Avobenzone

Avobenzone
File:Avobenzone.png
IUPAC name 1-(4-Methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione
Other names butylmethoxydibenzoylmethane; 4-tert-butyl-4'-methoxydibenzoylmethane
style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
CAS number	70356-09-1 Y
PubChem	51040
ChemSpider	46261
EC number	274-581-6
SMILES
InChI
InChI key	XNEFYCZVKIDDMS-UHFFFAOYAG
style="background: #F8EABA; text-align: center;" colspan="2" | Properties
Molecular formula	C20H22O3
Molar mass	310.39 g mol−1
Appearance	colorless crystal
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Avobenzone (trade names Parsol 1789, Eusolex 9020, Escalol 517 and others, INCI Butyl Methoxydibenzoylmethane) is an oil soluble ingredient used in sunscreen products to absorb the full spectrum of UVA rays. It is a dibenzoylmethane derivative. Avobenzone exists in the ground state as a mixture of the enol and keto forms, favoring the chelated enol. Its ability to absorb ultraviolet light over a wider range of wavelengths than many organic sunscreen agents has led to its use in many commercial preparations marketed as "broad spectrum" sunscreens. Avobenzone has an absorption maximum of 357 nm.

History

Avobenzone was patented in 1973 and was approved in the EU in 1978. It was approved by the FDA in 1988. Its use is approved world wide.

Avobenzone is sensitive to the properties of the solvent, being relatively stable in polar protic solvents and unstable in nonpolar environments. Also, when it is irradiated with UVA light, it generates a triplet excited state in the keto form which can either cause the avobenzone to degrade or it can transfer energy to biological targets and cause deleterious effects.

Avobenzone has been shown to degrade significantly in light, resulting in less protection over time. The UV-A light in a day of sunlight in a temperate climate is sufficient to break down most of the compound. Data presented to the Food and Drug Administration by the Cosmetic, Toiletry and Fragrance Association indicates a -36% change in avobenzone's UV absorbance following one hour of exposure to sunlight. This degradation can be reduced by using a photostabilizer, like octocrylene. Other photostabilizers include:

• 4-Methylbenzylidene camphor (USAN Enzacamene)
• Tinosorb S (USAN Bemotrizinol, INCI Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine)
• Tinosorb M (USAN Bisoctrizole, INCI Methylene Bis-Benzotriazolyl Tetramethylbutylphenol)
• Butyloctyl Salicylate (Tradename HallBrite BHB - [1])
• Hexadecyl Benzoate
• Butyloctyl Benzoate
• Mexoryl SX (USAN Ecamsule, INCI Terephthalylidene Dicamphor Sulfonic Acid)
• Corapan TQ (INCI Diethylhexyl 2,6-Naphthalate)
• Parsol SLX (INCI Polysilicone-15)
• Oxynex ST (INCI Diethylhexyl Syringylidene Malonate)
• Polycrylene (INCI Polyester-8)
• SolaStay S1 (INCI Ethylhexyl Methoxycrylene)

Complexing avobenzone with cyclodextrins may also increase its photostability.

According to some studies, "the most effective sunscreens contain avobenzone and titanium dioxide."

Avobenzone can degrade faster in light in combination with mineral UV absorbers like zinc oxide and titanium dioxide, though with the right coating of the mineral particles this reaction can be reduced. A manganese doped titanium dioxide may be better than undoped titanium dioxide to improve avobenzone's stability.

Avobenzone reacts with minerals to form colored complexes. Manufacturers of avobenzone, like DSM recommend to include a chelator to prevent this from happening. They also recommend to avoid the inclusion of iron and ferric salts, heavy metals, formaldehyde donors and PABA and PABA esters.

The makers of Coppertone advise that avobenzone binds iron and can cause staining of clothes washed in iron-rich water.

Avobenzone also reacts with boron trifluoride to form a stable crystalline complex that is highly fluorescent under UV irradiation. More interestingly, the emission color of the crystals relies on the molecular packing of the boron avobenzone complex. The photoluminescence may also be altered by mechanical force in the solid state, resulting in a phenomenon called "mechanochromic luminescence". The altered emission color recovers itself slowly at room temperature or more swiftly at higher temperatures.

See also

• Sun protection factor

External links

• Discussion of Parsol 1789 properties

nl:Avobenzon