated for their emollient properties and skin barrier interactions.
Eicosenoic acid is used as a model compound in oleochemical research to develop and test bio-based lubricants, surfactants, and functional lipids.
In industrial chemistry, Eicosenoic Acid serves as a starting material or intermediate for synthesizing specialty esters and fatty acid derivatives.
Eicosenoic Acid is also applied in plant and agricultural studies to investigate seed oil composition and genetic regulation of fatty acid biosynthesis.
HISTORICAL USE of EICOSENOIC ACID:
Eicosenoic acid itself has no direct historical use in herbal or traditional medicine, as it was identified and studied only in the 20th century, primarily through fatty acid analysis of oils and seeds.
However, Eicosenoic Acid's natural sources—especially jojoba oil—have a long tradition of use:
Jojoba oil was used by Indigenous peoples of the American Southwest for wound healing, skin hydration, and hair care.
Its ability to soothe dry, irritated, or inflamed skin has made Eicosenoic Acid a staple in modern cosmetic and therapeutic skin care.
Guarana, a source of paullinic acid, has been used in Amazonian herbal medicine for energy, cognition, and digestive support, though this use relates more to its caffeine content than its fatty acid profile.
Today, eicosenoic acid is most commonly encountered in natural skin care, dermatological products, and lipid research, where it supports skin health, hydration, and gentle anti-inflammatory effects, particularly in sensitive or dry skin conditions.
BENEFITS AND APPLICATIONS of EICOSENOIC ACID INCLUDE:
*Skin hydration and barrier repair, especially in cosmetic and dermatological products.
*Emollient and anti-inflammatory effects when applied topically.
*Potential cardiovascular support, due to its structural similarity to oleic acid (the main fatty acid in olive oil).
*Use in biomedical applications and biomimetic skin formulations, particularly via jojoba oil, which is chemically similar to human sebum.
EICOSENOIC ACID IS MAINLY OBTAINED FROM:
*Jojoba oil (Simmondsia chinensis) – rich in gondoic acid.
*Guarana (Paullinia cupana) – a natural source of paullinic acid.
*Some fish oils and other seed oils in minor amounts.
ALTERNATIVE PARENTS of EICOSENOIC ACID:
*Unsaturated fatty acids
*Straight chain fatty acids
*Monocarboxylic acids and derivatives
*Carboxylic acids
*Organic oxides
*Hydrocarbon derivatives
*Carbonyl compounds
SUBSTITUENTS of EICOSENOIC 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
PHYSICAL and CHEMICAL PROPERTIES of EICOSENOIC ACID:
General Chemical Formula: C20H38O2
Common Molecular Weight: 310.51 g/mol
Chemical Class: Long-chain monounsaturated fatty acids (fatty acyls, lipid-like compounds)
Selected CAS Numbers (isomer-specific)
cis-9-Eicosenoic acid (Gadoleic acid): 29204-02-2
cis-11-Eicosenoic acid (Gondoic acid): 5561-99-9
cis-5-Eicosenoic acid: 7050-07-9
trans-2-Eicosenoic acid: 109264-21-3
11(E)-Eicosenoic acid (trans): 62322-84-3
(E)-9-Eicosenoic acid variant: 506-31-0
EC Number: There is no single universal EC number assigned to “eicosenoic acid” as a class. Each specific isomer may have distinct registration entries in chemical inventories rather than a common EC listing.
Molecular formula: C20H38O2
Average molecular weight: 310.51 g/mol
Physical state: Generally colorless to light yellow viscous liquid at room temperature (cis-isomers), though some isomers solidify near ambient conditions.
Density: 0.88–0.90 g/cm³
Melting point: 23–24 °C
Boiling point: 420–430 °C
Refractive index: 1.46–1.47
Solubility: Practically insoluble in water; more soluble in organic solvents such as chloroform, methanol, ethanol, and hexane.
pKa: 4.7–4.8
LogP: 8.4–8.8
CAS Numbers (major naturally occurring isomers)
cis-9-Eicosenoic acid (Gadoleic acid, 20:1 n-11)
CAS No.: 29204-02-2
cis-11-Eicosenoic acid (Gondoic acid, 20:1 n-9)
CAS No.: 5561-99-9
cis-13-Eicosenoic acid (Paullinic acid)
CAS No.: 34316-64-8
cis-5-Eicosenoic acid
CAS No.: 7050-07-9
EC (EINECS) Number
EC No.: Not assigned as a single number for “eicosenoic acid” as a class
EC numbers, where available, are isomer-specific and depend on individual REACH/ECHA registrations
Many eicosenoic acid isomers are supplied without a standalone EC number, especially for research use
Molecular formula: C20H38O2
Molecular weight: 310.51 g/mol
Other safety information: No data available
Chemical name: Eicosenoic acid
Chemical class: Monounsaturated fatty acid (C20:1)
Molecular formula: C20H38O2
Molecular weight: 310.51 g/mol
CAS No. (cis-9): 29204-02-2
CAS No. (cis-11): 5561-99-9
CAS No. (cis-13): 34316-64-8
EC number: Not unique / isomer-dependent
Isomeric Smiles: C(C=CCCCCCCCCCC)CCCCCCC(O)=O
InChI: InChI=1S/C20H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h11-12H,2-10,13-19H2,1H3,(H,21,22)/b12-11-
InChIKey: InChIKey=LQJBNNIYVWPHFW-QXMHVHEDSA-N
Chemical Formula: C20H38O2
Average Molecular Weight: 310.5145
Monoisotopic Molecular Weight: 310.28718046
IUPAC Name: (11Z)-icos-11-enoic acid
Traditional Name: cis-11-eicosenoic acid
CAS Registry Number: 5561-99-9
SMILES: CCCCCCCCC=C/CCCCCCCCCC(O)=O
InChI Identifier: InChI=1S/C20H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h9-10H,2-8,11-19H2,1H3,(H,21,22)/b10-9-
InChI Key: BITHHVVYSMSWAG-KTKRTIGZSA-N
Physical state: liquid, clear
Color: colorless
Odor: No data available
Melting point: 23 - 24 °C
Flash point: >113.00 °C - closed cup
Density: 0.883 g/mL at 25 °C
Explosive properties: No data available
Oxidizing properties: No data available
Water Solubility: 5.0e-05 g/L
logP: 8.4
logP: 7.67
logS: -6.8
pKa (Strongest Acidic): 4.95
Physiological Charge: -1
Hydrogen Acceptor Count: 2
Hydrogen Donor Count: 1
Polar Surface Area: 37.3 Ų
Rotatable Bond Count: 17
Refractivity: 96.6 m³•mol⁻¹
Polarizability: 41.89 ų
Number of Rings: 0
Bioavailability: No
Rule of Five: No
Ghose Filter: No
Veber's Rule: No
MDDR-like Rule: No
Chemical Formula: C20H38O2
IUPAC Name: icos-11-enoic acid
InChI Identifier: InChI=1S/C20H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h9-10H,2-8,11-19H2,1H3,(H,21,22)
InChI Key: BITHHVVYSMSWAG-UHFFFAOYSA-N
Isomeric Smiles: CCCCCCCCC=CCCCCCCCCCC(O)=O
Average Molecular Weight: 310.5145
Monoisotopic Molecular Weight: 310.28718046
FIRST AID MEASURES of EICOSENOIC 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 EICOSENOIC 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 EICOSENOIC 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 EICOSENOIC 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 EICOSENOIC ACID:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed.
Dry.
STABILITY and REACTIVITY of EICOSENOIC ACID:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available
