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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
EC Number:
274-581-6
MDL number:
MFCD00210252
UNSPSC Code:
41116107
PubChem Substance ID:
329751311
NACRES:
NA.24

grade

analytical standard

Quality Level

100

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

SMILES string

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

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

InChI key

XNEFYCZVKIDDMS-UHFFFAOYSA-N

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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.

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).
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Hazard Statements

H413

Precautionary Statements

P273 - P501

Hazard Classifications

Aquatic Chronic 4

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBD8497V
1336972

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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)
Virginie Lhiaubet-Vallet et al.
Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 9(4), 552-558 (2010-04-01)
In most sunscreens, the presence of two UV filters usually leads to synergistic effects regarding both the final performance and photostabilization of the active principles. However, this may also result in an accelerated decomposition if a photoreaction occurs between the
Jing Yang et al.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V, 69(2), 605-612 (2008-01-30)
The objective of the present study was to determine the effects of hydroxypropyl-beta-cyclodextrin (HPCD) complexation on the transdermal penetration and photostability of a model ultraviolet A (UVA) absorber, butyl methoxydibenzoylmethane (avobenzone), and to determine the influence of complexation on in
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
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