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OCTOCRYLENE

Octocrylene is an organic compound used as an ingredient in sunscreens and cosmetics. It is an ester formed by the reaction of 3,3-diphenylcyanoacrylate with 2-ethylhexanol. It is a viscous, oily liquid that is clear and colourless.
The extended conjugation of the acrylate portion of the molecule absorbs UVB and short-wave UVA (ultraviolet) rays with wavelengths from 280 to 320 nm,[1] protecting the skin from direct DNA damage. The ethylhexanol portion is a fatty alcohol, adding emollient and oil-like (water-resistant) properties.

CAS NO:  6197-30-4
EC NUMBER: 228-250-8


IUPAC NAMES:
(RS)-2-Cyan-3,3-diphenylacrylsäure-2-ethylhexylester
2-cyano-3,3-diphenyl-acrylic acid 2-ethyl-hexyl ester
2-ethylhexyl 2-cyano-3, 3-diphenyl-prop-2-enoate
2-ethylhexyl 2-cyano-3,3- diphenyl-2-propenoate
2-ethylhexyl 2-cyano-3,3-diphenyl-2-propanoate
2-ETHYLHEXYL 2-CYANO-3,3-DIPHENYL-2-PROPENOATE
2-Ethylhexyl 2-Cyano-3,3-diphenylacrylate
2-Ethylhexyl 2-cyano-3,3-diphenylacrylate
2-ethylhexyl 2-cyano-3,3-diphenylacrylate
2-ethylhexyl 2-cyano-3,3-diphenylprop-2-enoate
2-Propenoic acid, 2-cyano-3,3-diphenyl-, 2-ethylhexyl ester
Octocrilene
octocrilene
octocrilene
OCTOCRYLENE
Octocrylene
Octocrylene


SYNONYMS
Octocrylene;6197-30-4;2-Ethylhexyl 2-cyano-3,3-diphenylacrylate;Octocrilene;2-Propenoic acid, 2-cyano-3,3-diphenyl-, 2-ethylhexyl ester;2-ethylhexyl 2-cyano-3,3-diphenylprop-2-enoate;2-Cyano-3,3-diphenylacrylic Acid 2-Ethylhexyl Ester;MLS002454364;Octocrilene (INN);Octocrilene [INN];UV-3039;NCGC00091585-03;NCGC00091585-05;SMR001371988;DSSTox_CID_5299;DSSTox_RID_77734;2-Ethylhexyl 2-cyano-3,3-diphenylacrylate, 97%;DSSTox_GSID_25299;Octocrileno;Octocrilenum;Octocrilenum [INN-Latin];Octocrileno [INN-Spanish];UV Absorber-3;CAS-6197-30-4;CCRIS 4814;EINECS 228-250-8;Octocrylene [USAN:USP];Octocrilen;2-Ethylhexyl 2-cyano-3,3-diphenyl-2-acrylate;2-Ethylhexyl 2-cyano-3,3-diphenyl-2-propenoate;Octocrylene (USP);Neo heliopan 303;Uvinul N539;Parsol 340;PubChem13147;Uvinul N-539;ACMC-209myd;2-ethylhexyl 2-cyano-3,3-diphenyl-acrylate;EC 228-250-8;SCHEMBL16483;cid_22571;Octocrylene, analytical standard;CHEMBL1201147;DTXSID9025299;BDBM74416;CHEBI:135526;HMS3039D04;BCP15293;HY-A008;Octyl ;2-Cyano-3,3-diphenylacrylate;Tox21_111153;Tox21_200236;ANW-34019;MFCD00059260;1750;SBB057163;AKOS015900539;Tox21_111153_1;AC-7027;CCG-268181;CS-4296;MCULE-9077867311;NCGC00091585-01;NCGC00091585-04;NCGC00091585-06;NCGC00257790-01;AK-78708;AS-13821;2-ethylhexyl alpha-cyano-beta-phenylcinnamate;2-ethylhexyl-alpha-cyano-beta-phenylcinnamate;FT-0612234;ST50997517;D05227;J10375
acid 2-ethylhexyl ester;2-cyano-3,3-diphenylacrylic acid-2-ethylhexyl ester;2-cyano-3,3-diphenyl-acrylic acid 2-ethyl-hexyl ester;(7-Methoxy-8-(3-methyl-2-buten-1-yl)-2H-chromen-2-one);Octocrylene, United States Pharmacopeia (USP) Reference Standard;Octocrylene, Pharmaceutical Secondary Standard; Certified Reference Material;OCTYL;2-CYANO-3,3-DIPHENYLACRYLATE;octocrilene;PARSOL 340;2-cyano-3,3-diphenyl-2-propenoicaci2-ethylhexylester;2-ethylhexylalpha-cyano-beta-phenylcinnamate;2-Propenoicacid,2-cyano-3,3-diphenyl-,2-ethylhexylester;EUSOLEX OCR;2-Ethyl-2-cyano-3,3-Diphenylacrylate;Octoctylene;2-ETHYLHEXYL 2-CYANO-3,3-DIPHENYL-ACRYLATE 95%-105%;Octocrylene,2-Ethylhexyl-2Cyano-3,3-DiphenylAcrylate;2-cyano-3,3-diphenyl-2-propanoic acid 2-ethylhexyl ester;2-CYANO-3,3-DIPHENYLACRYLIC ACID 2-ETHYLHEXYL ESTER;2-ETHYLHEXYL 2-CYANO-3,3-DIPHENYLACRYLATE;2-ethylhexyl 2-cyano-3,3-diphenylpropenoate;Aokelilin;Parsol 340 (2-Ethylhexyl 2-Cyano-3,3-Diphenylacrylate);OctocryleneUSP, 95.0-105.0% (Assay);LGB-OCT;JADEWIN UV 3039;octocrylen;2-ETHYLHEXYL-2-CYANO-3,3-DIPHENYL-2-PROPENOATE;2-CYANO-3,3-DIPHENYL-2-PROPENOICACID2-ETHYLHEXYLESTER;Octocrilen;2-Ethylhexyl-2-cyano-3,3-diphenylacrylate (OCTOCRYLENE);OCTOCRYLENE USP;3,3-Diphenyl-2-cyanoacrylic acid 2-ethylhexyl ester;Uvinul N-539;α-Cyano-β-phenylbenzeneacrylic acid 2-ethylhexyl ester;α-Cyano-β-phenylcinnamic acid 2-ethylhexyl ester;3-Diphenyl-2-Cyanoacrylic Acid 2-Ethyl-;Octocrylene (500 mg);2-Cyano-3,3-diphenylacrylic Acid 2-Ethylhexyl Ester Octyl 2-Cyano-3,3-diphenylacrylate;ANTHELIOS SX ( octocrylene);Ethylhexyl 2-cyano-3,3-diphenyl;UV-3039;2-Ethylhexyl 2-cyano-3,3-diphenylacrylate 97%;Parsol 340 0.2;UV Absorber 3039;2-Ethylhexyl 2-cyano-3,3-diphenylacrylate Solution, 100ppm;Mr Lin;2-Ethylhexyl 2-Cyano-3,3-diphenylacrylate >;Octocrilene Solution in Methanol/THF/Water, 1000μg/mL


USES 
Solvent for solid sunscreens. UV absorber for plastics and paints.        
octocrylene is a UVB sunscreen with strong water-resistant properties and a rather broad-band absorption range. It exhibits good photostability and is being evaluated by many companies as an effective SPF booster and waterproofing enhancer. This is an expensive ingredient with an approved usage level of 7 to 10 % in both the United States and the European Union. Although gaining in popularity among formulators, its cost and usage level can limit use. In addition, some studies are indicating it may cause allergic reactions in the skin with a history of photo allergy.


Octocrylene is chemically related to cinnamates. It can be used to boost SPF and improve water resistance in a given formulation. Octocrylene is photostable and can improve the photostability of other sunscreens.


•Materials used in the building process, such as flooring, insulation, caulk, tile, wood, glass, etc.
•Flooring materials (carpets, wood, vinyl flooring), or related to flooring such as wax or polish for floors
•Related to all forms of cleaning/washing, including cleaning products used in the home, laundry detergents, soaps, de-greasers, spot removers, etc; modifiers included when specific information is known, such as dry cleaning, laundry, soap, window/floor, etc 
•Drug product, or related to the manufacturing of drugs; modified by veterinary, animal, or pet.
-Includes antifoaming agents, coagulating agents, dispersion agents, emulsifiers, flotation agents, foaming agents, viscosity adjusters, etc
•Food for human consumption, does not include food additives; also includes the manufacture of food, facilities related to food (with appropriate modifiers) 
•Includes food packaging, paper plates, cutlery, small appliances such as roasters, etc.; does not include facilities that manufacture food.
•Plastic products, industry for plastics, manufacturing of plastics, plastic additives
•Related to bedding used in the home (e.g. mattresses, bed pillows)
•Manufacturing of or related to machinery, for production of cement or food, air/spacecraft machinery, electrical machinery, etc
•Plastic products, industry for plastics, manufacturing of plastics, plastic additives
•Various types of paint for various uses, modifiers included when more information is known.
•Personal care products, including cosmetics, shampoos, perfumes, soaps, lotions, toothpaste, etc
•General term for personal care products related to the eye (e.g. eye care products)
•Personal care products used on the face.
•Fragrances or odour agents, can be used in home products (cleaners, laundry products, air fresheners) or similar industrial products.
• Related to hair removal on the body (shaving products, waxing products, trimmers/clippers)
• Personal care products, including scouring cream, hand creams, shaving cream, and tanning cream
• personal care and cosmetics, lip care products
• personal care and cosmetics, lotions and moisturizers for consumer use
• Sunscreen, used on the skin to protect skin from the sun's rays
• Car wax/polish, floor wax, general polishing agents, polish for metals, plastics, rubber, lacquers, leather, furniture, etc.
•Shoes, shoe care products, etc.
•Leather products, and products/chemicals used in the process of tanning and dressing leather
•Sunscreens and blocks marketed to children or babies (spray or aerosol formulations specified

Consumer Uses
Octocrylene is used in the following products: cosmetics and personal care products and perfumes and fragrances.
Another release to the environment of Octocrylene is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use as a processing aid.

Another release to the environment of Octocrylene is likely to occur from, outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials) and indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment). Octocrylene can be found in products with material based on: plastic (e.g. food packaging and storage, toys, mobile phones) and paper (e.g. tissues, feminine hygiene products, nappies, books, magazines, wallpaper).

Widespread uses by professional workers
Octocrylene is used in the following products: cosmetics and personal care products, laboratory chemicals, perfumes and fragrances, pharmaceuticals and photo-chemicals.
Octocrylene is used in the following areas: formulation of mixtures and/or re-packaging.
Another release to the environment of Octocrilene is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use as a processing aid.
Formulation or re-packing
Octocrileneis used in the following products: cosmetics and personal care products and perfumes and fragrances.
Release to the environment of Octocrylene can occur from industrial use: formulation of mixtures.


Uses at industrial sites
Octocrylene is used in the following products: cosmetics and personal care products, laboratory chemicals, perfumes and fragrances, pharmaceuticals and photo-chemicals.
Octocrylene is used in the following areas: formulation of mixtures and/or re-packaging.
Octocrylene is used for the manufacture of plastic products.
Release to the environment of Octocrylene can occur from industrial use: in the production of articles, in processing aids at industrial sites, as an intermediate step in further manufacturing of another substance (use of intermediates), as a processing aid, for thermoplastic manufacture and as a processing aid.
Intermediates
Odour agents
Paint additives and coating additives not described by other categories


Industry Processing Sectors
•All other chemical product and preparation manufacturing
•Fragrances
•Plastic material and resin manufacturing


Manufacture
Release to the environment of Octocrylene can occur from industrial use: manufacturing of the substance.


Chemical Properties        
Clear yellow viscous liquid


Octocrylene is chemically related to cinnamates. It can be used to boost SPF and improve water resistance in a given formulation. Octocrylene is photostable and can improve the photostability of other sunscreens.


General Description        
Yellow viscous liquid. Insoluble in water.
Air & Water Reactions        Insoluble in water.


Reactivity Profile
Octocrilene is an ester derivative. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.


Octocrylene is an organic sun filter. This filter mainly absorbs UVB radiation, which is responsible for tanning but also for sunburn and skin cancer. 
Octocrylene protects the skin from the harmful effects of the sun and premature skin ageing. It helps prevent the risk of skin cancer.
This filter mainly absorbs UVB rays, and shorter UVA rays, which are responsible for ageing but also for skin cancer. 
Octocrylene remains stable and therefore effective during exposure to the sun. It stabilises avobenzone, a particularly effective filter against long UVA rays, enabling it to be used. 
It enables sunscreen products to be water-resistant.


What Is Octocrylene?
Octocrylene is an ingredient used in sunscreens for its ability to absorb UV rays, protecting the skin from sun damage. Octocrylene is a thick colourless ingredient; it is very chemically stable and can be used as an additive to cosmetics to preserve any natural chemical degradation that can occur when skincare products are exposed to sunlight for prolonged periods. 


Octocrylene is classed as a chemical sunscreen due to this ability to protect the skin from UV damage. Octocrylene is different from your physical based sunscreens such as; zinc or titanium dioxide which work to protect the skin by creating a physical barrier. Octocrylene is also thought to have skin-moisturizing effects because of its emollient properties. Emollients help to prevent moisture loss from the top layers of the skin. However, it’s important to remember that the primary purpose of this ingredient is to neutralize UV radiation, and any emollient properties are just an added benefit. If you’re looking to moisturize the skin specifically, octocrylene should not be the first ingredient on your list. Octocrylene is often used in formulations for products such as; hair sprays, tanning oils, BB creams, conditioners, and CC creams. 


Another useful chemical property of octocrylene is its ability to easily combine with other oils, which makes it helpful as an emulsifier – used to keep ingredients more thoroughly mixed to improve their effectiveness. In-vitro studies have shown that sunscreen combinations containing octocrylene may increase UVA protection levels without causing instability or significantly harming the skin and boosting the sun protection factor (SPF). 


Octocrylene is an effective oil-soluble liquid UV‐B filter. It has excellent dissolving properties for crystalline UV filters. Due to its outstanding photostability, it is used as a photostabilizer. The conjugated acrylate portion absorbs UVB and short-wave UVA (ultraviolet) rays with wavelengths in the range of 280-320 nm which protects the skin from direct DNA damage. The ethylhexanol portion is a fatty alcohol, which functions as an emollient due to its hydrophobicity.


General description
Octocrylene is a commercially used UVB filter, termed an environmental pollutant because of its stability, lipophilic nature, and resistance to sunlight degradation. It is employed as an ingredient in water-resistant sunscreen products and high SPF formulations.


Application
Octocrylene may be used as an analytical reference standard for the quantification of the analyte in the following:        
• Sunscreen formulations using reversed-phase high-performance liquid chromatography (RP-HPLC) technique.  
• Marine mammals using ultra-high-performance liquid chromatography (UHPLC).       
• Solid lipid nanoparticle systems using high-performance liquid chromatography (HPLC) technique.


Octocrylene is a compound often used as an additive in sunscreen and is thought to have skin moisturizing effects because of its emollient properties. What makes this chemical such a popular additive to sunblock, is its ability to neutralize UV radiation dissipated by sunlight, and to minimize skin damage from prolonged sun exposure. Octocrylene is also often combined with avobenzone, another common sunscreen ingredient often appearing on ingredient labels. Because of its effectiveness, the chemical has been approved across the globe for use in cosmetics and skincare products, but the concentrations of this ingredient are usually limited to no more than 10 or 12 %. However, the use of this chemical doesn’t just stop with sunscreen for the face and arms but can extend to a variety of other products, like hair spray, tannin oil, BB cream, conditioner, and CC cream, among others.


Octocrylene is an organic ultraviolet (UV) filter that absorbs mainly UVB radiation and short UVA wavelengths. Octocrylene has the potential for using in various cosmetic products to either provide an appropriate sun protection factor in sunscreen products or to protect cosmetic formulations from UV radiation.


What Is It?
Octocrylene is a clear, colourless oily liquid. In cosmetics and personal care products, Octocrylene is used in the formulation of sun protection products, as well as skin and nail care products.


Why is it used in cosmetics and personal care products?
Octocrylene, when applied to the skin, absorbs UV rays. In addition to causing sunburn, UV radiation is a significant cause of premature ageing of the skin and contributes to the development of melanoma and other forms of skin cancer. Octocrylene can also be used to protect cosmetics and personal care products from deterioration by absorbing, UV rays.


Octocrylene is an organic, oil-soluble sun filter that mainly absorbs UV-B radiation. Also provides protection against short UV-A radiation, which is a significant cause of skin cancer and ageing. Octocrylene 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.


Approved for the use in sun care preparations in many countries worldwide.


In Europe and America max. 10% and in Canada max. 12%.
Octocrylene is particularly suitable for water-resistant formulations, as it is hydrophobic and miscible with many emollients. Combine with other oil-soluble UV filters such as AakoSun OTZ or AakoSun BEMT to provide a higher SPF.


Octocrylene is also known under the names Octocrilene, 2-ethylhexyl 2-cyano-3 and 3-diphenylacrylate.


Octocrylene is a compound often used as an additive in sunscreen and is thought to have skin moisturizing effects because of its emollient properties.
What makes this chemical such a popular additive to sunblock, is its ability to neutralize UV radiation dissipated by sunlight, and to minimize skin damage from prolonged sun exposure.
Octocrylene is also often combined with avobenzone, another common sunscreen ingredient often appearing on ingredient labels.
Because of its effectiveness, the chemical has been approved across the globe for use in cosmetics and skincare products, but the concentrations of this ingredient are usually limited to no more than 10 or 12 %.
However, the use of this chemical doesn’t just stop with sunscreen for the face and arms but can extend to a variety of other products, like hair spray, tannin oil, BB cream, conditioner, and CC cream, among others.
Octocrylene may cause contact and photo contact allergy.


Rising demand for cosmetics and sunscreens due to increased incidences of skin cancer is expected to drive the octocrylene market.
Due to changing environment globally and increasing awareness about skin cancer, consumer groups are turning towards sunscreens.
Octocrylene is an important and indispensable component due to its advantageous properties.
With the increase in the sunscreen and cosmetics industries worldwide, demand for octocrylene is anticipated to expand at a significant growth rate


Octocrylene is an organic compound and ester formed by the condensation of a diphenylcyanoacrylate with 2-ethylhexanol (a fatty alcohol, adding emollient and oil-like, water resistant properties). It is primarily used as an active ingredient in sunscreens because of its ability to absorb UVB and short-wave UVA (ultraviolet) rays and protect the skin from direct DNA damage.


FUNCTIONS AND USES OF OCTOCRYLENE
Octocrylene can be used as a UV-B filter in sunscreen products at a concentration up to 10% (as acid) and is often used together with dibenzoylmethane derivatives to stabilise sunscreen products.
Octocrylene is also used in body and face care products, perfumes and fragrances.


It's a chemical sunscreen ingredient, used not only for its own ability to protect skin from both UVA and UVB rays but also for its ability to increase further the stability and efficacy of other chemical sunscreen ingredients, hence its popularity and prevalence.


Physical sunscreens
Physical sunscreens work by reflecting the UV rays from the sun, protecting the skin from the harmful rays.
These formulations rely on the use of ingredients such as zinc oxide and titanium dioxide to provide this protection.
Physical sunscreens create a barrier between the skin and the sun and aren’t absorbed into the skin.
They are generally broad-spectrum, meaning that they protect against both UVA and UVB rays.


Chemical sunscreens
Chemical sunscreens are absorbed into the skin and absorb the skin’s harmful rays before they can penetrate deep enough to cause damage to the skin.
Often chemical sunscreens are used in combination with another chemical sunscreen to provide broad-spectrum protection.
In the case of octocrylene, it is commonly used in conjunction with avobenzone.
Also, both types of sunscreens, physical and chemical, will often include ingredients such as vitamin C or E to protect against damage from free radicals.
Free radicals damage is more likely to occur with chemical sunscreens than with physical sunscreens, so these ingredients are important to look for in your sunscreen product.


Octocrylene or octocrylene (CAS n. 6197‐30‐4) is an organic compound with an aromatic structure which is also known as 2‐ethylhexyl 2‐cyano‐3,3‐diphenyl‐2‐propenoate; 2‐ethylhexyl 2‐cyano‐3,3‐diphenylacrylate or the 2‐ethylhexyl ester of 2‐cyano‐3,3‐diphenyl acrylic acid.</p>


It is an organic ultraviolet (UV) filter, which absorbs mainly UVB radiation and short UVA wavelengths.
Due to its UV radiation absorption properties, it is used in sunscreens with other UV filters to provide an adequate sun protection factor (SPF).
It is also used to stabilize other UV filters such as avobenzone, a filter particularly effective against UVA2; this association thus provides optimal UV protection.
Various cosmetic products such as facial creams or lip care products contain octocrylene to either provide an adequate SPF or to protect the cosmetic formulation from UV radiation.


In Europe, UV filters allowed in cosmetic products are regulated in Annex VI of Cosmetics Regulation (EC) No. 1223/2009.
According to this regulation, octocrylene is authorized as a UV filter in cosmetic formulations at a maximum concentration of 10.0% as an acid form in Europe (Annex VI/10). Of note, octocrylene is also authorized as a UV filter in sunscreen products in the same conditions in the USA.


Octocrylene is chemically related to cinnamates. It can be used to boost SPF and improve water resistance in a given formulation. Octocrylene is photostable and can improve the photostability of other sunscreens. It is expensive and can present difficulties in the formulation.


Octocrylene is an ester of diphenylcyanoacrylate and 2-ethylhexanol formed by the condensation process.
The organic compound is a colourless, oily and viscous liquid. Octocrylene is primarily used in sunscreens owing to its skin moisturizing properties.
Octocrylene can neutralize UV radiation emitted by the sun and minimizes skin damage caused by prolonged sun exposure.
The compound is approved by various regulatory organizations across the globe; however, its concentration is limited to 10-12% in any formulation.
It is not used to protect the face and arms. It is widely used in the products such as BB cream, CC cream, hair spray, conditioner and tannin oil.It is an ester formed by the


Octocrylene is an oil-miscible UV-B filter that is approved in the USA, Europe and in Japan for use in sun care preparations. As octocrylene is miscible with many cosmetic oils, octocrylene can easily be incorporated in the oily phase of an emulsion. Because octocrylene is hydrophobic and oil-soluble, octocrylene is preferred for
water-resistant and water-repellant formulations octocrylene is also compatible with all common plasticizers.


On the basis of safety assessment, and considering the concerns related to potential endocrine-disrupting properties of Octocrylene, the SCCS is of the opinion that Octocrylene is safe as a UV-filter at concentrations up to 10% in cosmetic products when used individually.
Octocrylene is also considered safe for combined use of sunscreen cream/lotion, sunscreen pump spray, face cream, hand cream and lipstick at a concentration up to 10%. However, the use of Octocrylene at 10% or above in sunscreen propellant spray is not considered safe for the combined use.


The use of Octocrylene in sunscreen propellant spray is considered safe when its concentration does not exceed 9% when used together with face cream, hand cream, and lipstick containing 10% Octocrylene. 


Octocrylene is a pale yellow liquid with a melting point of 96-98ºC. An oil-miscible UV-B filter that is approved in the USA, Europe and Japan for use in suncare preparations. As it is miscible with many cosmetic oils, it can easily be incorporated into the oily phase of an emulsion. Because it is hydrophobic and oil-soluble, it is preferred for water-resistant and water-repellant formulations. Also features excellent photostability, and its ability to stabilize Butyl Methoxydibenzoylmethane.
 

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