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415820

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:
Molecular Weight:
361.48
EC Number:
MDL number:
UNSPSC Code:
12162002
PubChem Substance ID:
NACRES:
NA.23

Quality Level

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

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

453.2 °F - closed cup

Flash Point(C)

234 °C - closed cup


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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)
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)
Sunscreen enhancement of UV-induced reactive oxygen species in the skin
Hanson KM, et al.
Free Radical Biology & Medicine, 41(8), 1205-1212 (2006)
Martine Avenel-Audran et al.
Archives of dermatology, 146(7), 753-757 (2010-07-21)
Octocrylene is a new emerging photoallergen. We report and discuss 50 cases of photoallergic contact dermatitis from octocrylene use and/or positive photopatch test reactions to this UV filter and draw attention to the unexpected association in adults with a history
Morgane Bachelot et al.
The Science of the total environment, 420, 273-279 (2012-02-15)
The accumulation of EHMC, OCT and OD-PABA, three common UV filter compounds, was investigated in marine mussels. Wild Mytilus edulis and Mytilus galloprovincialis were sampled in ten sites along the French Atlantic and Mediterranean coasts from June to November. In

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