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SMB00953

Sigma-Aldrich

2-Cyano-3,3-diphenylacrylic acid

≥95%

Synonym(s):

α-Cyano-β-diphenylacrylic acid, 2-Cyano-3,3-diphenylpropenoic acid

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About This Item

Empirical Formula (Hill Notation):
C16H11NO2
CAS Number:
10380-41-3
Molecular Weight:
249.26
UNSPSC Code:
12352106
NACRES:
NA.22

biological source

synthetic

Quality Level

200

Assay

≥95%

form

solid

mol wt

249.26 g/mol

storage condition

(Tightly closed. Dry.)

technique(s)

HPLC: suitable

color

white to off-white

storage temp.

2-8°C

InChI

1S/C16H11NO2/c17-11-14(16(18)19)15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10H,(H,18,19)

InChI key

VSXIZXFGQGKZQG-UHFFFAOYSA-N

General description

2-Cyano-3,3-diphenylacrylic acid (CDA) belongs to the class of α,β-unsaturated carboxylic acids. It is a primary metabolite of Octocrylene, an organic sunscreen that functions by absorbing UVB radiation and short UVA wavelengths, commonly utilized in cosmetics for sun protection. CDA exhibits prolonged systemic availability after dermal exposure which may accumulate in the body. It can be used to study skin-permeable selective cyclooxygenaswe-2 inhibitor composition, and to study hydrophilic components of cosmetic compositions, such as in sunscreen.

Application

2-Cyano-.3-diphenylacrylic acid finds application in metabolomics, cosmetics and cancer research

Biochem/physiol Actions

Within the human body, Octocrylene, a non-polar compound, undergoes metabolism to become a water-soluble metabolite 2-cyano-3,3-diphenylacrylic acid, which is excreted through the kidneys. A pilot study in the general population has consistently detected CDAA, and its levels have been linked to recent sunscreen application.

Features and Benefits

  • High quality compound suitable for multiple research applications
  • Compatible with a wide variety of chromatographic and spectrometry techniques

Other Notes

For additional information on our range of Biochemicals, please complete this form.
This product is intended for research purposes only, and it is not meant for human consumption.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Deleterious substance

JAN Code

SMB00953-25MG:
SMB00953-VAR:
SMB00953-BULK:
SMB00953-100MG:

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Certificates of Analysis (COA)

Lot/Batch Number
0000185453
0000105042

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Julia Hiller et al.
Environment international, 132, 105068-105068 (2019-08-31)
Chemical UV filters are common components in sunscreens and cosmetic products and used to protect the skin against harmful effects of sunlight like sunburn. However, the effectiveness of sunscreens in the prevention of skin cancer is in some parts still
Daniel Bury et al.
Analytical chemistry, 90(1), 944-951 (2017-12-01)
Octocrylene (OC) is an emerging UV filter, which is used in the majority of sunscreens as well as other personal care products (PCP) and consumer products. Its presence in various environmental matrices has been reported. However, information on the internal
Murali K Matta et al.
JAMA, 323(3), 256-267 (2020-01-22)
A prior pilot study demonstrated the systemic absorption of 4 sunscreen active ingredients; additional studies are needed to determine the systemic absorption of additional active ingredients and how quickly systemic exposure exceeds 0.5 ng/mL as recommended by the US Food
Quantification of prominent organic UV filters and their metabolites in human urine and plasma samples
Klotz et al.
Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences, 1125, 121706-121706 (2019)

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