Octocrylene

HCID 22571

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

Octocrylene6197-30-42-Ethylhexyl 2-cyano-3,3-diphenylacrylateOctocrilene2-ETHYLHEXYL-2-CYANO-3,3-DIPHENYLACRYLATEOctocrileno2-Propenoic acid, 2-cyano-3,3-diphenyl-, 2-ethylhexyl esterOctocrilenumDTXSID90252995A68WGF6WM2-Ethylhexyl 2-cyano-3,3-diphenyl-2-propenoateNSC-760433
Show more names
UV-3039PARSOL 340OctocrilenMr LinLGB-OCTAokelilinoctocrylenEUSOLEX OCR
DTXCID2052992-cyano-3,3-diphenyl-acrylic acid 2-ethylhexyl esterDT CollagenOCTOCRKYENERefChem:55765VUINT TINTED SUNSCREENW.SKIN TRIPLE CARE SUNBest of Glow SPF Discovery Kit

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

Experimental & physicochemical properties

Chemical ClassesUV filter
CosmeticsUv absorber; Uv filter
FragrancesFragrance Ingredient (2-_Propenoic acid, 2-_cyano-_3,_3-_diphenyl-_, 2-_ethylhexyl ester) -> IFRA transparency List
SolubilityInsoluble (NTP, 1992)
Human Drugs · 2 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Food Contact Substances · 2 items

FCS -> FDA Cumulative Estimated Daily Intake (CEDI)

FCS -> FDA Inventory of Effective Food Contact Substance (FCS) Notifications

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

Safety & regulation

GHS classification

GHS Classification · 5 items

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 · 4 items

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

Fire HazardsFlash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
Reactive GroupNitriles
Reactivity AlertsPolymerizable
Reactivity Profile · 1 item

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.

Air and Water ReactionsInsoluble in water.

Safety & protection

Fire Fighting · 1 item

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 · 1 item

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 · 1 item

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) · 1 item

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

Chemistry & industry

Pharmacology

Mechanism of Action · 1 item

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

U.S. Production2023: 550,000 - <700,000 lb
Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesNot Known or Reasonably Ascertainable
Household ProductsInformation on 77 consumer products that contain Octocrylene in the following categories is provided:
Use Classification · 2 items

Fragrance Ingredients

Cosmetics -> Uv absorber; Uv filter

General Manufacturing Information · 2 items

All Other Basic Organic Chemical Manufacturing

2-Propenoic acid, 2-cyano-3,3-diphenyl-, 2-ethylhexyl ester: ACTIVE

Applications · 3 items

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

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
福建帝盛科技股份有限公司0571-88226505 17757185101 · [email protected]

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

6 records

Compound notes

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