ELAIDIC ACID
Elaidic acid is a colorless solid and its salts and esters are called elaidates.
Elaidic acid is the trans isomer of oleic acid and belongs to the family of trans fats.
Elaidic acid is commonly found in partially hydrogenated vegetable oils and certain processed foods such as margarine, fried foods, and commercially baked goods.
CAS Number: 112-79-8
EC Number: 204-006-6
Chemical Formula: C18H34O2
Molecular Weight: 282.46
Synonyms: Elaidic acid, 112-79-8, trans-9-Octadecenoic acid, trans-Oleic acid, (E)-octadec-9-enoic acid, 9-octadecenoic acid, (E)-Oleic acid, 9-Octadecenoic acid, (E)-, 9-octadecenoic acid, (9E)-, trans-Elaidic acid, trans-Octadec-9-enoic acid, (9E)-octadec-9-enoic acid, Elaidinsaeure, Elaidinsaure, acide elaidique, Elaidinic acid, (9E)-Octadecenoic acid, 9-trans-Octadecenoic acid, Octadec-9-enoic acid, (E)-9-Octadecenoic acid, 9-elaidic acid, trans-.DELTA.9-Octadecenoic acid, D9-trans-Octadecenoic acid, trans-D9-Octadecenoic acid, EINECS 204-006-6, NSC 26988, trans-delta(sup 9)-Octadecenoic acid, 9E-octadecenoic acid, CHEBI:27997, AI3-15840, trans-Delta(9)-octadecenoic acid, UNII-4837010H8C, MFCD00063954, NSC-26988, 9-TRANS-OLEIC ACID, Delta(9)-octadecenoic acid, CHEMBL460657, 4837010H8C, NSC26988, C18:1 N-9T, C18:1, n-9, trans-.delta.(sup 9)-Octadecenoic acid, 18:1, n-9, OLEIC-13C18 ACID, 9-octadecenoicacid, OLEIC ACID (9,10-D2), 9-Octadecenoic acid,(9E)-, cis 9 Octadecenoic Acid, delta9-Octadecenoic acid, Delta(9)-octadecenoate, oleic_acid, 1lfo, EINECS 217-977-6, 9-octadecaenoic Acid, 1fe3, Elaidic acid, ?99%, Elaidic acid (Standard), bmse000643, ELAIDIC ACID [MI], Octadec-9-enoic acid anion, SCHEMBL1139, SCHEMBL6693, WLN: QV8U9-T, trans-delta9-Octadecenoic acid, Fatty Acid 18:1 n-9 trans, DTXSID8058619, CHEBI:36021, Elaidic acid, analytical standard, HMS3649H19, Elaidic acid, >=99.0% (GC), BDBM50250904, CCG-35462, LMFA01030073, s3357, STL282737, Elaidic acid, analytical sample grade, AKOS000278123, DB04224, FS-4659, HY-113016R, NCGC00344330-02, NCGC00344330-03, AC-33773, FE137758, LS-14685, HY-113016, CS-0059361, CS-0368443, NS00070410, O0010, EN300-19543, C01712, D78470, EN300-1697685, A905948, L001099, Q413491, SR-01000946663, SR-01000946663-1, D89C6CAA-1C31-4C71-BD3B-EA155A22E10C, 204-006-6, InChI=1/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9, (9E)-9-Octadecenoic acid, (9E)-9-Octadecensäure, (9E)-Octadec-9-enoic acid, (9E)-Octadecenoic acid, (E)-9-Octadecenoic acid, (E)-Oleic acid, (±)-Propylene glycol, 112-79-8, 1726543, 204-006-6, 9-elaidic acid, 9-Octadecenoic acid, 9-Octadecenoic acid, (9E)-, 9-Octadecenoic acid, (E)-, 9-Octadecenoic acid,(9E)-, 9-trans-Octadecenoic acid, 9E-octadecenoic acid, Acide (9E)-9-octadécénoïque, Acide elaidique, Elaidic Acid, MFCD00063954, octadec-9-enoic acid, trans-9-Octadecenoic acid, trans-Octadec-9-enoic acid, trans-Oleic acid, (9E)octadec-9-enoic acid, (E)-octadec-9-enoic acid, (E)-Palmitoleic acid, (Z)-9-Octadecenoic Acid, 18:1, n-9, 223487-44-3, 287100-82-7, 5711-29-5, 9 Octadecenoic Acid, 9 trans - ácido octadecanoico, 9-Octadecenoate, Acide elaidique, C18:1, n-9, C18:1n-9, Canola Fatty Acid 790, cis 9 Octadecenoic Acid, cis-9-Octadecenoic acid, D9-trans-Octadecenoic acid, EINECS 204-006-6, EINECS 214-309-5, EINECS 217-977-6, ELAIDIC ACID (9tr), elaidic acid(c18:1t), Elaidicacid, Elaidinic acid, Elaidinsaeure, Elaidinsaure, MFCD00064242, octadec-9-enoate, Oleic Acid 213 NF, Oleic Acid 221 NF, Oleic Acid 233 LL, Oleic acid, from tall oil fatty acids, Oleic Acid-13C, Oleic acid-13C18, Oleic Acid-d17, Oleic acid-d2, Oleyl Alcohol, QV8U9-T, trans-D9-Octadecenoic acid, trans-Elaidic acid, trans-Δ(9)-octadecenoic acid, trans-δ(sup 9)-Octadecenoic acid, trans-Δ9-Octadecenoic acid, Δ(9)-octadecenoate, Δ(9)-octadecenoic acid, δ9-Octadecenoic acid
Elaidic acid is a monounsaturated trans fatty acid (trans-9-octadecenoic acid) with the molecular formula C18H34O2.
Elaidic acid is the trans isomer of oleic acid and belongs to the family of trans fats.
Elaidic acid is commonly found in partially hydrogenated vegetable oils and certain processed foods such as margarine, fried foods, and commercially baked goods.
This fatty acid is produced during the industrial hydrogenation process, where unsaturated fats are artificially converted into trans fats to improve shelf life and stability.
Structurally, elaidic acid differs from its cis counterpart, oleic acid, due to the presence of a trans double bond at the ninth carbon position, which results in a more linear conformation.
This structural change significantly impacts Elaidic acid's biological properties and metabolic effects.
Elaidic acid has been widely studied due to its potential health implications.
High intake of trans fats, including elaidic acid, has been linked to increased levels of low-density lipoprotein (LDL) cholesterol and decreased levels of high-density lipoprotein (HDL) cholesterol, contributing to a higher risk of cardiovascular diseases.
Additionally, excessive consumption of trans fats has been associated with inflammation, insulin resistance, and a greater likelihood of developing metabolic disorders such as type 2 diabetes.
Regulatory agencies in various countries have implemented strict policies to limit or ban the use of artificial trans fats in food products to mitigate these health risks.
Despite its negative health effects, elaidic acid is sometimes used as a reference standard in scientific research, particularly in lipid analysis and metabolic studies.
Elaidic acid is also found naturally in small amounts in ruminant fats, such as dairy and meat products from cows, sheep, and goats.
However, the levels of trans fats in these natural sources are significantly lower than those found in industrially processed foods.
Ongoing research continues to explore the biological functions and metabolic pathways of elaidic acid to further understand its role in human health and disease.
Elaidic acid is a chemical compound with the formula C18H34O2, specifically the fatty acid with structural formula HOOC−(CH2)7−CH=CH−(CH2)7−CH3, with the double bond (between carbon atoms 9 and 10) in trans configuration.
Elaidic acid is a colorless solid.
Elaidic acid's salts and esters are called elaidates.
Elaidic acid is an unsaturated trans fatty acid, with code C18:1 trans-9.
Elaidic acid has attracted attention because it is a major trans fat found in hydrogenated vegetable oils, and trans fats have been implicated in heart disease.
Elaidic acid is the trans isomer of oleic acid.
The name of the elaidinization reaction comes from elaidic acid.
Elaidic acid's name comes from the Ancient Greek word ἔλαιον (elaion), meaning oil.
Elaidic acid is a 9-octadecenoic acid and the trans-isomer of oleic acid.
Elaidic acid has a role as a food component.
Elaidic acid is a conjugate acid of an elaidate and an Octadec-9-enoic acid anion.
Elaidic acid derives from a hydride of a trans-octadec-9-ene.
In human platelets incubated with arachidonic acid, elaidic acid inhibits HHT and HETE formation while inducing prostaglandin and thromboxane synthesis.
Elaidic acid, a transdiomer of oleic acid, is an unsaturated fatty acid.
In its pure state, Elaidic acid is a colorless, oily liquid that is barely soluble in water and oxidizes easily in air, turning into a yellowish liquid and smelling rancid.
Salts of oleic acid are called oleates.
Oleic acid dissolves well in methyl alcohol, ethyl alcohol, diethyl ether and fatty and essential oils.
Stearic acid is obtained from oleic acid during fat hardening.
Oleic acid is the most important unsaturated, essential fatty acid in food.
Elaidic acid is found in olive oil and sunflower oil.
There is a cis-trans isomerism with elaidic acid.
In cosmetic products, oleic acid serves as an acid component of emulsifiers.
Elaidic 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.
Elaidic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Elaidic acid is the major trans fat found in hydrogenated vegetable oils and occurs in small amounts in caprine and bovine milk (very roughly 0.1 % of the fatty acids) and some meats.
Elaidic acid is the trans isomer of oleic acid.
The name of the elaidinization reaction comes from elaidic acid.
Elaidic acid increases CETP activity, which in turn raises VLDL and lowers HDL cholesterol.
Elaidic acid is the 9-trans isomer of oleic acid.
Elaidic acid is a monounsaturated trans-fatty acid, which can be found in partially hydrogenated cooking oils.
Elaidic acid was revealed, that elaidic acid inhibits HHT and HETE formation in human platelets incubated with arachidonic acid.
Also was shown, that trans oleic acid increased plasma CETP activity, which increases low-density lipoprotein (LDL) cholesterol and decreases high-density lipoprotein (HDL).
Elaidic acid is the major trans fat found in hydrogenated vegetable oils and can be used as a pharmaceutical solvent.
Elaidic acid is a trans-unsaturated fatty acid.
In vitro investigations have been undertaken to delve into Elaidic acid's impact on cell proliferation, apoptosis, and gene expression.
Researchers have discovered that elaidic acid acts as an agonist for the peroxisome proliferator-activated receptor gamma (PPARγ), a nuclear receptor responsible for regulating lipid and glucose metabolism.
Additionally, elaidic acid has been found to act as an agonist for the PPARα receptor.
Elaidic acid is a monounsaturated trans fatty acid, specifically trans-9-octadecenoic acid, with the molecular formula C18H34O2.
Elaidic acid is the trans isomer of oleic acid, meaning that while both share the same chemical composition, they differ in the spatial configuration of their double bond.
Unlike oleic acid, which has a naturally occurring cis configuration, elaidic acid possesses a trans configuration at the ninth carbon.
This structural difference results in elaidic acid adopting a more linear shape, as opposed to the bent structure of oleic acid.
This seemingly small molecular variation significantly affects Elaidic acid's physical properties, metabolic pathways, and biological effects.
The linear structure of elaidic acid allows it to behave more like saturated fats, leading to potential health concerns when consumed in large amounts.
Elaidic acid is most commonly found in partially hydrogenated vegetable oils, which were historically used in the food industry due to their ability to extend the shelf life and stability of food products.
The process of hydrogenation involves the addition of hydrogen atoms to unsaturated fatty acids, converting some cis double bonds into trans double bonds.
This industrial process was widely employed in the production of margarine, shortenings, fried foods, and various baked goods such as cookies, crackers, and pastries.
The stability and resistance to oxidation of trans fats like elaidic acid made them an attractive alternative to natural fats, particularly in processed and fast foods.
Despite its widespread use in the food industry, elaidic acid and other trans fatty acids have been heavily scrutinized due to their adverse health effects.
Research has shown that trans fats contribute to cardiovascular diseases by increasing levels of low-density lipoprotein (LDL) cholesterol, often referred to as "bad cholesterol," while simultaneously reducing levels of high-density lipoprotein (HDL) cholesterol, the "good cholesterol."
This imbalance in cholesterol levels leads to an increased risk of atherosclerosis, which is the buildup of fatty deposits in the arteries, potentially resulting in heart attacks and strokes.
In addition to cardiovascular issues, high consumption of trans fats has been associated with increased systemic inflammation, insulin resistance, and a higher likelihood of developing metabolic disorders such as type 2 diabetes.
Some studies have also suggested that trans fats may play a role in obesity, non-alcoholic fatty liver disease, and even cognitive decline, although more research is needed in these areas.
Due to these significant health risks, regulatory agencies and health organizations worldwide have taken steps to reduce or eliminate artificial trans fats from the food supply.
The World Health Organization (WHO) has called for a global elimination of industrially produced trans fats, recommending policies that limit their use in food manufacturing.
Many countries, including the United States, Canada, and members of the European Union, have imposed strict regulations or outright bans on partially hydrogenated oils, which are the primary source of elaidic acid in processed foods.
These regulations have led to a significant decline in trans fat consumption in many regions, reducing the prevalence of trans fat-related health issues.
While industrial sources of elaidic acid are being phased out, it is important to note that small amounts of trans fats occur naturally in certain foods.
Ruminant animals, such as cows, sheep, and goats, produce small quantities of trans fats, including elaidic acid, through bacterial fermentation in their digestive systems.
As a result, dairy products, beef, and lamb contain trace amounts of naturally occurring trans fatty acids.
However, studies suggest that these naturally occurring trans fats do not have the same harmful health effects as their industrially produced counterparts.
The differences in how these trans fats are metabolized in the body may account for the variations in their impact on health.
Beyond its presence in food, elaidic acid is also used in scientific research, particularly in lipid metabolism studies and analytical chemistry.
Researchers use Elaidic acid as a reference standard when analyzing fatty acid compositions in various biological samples.
Elaidic acid's distinct structural properties make it useful for investigating the effects of trans fats on cell membranes, lipid signaling pathways, and metabolic processes.
Some studies have explored the impact of elaidic acid on gene expression related to inflammation and lipid metabolism, further deepening our understanding of how trans fats influence human health at the molecular level.
In conclusion, elaidic acid is a notable trans fatty acid that has played a significant role in the food industry and public health discourse.
While Elaidic acid's stability and extended shelf life made it a popular ingredient in processed foods, its negative health effects have led to widespread regulatory action aimed at eliminating artificial trans fats from diets worldwide.
Continued research into Elaidic acid's biological effects and metabolic pathways will further inform public health policies and nutritional recommendations.
As awareness of the dangers of trans fats grows, efforts to replace them with healthier alternatives continue, paving the way for improved dietary standards and overall public health outcomes.
Market Overview of Elaidic Acid:
Elaidic acid, a monounsaturated trans fatty acid (trans-9-octadecenoic acid), has historically played a significant role in the food industry due to its stability and resistance to oxidation.
Elaidic acid is primarily found in partially hydrogenated vegetable oils, which have been widely used in margarine, baked goods, fried foods, and various processed food products.
However, increasing awareness of the negative health effects associated with trans fats, including elevated risks of cardiovascular disease, inflammation, and metabolic disorders, has led to global regulatory restrictions aimed at reducing or eliminating artificial trans fats from the food supply.
As a result, the market for elaidic acid has undergone a drastic transformation, shifting from widespread industrial use to a more niche market focused on scientific research and analytical applications.
The global market for elaidic acid is significantly influenced by strict food safety regulations, particularly in developed regions such as North America and Europe, where governmental agencies like the U.S. Food and Drug Administration (FDA) and the European Food Safety Authority (EFSA) have banned or limited the use of artificial trans fats.
In response, food manufacturers have reformulated products to remove trans fats and replace them with healthier alternatives, such as high-oleic vegetable oils, fully hydrogenated oils, and other lipid substitutes.
This shift has dramatically reduced the demand for industrially produced elaidic acid, making Elaidic acid less relevant in the commercial food sector.
However, despite these regulations, small amounts of elaidic acid still occur naturally in dairy products and ruminant meat, though these sources contain significantly lower levels compared to industrially produced trans fats.
While the demand for elaidic acid in food applications continues to decline, the compound maintains a role in the scientific research sector.
Elaidic acid is commonly used as a reference standard in lipid analysis, biochemical research, and metabolic studies.
Researchers utilize elaidic acid to study the effects of trans fats on lipid metabolism, cholesterol regulation, and inflammatory pathways, furthering our understanding of how these compounds influence human health.
In addition, Elaidic acid's distinct molecular structure makes Elaidic acid a valuable tool for exploring the differences in biological impact between trans and cis fatty acids, particularly in relation to their influence on cell membrane integrity and function.
Despite its declining commercial viability, elaidic acid remains relevant in laboratory settings, where it contributes to ongoing studies in nutrition and health sciences.
The regional dynamics of the elaidic acid market vary depending on the regulatory landscape and consumer awareness.
In North America and Europe, where trans fat bans have been fully implemented, the use of industrial elaidic acid has been virtually eliminated.
However, in regions such as Asia-Pacific, Latin America, and parts of Africa, where trans fat regulations are still evolving or not as strictly enforced, there remains some demand for partially hydrogenated oils, albeit at decreasing rates.
Governments in these regions are beginning to implement policies that align with the World Health Organization’s (WHO) global initiative to eliminate industrially produced trans fats by 2023, which is expected to further reduce market opportunities for elaidic acid in food production.
As more countries adopt these health-driven regulations, the global landscape of elaidic acid will continue shifting toward non-food applications, primarily within scientific research.
Despite its declining role in food manufacturing, the market for elaidic acid is not entirely disappearing.
The pharmaceutical industry, for instance, has shown interest in studying the metabolic effects of trans fatty acids, and ongoing research continues to explore their role in conditions such as diabetes, obesity, and neurodegenerative diseases.
While elaidic acid itself is not used as a therapeutic compound, its presence in laboratory research helps inform future nutritional guidelines and public health recommendations.
Additionally, as the field of lipidomics expands, researchers are investigating novel lipid profiles and their potential applications in medicine, further sustaining the need for elaidic acid in controlled experimental settings.
Looking ahead, the future of the elaidic acid market appears to be one of continued decline in commercial food applications but stable relevance in the realm of scientific research.
With regulatory bodies enforcing stricter trans fat bans, manufacturers are innovating new fat substitutes to replace partially hydrogenated oils, further reducing the need for industrial elaidic acid.
Meanwhile, ongoing studies into lipid metabolism and the health effects of trans fats ensure that elaidic acid remains a subject of scientific interest.
As consumer awareness grows and global food standards evolve, the presence of trans fats, including elaidic acid, in the human diet is expected to diminish further, making its market primarily focused on academic and clinical research rather than commercial production.
Uses of Elaidic Acid:
Elaidic acid is the 9-trans isomer of oleic acid.
Elaidic acid is a monounsaturated trans-fatty acid which can be found in partially hydrogenated cooking oils.
In human platelets incubated with arachidonic acid, elaidic acid inhibits HHT and HETE formation while inducing prostaglandin and thromboxane synthesis.
Elaidic acid is the major trans fat found in hydrogenated vegetable oils.
Elaidic acid increases CETP activity, which in turn raises VLDL and lowers HDL cholesterol.
Elaidic acid has historically been used in various industries, primarily in food production, scientific research, and biochemical studies.
In the past, Elaidic acid was a key component of partially hydrogenated vegetable oils, which were widely used in margarine, baked goods, fried foods, and processed snacks due to their stability and long shelf life.
However, as research revealed the harmful effects of trans fats, including increased LDL cholesterol and heightened risks of cardiovascular disease, regulatory bodies worldwide imposed strict restrictions, leading to a significant decline in its use in food production.
Despite this, elaidic acid continues to be utilized in scientific research, particularly in lipid metabolism studies, where it serves as a reference compound for analyzing the impact of trans fats on human health.
Elaidic acid is also used in cell membrane studies to examine how trans fats affect membrane fluidity and function.
Additionally, elaidic acid plays a role in analytical chemistry, where it is employed as a standard for lipid profiling and chromatography in food and biological samples.
While industrial applications of elaidic acid have largely disappeared, it remains naturally present in small amounts in dairy and ruminant meat products, though these natural trans fats are considered less harmful than their industrially produced counterparts.
Moving forward, Elaidic acid's relevance is expected to remain primarily in research and biochemical studies rather than commercial food production.
Elaidic acid, a trans isomer of oleic acid, has historically been utilized in various industries, primarily in food production, scientific research, and biochemical studies.
However, due to increasing health concerns and regulatory restrictions, Elaidic acid's applications have shifted away from commercial food production toward more specialized uses in research and lipid analysis. Below are the primary uses of elaidic acid:
Food Industry (Declining Use):
Previously Used in Processed Foods:
Elaidic acid was a major component of partially hydrogenated vegetable oils, which were used in margarine, baked goods, fried foods, and packaged snacks.
These oils provided stability, extended shelf life, and improved texture in food products.
Replacement of Natural Fats:
Elaidic acid was used as a cheaper alternative to natural saturated fats, enhancing the consistency of food products.
Decline Due to Health Risks:
Due to Elaidic acid's association with increased LDL cholesterol and cardiovascular disease, regulatory agencies have restricted its use, leading to a significant decline in its application in the food industry.
Scientific Research & Biochemical Studies:
Lipid Metabolism Research:
Elaidic acid is used as a reference compound in lipid metabolism studies to understand how trans fats affect the human body.
Researchers analyze Elaidic acid's impact on cholesterol levels, insulin resistance, and inflammatory markers.
Cell Membrane Studies:
Elaidic acid's structural differences from cis fatty acids make it useful for studying how trans fats alter cell membrane fluidity, permeability, and function.
Nutritional & Medical Studies:
Scientists use elaidic acid to examine its effects on diseases such as cardiovascular disorders, obesity, diabetes, and neurodegenerative conditions.
Chemical & Industrial Applications:
Analytical Standards:
Elaidic acid is used in chromatography and lipid analysis as a chemical standard to identify and quantify trans fatty acids in food and biological samples.
Fatty Acid Profiling:
In biochemical assays, elaidic acid helps determine fatty acid composition in various substances, including food, biological tissues, and environmental samples.
Industrial Lubricants & Surfactants:
While not a primary use, some fatty acids, including elaidic acid derivatives, have been explored for applications in lubricants, emulsifiers, and surfactants in chemical manufacturing.
Presence in Natural Products:
Naturally Occurring in Animal Products:
Elaidic acid is found in small amounts in dairy products, beef, and lamb due to bacterial fermentation in ruminant animals.
These natural trans fats are perceived as less harmful compared to industrially produced trans fats.
Future Trends in Use:
With the global phase-out of artificial trans fats, the primary uses of elaidic acid have shifted toward scientific research and biochemical applications.
Elaidic acid's role in food production has largely diminished due to regulatory bans, while its importance in lipid studies remains steady.
Ongoing research into lipid metabolism, cardiovascular health, and alternative fat sources may continue to utilize elaidic acid for controlled experimental studies.
Potential Benefits of Elaidic Acid:
While elaidic acid is primarily known for its negative health effects, particularly its role in increasing the risk of cardiovascular diseases, it has some limited benefits in specific contexts, particularly in research and biochemical studies.
Below are some potential benefits associated with elaidic acid:
Role in Scientific Research and Biochemical Studies:
Elaidic acid serves as a valuable tool in lipid metabolism research, helping scientists understand how trans fats affect human health.
Elaidic acid is used in studies on cholesterol metabolism, insulin resistance, and inflammation, contributing to broader nutritional and medical research.
By analyzing Elaidic acid's effects, researchers can develop better dietary guidelines and explore healthier fat alternatives.
Use in Analytical Chemistry:
Elaidic acid is commonly used as a chemical reference in chromatography and lipid profiling.
Elaidic acid helps scientists identify and quantify trans fatty acids in food, biological tissues, and environmental samples, improving food safety and quality control measures.
This contributes to public health efforts by ensuring accurate monitoring of trans fat levels in food products.
Stability in Industrial Applications (Historical Use):
In the past, elaidic acid was valued in the food industry for its stability, resistance to oxidation, and ability to extend the shelf life of processed foods.
Elaidic acid was widely used in margarine, baked goods, and frying oils due to its ability to enhance texture and consistency.
However, this benefit has been outweighed by Elaidic acid's adverse health effects, leading to regulatory restrictions and a decline in its use.
Naturally Occurring in Ruminant Products:
Small amounts of elaidic acid occur naturally in dairy products and meat from ruminant animals, where it is considered less harmful than industrial trans fats.
Unlike artificially produced trans fats, which are linked to severe health risks, naturally occurring trans fats may have a different metabolic effect and do not appear to be as strongly associated with cardiovascular diseases.
Although elaidic acid has been largely phased out of food production due to its negative health effects, it remains an important compound in scientific research, analytical chemistry, and lipid metabolism studies.
Elaidic acid's role in helping researchers understand the impact of trans fats on human health is one of its most significant contributions, leading to better dietary recommendations and regulatory policies.
However, in terms of direct health benefits, elaidic acid has limited advantages, and its consumption is generally discouraged.
Occurrence and Bioactivity of Elaidic Acid:
Elaidic acid occurs mostly in industrial hydrogenation of polyunsaturated fatty acids.
It's also present in small amounts in caprine and bovine milk (very roughly 0.1% of the fatty acids) and in some meats.
Elaidic acid increases plasma cholesterylester transfer protein (CETP) activity which lowers HDL cholesterol.
Pharmacology and Biochemistry of Elaidic Acid:
Human Metabolite Information:
Tissue Locations:
Adipose Tissue
Fibroblasts
Cellular Locations:
Cytoplasm
Extracellular
Membrane
Production of Elaidic Acid:
Elaidic acid is primarily produced through the partial hydrogenation of vegetable oils, a process that alters the structure of unsaturated fatty acids by converting some naturally occurring cis bonds into trans bonds.
This method, historically used in the food industry, involves heating vegetable oils such as soybean or sunflower oil and introducing hydrogen gas in the presence of a metal catalyst like nickel.
The result is a more stable fat with improved texture and shelf life, making Elaidic acid suitable for processed foods like margarine and baked goods.
However, due to the well-documented health risks associated with trans fats, the industrial production of elaidic acid has significantly declined, with many countries banning or restricting its use.
Despite this, elaidic acid still occurs naturally in small amounts in dairy products and meat from ruminant animals, where it is formed through microbial biohydrogenation in the stomach.
Additionally, elaidic acid can be synthesized in laboratory settings for scientific research, particularly in lipid metabolism studies.
While Elaidic acid's industrial significance has diminished, its role in biochemical research remains relevant for understanding the impact of trans fats on human health.
Synthesis of Elaidic Acid:
The synthesis of elaidic acid primarily involves the isomerization of oleic acid, a naturally occurring cis monounsaturated fatty acid, into its trans form.
This transformation can be achieved through chemical or catalytic processes.
While elaidic acid was historically produced as a byproduct of partial hydrogenation in the food industry, modern synthesis is primarily conducted for research and analytical applications.
Isomerization of Oleic Acid:
Elaidic acid can be synthesized in the laboratory by chemically altering oleic acid (cis-9-octadecenoic acid) into its trans isomer.
The key steps include:
Selection of Substrate:
Oleic acid, derived from vegetable oils, serves as the starting material.
Catalytic Isomerization:
The conversion of the cis double bond to a trans configuration is facilitated using metal catalysts such as palladium, rhodium, or iodine-based reagents.
Heat Treatment:
Controlled heating in the presence of catalysts accelerates the isomerization process, yielding elaidic acid.
Partial Hydrogenation (Historical Method):
In the past, elaidic acid was produced as a byproduct during the partial hydrogenation of unsaturated fats, where controlled hydrogenation resulted in the conversion of some cis double bonds to trans without fully saturating the molecule.
This method was widely used in the food industry but has been largely discontinued due to health concerns and regulatory restrictions.
Laboratory Synthesis for Research:
Elaidic acid is synthesized in controlled laboratory settings for use as a reference standard in lipid metabolism studies, trans fat analysis, and biochemical research.
High-purity elaidic acid can be obtained through chemical synthesis or extraction and purification from naturally occurring sources.
With the decline of industrial trans fat production, the synthesis of elaidic acid is now primarily limited to scientific applications, where it remains an essential compound in lipid research and analytical studies.
History of Elaidic Acid:
Elaidic acid's history is closely tied to the development of the hydrogenation process in the early 20th century, which allowed the transformation of liquid vegetable oils into solid fats.
This process, while increasing the shelf life and stability of oils, also produced trans fats, including elaidic acid, as byproducts.
By the mid-1900s, elaidic acid was widely used in processed foods such as margarine, shortening, and baked goods, due to its cost-effectiveness and desirable properties like extended shelf life and improved texture.
However, as research began to link trans fats to increased risks of cardiovascular disease, diabetes, and other health issues, public awareness grew, and regulatory bodies began implementing restrictions.
The U.S. Food and Drug Administration (FDA) banned partially hydrogenated oils in 2015, leading to a sharp decline in the use of elaidic acid in food production.
Today, elaidic acid is no longer widely used in the food industry but continues to play a role in scientific research, particularly in studies related to lipid metabolism and the effects of trans fats on human health.
Handling and Storage of Elaidic Acid:
Handling:
Elaidic acid should be handled with care in a well-ventilated area.
Avoid contact with skin, eyes, and clothing.
Elaidic acid should be stored in tightly sealed containers to prevent contamination.
Use proper safety equipment, including gloves and eye protection, when handling Elaidic acid.
Storage:
Store elaidic acid in a cool, dry, and well-ventilated area away from direct sunlight, moisture, and heat sources.
Elaidic acid should be kept in a container made of materials compatible with fatty acids, such as stainless steel or certain plastics.
Ensure containers are tightly sealed to avoid exposure to air and moisture, which may affect the quality of the substance.
Stability and Reactivity of Elaidic Acid:
Stability:
Elaidic acid is stable under normal handling and storage conditions.
However, Elaidic acid may undergo slow oxidation over time when exposed to air and light, especially if stored improperly.
Reactivity:
Elaidic acid is chemically stable but may react with strong oxidizing agents, such as concentrated hydrogen peroxide and potassium permanganate, which could lead to decomposition.
Avoid contact with these and other reactive substances to prevent dangerous reactions.
Decomposition Products:
Decomposition of elaidic acid can release toxic fumes, including carbon oxides and other volatile compounds.
First Aid Measures of Elaidic Acid:
Inhalation:
If inhaled, move the affected person to fresh air immediately.
If symptoms like coughing or difficulty breathing occur, seek medical attention.
Skin Contact:
In case of skin contact, wash the affected area thoroughly with soap and water.
Remove contaminated clothing.
If irritation persists, seek medical attention.
Eye Contact:
In case of eye contact, rinse the eyes immediately with plenty of water for at least 15 minutes, ensuring that the eyelids are lifted to wash underneath.
Seek medical attention if irritation persists.
Ingestion:
If ingested, do not induce vomiting unless directed by medical personnel.
Rinse the mouth with water and seek medical advice immediately.
Fire Fighting Measures of Elaidic Acid:
Suitable Extinguishing Media:
Use dry chemical powder, foam, or carbon dioxide (CO2) to extinguish fires involving elaidic acid.
Unsuitable Extinguishing Media:
Avoid using water directly on fires involving elaidic acid, as Elaidic acid may spread the fire or cause an exothermic reaction.
Special Fire Fighting Procedures:
Firefighters should wear self-contained breathing apparatus (SCBA) and protective clothing to avoid inhalation of toxic fumes and skin contact with hot substances.
In case of large fires, cool containers with water spray to prevent rupture.
Hazardous Combustion Products:
Burning elaidic acid may produce smoke, carbon monoxide, carbon dioxide, and other hazardous decomposition products.
Accidental Release Measures of Elaidic Acid:
Personal Precautions:
Wear appropriate personal protective equipment (PPE) such as gloves, safety goggles, and a lab coat when handling spills.
Ensure adequate ventilation in the affected area.
Environmental Precautions:
Prevent the release of elaidic acid into waterways, soil, or drains.
If large quantities are spilled, contact emergency response teams immediately.
Methods for Containment and Cleanup:
For small spills, absorb the liquid with inert material like sand, vermiculite, or absorbent pads and dispose of Elaidic acid properly.
For larger spills, contain the spill with dikes or barriers to prevent Elaidic acid from spreading and clean up using mechanical means, such as a vacuum or absorbent material.
Dispose of waste in accordance with local regulations.
Exposure Controls / Personal Protective Equipment of Elaidic Acid:
Exposure Limits:
There are no specific exposure limits for elaidic acid in most regions.
However, Elaidic acid is recommended to limit exposure to the skin, eyes, and inhalation as a precaution.
Ventilation:
Use adequate ventilation in the workspace to avoid inhalation of fumes, vapors, or dust from elaidic acid.
Personal Protective Equipment (PPE):
Eye Protection:
Wear safety goggles or face shields to prevent eye contact.
Skin Protection:
Use gloves made of chemical-resistant material (e.g., nitrile or neoprene) and wear protective clothing to prevent skin contact.
Respiratory Protection:
If ventilation is inadequate or there is a risk of inhalation, use an approved respirator equipped with a chemical filter.
Other Protective Measures:
Ensure that workers have access to safety showers and eyewash stations in case of accidental exposure.
Identifiers of Elaidic Acid:
CAS Number: 112-79-8
ChEBI: CHEBI:27997
ChEMBL: ChEMBL460657
ChemSpider: 553123
DrugBank: DB04224
ECHA InfoCard: 100.003.642
KEGG: C01712
PubChem CID: 637517
UNII: 4837010H8C
CompTox Dashboard (EPA): DTXSID8058619
InChI: InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9+
Key: ZQPPMHVWECSIRJ-MDZDMXLPSA-N
InChI=1/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9+
Key: ZQPPMHVWECSIRJ-MDZDMXLPBT
SMILES: O=C(O)CCCCCCC/C=C/CCCCCCCC
Linear Formula: CH3(CH2)7CH=CH(CH2)7COOH
CAS Number: 112-79-8
Molecular Weight: 282.46
Beilstein: 1726543
EC Number: 204-006-6
MDL number: MFCD00063954
UNSPSC Code: 12352211
PubChem Substance ID: 24894568
NACRES: NA.25
Properties of Elaidic Acid:
Chemical formula: C18H34O2
Molar mass: 282.46 g/mol
Appearance: colorless waxy solid
Density: 0.8734 g/cm3
Melting point: 45 °C (113 °F)
Magnetic susceptibility (χ): −204.8·10−6 cm3/mol
Molecular Weight: 282.5 g/mol
XLogP3: 6.5
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 15
Exact Mass: 282.255880323 Da
Monoisotopic Mass: 282.255880323 Da
Topological Polar Surface Area: 37.3 Ų
Heavy Atom Count: 20
Complexity: 234
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 1
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
biological source: semisynthetic
Quality Level: 200
Assay: ≥99.0% (GC)
form: powder
bp: 288 °C/100 mmHg (lit.)
mp: 42-44 °C (lit.)
functional group: oleic acid
lipid type: unsaturated FAs
shipped in: ambient
storage temp.: −20°C
SMILES string: CCCCCCCC\C=C\CCCCCCCC(O)=O
InChI: 1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9+
InChI key: ZQPPMHVWECSIRJ-MDZDMXLPSA-N
Names of Elaidic Acid:
IUPAC name:
(E)-octadec-9-enoic acid
Other names:
(E)-9-octadecenoic acid
(9E)-octadecenoic acid
trans-9-octadecenoic acid
18:1 trans-9
C18:1 trans-9
MeSH Entry Terms of Elaidic Acid:
elaidate
elaidic acid
elaidic acid, 1-(14)C-labeled, (E)-isomer
elaidic acid, 10-(14)C-labeled, (E)-isomer
elaidic acid, 14C-labeled, (E)-isomer
elaidic acid, 9-(14)C-labeled
elaidic acid, potassium salt, (E)-isomer
elaidic acid, sodium salt, (E)-isomer
