Avobenzone - CAS 70356-09-1
Catalog number: 70356-09-1
Category: Inhibitor
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Molecular Formula:
C20H22O3
Molecular Weight:
310.39
COA:
Inquire
Targets:
Others
Description:
Avobenzone is an oil soluble ingredient used in sunscreen products to absorb the full spectrum of UVA rays and a dibenzoylmethane derivative.
Purity:
>98%
Synonyms:
Avobenzone, Avobenzonum, Parsol 1789, Parsol1789, Parsol-1789, HSDB 7423, HSDB-7423, HSDB7423
MSDS:
Inquire
InChIKey:
XNEFYCZVKIDDMS-UHFFFAOYSA-N
InChI:
InChI=1S/C20H22O3/c1-20(2,3)16-9-5-14(6-10-16)18(21)13-19(22)15-7-11-17(23-4)12-8-15/h5-12H,13H2,1-4H3
Canonical SMILES:
CC(C)(C)C1=CC=C(C=C1)C(=O)CC(=O)C2=CC=C(C=C2)OC
1.A sensitive LC-ESI-MS/MS method for the quantification of avobenzone in rat plasma and skin layers: Application to a topical administration study.
Kim MG1, Kim TH1, Shin BS2, Kim MG1, Seok SH1, Kim KB3, Lee JB1, Choi HG1, Lee YS1, Yoo SD4. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Oct 15;1003:41-6. doi: 10.1016/j.jchromb.2015.09.014. Epub 2015 Sep 15.
This study describes the development of a sensitive high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry (LC-ESI-MS/MS) method for the quantification of avobenzone in rat plasma and skin layers. Separations were performed on a Zorbax SB C8 column using a binary gradient mobile phase composed of acetonitrile and 0.1% formic acid in water. The assay achieved LLOQ of 0.5ng/ml for plasma, 5ng/ml for stratum corneum, and 10ng/ml for epidermis and dermis. This method was applied to a percutaneous absorption study of avobenzone in rats. At 12h following topical application of emulsion and lotion (applied amount of avobenzone 11.7mg/kg), avobenzone was found primarily in the stratum corneum (16.3-17.8%) followed by epidermis (2.0-3.4%) and dermis (0.11-0.15%). Avobenzone was not quantifiable in the plasma samples collected over a 12h sampling period. Given the excellent plasma assay sensitivity, this study provides evidence that the systemic absorption of avobenzone is insignificant, if any, after topical application.
2.Mangiferin and naringenin affect the photostability and phototoxicity of sunscreens containing avobenzone.
Kawakami CM1, Gaspar LR2. J Photochem Photobiol B. 2015 Oct;151:239-47. doi: 10.1016/j.jphotobiol.2015.08.014. Epub 2015 Aug 15.
Efficient UV-absorbing molecules are designed to protect against UV-light exposure. However, the development of photostable sunscreens is important to preserve the photoprotective efficacy and to prevent the formation of reactive oxygen species (ROS) and photodegradation products, which can promote phototoxic or photoallergic contact dermatitis. The aim of this study was to evaluate the effects of mangiferin and naringenin on the photostability and phototoxicity of sunscreens containing avobenzone. Cosmetic sunscreen formulations containing octocrylene (OCT), octyl methoxycinnamate (OMC) and avobenzone (AVO) were prepared and supplemented or not with mangiferin, naringenin, or with both compounds in combination. For photostability studies, samples of the formulations were spread onto glass plates, exposed to UVA radiation and then analyzed by high performance liquid chromatography (HPLC) to determine UV filters and the antioxidants recovery.
3.Electronic and spectroscopic properties of avobenzone derivatives attached to ditungsten quadruple bonds.
Chisholm MH1, Gustafson TL1, Kender WT1, Spilker TF2, Young PJ1. Inorg Chem. 2015 Oct 5;54(19):9438-46. doi: 10.1021/acs.inorgchem.5b01221. Epub 2015 Sep 21.
From the reactions between W2(T(i)PB)4, where T(i)PB is 2,4,6-triisopropylbenzoate, and 2 equiv of acid, 4-formylbenzoic acid, HBzald, 4-(3-oxo-3-phenylpropanoyl)benzoic acid, HAvo, or 4-(2,2-difluoro-6-phenyl-2H-1λ(3),3,2λ(4)-dioxaborinin-4-yl)benzoic acid, HAvoBF2, three new compounds W2(T(i)PB)2(Bzald)2, I, W2(T(i)PB)2(Avo)2, II, and W2(T(i)PB)2(AvoBF2)2, III, have been prepared. As solid compounds I and II are blue while compound III is green. Characterization of these compounds has been carried out by means of (1)H NMR, MALDI-TOF MS, steady-state absorption and emission spectroscopies, and femtosecond and nanosecond transient absorption and time-resolved infrared spectroscopies. Compounds I and II have strong metal to ligand charge transfer, MLCT, transitions in the visible region of their spectra while compound III exhibits MLCT absorption in the near-infrared (λmax = 1017 nm). All three have S1 states that have corresponding lifetimes of ∼3-30 ps and are (1)MLCT in character.
4.Theoretical study of tautomers and photoisomers of avobenzone by DFT methods.
Trossini GH1, Maltarollo VG2, Garcia RD2, Pinto CA2, Velasco MV2, Honorio KM3,4, Baby AR2. J Mol Model. 2015 Dec;21(12):319. doi: 10.1007/s00894-015-2863-2. Epub 2015 Dec 2.
Organic ultraviolet (UV) filters such as cinnamates, benzophenones, p-aminobenzoic derivatives, and avobenzone (which have well-established and recognized UV-filtering efficacies) are employed in cosmetic/pharmaceutical products to minimize the harm caused by exposure of the skin to sunlight. In this study, a detailed investigation of the photostability and tautomerism mechanisms of avobenzone was performed utilizing DFT methods. The UV spectral profile of avobenzone was also simulated, and the results showed good agreement with experimental data. Furthermore, the calculations were able to distinguish tautomers and photoisomers of the studied organic filter based on their properties, thus showing the potential to develop new organic UV filters. Graphical Abstract Theoretical studies of avobenzone and its tautomers by TD-DFT.
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CAS 70356-09-1 Avobenzone

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