6197-30-4

Basic information

• Product Name: Octocrilene
• Synonyms: OCTYL 2-CYANO-3,3-DIPHENYLACRYLATE;octocrilene;OCTOCRYLENE;PARSOL 340;2-cyano-3,3-diphenyl-2-propenoicaci2-ethylhexylester;2-ethylhexylalpha-cyano-beta-phenylcinnamate;2-Propenoicacid,2-cyano-3,3-diphenyl-,2-ethylhexylester;2-cyano-3,3-diphenyl-2-propanoic acid 2-ethylhexyl ester
• CAS NO: 6197-30-4
• Molecular Formula: C₂₄H₂₇NO₂
• Molecular Weight: 361.48
• EINECS: 228-250-8
• Product Categories: cosmetic raw material;UV-Absorber;Stabilizers;Polymer Additives;Polymer Science;API;PARAPLATIN
• Mol File: 6197-30-4.mol

Chemical Properties

• Melting Point: −10 °C(lit.)
• Boiling Point: 218 °C1.5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Yellow viscous liquid
• Density: 1.051 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.56E-09mmHg at 25°C
• Refractive Index: n20/D 1.567(lit.)
• Storage Temp.: 15-25°C
• Solubility: Chloroform (Slightly), Methanol (Sparingly)
• Merck: 14,6756
• CAS DataBase Reference: Octocrilene(CAS DataBase Reference)
• NIST Chemistry Reference: Octocrilene(6197-30-4)
• EPA Substance Registry System: Octocrilene(6197-30-4)

Safety Data

• Statements: 52
• Safety Statements: 29/56
• WGK Germany: 1
• RTECS: UD3328750
• Hazardous Substances Data: 6197-30-4(Hazardous Substances Data)

Usage

Uses

Used in Sunscreen Industry:
Octocrylene is used as a UVB sunscreen for its ability to absorb UV rays, protecting the skin from sun damage. It is chemically related to cinnamates and is employed to boost SPF and improve water resistance in a given formulation. Octocrylene is photostable and can enhance the photostability of other sunscreens.
Octocrylene is used as an effective SPF booster and waterproofing enhancer for its strong water-resistant properties and broad-band absorption range. It is being evaluated by many companies for its potential in the sunscreen industry. However, its cost and approved usage level of 7 to 10 percent in both the United States and the European Union can limit its use. Additionally, some studies indicate that it may cause allergic reactions in skin with a history of photoallergy.

benefits

Octocrylene is a compound often used as an additive in sun screen, and is thought to have skin moisturizing effects because of its emollient properties. What makes this chemical such a popular additive to sun block, is its ability to neutralize UV radiation dissipated by sunlight, and to minimize skin damage from prolonged sun exposure. Octocrylene protects the skin from the harmful effects of the sun and premature skin aging. It helps prevent the risk of skin cancer. This filter mainly absorbs UVB rays, and shorter UVA rays, which are responsible for aging but also for skin cancer.

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.

Fire Hazard

Flash point data for Octocrilene are not available. Octocrilene is probably combustible.

Flammability and Explosibility

Nonflammable

Contact allergens

Octocrylene is an anti-UVB filter used in cosmetics that may induce photoallergic contact dermatitis.

Side effects

Some people are concerned about the body’s ability to absorb octocrylene, which can present in the blood, urine, and breast milk. It may promote the production of free radicals, which can damage DNA, potentially increasing the risk of melanoma. However, further research is necessary.People with sensitive skin or skin conditions, such as eczema, may prefer to avoid products containing octocrylene. Alternatively, a person can perform a patch test before using a product containing octocrylene for the first time. The patch test should indicate if an individual is allergic or sensitive to an ingredient in the product.The Food and Drug Administration (FDA) evaluated the safety of octocrylene for use in sunscreen products and found that concentrations of up to 10% are safe.The European Scientific Committee on Consumer Safety (SCCS) also stated that octocrylene is safe in products containing concentrations of no more than 10%.Berardesca, E.,et al.(2019). Review of the safety of octocrylene used as an ultraviolet filter in cosmetics.https://onlinelibrary.wiley.com/doi/full/10.1111/jdv.15945

Safety Profile

Low toxicity by ingestion. Whenheated to decomposition it emits toxic vapors of NOx.

InChI:InChI=1/C24H27NO2/c1-3-5-12-19(4-2)18-27-24(26)22(17-25)23(20-13-8-6-9-14-20)21-15-10-7-11-16-21/h6-11,13-16,19H,3-5,12,18H2,1-2H3

Synthetic route

2-Ethylhexyl alcohol (104-76-7) + etocrylene (5232-99-5) → octocrylene (6197-30-4)

Conditions	Yield
In sodium carbonate	99.8%
With sodium methylate In toluene for 8h; Reflux;	144.3 g

benzophenone (119-61-9) + 2'-ethylhexyl cyanoacetate (13361-34-7) → octocrylene (6197-30-4)

Conditions	Yield
With ammonium acetate; acetic acid In water at 85 - 90℃; under 400 - 420 Torr; for 16h; Reagent/catalyst;	76.3%
With propionic acid; ammonium acetate In n-heptane at 110℃; under 760.051 Torr; for 5h; Product distribution / selectivity;	66.18%

benzophenone (119-61-9) + 2'-ethylhexyl cyanoacetate (13361-34-7) → 2-cyano-3,3-diphenylacrylamide (731-48-6) + octocrylene (6197-30-4)

Conditions	Yield
With propionic acid; ammonium acetate In n-heptane at 95 - 110℃; under 525.053 - 760.051 Torr; for 6h; Product distribution / selectivity; Heating / reflux;	A 0.42 - 0.7 %Chromat. B n/a

benzophenone (119-61-9) → octocrylene (6197-30-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonium acetate; pyrographite / n-heptane / 15 h / Ionic liquid; Reflux 2: sodium methylate / toluene / 8 h / Reflux View Scheme

octocrylene (6197-30-4) → 2-cyano-3,3-diphenyl-propionic acid 2-ethylhexyl ester

Conditions	Yield
With hydrogen; 5%-palladium/activated carbon In tetrahydrofuran at 20℃;

ethanol (64-17-5) + octocrylene (6197-30-4) → etocrylene (5232-99-5) + 2-ethylhexyl 2-ethoxy-4-phenylquinoline-3-carboxylate

Conditions	Yield
for 6h; Photolysis;

benzylamine (100-46-9) + octocrylene (6197-30-4) → N-benzyl-2-cyano-3,3-diphenylacrylamide

Conditions	Yield
In cyclohexane for 3h; Photolysis;

octocrylene (6197-30-4) → C41H51NO5

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide; water / ethanol / 24 h / 20 °C 2.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 2 h / 25 °C / Inert atmosphere 2.2: 5 h / 25 °C / Inert atmosphere View Scheme

octocrylene (6197-30-4) → 2-cyano-3,3-diphenylacrylic acid (10380-41-3)

Conditions	Yield
With water; sodium hydroxide In ethanol at 20℃; for 24h;

Upstream product

• 104-76-7 2-Ethylhexyl alcohol 
• 5232-99-5 etocrylene 
• 119-61-9 benzophenone 
• 13361-34-7 2'-ethylhexyl cyanoacetate 

Downstream Products

• 5232-99-5 etocrylene 
• 10380-41-3 2-cyano-3,3-diphenylacrylic acid 

Relevant articles and documents

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The invention provides a preparation method of a cyanoacrylate ultraviolet light absorber. Benzophenone compounds represented by general formula I with cyanoacetate under a weakly alkaline condition by using activated carbon grafted acidic ionic liquid as a catalyst to generate a compound represented by general formula II. The preparation method of the cyanoacrylate ultraviolet light absorber adopts the activated carbon grafted acidic ionic liquid catalyst to replace acetic acid, so that the preparation method has the advantages of easiness in recycling of the catalyst, high product yield, fewthree wastes, and convenience in post-treatment, and is an economical, practical and environment-friendly technology.

Method to reduce substantivity of cloth staining caused by sunscreens

Suggested is a cosmetic and/or pharmaceutical preparation, especially dermatological preparation and its used for the protection of the human skin and human hair against the harmful effects of ultraviolet solar radiation comprising the water soluble UVA absorbing substance disodium phenyl dibenzimidazole tetrasulfonate, wherein the preparation is free from the UVA filters selected from the group consisting of 2,4-bis[{(4-(2-ethylhexyloxy)-2-hydroxy}phenyl]--6-(4-methoxyphenyl)-1,3,5-triazine, (Tinosorb?S), hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate (Uvinul? A Plus), 2-hydroxy-4-methoxybenzo-phenone (Benzophenone-3, Oxybenzone, Neo Heliopan? BB), Tris-Biphenyl Triazine (Tinosorb? A2B) or mixtures thereof.

A NOVEL PROCESS FOR THE PREPARATION OF 2-CYANO- 3,3- DIARYLACRYLATES

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Suggested is a cosmetic compositions comprising (a) a crosspolymer obtained from copolymerisation of at least two different polyols and at least one dicarboxylic acid and (b) at least one fragrance.

A composition for lightening skin and hair

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ALPHA-AMINO ACID DERIVATIVES FOR IMPROVING SOLUBILITY

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USE OF CHROMAN-4-ONE DERIVATIVES

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UV FILTER CAPSULE

The present invention relates to UV filter capsules, to the use thereof for the preparation of cosmetic or dermatological formulations or dispersions, and to cosmetic or dermatological formulations which comprise the capsules, and to a process for the production thereof.

TYROSINASE INHIBITORS

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