CAS Number: 544-31-0
EC Number: 208-869-6
Molecular Formula: C₁₈H₃₇NO₂
Molecular Weight: 299.49 g/mol
Synonyms:
Palmitoyl monoethanolamide,N-(2-Hydroxyethyl)palmitamide,Hexadecanoyl ethanolamide,Palmityl MEA,Cetyl MEA
Physical and Chemical Properties:
Palmitamide MEA typically appears as white to off-white flakes or powder with a faint characteristic odor. It exhibits a melting point of 92-96°C and demonstrates amphiphilic character due to the combination of long hydrocarbon chain and polar ethanolamide head group. Solubility characteristics include limited water solubility (<0.1 g/L at 25°C), moderate solubility in ethanol (5-10 g/L), and excellent solubility in oils and lipid phases. The amide bond provides chemical stability over a wide pH range (3-10), with hydrolysis becoming significant only under strongly acidic or basic conditions at elevated temperatures.
Alternative Methods:
Transamidation: Methyl palmitate with monoethanolamine at 100-120°C
Enzymatic Synthesis: Using immobilized lipases (Candida antarctica) at 60-80°C
Schotten-Baumann Reaction: Palmitoyl chloride with monoethanolamine (lower temperature but higher cost)
Purification and Quality Control:
Crude product undergoes multiple purification steps:
Crystallization: From ethanol or acetone to remove unreacted starting materials
Bleaching: Activated carbon treatment for color improvement
Drying: Vacuum drying at 50-60°C to achieve moisture content <0.5%
Milling: To achieve desired particle size (typically 80-200 mesh)
Quality Specifications:
Purity: >98% by HPLC
Melting Point: 92-96°C
Acid Value: <2.0 mg KOH/g
Amine Value: <5.0 mg KOH/g
Color: White to cream (Gardner <2)
Heavy Metals: <10 ppm
Residual Solvents: <500 ppm
Global production capacity is estimated at 5,000-8,000 metric tons annually, with major producers including Nippon Fine Chemical (Japan), Kawaken Fine Chemicals (Japan), Zschimmer & Schwarz (Germany), and several Chinese manufacturers. Pricing ranges from $8-12/kg for standard grades to $15-25/kg for high-purity cosmetic and pharmaceutical grades.
Functional Properties and Mechanism of Action
Surface Activity:
Palmitamide MEA exhibits mild surfactant properties with a critical micelle concentration (CMC) of approximately 0.5-1.0 mM. The amide group provides hydrogen bonding capability while the long alkyl chain contributes to hydrophobic interactions, enabling formation of stable interfacial films.
Skin Compatibility Mechanisms:
Barrier Function Enhancement: Integrates into stratum corneum lipid lamellae, improving barrier properties
Moisturization: Forms occlusive film reducing transepidermal water loss (TEWL)
Emolliency: Provides smooth, velvety skin feel without greasiness
Compatibility: With skin's natural lipid composition (similar chain length to naturally occurring ceramides)
Rheological Effects:
In formulations, palmitamide MEA can function as:
Thickener: Through formation of crystalline networks in oil phases
Stabilizer: For emulsions through interfacial film reinforcement
Opacifier: Due to its crystalline nature and refractive index (≈1.45)
Comprehensive Application Spectrum
Skin Care Formulations (60% of consumption):
Moisturizers and Creams: At 1-5% concentration, provides long-lasting hydration and improves skin barrier function.
Anti-Aging Products: As matrix component in wrinkle-reducing formulations (2-4%).
Body Lotions: Enhances spreadability and after-feel (1-3%).
Lip Care: In balms and treatments for barrier protection (3-8%).
Case Example: In barrier repair creams for eczema-prone skin, palmitamide MEA (3-5%) significantly reduces TEWL (by 30-40%) and improves hydration levels within 1-2 weeks of regular use.
Hair Care Products (25%):
Conditioners: Provides detangling and shine enhancement (1-3%).
Hair Masks: For deep conditioning treatments (2-5%).
Styling Products: Improves hold and manageability (0.5-2%).
Scalp Treatments: For dry, flaky scalp conditions (1-2%).
Case Example: In leave-in conditioners for chemically treated hair, palmitamide MEA (1.5-2.5%) reduces combing force by 40-50% and improves shine measurements by 20-30%.
Color Cosmetics (10%):
Foundations: Improves spreadability and wear (0.5-2%).
Lipsticks: Enhances texture and application smoothness (2-5%).
Mascara: Conditions lashes and improves product deposition (1-3%).
Case Example: In long-wear liquid foundations, palmitamide MEA (1-2%) improves pigment dispersion while providing a natural matte finish that resists transfer for 8+ hours.
Other Applications (5%):
Pharmaceutical Ointments: As emollient and drug release modifier (2-6%).
Sun Care: Enhances water resistance and skin feel (1-4%).
Shaving Products: Improves razor glide and post-shave feel (2-5%).
Baby Care: In diaper rash creams and baby lotions (1-3%).
Market Dynamics and Future Trends
Current Market Status:
The palmitamide MEA market is growing at 4-6% annually, driven by increasing demand for multifunctional ingredients in personal care. Key market drivers include:
Multifunctionality Trend: Formulators seeking ingredients with multiple benefits
Natural/Bio-based Movement: Despite synthetic production, fits "natural" positioning
Performance Demands: Need for ingredients with proven efficacy
Regional Expansion: Growing personal care markets in Asia and Latin America
Sustainability Considerations:
Raw Material Sourcing: Palm oil-derived palmitic acid sustainability concerns
Green Chemistry: Enzymatic synthesis methods gaining attention
Carbon Footprint: Petrochemical vs. bio-based monoethanolamine
Competitive Landscape:
Direct Alternatives: Other fatty acid ethanolamides (stearamide MEA, behenamide MEA)
Functional Competitors: Synthetic ceramides, phytosphingosine derivatives
Differentiation Factors: Purity, particle size, technical support
Innovation Frontiers:
Delivery Systems: Encapsulated or complexed forms for controlled release
Derivatization: Ethoxylated or other modified forms with enhanced properties
Biotechnological Production: Fermentation-derived alternatives
Clinical Validation: More extensive efficacy studies for specific claims
Strategic Outlook:
Palmitamide MEA will maintain its position as a versatile, cost-effective ingredient for personal care formulations. Future growth will be strongest in premium skin care and treatment products where its barrier-enhancing properties are particularly valued. Challenges include increasing scrutiny of palm oil derivatives and competition from novel lipid ingredients. Success will depend on demonstrating clear value through clinical studies, improving sustainability credentials, and developing innovative formulations that leverage its unique properties.
SAFETY INFORMATION ABOUT PALMITAMIDE MEA
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