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Merck
CN

16633

Avobenzone

analytical standard

Synonym(s):

1-(4-Methoxyphenyl)-3-(4-tert-butylphenyl)-1,3-propanedione, Butyl methoxydibenzoylmethane

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About This Item

Empirical Formula (Hill Notation):
C20H22O3
CAS Number:
70356-09-1
Molecular Weight:
310.39
NACRES:
NA.24
PubChem Substance ID:
329751311
UNSPSC Code:
41116107
EC Number:
274-581-6
MDL number:
MFCD00210252

Key Documents

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Product Name

Avobenzone, analytical standard

InChI key

XNEFYCZVKIDDMS-UHFFFAOYSA-N

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

SMILES string

COc1ccc(cc1)C(=O)CC(=O)c2ccc(cc2)C(C)(C)C

grade

analytical standard

assay

≥99.0% (GC)

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

81-84 °C

application(s)

cleaning products
cosmetics
environmental
food and beverages
personal care

format

neat

Quality Level

100

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Application

Avobenzone may be used as an analytical reference standard for the quantification of the analyte in the following:
  • Sunscreen formulations using reversed-phase high-performance liquid chromatography with diode array detection (RP-HPLC-DAD).
  • Freshwater, saline water samples, rat plasma and skin layers using liquid chromatography-positive electrospray ionization-tandem mass spectrometry (LC-ESI-MS/MS) in multiple reaction monitoring mode (MRM).

Avobenzone may be used to study the photophysical characteristics, photosensitizing activity of a blocked diketo form derived from 4-tert-butyl-4′-methoxydibenzoylmethane (BM-DBM).
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General description

Avobenzone is an UVA filter. It is used in sunscreen lotions and cosmetic formulations. It has maximum absorption at ca 340–350 nm, decreasing under UV irradiation resulting in loss of the UVA protecting effect. Its photostability is very sensitive as it is stable in polar protic solvent and is photolabile in nonpolar solvents.

hcodes

H413

Hazard Classifications

Aquatic Chronic 4

Storage Class

11 - Combustible Solids

wgk

WGK 2

ppe

Eyeshields, Gloves

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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 GM, et al.
Journal of Chromatography. B, Biomedical Sciences and Applications, 1003, 41-46 (2015)
Analytical method development for simultaneous estimation of Oxybenzone, Octocrylene, Octinoxate and Avobenzone in sunscreen by high performance liquid chromatography and its validation
Bhuva C, et al.
Pharmacophore, 3(2) (2012)
Determination of seven commonly used organic UV filters in fresh and saline waters by liquid chromatography-tandem mass spectrometry
Bratkovics S and Sapozhnikova Y
Analytical Methods : Advancing Methods and Applications, 3(12), 2943-2950 (2011)
Daniele Dondi et al.
Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 5(9), 835-843 (2006-10-19)
A systematic investigation of two well-known and popular commercial suncreams reveals significant degradation when exposed to simulated UV sunlight at an irradiance corresponding to natural sunlight. We have examined the photochemistry of two widely used sunscreen active agents in pure
Woan-Ruoh Lee et al.
Toxicology letters, 211(2), 150-158 (2012-04-10)
While laser skin resurfacing is expected to result in reduced barrier function and increased risk of drug absorption, the extent of the increment has not yet been systematically investigated. We aimed to establish the skin permeation profiles of tetracycline and
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