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DESCRIPTION
Lauric acid is a saturated fatty acid with a 12-carbon backbone, commonly found in coconut oil, palm kernel oil, and in smaller amounts in other animal fats and milk.
Its chemical formula is C12H24O2, and it is known for its antimicrobial properties, which is why it is often used in soaps and cosmetic products.
Cas Number
143-07-7
Synonyms
Dodecanoic acid,1-Dodecanoic acid, Decyl acetic acid,Dodecylic acid,N-dodecanoic acid
Lauric acid (C12H24O2), a medium-chain fatty acid (MCFA), is a saturated fat commonly found in natural oils like coconut oil and palm kernel oil.
It has a significant presence in both food and industrial products due to its unique properties.
It is often cited for its health benefits, antimicrobial effects, and versatility in various chemical applications. In the scientific community, Lauric acid is of interest due to its ability to influence metabolic processes, fight infections, and support the body's immune system.
Chemical Properties
Molecular Structure and Chemical Composition
Lauric acid is a straight-chain saturated fatty acid composed of a 12-carbon chain with a carboxyl group (-COOH) at one end.
Its chemical formula is C12H24O2, and it has a molecular weight of approximately 200.32 g/mol.
The presence of a carboxyl group allows Lauric acid to form esters with alcohols and glycerol, contributing to its role in various industrial applications.
Physical Properties
Melting point: Lauric acid has a melting point of approximately 44.2°C, making it solid at room temperature.
Boiling point: The boiling point is around 249°C under normal pressure.
Solubility: Lauric acid is soluble in organic solvents like ethanol, chloroform, and ether, but it has limited solubility in water.
Chemical Reactivity
Lauric acid undergoes typical reactions for fatty acids, such as:
Oxidation: It can be oxidized into aldehydes, ketones, and acids under certain conditions, though it is relatively stable compared to unsaturated fatty acids.
Esterification: It readily forms esters with alcohols to produce biodiesel, soaps, and other chemicals.
Decarboxylation: Lauric acid can undergo decarboxylation under extreme conditions, particularly when subjected to high temperatures or in the presence of a catalyst.
Natural Sources of Lauric Acid
Coconut Oil and Palm Kernel Oil
Lauric acid makes up about 45-50% of the total fatty acids in coconut oil and palm kernel oil. These oils are considered the primary sources of Lauric acid due to their high concentrations of this fatty acid.
Other Natural Sources
Breast milk: Lauric acid is naturally present in human breast milk, contributing to the health of infants, particularly in terms of immune defense and energy provision.
Dairy products: It is found in small quantities in dairy fats, especially in the milk of ruminants.
Other plants: While coconut and palm oil are the primary sources, Lauric acid can also be extracted from smaller quantities of other plant oils.
Extraction Methods
The most common methods for extracting Lauric acid from coconut and palm kernel oil involve:
Hydrolysis: The oils are subjected to hydrolysis, breaking down triglycerides into their constituent fatty acids.
Fractionation: This involves separating Lauric acid from other fatty acids by distillation or crystallization.
Supercritical CO2 extraction: A more advanced and eco-friendly method to extract oils at lower temperatures.
Biosynthesis of Lauric Acid
Biosynthesis in Plants
In plants, Lauric acid is produced as part of the fatty acid biosynthesis pathway.
Acetyl-CoA is the precursor molecule for the synthesis of longer-chain fatty acids.
The acetyl-CoA carboxylase enzyme plays a role in the elongation process, leading to the formation of Lauric acid as one of the primary products.
Biosynthesis in Animals
In animals, Lauric acid is synthesized from other saturated fatty acids via a process involving fatty acid synthase (FAS) and acyl-CoA dehydrogenase.
The majority of Lauric acid found in the body originates from dietary intake, as mammals, including humans, cannot produce it in significant quantities from scratch.
Fatty Acid Biosynthesis Pathways
The fatty acid synthesis pathway starts with acetyl-CoA, which is then converted to malonyl-CoA.
The malonyl-CoA is used in the Fatty Acid Synthase complex, where a chain of reactions elongates the carbon chain by two carbon units at a time.
Lauric acid, having 12 carbon atoms, is a medium-chain fatty acid compared to others like stearic acid (18 carbons).
Biological Activity and Health Benefits
Antimicrobial Properties
One of Lauric acid's most well-known characteristics is its antimicrobial activity.
Upon entering the body, Lauric acid is converted into monolaurin, a compound that has been shown to effectively combat viruses, bacteria, and fungi.
It has been found to exhibit strong activity against pathogens like Staphylococcus aureus, Candida albicans, and herpes simplex virus (HSV).
Effects on Cholesterol and Cardiovascular Health
Research indicates that Lauric acid, unlike other saturated fats, may increase HDL cholesterol (good cholesterol) without significantly raising LDL cholesterol (bad cholesterol).
This suggests a potentially beneficial role in cardiovascular health.
However, studies are mixed, and the impact on long-term heart health is still debated.
Role in Metabolic Processes
Lauric acid is metabolized more rapidly than long-chain fatty acids, providing a quicker source of energy.
It has been proposed that medium-chain fatty acids like Lauric acid can support weight management by enhancing fat oxidation and increasing thermogenesis.
Impact on Immune System
Lauric acid and its derivative, monolaurin, support the immune system by exhibiting antiviral, antibacterial, and antifungal properties.
Studies have shown that Lauric acid supplementation can reduce inflammation, support gut health, and strengthen the immune system's defenses against various pathogens.
Industrial Applications of Lauric Acid
Soaps and Cosmetics
Lauric acid is a key ingredient in the production of soaps due to its ability to form lather and act as a surfactant.
It is also used in the production of shampoos, conditioners, and skin creams, where its antimicrobial and emulsifying properties provide added benefits.
Food and Beverages
Lauric acid is often included in food products, particularly in coconut oil, due to its stability at high temperatures.
It is used in margarine, processed foods, and confectionery. In addition, Lauric acid and its derivatives can be used in flavoring agents and food preservatives.
Biodiesel Production
Lauric acid is a precursor in the production of biodiesel through esterification reactions, where it reacts with methanol or ethanol.
Its shorter carbon chain length compared to long-chain fatty acids makes Lauric acid an attractive feedstock for biodiesel production.
Pharmaceuticals and Detergents
In the pharmaceutical industry, Lauric acid serves as a component of certain topical ointments and antiseptic products.
It is also used in the production of industrial detergents, where its emulsifying and foaming properties come into play.
Lauric Acid and Human Health
Relationship with Metabolic Syndrome and Obesity
Although Lauric acid has been linked to several health benefits, there is some concern about its role in metabolic syndrome and obesity.
Excessive consumption of Lauric acid could contribute to fat deposition and lead to insulin resistance in some individuals.
However, it is thought to be less problematic than other saturated fats, especially when consumed as part of a balanced diet.
Impact on the Gut Microbiome
Research suggests that Lauric acid influences the gut microbiome by promoting the growth of beneficial bacteria while suppressing harmful ones.
It may contribute to the overall health of the digestive system and reduce the risk of gastrointestinal infections.
Studies on Weight Management
Lauric acid, through its medium-chain triglycerides (MCT) content, may support weight management efforts by increasing energy expenditure and promoting fat oxidation.
However, its role is still under investigation, with some studies showing limited impact.
Risk Factors and Adverse Effects
High doses of Lauric acid could result in digestive discomfort, such as bloating or diarrhea.
People with specific metabolic conditions should be cautious about its consumption, especially if they have issues with fat digestion or absorption.
Research Studies and Clinical Trials
Numerous studies have investigated Lauric acid's health benefits and biological activity.
Some of the most significant research has focused on its antimicrobial properties and its effects on lipid metabolism.
Clinical trials have also examined Lauric acid's ability to prevent or reduce the severity of infections like the common cold, herpes simplex, and other viral or bacterial infections.
Environmental Considerations
Sustainability of Lauric Acid Production
The environmental impact of Lauric acid production is tied to the agricultural practices surrounding coconut and palm oil plantations.
While coconut oil is generally considered sustainable, palm oil production has been associated with deforestation and habitat loss in some regions, raising ethical concerns about large-scale production.
Ethical Concerns and Eco-Friendly Practices
Efforts to address environmental concerns have led to certification programs like the Roundtable on Sustainable Palm Oil (RSPO), which aims to minimize the environmental impact of palm oil production.
These programs are increasingly important in ensuring that Lauric acid production remains environmentally responsible.
Lauric acid is a versatile and essential fatty acid with significant applications in health, industry, and agriculture.
Its unique properties make it valuable in fighting infections, improving metabolic processes, and supporting immune health.
However, more research is needed to fully understand its potential and limitations.
As industries continue to harness Lauric acid's benefits, it is essential to consider its environmental impact and work toward more sustainable production methods.
SAFETY INFORMATION ABOUT LAURIC ACID
First aid measures:
Description of first aid measures:
General advice:
Consult a physician.
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
If inhaled:
If breathed in, move person into fresh air.
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately.
Wash off with soap and plenty of water.
Consult a physician.
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
If swallowed:
Do NOT induce vomiting.
Never give anything by mouth to an unconscious person.
Rinse mouth with water.
Consult a physician.
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment.
Avoid breathing vapours, mist or gas.
Evacuate personnel to safe areas.
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste.
Keep in suitable, closed containers for disposal.
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place.
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles.
Faceshield (8-inch minimum).
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection:
Handle with gloves.
Gloves must be inspected prior to use.
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product.
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls.
If the respirator is the sole means of protection, use a full-face supplied air respirator.
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions.
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product.
