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6197-30-4

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6197-30-4 Usage

Chemical Properties

Clear yellow viscous liquid with mild characteristic odor, Miscible in methanol, n-butanol, ethyl acetate, mineral oil, hexane, toluene. Immiscible in water. Octocrylene is an effective oil soluble liquid UV‐B filter. It has excellent dissolving properties for crystalline UV filters.

Uses

Octocrylene is an ingredient used in sunscreens for its ability to absorb UV rays, protecting the skin from sun damage. It 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 formulation.

Definition

ChEBI: Octocrylene is a diarylmethane. It is an ester formed by the condensation of a diphenylcyanoacrylate with 2-ethylhexanol, used in sunscreens and cosmetics.

Application

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 percent 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 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.

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.

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.

Check Digit Verification of cas no

The CAS Registry Mumber 6197-30-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,1,9 and 7 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 6197-30:
(6*6)+(5*1)+(4*9)+(3*7)+(2*3)+(1*0)=104
104 % 10 = 4
So 6197-30-4 is a valid CAS Registry Number.
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

6197-30-4 Well-known Company Product Price

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  • Sigma-Aldrich

  • (PHR1083)  Octocrylene  pharmaceutical secondary standard; traceable to USP

  • 6197-30-4

  • PHR1083-1G

  • 732.19CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1083)  Octocrylene  pharmaceutical secondary standard; traceable to USP

  • 6197-30-4

  • PHR1083-10G

  • 4,312.04CNY

  • Detail
  • Sigma-Aldrich

  • (02343)  Octocrylene  analytical standard

  • 6197-30-4

  • 02343-1ML

  • 1,437.93CNY

  • Detail
  • USP

  • (1477411)  Octocrylene  United States Pharmacopeia (USP) Reference Standard

  • 6197-30-4

  • 1477411-500MG

  • 4,662.45CNY

  • Detail
  • Aldrich

  • (415820)  2-Ethylhexyl2-cyano-3,3-diphenylacrylate  97%

  • 6197-30-4

  • 415820-50ML

  • 586.17CNY

  • Detail
  • Aldrich

  • (415820)  2-Ethylhexyl2-cyano-3,3-diphenylacrylate  97%

  • 6197-30-4

  • 415820-250ML

  • 1,852.11CNY

  • Detail

6197-30-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Ethylhexyl 2-cyano-3,3-diphenylacrylate

1.2 Other means of identification

Product number -
Other names Octocrilene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Paint additives and coating additives not described by other categories
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:6197-30-4 SDS

6197-30-4Synthetic route

2-Ethylhexyl alcohol
104-76-7

2-Ethylhexyl alcohol

etocrylene
5232-99-5

etocrylene

octocrylene
6197-30-4

octocrylene

Conditions
ConditionsYield
In sodium carbonate99.8%
With sodium methylate In toluene for 8h; Reflux;144.3 g
benzophenone
119-61-9

benzophenone

2'-ethylhexyl cyanoacetate
13361-34-7

2'-ethylhexyl cyanoacetate

octocrylene
6197-30-4

octocrylene

Conditions
ConditionsYield
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

benzophenone

2'-ethylhexyl cyanoacetate
13361-34-7

2'-ethylhexyl cyanoacetate

A

2-cyano-3,3-diphenylacrylamide
731-48-6

2-cyano-3,3-diphenylacrylamide

B

octocrylene
6197-30-4

octocrylene

Conditions
ConditionsYield
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

benzophenone

octocrylene
6197-30-4

octocrylene

Conditions
ConditionsYield
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

octocrylene

2-cyano-3,3-diphenyl-propionic acid 2-ethylhexyl ester

2-cyano-3,3-diphenyl-propionic acid 2-ethylhexyl ester

Conditions
ConditionsYield
With hydrogen; 5%-palladium/activated carbon In tetrahydrofuran at 20℃;
ethanol
64-17-5

ethanol

octocrylene
6197-30-4

octocrylene

A

etocrylene
5232-99-5

etocrylene

B

2-ethylhexyl 2-ethoxy-4-phenylquinoline-3-carboxylate

2-ethylhexyl 2-ethoxy-4-phenylquinoline-3-carboxylate

Conditions
ConditionsYield
for 6h; Photolysis;
benzylamine
100-46-9

benzylamine

octocrylene
6197-30-4

octocrylene

N-benzyl-2-cyano-3,3-diphenylacrylamide

N-benzyl-2-cyano-3,3-diphenylacrylamide

Conditions
ConditionsYield
In cyclohexane for 3h; Photolysis;
octocrylene
6197-30-4

octocrylene

C41H51NO5

C41H51NO5

Conditions
ConditionsYield
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

octocrylene

2-cyano-3,3-diphenylacrylic acid
10380-41-3

2-cyano-3,3-diphenylacrylic acid

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

6197-30-4Relevant articles and documents

Preparation method of cyanoacrylate ultraviolet light absorber

-

, (2020/04/29)

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.

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

-

Page/Page column 9; 10, (2014/11/13)

The present invention relates to a novel process for preparation of 2-Cyano-3,3- diarylacrylates of Formula I by the Knoevenagel condensation of Cyanoacetic esters and Arylketones using ammonium compound and acetic acid and without the use of organic solvent.

A composition for lightening skin and hair

-

, (2014/10/28)

Suggested is a composition comprising (a) sclareolide and (b1) at least one tyrosinase inhibitor; and/or (b2) at least one sun protection factor; and/or (b3) at least one anti-oxidants; and/or (b4) at least one anti-inflammatory agent; and/or (b5) at least one desquamating agent.

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