Photochemistry of dibenzoyl methane UVA filters Part 1

Schwack, Wolfgang; Rudolph, T.

doi:10.1016/1011-1344(95)07118-l

Cited by 162 publications

(143 citation statements)

References 3 publications

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“…However, avobenzone photoprotective effects are reduced when the compound is under UV radiation due to tautomerization, fragmentation and generation of photoproducts (Damiani et al, 2006;Paris et al, 2009;Schwack and Rudolph, 1995). The difficulty to obtain broad spectrum sunscreens containing avobenzone justifies the search by the scientific community and the Research & Development centers in the industry for new UV-filters and molecules able to improve avobenzone photostability.…”

Section: Introductionmentioning

confidence: 97%

Combination of retinyl palmitate and UV-filters: Phototoxic risk assessment based on photostability and in vitro and in vivo phototoxicity assays

Benevenuto

Guerra²,

Gaspar

2015

European Journal of Pharmaceutical Sciences

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Section: Introductionmentioning

confidence: 97%

Combination of retinyl palmitate and UV-filters: Phototoxic risk assessment based on photostability and in vitro and in vivo phototoxicity assays

Benevenuto

Guerra²,

Gaspar

2015

European Journal of Pharmaceutical Sciences

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“…Because of antitumor and anti-inflammatory effects, dibenzoylmethane and its derivatives have attracted attention considering their potential use as a chemopreventive agents [2]. Furthermore, powerful sunscreen activity of DBM derivatives allows to use these compounds in the cosmetic industry as sunscreen agents [3,4]. The keto-enol tautomerization of b-diketones has attracted great interest and has been investigated extensively.…”

mentioning

confidence: 99%

Tautomeric and conformational properties of dibenzoylmethane, C6H5–C(O)–CH2–C(O)–C6H5: gas-phase electron diffraction and quantum chemical study

2010

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Tautomeric and structural properties of dibenzoylmethane, C 6 H 5 -C(O)-CH 2 -C(O)-C 6 H 5 , have been investigated by gas-phase electron diffraction (GED) and quantum chemical calculations (B3LYP and MP2 approximation with different basis sets up to cc-pVTZ). Analysis of GED intensities resulted in the presence of 100(5)% enol tautomer at 380(5) K. The enol ring possesses C S symmetry with a strongly asymmetric hydrogen bond. The two phenyl rings are rotated with respect to the enol ring by 15.1(5.0) and 12.1(5.8)°. The experimental geometric parameters are reproduced very closely by the B3LYP/ cc-pVTZ method.

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“…Among the authorized UV-A absorbers, butyl methoxydibenzoylmethane (BMDBM) is the most efficient and widely used compound. However, it decomposes under sunlight exposure, leading to decreased protective ability as well as to free radical production which can provide DNA damage [4][5][6] .…”

Section: Introductionmentioning

confidence: 99%

In vivo and in vitro Skin Permeation of Butyl Methoxydibenzoylmethane from Lipospheres

Iannuccelli

Coppi²,

Sergi³

et al. 2007

Skin Pharmacol Physiol

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Lipid microparticles (lipospheres) loaded with butyl methoxydibenzoylmethane (BMDBM), a widely used UV-A sunscreen agent, were prepared by melt technique and evaluated for skin permeation both in vivo, by tape stripping method, and in vitro, by a flow-through diffusion chamber. Following in vivo human skin application of an O/W emulsion containing 2% of BMDBM loaded in lipospheres, 15% of the applied sunscreen accumulated in the uppermost layers of the stratum corneum without remarkably modifying the skin permeation of the unencapsulated sunscreen. These results were found to be predicted by an in vitro methodology involving the diffusion of BMDBM through a lipophilized synthetic membrane into a hydrophilic receptor phase, simulating the viable epidermis better than an ethanolic receptor phase.

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Photochemistry of dibenzoyl methane UVA filters Part 1

Cited by 162 publications

References 3 publications

Combination of retinyl palmitate and UV-filters: Phototoxic risk assessment based on photostability and in vitro and in vivo phototoxicity assays

Combination of retinyl palmitate and UV-filters: Phototoxic risk assessment based on photostability and in vitro and in vivo phototoxicity assays

Tautomeric and conformational properties of dibenzoylmethane, C6H5–C(O)–CH2–C(O)–C6H5: gas-phase electron diffraction and quantum chemical study

In vivo and in vitro Skin Permeation of Butyl Methoxydibenzoylmethane from Lipospheres

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