OCTYL METHOXYCINNAMATE (OMC)
Octyl methoxycinnamate or ethylhexyl methoxycinnamate (INCI) is an organic compound that is an ingredient in some sunscreens and lip balms.
Octyl methoxycinnamate is an ester formed from methoxycinnamic acid and 2-ethylhexanol.
Octyl methoxycinnamate is a liquid that is insoluble in water.
Octyl methoxycinnamate is primarily used in sunscreens and other cosmetics to absorb UV-B rays from the sun, protecting the skin from damage.
Octyl methoxycinnamate is also used to reduce the appearance of scars.
CAS: 5466-77-3
EINECS: 226-775-7
IUPAC Name: 2-ethylhexyl (E)-3-(4-methoxyphenyl)prop-2-enoate
Molecular Formula: C18H26O3
Molecular weight: 290.397
Tinosorb OMC, Octyl methoxycinnamate, Uvinul 3088, 2-Ethylhexyl-4-methoxycinnamate, Sunscreen AV, Eusolex 2292, Ethylhexyl methoxycinnamate, 2-ethylhexyl 3-(4-methoxyphenyl)prop-2-enoate, Parsol mcx-sa, octylmethoxycinnamate, NSC 26466, (E)-Octyl methoxycinnamate, 2-Ethylhexyl methoxycinnamate, Octinoxate [USAN:USP:INN], CCRIS 6200, HSDB 7459, EINECS 226-775-7, 2-ethylhexyl 3-(4-methoxyphenyl)-2-propenoate, AI3-05710, isooctyl 4-methoxycinnamate, CHEMBL3183184, CHEBI:134750, AKOS028110087, NS00004841, 3-(4-Methoxyphenyl)-2-propenoic acid, 2-ethylhexyl ester
Octyl Methoxycinnamate (OMC), also known as Ethylhexyl Methoxycinnamate, is a synthetic compound that has made a mark in the personal care industry.
Octyl methoxycinnamate is lauded for its remarkable sun protection characteristics, alongside other properties that have made it an essential ingredient in an array of personal care products.
Octyl Methoxycinnamate, a compound derived from cinnamic acid, is an organic UVB filter.
UVB rays are the ultraviolet rays that cause sunburn and play a significant role in developing skin cancer.
Octyl methoxycinnamate has been primarily used in sunscreens and lip balms to absorb UVB radiation, thus protecting the skin from damage.
Unlike inorganic sunscreens, its organic nature ensures it does not leave a white residue, making it cosmetically appealing.
Octyl methoxycinnamate is also known as Ethylhexyl methoxycinnamate.
Octyl methoxycinnamate is an ester formed from methoxycinnamic acid and 2-ethylhexanol.
Ethylhexyl Methoxycinnamate (Octyl Methoxycinnamate or OMC) is an ester of 4-methoxycinnamic acid and 2-ethyl hexanol, a strong UVB absorber and is one of the most widely used UV-B filters with excellent protection potential.
Octyl methoxycinnamate is an oil-soluble (insoluble in water), colorless to pale yellow (yellowing when exposed to light), practically odorless, oily liquid that can be easily incorporated into the sunscreen formulation.
Octyl methoxycinnamate has a refractive index (at 20 °C) of 1.542–1.548 and boosts the SPF when combined with other UV filters.
Ethylhexyl Methoxycinnamate is ideal for water-resistant sunscreens, lipsticks, protective hair care, and daycare products for everyday protection against UV-B rays.
In addition, Octyl methoxycinnamate is compatible with most cosmetic ingredients and an excellent solubilizer for many solid UV filters such as Ethylhexyl Triazone, Diethylhexyl Butamido Triazone, Diethylamino Hydroxybenzoyl Hexyl Benzoate, and Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine.
Due to Octyl Methoxycinnamate is a derivative of cinnamate acid (unsaturated fatty acid), an antioxidant should be added to the cosmetic composition, to guarantee the oxidative stability of the product.
Antioxidants could be, for example, vitamin E or BHT.
Ethylhexyl Methoxycinnamate is approved worldwide in various concentrations.
Ethylhexyl Methoxycinnamate is one of the well-studied ingredients.
Several studies showed that it has cytotoxic, estrogenic, and neurological adverse effects.
But, applied topically, Octyl methoxycinnamate practically doesn't adsorb into the epidermis, and it is safe for external use and approved by the FDA for use in sunscreens and protective applications.
Octyl methoxycinnamate (Ethylhexyl methoxycinnamate) is an ultra violet absorber.
Octyl methoxycinnamate has a broad UV-B radiation absorbance profile and functions as UV-B blocker.
Octyl methoxycinnamate has a wide use in sunscreen and skin care products to give UV-B radiation protection.
Octyl methoxycinnamate also acts as a photo stabiliser in cosmetic products.
Ethylhexyl Methoxycinnamate is organic, oil-soluble and absorbs UV-B radiation at wavelengths from 280 to 320nm, with a peak protection at 310nm.
Ethylhexyl Methoxycinnamate is being used in a wide range of cosmetic products to provide an appropriate Sun Protection Factor (SPF) in sunscreens or to protect cosmetics against UV radiation.
In cosmetic products Octyl methoxycinnamate also acts as a photo stabilizer and it helps to protect colors and fragrances.
Approved for the use in sun care preparations in many countries worldwide.
In America max. 7.5% and in Europe max. 10%
Ethylhexyl methoxycinnamate is an ultraviolet (UV) protection agent commonly used in sunscreens, face foundations, and lip care products.
Octyl methoxycinnamate acts as a UV filter and blocks the Sun’s UV-B rays which have been associated with sunburn and skin cancer, thus protecting the skin.
Octyl methoxycinnamate is an effective UV-B filter.
UV-A radiation (320-400nm) is linked with the loss of skin elasticity, wrinkling and premature ageing, whilst the more powerful UV-B radiation (290-320nm) is linked to sunburn, cell damage and skin cancer.
Octyl methoxycinnamate is soluble in most organic solvents facilitating good incorporation particularly into high SPF skin care and sunscreen product where a level of water resistance is desirable.
Octyl methoxycinnamate is compatible with most of the cosmetic ingredients.
For total UV range protection, Octyl methoxycinnamate is formulated with Avobenzone (UV-A blocking).
Octyl methoxycinnamate is highly effective UV-B filter which absorbs the UV-B rays in the range of 290-340nm.
Ethylhexyl Methoxycinnamate (OMC) Octyl 4-methoxycinnamate CAS 5466-77-3 is a UV-B category 1 sunscreen used for OTC sun protection products such as sunscreens, personal care products, sun care, baby sun care, daily skin care, decorative cosmetic with sun protection and broad spectrum UV- B filter.
Ethylhexyl Methoxycinnamate (also called Octyl Methoxycinnamate) is an active ingredient in OTC sunscreen products.
Octyl methoxycinnamate is widely utilized in commodities which are applied to the skin to absorb, reflect or scatter UV rays; it protects the skin from sunburn and other damaging effects of the sun.
Ethylhexyl Methoxycinnamate (OMC) Octyl 4-methoxycinnamate CAS 5466-77-3 also protects cosmetics and personal care products from deterioration caused by UV rays and allows them to last longer in high UV conditions.
- Octyl methoxycinnamate is used in sunscreen as a UV filter
- Octyl methoxycinnamate is often listed on sunscreen products as Octinoxate
Octyl methoxycinnamates primary application is in sunscreens and other cosmetics to absorb UV-B rays from the sun, protecting the skin from damage.
Octyl methoxycinnamate is also used to reduce the appearance of scars.
Octyl Methoxycinnamate (OMC), also known as ethylhexyl methoxycinnamate or octinoxate, is a widely used organic compound found in many sunscreen formulations.
Octyl methoxycinnamate serves as a primary UVB filter, protecting the skin from harmful ultraviolet radiation.
Octyl methoxycinnamate is an organic compound with the chemical formula C18H26O3.
Octyl methoxycinnamate appears as a colorless to pale yellow liquid with a characteristic odor.
This UV filter is highly soluble in organic solvents like ethanol and acetone but has limited solubility in water.
Octyl methoxycinnamate absorbs UVB radiation in the range of 290-320 nanometers, effectively shielding the skin from these harmful rays.
However, Octyl methoxycinnamate offers minimal protection against UVA radiation, necessitating the use of additional sunscreen agents for broad-spectrum coverage.
Octyl Methoxycinnamate is an organic compound that is a component of sunscreens and lipsticks, mainly used in cosmetics such as sunscreens to absorb UV-B rays from the sun, protect skin from damage, and can also be used to reduce the appearance of scars.
Functions and Usages
As a UVB filter, Octyl methoxycinnamate plays a crucial role in sunscreens and other skincare products designed to protect against sunburn and UV-induced skin damage.
Octyl methoxycinnamate absorbs UVB radiation, preventing it from penetrating the skin and causing DNA damage, erythema, and premature aging.
Octyl methoxycinnamate is commonly used in combination with other UV filters to achieve broad-spectrum protection against both UVB and UVA rays.
Octyl methoxycinnamates compatibility with various cosmetic ingredients makes it a popular choice in sunscreen formulations, offering consumers effective sun protection with desirable sensory attributes.
Synthesis Methods
Octyl methoxycinnamate is typically synthesized through esterification of methoxycinnamic acid with 2-ethylhexanol.
This reaction is catalyzed by acidic or basic conditions, resulting in the formation of Octyl methoxycinnamate along with water as a byproduct.
The process involves careful control of temperature and reaction time to ensure optimal yield and purity of the product.
After synthesis, Octyl methoxycinnamate undergoes purification steps to remove impurities and obtain a high-quality ingredient suitable for cosmetic and sunscreen formulations.
Use of Octyl Methoxycinnamate in Personal Care
UV filters minimize the undesired effects of UV radiation on the skin and are an essential component of sunscreens.
By protecting the skin against dangerous sun radiation, they contribute to preventing premature light-caused skin aging and skin cancer.
Chemical sunscreens, or organic UV filters, are generally aromatic compounds.
Their molecular structure is responsible for absorbing UV energy. Organic filters absorb UV rays, which produce excitation of the sunscreen chemical to a higher energy state.
Then, they return to the ground state and convert the absorbed energy into longer, lower energy wavelengths (heat).
Examples of organic UVB absorbing filters include octinoxate. Organic filters are often combined to achieve the desired broad-spectrum protection.
Octyl methoxycinnamate is a soluble organic UVB filter.
Octyl methoxycinnamate absorbs UVB radiation from approximately 280 to 320 nm.
Ethylhexyl Methoxycinnamate.
Octyl Methoxycinnamate-OMCX is a highly effective oil soluble UV-B filter and an excellent solubilizer for solid UV absorbers.
Octyl methoxycinnamate is used in sun care formulations.
Applications in Personal Care Products
UV Absorber: Octyl methoxy cinnamate (OMC) is one of sunscreens’ most used UVB filters.
Octyl methoxycinnamate is commonly used to absorb from 280 to 320 nm.
UV Filter: Soluble organic UV filters absorb the UV radiation, transform it into heat and form an invisible protective shield in the upper skin layer.
Light Stabilizer: Octyl methoxycinnamates cosmetic function intends to protect the product from light-induced deterioration.
Octyl Methoxycinnamate is an invaluable component in the personal care industry, predominantly for its sun-protecting capabilities.
Octyl methoxycinnamate’s chemical properties make it ideal for inclusion in various products, including sunscreens, cosmetics, and hair care products.
Sun Care Products: Sunscreens, Sunscreen gels, Baby sunscreen
Color Cosmetics: Foundation with SPF Claim, Lip Balms, Primer, Lipsticks
Skin Care: Face and Hand Moisturizers, Aftershaves
Hair Care: Hair Styling Gel, Hair Sprays, Pomade
What are the benefits of Octyl methoxycinnamate on the skin?
Octyl methoxycinnamate (also known as octinoxate and ethylhexyl methoxycinnamate) is an ‘organic’ UV filter or sunscreen agent.
This clear liquid has the ability to absorb some of the sun's UVB rays and protect the skin against their burning effect.
Invented in 1994, it has been extensively used in cosmetics.
Technical Data
Appearance: Colourless to Pale yellow, oily liquid
Odor: Practically Odorless
Purity by GLC: Minimum 98.0 %
Absorbance (λ) (E 1%, 1cm, in methanol: Min 835 at 310 ± 2 nm
Acid Value: 1.0 Max
Refractive Index (at 20 °C) : 1.5420-1.5480
Specific gravity (at 20 °C): 1.008-1.020
Lovibond color 5 ¼ cell Not more than 2.0
Solubility: Soluble in Ethanol, Propylene Glycol, Isopropanol
Uses
Octyl methoxycinnamate is the most common active ingredient in sunscreens for protection against UV-B rays.
Octyl methoxycinnamate may be combined with oxybenzone and titanium oxide.
Studies have evaluated the efficacy of octyl methoxycinnamate in preventing postoperative peritoneal adhesions and determined that octyl methoxycinnamate covering peritoneal surfaces decreases adhesion formation.
This effect is more notable when octyl methoxycinnamate is applied before the induction of trauma.
Chromophore groups, such as C=C, C=O, and O-N=O, have loosely held electrons that are excited by radiation.
Hence, octyl methoxycinnamate is able to absorb radiation when the electron energy level is increased to an excited state.
Properties of Octyl Methoxycinnamate
Appearance at 25 °C: Clear Colorless to Yellow Liquid
Molecular Weight (g/ml): 290.4
Density at 18°C (g/cm3): 1.009
Specific Gravity: 1.01-1.02
Solubility: Insoluble in water, miscible in alcohols, propylene glycol mono myristate, and various oils.
Melting Point: <-25℃
Boiling Point: 198-200°C
Refractive Index: 1.543-1.547
Odour: Odorless
Shelf Life: 12-18 months
Storage Conditions: Store in well-filled, tightly sealed containers in a cool, dry place.Sensitive to light.
Ideal Storage Temperature – 2-8°C
Synthesis
Olefin metathesis has been widely studied.
One of the synthesis pathways for octyl methoxycinnamate includes cross metathesis.
The high efficiency of the nitro-Grela catalyst has been used in the cross metathesis of trans-anethole with 2-ethylhexyl acrylate to produce octyl methoxycinnamate (86% yield).
Typical Formulations
Here is an example of a personal care products table with Ethylhexyl Methoxycinnamate along with the % weight of ingredients:
Sunscreens: 1-10%
Face Moisturizers: 4-6%
Foundations: Up to 7.5%
Lip Balms, Lipsticks: Up to 5%
Octyl Methoxycinnamate Formulation Considerations
Organic sunscreens can penetrate the skin due to their lipophilic nature, which may cause safety concerns.
An issue with many organic sunscreens is their photostability.
Upon exposure to UV radiation, the structure of UV filters may be negatively affected and destroyed.
As a result, instead of returning to the ground state, they lose their absorption capacity.
Therefore, most formulations contain photo stabilizers.
Octyl Methoxycinnamate is incompatible with potent oxidizing agents.
Unlike other sunscreens that leave a white residue, Octyl Methoxycinnamate is clear on the skin, making it a popular choice for everyday wear.
Octyl methoxycinnamate improves the texture and feel of personal care products, contributing to a non-greasy, lightweight, and aesthetically pleasing formulation.
In addition to skin, Octyl methoxycinnamate is used in some hair care products to protect hair from sun damage.
This protection helps maintain the health and color of hair, especially for dyed hair which is more susceptible to color fading with UV exposure.
Octyl methoxycinnamate is photostable, which means it retains its protective capacity even after being exposed to sunlight for extended periods.
Functions:
As an oil-soluble UV-B filter in sun-care and cosmetic preparations, Ethylhexyl Methoxycinnamate (OMC) Octyl 4-methoxycinnamate CAS 5466-77-3 is one of the most tested and most widely used UV-B filters.
Octyl methoxycinnamate is ideal for use in sun-care and skin-care products for everyday protection.
Ethylhexyl Methoxycinnamate (OMC) Octyl 4-methoxycinnamate CAS 5466-77-3 is suitable for the formulation of protective hair-care products.
Applications:
Ethylhexyl Methoxycinnamate (OMC) Octyl 4-methoxycinnamate CAS 5466-77-3 is widely used in the preparation of sunscreen (cream, milk, liquid) and other skin care cosmetics, can effectively absorb the sun in the UV, to prevent the human skin sun red, sunburn, sun ink, but also light-sensitive dermatitis treatment.
In the industry, Octyl methoxycinnamate can be used as plastic, ink anti-aging agent and UV absorber.
Beside the usage in personal care products, in some conditions, Ethylhexyl Methoxycinnamate (OMC) Octyl 4-methoxycinnamate CAS 5466-77-3 is found to be sued in pharmaceutical area, too.
Octyl methoxycinnamate is used in products that are applied to the skin to absorb, reflect or scatter UV rays.
This serves to protect the skin from sunburn as well as other damaging effects of the sun.
Ethylhexyl Methoxycinnamate (OMC) also protects cosmetics and personal care products from deterioration caused by UV rays.