Basic information
- CAS
6197-30-4- Standard SMILES
CCCCC(CC)COC(=O)C(C#N)=C(c1ccccc1)c1ccccc1- InChIKey
FMJSMJQBSVNSBF-UHFFFAOYSA-N- Molecular formula
- C24H27NO2
- Average molar mass
- 361.5 g/mol
- Monoisotopic mass
- 361.2041791
Overview
2-ethylhexyl-2-cyano-3,3-diphenylacrylate is a yellow viscous liquid. Insoluble in water. (NTP, 1992)
Names & identifiers
- Preferred name
- Octocrylene
- IUPAC
- 2-ethylhexyl 2-cyano-3,3-diphenylprop-2-enoate
- English name
- Octocrylene
- Molecular formula
- C24H27NO2
- Molecular weight
- 361.48
Names & synonyms
Show more names
Database identifiers
- CAS
6197-30-4- PubChem CID
- 22571
- DTXSID
DTXSID9025299- ChEMBL
CHEMBL1201147- ChEBI
CHEBI:135526- UNII
- 5A68WGF6WM
- EC Number
- 228-250-8
- Nikkaji
- J8.358E
Properties
Computed structural properties
- XLogP
- 7.1
- Topological polar surface area
- 50.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 10
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 510
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Food Contact Substances
FCS -> FDA Cumulative Estimated Daily Intake (CEDI)
FCS -> FDA Inventory of Effective Food Contact Substance (FCS) Notifications
Physical Description
2-ethylhexyl-2-cyano-3,3-diphenylacrylate is a yellow viscous liquid. Insoluble in water. (NTP, 1992)
Liquid
Physicochemical properties
- Melting point
- -10 °C · -10 °C (lit.)
- Boiling point
- 218 °C/1.5 · 218 °C/1.5 mmHg (lit.)
- Density
- 1.051 g/mL · 1.051 g/mL at 25 °C (lit.)
- vapor pressure
- 0 Pa · 0Pa at 25℃
- refractive index
- 20 · n20/D 1.567(lit.)
- Flash point
- 230 °F · >230 °F
- storage temp.
- 15 · 15-25°C
- solubility
- Chloroform (Slightly), Methanol (Sparingly)
- form
- Oil
- color
- Colourless to Light Yellow
- Odor
- Mild characteristic odor
- Merck
- 14 · 14,6756
- Cosmetics Ingredients Functions
- LIGHT STABILIZERUV ABSORBERUV FILTER
- InChI
- 1S/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
- InChIKey
- FMJSMJQBSVNSBF-UHFFFAOYSA-N
- SMILES
- CCCCC(CC)COC(=O)\C(C#N)=C(/c1ccccc1)c2ccccc2
- LogP
- 6.1 at · 6.1 at 23℃
- CAS DataBase Reference
- 6197 · 6197-30-4(CAS DataBase Reference)
- EWG's Food Scores
- 2 · 2-3
- FDA UNII
- 5 A68WGF6WM · 5A68WGF6WM
- EPA Substance Registry System
- 2 · 2-Ethylhexyl 2-cyano-3,3-diphenylacrylate (6197-30-4)
- Absorption
- 303 nm · uv max: 303 nm
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 413 · H413
- Precautionary statements
- 273 · P273-P501
- Risk Statements
- 52 · 52
- Safety Statements
- 29 · 29/56
- WGK Germany
- 1 · 1
- RTECS
- 3328750 · UD3328750
- TSCA
- TSCA listed
- HS Code
- 29269095 · 29269095
- Storage Class
- 10 · 10 - Combustible liquids
- Hazard Classifications
- 1 Aquatic · Aquatic Acute 1Aquatic Chronic 1
- Toxicity
- 50 orl-rat: · LD50 orl-rat: >5 g/kg NTIS** OTS0556792
- REACH Registrations
- Active
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 2.5% (16 of 645) of reports.
Warning
H410 (42.6%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]
P273, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 645 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 2-Propenoic acid, 2-cyano-3,3-diphenyl-, 2-ethylhexyl ester
2-Propenoic acid, 2-cyano-3,3-diphenyl-, 2-ethylhexyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 2-cyano-3,3-diphenyl-, 2-ethylhexyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 09-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14858
Octocrylene: Does not have an individual approval but may be used under an appropriate group standard
Reactivity Profile
2-ETHYLHEXYL-2-CYANO-3,3-DIPHENYLACRYLATE is an acrylate 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.
Safety & protection
Fire Fighting
This compound is not very flammable but any fire involving this compound may produce dangerous vapors. You should evacuate the area. All firefighters should wear full-body protective clothing and use self-contained breathing apparatuses. You should extinguish any fires involving this chemical with a dry chemical, carbon dioxide, foam, or halon extinguisher. (NTP, 1992)
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with toluene followed by washing with a strong soap and water solution. Do no reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Safety data
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- UD3328750
- hs_code
- 29269095
- Toxicity
- LD50 orl-rat: >5 g/kg NTIS** OTS0556792
- risk_code
- 52
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 29/56
- Storage Class
- 10 - Combustible liquids
- Hazard statements
- H413
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- REACH Registrations
- Active
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1
- Precautionary statements
- P273-P501
Chemistry & industry
Pharmacology
Mechanism of Action
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 photostabilizer. 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 it's hydrophobicity.
Uses & manufacturing
Use Classification
Fragrance Ingredients
Cosmetics -> Uv absorber; Uv filter
General Manufacturing Information
All Other Basic Organic Chemical Manufacturing
2-Propenoic acid, 2-cyano-3,3-diphenyl-, 2-ethylhexyl ester: ACTIVE
Applications
DescriptionOctocrylene (OCT) is a viscous, clear, colorlesss oi introduced in commercial sunscreens and anti-ageing creams about 15 years ago. It is the 2-ethylhexyl ester of 2-cyano-3,3-diphenylacrylic acid, with the extended conjugation of the acid portion that absorbs UVB and short-wave UVA (ultraviolet) rays, with wavelengths from 280 to 320 nm, which promote tanning but also contribute to the onset of sunburn and skin cancer. It is used in various body care products, in concentrations up to 10%, to provide an adequate sun-protection factor or to protect the body care formulations themselves from UV radiation[1].
UsesOctocrylene 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.
General DescriptionYellow viscous liquid. Insoluble in water.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Additional notes
DefinitionChEBI: Octocrylene is a diarylmethane. It is an ester formed by the condensation of a diphenylcyanoacrylate with 2-ethylhexanol, used in sunscreens and cosmetics.
Related reactions
Compound notes
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