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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:
Molecular Weight:
310.39
EC Number:
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.24

grade

analytical standard

Quality Level

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

Precautionary Statements

Hazard Classifications

Aquatic Chronic 4

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), 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)
Robert M Sayre et al.
Photochemistry and photobiology, 81(2), 452-456 (2004-11-25)
A major concern raised about photostability studies of sunscreen products is that the photodegradation of sunscreens does not readily translate into changes in product performance. This study examines the correlation between photochemical degradation of sunscreen agents and changes in protection
Tatiana Armeni et al.
Toxicology, 203(1-3), 165-178 (2004-09-15)
As an extension of our previous investigations on sunscreen ingredients, the present work was aimed at assessing the possible protective effects of a common UVA-absorbing agent, Parsol 1789 (4-tert-butyl-4'-methoxydibenzoylmethane) in contact with human keratinocytes under UVA illumination. Cell viability was
Serge Forestier
Journal of the American Academy of Dermatology, 58(5 Suppl 2), S133-S138 (2008-04-25)
The risks associated with cumulative or overexposure to ultraviolet (UV) radiation are now well identified. They involve both UVB (290-320 nm) and UVA (320-400 nm) components. UVB radiation is still considered to be the major factor responsible for most harmful

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