Design of a Photostabilizer Having Built-in Antioxidant Functionality and Its Utility in Obtaining Broad-spectrum Sunscreen Formulations†

@inproceedings{Chaudhuri2006DesignOA,
  title={Design of a Photostabilizer Having Built-in Antioxidant Functionality and Its Utility in Obtaining Broad-spectrum Sunscreen Formulations†},
  author={Ratan K. Chaudhuri and Zoia Lascu and Germain Puccetti and A. A. Deshpande and Sashikumar Keshav Paknikar},
  booktitle={Photochemistry and photobiology},
  year={2006}
}
Abstract Di-2,2′-diethylhexyl-3,5-dimethoxy-4-hydroxy-benzylidenemalonate (INCI name diethylhexyl syringylidene malonate, DESM), the target photostabilizer, was synthesized in one step by condensation of 3,5-dimethoxy-4-hydroxy benzaldehyde (Syringaldehyde) with di-2,2′-diethylhexyl malonate. Photostability data in sunscreen formulations showed that DESM is photostable and improves the photostability of avobenzone significantly when compared to control (without a photostabilizer). Photostable… Expand
Photostability of the sunscreening agent 4-tert-butyl-4′-methoxydibenzoylmethane (avobenzone) in solvents of different polarity and proticity
The most widely used UVA absorber in broad-spectrum sunscreens is 4-tert-butyl-4� -methoxydibenzoylmethane (avobenzone). However, the photostability of avobenzone is solvent-dependent. The aim ofExpand
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TLDR
Irradiation of the avobenzone derivative in the presence of a triazine UV‐B filter diminished the undesirable effects of the compound by an efficient quenching of the triplet excited state, which means sunscreen formulations including triplet quenchers could provide effective protection from the potential phototoxic and photoallergic effects derived from poor photostability of avOBenzone. Expand
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Comparison photodegradation studies demonstrated that quercetin was much more effective and at a lower concentration than commonly used stabilizer (octocrylene) and antioxidants (vitamin E, butylated hydroxyanisole). Expand
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The thiol group of glutathione plays a vital role in exhibiting the photoprotection activity, which was further supported by the studies on photodegradation of avobonzone in the presence of β-mercaptoethanol. Expand
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  • C. Benevenuto, L. Guerra, L. R. Gaspar
  • Chemistry, Medicine
  • European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences
  • 2015
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References

SHOWING 1-10 OF 33 REFERENCES
An in vitro systematic spectroscopic examination of the photostabilities of a random set of commercial sunscreen lotions and their chemical UVB/UVA active agents.
The photostabilities of a random set of commercially available sunscreen lotions and their active ingredients are examined spectroscopically subsequent to simulated sunlight UV exposure. Loss ofExpand
Increased oxidative modification of albumin when illuminated in vitro in the presence of a common sunscreen ingredient: protection by nitroxide radicals.
TLDR
The results obtained corroborate the fact that Parsol 1789 generates free radicals upon illumination and that these are, most probably, responsible for the protein damage observed under the conditions used in the system. Expand
A NEW METHOD FOR THE DETECTION OF SINGLET OXYGEN IN AQUEOUS SOLUTIONS
Abstract— In experiments on the interception of reactive intermediates of strongly oxidizing character in dye (S) sensitized photooxidations using p‐nitrosodimethylaniline (RNO) as a selectiveExpand
Photochemical studies of 4-tert-butyl-4'-methoxydibenzoylmethane (BM-DBM).
TLDR
It is shown for the first time that 266 nm laser photolysis of BM-DBM solutions leads to formation of the triplet state of the keto (K) form with a lifetime of approximately 500 ns. Expand
The triplet energy levels of UVA and UVB sunscreens.
TLDR
It is suggested that there could be drawbacks in using sunscreens whose lowest triplet is higher than or similar to thymine, and e.g. as thymine monophosphate (IMP), which is in good agreement with early phosphorescence data. Expand
Photo-oxidation of lipids by singlet oxygen: a theoretical study
Abstract The photo-oxidation reactions between lipid model nona-3,6(c,c)-diene and singlet molecular oxygen are investigated using density functional theory and polarized continuum models. AdditionsExpand
Mechanistic aspects of the oxidation of DNA constituents mediated by singlet molecular oxygen.
TLDR
The combined use of the thermolysis of a water-soluble naphthalene endoperoxide as a generator of 18O-singlet oxygen and the sensitivity of electrospray ionization-tandem mass spectrometry has allowed us to better understand the reactivity of 1O2 toward dGuo and 8-oxodGuo. Expand
Nitroxide radicals protect DNA from damage when illuminated in vitro in the presence of dibenzoylmethane and a common sunscreen ingredient.
TLDR
Indolinonic nitroxides and the piperidines TEMPO and TEMPOL are compared for their ability to inhibit strand breaks inflicted on DNA when it is illuminated in vitro in the presence of dibenzoylmethane and a relative, Parsol 1789, used as a UVA-absorbing sunscreen. Expand
A UVA FILTER (4-TERT-BUTYL-4'-METHOXYDIBENZOYLMETHANE): PHOTOPROTECTION REFLECTS PHOTOPHYSICAL PROPERTIES
Abstract A dibenzoylmethane-based UVA sunscreen, 4- tert -butyl-4′-methoxydibenzoylmethane has been shown to protect human lymphoid cells efficiently when present in high concentration (10 −2 M). TheExpand
Photochemistry of dibenzoyl methane UVA filters Part 1
Abstract Two dibenzoyl methane derivatives, 4-isopropyldibenzoyl methane (I-DBM) and 4-t-butyl-3′-methoxydibenzoyl methand (BM-DBM), have been found to be photolabile towards UVA light in non-polarExpand
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