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Sigma-Aldrich

2-Ethylhexyl 2-cyano-3,3-diphenylacrylate

97%

Synonym(s):

2-Cyano-3,3-diphenylacrylic acid 2-ethylhexyl ester, 2-Ethylhexyl α-cyano-β-phenylcinnamate, 2-Ethylhexyl 2-cyano-3,3-diphenyl-2-propenoate, Octocrylene

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About This Item

Linear Formula:
(C6H5)2C=C(CN)CO2CH2CH(C2H5)(CH2)3CH3
CAS Number:
6197-30-4
Molecular Weight:
361.48
EC Number:
228-250-8
MDL number:
MFCD00059260
UNSPSC Code:
12162002
PubChem Substance ID:
24866036
NACRES:
NA.23

Quality Level

200

Assay

97%

form

viscous liquid

refractive index

n20/D 1.567 (lit.)

bp

218 °C/1.5 mmHg (lit.)

mp

−10 °C (lit.)

density

1.051 g/mL at 25 °C (lit.)

SMILES string

CCCCC(CC)COC(=O)\C(C#N)=C(/c1ccccc1)c2ccccc2

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

InChI key

FMJSMJQBSVNSBF-UHFFFAOYSA-N

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General description

2-Ethylhexyl 2-cyano-3,3-diphenylacrylate is an ester-based UV filter formed by reacting 3,3-diphenylcyanoacrylate and 2-ethylhexanol. It is commercially used as a UV absorber in sunscreens and other cosmetic formulations.

Application

  • Photochemical response of the scleractinian coral Stylophora pistillata to some sunscreen ingredients: This study investigates the impact of octocrylene on the photosynthetic efficiency of coral symbionts, raising concerns about environmental effects (JP Fel et al., 2019).
  • Preparation of O/I1-type emulsions and S/I1-type dispersions encapsulating UV-absorbing agents: Explores formulations for incorporating octocrylene into cosmetic products, enhancing UV protection capabilities (K Aramaki et al., 2015).

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

WGK

WGK 2

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Changes in ultraviolet absorbance and hence in protective efficacy against lipid peroxidation of organic sunscreens after UVA irradiation
Damiani E, et al.
Journal of Photochemistry and Photobiology. B, Biology, 82(3), 204-213 (2006)
Dispersive solid-phase extraction based on oleic acid-coated magnetic nanoparticles followed by gas chromatography-mass spectrometry for UV-filter determination in water samples
Roman IP, et al.
Journal of Chromatography A, 1218(18), 2467-2475 (2011)
Sunscreen enhancement of UV-induced reactive oxygen species in the skin
Hanson KM, et al.
Free Radical Biology & Medicine, 41(8), 1205-1212 (2006)
Rosario Rodil et al.
Journal of chromatography. A, 1179(2), 81-88 (2007-12-22)
Stir bar sorptive extraction (SBSE) in combination with thermal desorption-gas chromatography-mass spectrometry (TD-GC-MS) was applied for the determination of 9 UV filters in water samples. The stir bar coated with polydimethylsiloxane (PDMS) was added to 20 mL of water sample
N Negreira et al.
Analytical and bioanalytical chemistry, 400(2), 603-611 (2011-02-22)
This work describes an effective, low solvent consumption and affordable sample preparation approach for the determination of eight UV filters in surface and wastewater samples. It involves sorptive extraction of target analytes in a disposable, technical grade silicone disc (5 mm
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