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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

Storage Class Code

11 - Combustible Solids

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)
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
Ibrahim Hanno et al.
Pharmaceutical research, 29(2), 559-573 (2011-09-23)
To prepare polyamide nanocapsules for skin photo-protection, encapsulating α-tocopherol, Parsol®MCX (ethylhexyl methoxycinnamate) and/or Parsol®1789 (butyl methoxydibenzoylmethane). Nanocapsules were obtained by combining spontaneous emulsification and interfacial polycondensation reaction between sebacoyl chloride and diethylenetriamine. Nano-emulsions used as control were obtained by the
Esther J H Collaris et al.
International journal of dermatology, 47 Suppl 1, 35-37 (2008-11-15)
Over the last decade, a change in the public awareness regarding the possible danger of excessive sunlight exposure has resulted in an increased consumption of sunscreens. These products contain a broad spectrum of putative sensitizers that can cause contact dermatitis
Cecilia Paris et al.
Photochemistry and photobiology, 85(1), 178-184 (2008-08-05)
Novel sunscreens are required providing active protection in the UVA and UVB regions. On the other hand, there is an increasing concern about the photosafety of UV filters, as some of them are not sufficiently photostable. Avobenzone is one of
View All Related Papers

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