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OCTYL METHOXYCINNAMATE

Octyl methoxycinnamate is an organic compound that is an ingredient in some sunscreens and lip balms, formed from methoxycinnamic acid and 2-ethylhexanol.
Octyl methoxycinnamate is a highly effective oil-soluble UV-B filter and an excellent solubilizer for solid UV absorbers.
Octyl methoxycinnamate is commonly found in hair color, shampoos, sunscreen, lipstick, nail paint, and skin lotions.

CAS Number: 5466-77-3
EC Number: 226-775-7
Molecular Formula: C18H26O3
Molar mass: 290.403 g·mol−1

Synonyms: (RS)-2-Ethylhexyl (2E)-3-(4-methoxyphenyl)prop-2-enoate, Ethylhexyl methoxycinnamate, Octinoxate, Uvinul MC80, (E)-3-(4-methoxyphenyl) prop-2-enoic acid 2-ethylhexyl ester, Octinoxate, OMC, Octyl methoxycinnamate, 2-ETHYLHEXYL TRANS-4-METHOXYCINNAMATE, MC80, PARSOL MCX, Neo Heliopan AV, 2-ETHYLHEXYL P-METHOXYCINNAMATE, OCTYL P-METHOXYCINNAMATE, 2-ETHYLHEXYL 4-METHOXYCINNAMATE, Ethylhexyl methoxycinnamate, Octinoxate, OM-Cinnamate, OM Cinnamate, Octyl methoxycinnamate, 2-Ethylhexyl 4-methoxycinnamate, Parsol MCX, OMCU, Uvinul MC80, ETHYLHEXYL METHOXYCINNAMATE, 2-ETHYLHEXYL P-METHOXYCINNAMATE, 2-ETHYLHEXYL 4-METHOXYCINNAMATE, 2-ETHYLHEXYL ESTER P-METHOXYCINNAMIC ACID, 2-ETHYLHEXYL METHOXYCINNAMATE, 2-ETHYLHEXYL P-METHOXYCINNAMATE, 2-ETHYLHEXYL-4-METHOXYCINNAMATE, AI3-05710, CCRIS 6200, EINECS 226-775-7, ESCALOL, NEO HELIOPAN, 2-Ethylhexyl-4-methoxycinnamate, 4-Methoxycinnamic Acid 2-Ethylhexyl Ester, EHMC, Octinoxat (INN)

Octyl methoxycinnamate is an old-school chemical sunscreen agent.
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 a commercial sunscreen known as octinoxate with excellent UVB filter properties.

However, Octyl methoxycinnamate is known to undergo a series of photodegradation processes that decrease its effectiveness as a UVB filter.
In particular, the trans (E) form—which is considered so far as the most stable isomer—converts to the cis (Z) form under the effect of light.

In this work, by using post-Hartree–Fock approaches [CCSD, CCSD(t), and CCSD + T(CCSD)] on ground state Octyl methoxycinnamate geometries optimized at the MP2 level, we show that the cis and trans forms of the gas-phase Octyl methoxycinnamate molecule have comparable stability.
Test calculations on the same structures with a series of dispersion-corrected density functional theory-based approaches including the B2PLYP double hybrid predict the trans structures to be energetically favored, missing the subtle stabilization of cis-Octyl methoxycinnamate.

Octyl methoxycinnamate is a clear, oil-soluble, "cosmetically-elegant" liquid that is the most commonly used chemical sunscreen.
Octyl methoxycinnamate absorbs UVB radiation (at wavelengths: 280-320 nm) with a peak protection at 310nm.
Octyl methoxycinnamate only protects against UVB and not UVA rays (the 320-400 nm range) – so always choose products that contain other sunscreens too.

Octyl methoxycinnamate is not very stable either, when exposed to sunlight, it kind of breaks down and loses its effectiveness (not instantly, but over time - it loses 10% of its SPF protection ability within 35 mins).
To make Octyl methoxycinnamate more stable it can be - and should be - combined with other sunscreen agents to give stable and broad-spectrum protection (the new generation sunscreen agent, Tinosorb S is a particularly good one for that).

Overall, Octyl methoxycinnamate is an old-school chemical sunscreen agent.
There are plenty of better options for sun protection today, but Octyl methoxycinnamate is considered "safe as used" (and sunscreens are pretty well regulated) and it is available worldwide (can be used up to 10% in the EU and up to 7.5% in the US).

Octyl 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 in the form of a slightly yellow and viscous liquid.

Octyl methoxycinnamate dissolves well in organic solvents, especially alcohol.
Octyl methoxycinnamate or octinoxate (USAN), trade names Eusolex 2292 and Uvinul MC80, 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 a highly effective oil soluble UV-B filter and an excellent solubilizer for solid UV absorbers.
Octyl methoxycinnamate, one of the most used sun filters in the world.

Octyl methoxycinnamate is organic, oil-soluble and absorbs UV-B radiation at wavelengths from 280 to 320nm, with a peak protection at 310nm.
In cosmetic products Octyl methoxycinnamate also acts as a photo stabilizer and it helps to protect colors and fragrances.

Octyl methoxycinnamate is water-insoluble and therefore ideal to use in non-aqueous water-resistant and waterproof sunscreen preparations.
Octyl methoxycinnamate is also known under the names Octinoxate.

Octyl methoxycinnamate 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.
This sunscreen active, Octyl methoxycinnamate, is one of several currently undergoing further safety testing under the purview of the United States Food and Drug Administration (FDA).

This testing is to gain a better understanding of the systemic absorption, metabolism, and elimination of these sunscreen actives when small amounts enter the body via topical use.
It’s important to know that the presence of Octyl methoxycinnamate or other sunscreen actives in the body does not mean your health is at risk.

It is anticipated that the additional testing being done will reaffirm the safety of these ingredients; however, those who remain concerned can choose sunscreens with mineral actives (titanium dioxide and zinc oxide) which are not included in the FDA’s new call for additional testing.
Octyl methoxycinnamate is a sunscreen agent used to protect skin primarily from the sun’s UVB rays, it is one of the most commonly used sunscreen agents.

Octyl methoxycinnamate 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.
Octyl methoxycinnamate can be combined with other sunscreens that protect from UVA rays.

Octyl methoxycinnamate is pale yellow oily liquid.
Octyl methoxycinnamate 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.

Octyl 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.

Octyl methoxycinnamate is approved worldwide in various concentrations.
Octyl methoxycinnamate or octinoxate (USAN), 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 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.

Octyl methoxycinnamate 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 clear liquid that is insoluble in water.
Octyl methoxycinnamate is a clear liquid that is insoluble in water.

In the United States, these products are regulated as Over-the-Counter (OTC) drugs.
Octyl 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 Octyl methoxycinnamate 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.

People can find Octyl methoxycinnamate on product labels under various names.
Octyl methoxycinnamate or octinoxate (USAN), 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 a common UV filter.
Octyl methoxycinnamate is quickly absorbed through the skin.

Octyl methoxycinnamate has been found in human urine, blood, and breast milk, indicating that people are exposed to this molecule on a systemic level.
Octyl methoxycinnamate is a pale yellow oily liquid, practically odorless and is soluble in Ethanol, Propylene Glycol, Iso-propanol.

Octyl methoxycinnamate is a UVB Category 1 sunscreen used for OTC sun protection products.
Octyl methoxycinnamate brings about a considerable retardation in the aging of the skin with excellent tolerance and stability.

Octyl methoxycinnamate is an organic sunscreen.
Octyl methoxycinnamate is derived from Cinnamic Acid (an acid found in the Cinnamon plant) that is effective in protecting against UVB light.

Octyl methoxycinnamate is an organic compound that is an ingredient in some sunscreens and lip balms as a UV absorber/filter.
Octyl methoxycinnamate is an ester formed frommethoxycinnamic acid and (RS)-2-ethylhexanol.
Octyl methoxycinnamate is a clear liquid that is insoluble in water.

Octyl methoxycinnamate is a versatile sunscreen agent with UVB filter properties.
Octyl methoxycinnamate may be formulated into creams, lotions, gels, lip balms and anhydrous (water-free) products.

Uses of Octyl Methoxycinnamate:
Octyl methoxycinnamate is a UV filter used to protect the skin against the harmful effects of sunlight.
Octyl methoxycinnamate protects the skin against burns and sun damage, especially by absorbing UVB (ultraviolet B) rays.

In addition to providing sun protection, Octyl methoxycinnamate works together with other ingredients in cosmetic products to help moisturize, protect and add aesthetic properties to the skin.
The usage rate of Octyl methoxycinnamate varies between 2% and 15% depending on the effect of the product and its interaction with other compounds.

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.

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.

Octyl methoxycinnamate is an organic ester used in sunscreens (and lip balms) formed from methoxycinnamic acid and 2-ethylhexanol.
Octyl methoxycinnamate is a sun blocking agent that absorbs UVB rays, but not UVA rays.

Octyl 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.
Octyl methoxycinnamate is used in sun care formulations.

Octyl methoxycinnamate is often used as an active ingredient in sunscreens combined with AakoSun BP3 or AakoSun TiO2.
Octyl methoxycinnamate is used sun care & after-sun products, hair care products, protective creams & lotions, makeup products.

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.
Octyl methoxycinnamate's primary use is in suncreens and other cosmetics to absorb UV-B rays from the sun, protecting the skin from damage.

Octyl methoxycinnamate is an organic compound that is an ingredient in some sunscreens and lip balms, primarily used is in sunscreens and other cosmetics to absorb UV-B rays from the sun, protecting the skin from damage and can be used to reduce the appearance of scars.
Octyl methoxycinnamate also has a complex androgenic and estrogenic effect.

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.
Octyl methoxycinnamate also protects cosmetics and personal care products from deterioration caused by UV rays.

When used to protect the product, this ingredient is called Octyl methoxycinnamate.
Octyl methoxycinnamate is used in the formulation of a wide variety of product types including sunscreens and makeup products that contain ingredients to protect the skin from the sun.

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, also known as Octinoxate, is a commonly used organic compound found in sunscreens and skincare products. Octyl methoxycinnamate functions as a chemical sunscreen agent, primarily offering protection against harmful UVB rays from the sun.

One of the key advantages of Octyl methoxycinnamate is its ability to effectively absorb and filter UVB radiation, thereby reducing the risk of sunburn and shielding the skin from damage caused by excessive sun exposure.
Octyl methoxycinnamate can be found in hair color products and shampoos, sunscreen, lipstick, nail polish, skin creams.

A recent study concluded that Octyl methoxycinnamate and other sun screening agents do not penetrate the outer skin in sufficient concentration to cause any significant toxicity to the underlying human keratinocytes.
Octyl methoxycinnamate is one of the most frequently used chemical UV filters worldwide and has been reported to cause photosensitisation and photoallergic effects.

Octyl methoxycinnamate easily penetrates the upper layer of the skin and, when exposed to UV radiation, generates free radicals in skin cells.
Octyl methoxycinnamate's primary use 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.
Moreover, Octyl methoxycinnamate demonstrates excellent photostability, meaning it remains effective even when exposed to sunlight for extended periods.

This ensures that the sun protection provided by products containing this ingredient lasts longer.
An added benefit is that Octyl methoxycinnamate has a relatively low risk of causing skin irritation, making it suitable for use in various skincare and cosmetic formulations.

Octyl methoxycinnamate is often combined with other sunscreen agents to create broad-spectrum protection against both UVB and UVA rays.
However, it's important to note that Octyl methoxycinnamate may not provide complete protection across the entire UV spectrum.
Therefore, Octyl methoxycinnamate is commonly used alongside other sunscreen ingredients to ensure comprehensive sun protection.

In summary, Octyl methoxycinnamate is a valuable component of sunscreens and skincare products, offering effective UVB protection, photostability, and compatibility with the skin.
Octyl methoxycinnamate is also used to reduce the appearance of scars.

Octyl methoxycinnamate's inclusion in these products helps individuals safeguard their skin from the sun's harmful rays and maintain healthy skin during daily activities and outdoor adventures.
Octyl methoxycinnamate is commonly found in hair color, shampoos, sunscreen, lipstick, nail paint, and skin lotions.

Octyl methoxycinnamate is primarily used as a sun-protection agent that works on UV-B rays of the Sun and prevents skin damage.
Octyl methoxycinnamate is also used in cosmetics and personal care products to keep the other ingredients fresh and effective.

Octyl methoxycinnamate is used in sunscreens and other products like foundations, lip balms, and makeup to block the harmful UV-B rays from the Sun and protect the skin against sunburn and skin cancer.
Octyl methoxycinnamate also may help the skin to absorb other ingredients.
The maximum concentration of Octyl methoxycinnamate in ready-for-use products is 7.5% in the United States (U.S.) and 10% in the European Union (E.U.).

Functions of Octyl Methoxycinnamate:

Light Stabilizer:
Protecting the cosmetic product from deterioration effects of light.

UV Absorber:
Octyl methoxycinnamate protects the cosmetic product from damage caused by UV light.

UV Filter:
Octyl methoxycinnamate protects skin or hair from harmful UV radiation.

Benefits of Octyl Methoxycinnamate:
As a sunscreen, it offers broad-spectrum UV-B protection, but Octyl methoxycinnamate does not protect against UV-A rays.
Octyl methoxycinnamate aids in the prevention of sunburn and premature aging, such as wrinkles and leathery skin.

Sunscreens with Octyl methoxycinnamate can also assist in reducing the incidence of skin cancer and sunburn-like UV sensitivity induced by some drugs.
Octyl methoxycinnamate is utilized as a UV filter in items other than sunscreens to keep the products from deteriorating when exposed to sunlight.

Manufacturers commonly use Octyl methoxycinnamate in a variety of cosmetic and personal care products to help keep their contents fresh and active.
Octyl methoxycinnamate can also aid in the absorption of other chemicals by your skin.

Synthesis of Octyl Methoxycinnamate:
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)

Origin of Octyl Methoxycinnamate:
Octyl methoxycinnamate is an ester that is made by mixing methoxycinnamic acid and 2-ethylhexanol together.

Concentration And Solubility of Octyl Methoxycinnamate:
Octyl methoxycinnamate is recommended that it should be used at a concentration of 0.5–7.5%.
Octyl methoxycinnamate is insoluble in water but soluble in oils.

Scientific Facts of Octyl Methoxycinnamate:
UV light has a wavelength shorter than visible light.
Prolonged exposure to UV light may result in health effects in the skin, eye and immune system.

UV light damages collagen and contributes to aging of skin.
Octyl methoxycinnamate (Octinoxate) can help protect against sunburn and other skin damage caused by UV light by absorbing UV radiation.

Alternatives of Octyl Methoxycinnamate:
Titanium Dioxide
Zinc Oxide
Hydrogenated Coconut Oil
Hydrogenated Shea Butter

Handling And Storage of Octyl Methoxycinnamate:

Conditions for safe storage, including any incompatibilities:

Storage conditions:
Tightly closed.
Light sensitive.

Stability And Reactivity of Octyl Methoxycinnamate:

Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature) .

Incompatible materials:
No data available

Safety Profile of Octyl Methoxycinnamate:
Octyl methoxycinnamate is considered safe for use in cosmetics in the E.U. and the U.S. if it is used in the recommended concentrations, it is safe.

First Aid Measures of Octyl Methoxycinnamate:

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.
Remove contact lenses.

If swallowed:

After swallowing:
Make victim drink water (two glasses at most).
Consult doctor if feeling unwell.

Indication of any immediate medical attention and special treatment needed:
No data available

Fire Fighting Measures of Octyl Methoxycinnamate:

Suitable extinguishing media:
Foam
Carbon dioxide (CO2)
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.

Accidental Release Measures of Octyl Methoxycinnamate:

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 with liquid-absorbent material.
Dispose of properly.
Clean up affected area.

Exposure Controls/Personal Protection of Octyl Methoxycinnamate:

Personal protective equipment:

Eye/face protection:
Use equipment for eye protection.
Safety glasses

Skin protection:
not required

Respiratory protection:
Not required.

Control of environmental exposure:
Do not let product enter drains.

Identifiers of Octyl Methoxycinnamate:
IUPAC name: 2-Ethylhexyl (E)-3-(4-methoxyphenyl)prop-2-enoate
CAS number: 5466-77-3
Molecular formula: C18H26O3
Molar mass: 290.40 g/mol
PubChem CID: 5355130
EC number: 226-775-7
UNII: 4Y5P7MUD51
ChemSpider ID: 4514659
InChI Key: DXHHMQPQHTVDFZ-ZHACJKMWSA-N
SMILES: CCC(CC)CCCCOC(=O)/C=C/c1ccc(OC)cc1

CAS Number: 5466-77-3
EC Number: 226-775-7
MDL Number: MFCD00072582
Chem/IUPAC Name: 2-ethylhexyl 3-(4-methoxyphenyl)prop-2-enoate
Molecular Formula : C18H26O3
Molar mass: 290.403 g·mol−1

Porperties of Octyl Methoxycinnamate:
Boiling Point: 198-200°C
Melting Point: -25°C
Solubility: Insoluble in water, soluble in oil
Physical state: Viscous liquid
Color: Not available
Odor: Not available
Flammability (solid, gas): Not available
Upper/lower flammability or explosive limits: Not available
Flash Point: 193°C - DIN 51758
Autoignition temperature: Not available
Decomposition temperature: Not available
pH: Not available

Kinematic viscosity: Not available
Dynamic viscosity: Not available
Water solubility: 0.0002 g/l at 20°C
Partition coefficient: n-octanol/water (log Pow): 6.1 - Indicates potential bioaccumulation
Vapor pressure: Not available
Density: 1.01 g/cm3
Relative density: Not available
Relative vapor density: Not available
Particle characteristics: Not available
Explosive properties: Not available
Oxidizing properties: None
Other safety information: Not available
Chemical Information:
Chemical formula: C18H26O3
Molar mass: 290.403 g·mol−1
Beilstein Number: 5946632
MDL: MFCD00072582
XlogP3-AA: 5.30 (estimated)

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