Journal of Photochemistry and Photobiology B: Biology 140 (2014) 36–40

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Journal of Photochemistry and Photobiology B: Biology

journal homepage: www.elsevier.com/locate/jphotobiol

Photodegradation of avobenzone: Stabilization effect of antioxidants

S. Afonso a, K. Horita a, J.P. Sousa e Silva a,⇑, I.F. Almeida a, M.H. Amaral a, P.A. Lobão a, P.C. Costa a,
Margarida S. Miranda b, Joaquim C.G. Esteves da Silva b, J.M. Sousa Lobo a
a
Laboratory of Pharmaceutical Technology, Department of Drug Sciences, Faculty of Pharmacy, University of Porto, Rua Jorge de Viterbo Ferreira, n.° 228, 4050-313 Porto, Portugal
b
Centro de Investigação em Química, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre s/n, P-4169-007 Porto, Portugal

a r t i c l e i n f o a b s t r a c t

Article history: Avobenzone is one of the most common UVA-filters in sunscreens, and is known to be photounstable.
Received 16 April 2014 Some of the strategies used to stabilize this filter present some drawbacks like photosensitization reac-
Received in revised form 3 July 2014 tions. Antioxidants are widely used as cosmetic ingredients that prevent photoageing and complement
Accepted 7 July 2014
the photoprotection offered by the UV-filters preventing or reducing photogenerated reactive species.
Available online 15 July 2014
The purpose of this work was to study the effect of antioxidants in the photostabilization of avobenzone.
The filter dissolved in dimethyl sulfoxide or incorporated in a sunscreen formulation was irradiated with
Keywords:
simulated solar radiation (750 W/m2). The tested antioxidants were vitamin C, vitamin E, and ubiqui-
Avobenzone
Photostability
none. The area under the curve of the absorption spectrum for UVA range and the sun protection factor
Antioxidants (SPF) were calculated. Vitamin E (1:2), vitamin C (1:0.5) and ubiquinone (1:0.5) were the more effective
Sunscreens UV-filters concentrations increasing the photostability of avobenzone. In sunscreen formulations, the most effective
photostabilizer was ubiquinone which also promoted an increase in SPF.
This knowledge is important to improve effectiveness of sunscreen formulation. Antioxidants can be
valuable ingredients for sunscreens with a triple activity of filter stabilization, SPF boosting and
photoageing prevention.
Ó 2014 Elsevier B.V. All rights reserved.

1. Introduction Avobenzone (4-tert-butyl-40 -methoxydibenzoylmethane) is one

of the most common UVA-filters in sunscreens, and is known to be
Nowadays, there is a need to develop more effective sunscreens photounstable. The photochemical behaviour of this filter has been
to ensure optimal photoprotection. Chemical UV-filters are com- extensively studied and it has been found that its photostability is
pounds incorporated on sunscreen formulations to absorb specific highly dependent on the polarity and proticity of the solvent [7–9].
wavelengths of ultraviolet radiation, UVA (320–400 nm), UVB Photoallergic and cytotoxic reactions have often been associated
(290–320 nm) or both. The high capacity of UV-filters to absorb to avobenzone due to the photodegradation products such as
UV should remain stable for the entire period of sun exposure in arylglyoxals and benzils [4].
order to achieve the expected photoprotection for commercial sun- Several strategies have been explored in order to improve
screen products [1]. Some UV-filters are photochemically unstable, avobenzone-containing sunscreens. For example, it is well known
which impair their absorbance after UV exposure. UV-filters mole- that avobenzone–octocrylene association improves avobenzone
cules absorb the incoming UV radiation and reach an excited state. photostability [2]. Octocrylene, among other triplet quenchers like
However, the excited molecules return to the basal state by differ- methylbenzylidene camphor, is the most effective at stabilizing
ent mechanisms. These mechanisms can lead to the formation of avobenzone [10] but it is expensive and difficult to incorporate into
new compounds or photoproducts which can be inactive, decreas- sunscreens [11]. Such as octocrylene, there are many available
ing sunscreen effectiveness [2], can interact with skin biocompo- molecules stabilizing avobenzone but unable to quench reactive
nents causing photoallergy and phototoxicity reactions [2–4] or species generated due to photofragmentation [12]. Actually, safety
even interact with other UV-filters [5] or other ingredients present issues have arisen regarding octocrylene and such as the genera-
in sunscreen formulations leading to the formation of another tion of reactive oxygen species (ROS) in human epidermis keratino-
compounds with unknown toxicity [1,2,6]. cytes as a result of UV irradiation [13]. Furthermore, reports of
positive patch test and photopatch test reactions to octocrylene
have increased during the last decade [14,15]. Following these data
⇑ Corresponding author. Tel.: +351 220428620. it is of utmost importance to develop new strategies for avobenz-
E-mail address: paulo.silva@ffup.pt (J.P. Sousa e Silva). one photostabilization.

http://dx.doi.org/10.1016/j.jphotobiol.2014.07.004
1011-1344/Ó 2014 Elsevier B.V. All rights reserved.
 S. Afonso et al. / Journal of Photochemistry and Photobiology B: Biology 140 (2014) 36–40 37

Antioxidants are often used in the cosmetic industry to reduce were characterized for their appearance. The pH of the formulation
skin ageing due to UV radiation and in sunscreen formulations to containing vitamin C was determined.
complement the photoprotection offered by the UV-filters [16],
preventing or reducing potentially photogenerated reactive species 2.3. Irradiation
[17–19]. The question that arises is whether these antioxidants
may also be involved in the chemical stabilization of UV-filters. Avobenzone solutions were contained in screw cap quartz cells
The aim of this study was to evaluate the photodegradation of and formulations were spread in polymethylmethacrylate (PMMA)
avobenzone after exposure to simulated solar radiation and study plates (1 mg/cm2). The samples were irradiated at 750 W/m2 using
the effect of antioxidants vitamin C, vitamin E and ubiquinone on a xenon lamp equipped with a special UV-filter used to simulate
its photostability. To the best of our knowledge there are very UV radiation that reaches the earth and IR-block filter to neutralize
few research works that addressed the use of antioxidants to temperature effects (Atlas, Suntest CPS+). The irradiation time was
photostabilize avobenzone, and this one performed a systematic 1 h and the incident dose of UV was 2700 kJ/m2.
study of the use of antioxidants. The results of this research can
be useful to improve the formulation of sunscreens incorporating 2.4. UV measurements
avobenzone.
The spectra of avobenzone solutions were obtained in a spectro-
photometer (Jasco V-650). To measure the decrease in absorbance
2. Experimental
of avobenzone the spectra were recorded before and two hours
after irradiation, from 250 nm to 400 nm. The area under the curve
2.1. Materials
(AUC) was calculated for UVA range, before and after irradiation.
The AUC ratio (AUC R) was used to calculate the photostability
Avobenzone (Eusolex 9020) and EDTA were obtained from
increase (PI) in %. If the AUC ratio was higher than 0.80 the
MerckÒ. Vitamin E acetate, vitamin C, ubiquinone, isopropyl myris-
UV-filter was considered photostable [20].
tate, paraffinum liquidum and glycerine were obtained from
AcofarmaÒ and tweenÒ 60, sodium benzoate and nipaginÒ from AUC after
Vaz PereiraÒ. Cetostearyl alcohol from GuinamaÒ, spanÒ 60 from AUC R ¼ ð1Þ
AUC before
Roig FarmÒ and dimethylsulfoxide (DMSO) from Acrõs OrganicsÒ.
AUC R ðsampleÞ  AUC R ðcontrolÞ
PI ð%Þ ¼  100 ð2Þ
2.2. Sample preparation AUC R ðcontrolÞ

2.2.1. Avobenzone solutions

2.5. In vitro sun protection factor (SPF) measurement
Avobenzone solutions (5 lg/mL) with antioxidants (vitamin E,
vitamin C, ubiquinone) at different concentrations were prepared
The in vitro determination of the SPF of the sunscreen formula-
in dimethyl sulfoxide using amber volumetric flasks. These solu-
tions was carried out according to the Diffey and Robson method
tions were prepared by mixing avobenzone’s and antioxidants’
[21], with minor modifications. The transmission spectrum of the
stock solutions, so that the final concentrations were those shown
UV radiation (290–400 nm) was measured after application
in Table 2. A solution of avobenzone was used as control.
(1 mg/cm2) of the sunscreen formulation on a roughened PMMA
plate. The plate was placed into the spectrophotometer (Jasco
2.2.2. Sunscreen formulations V-650) sample compartment, facing the light emission source. A
Five formulations were prepared (Table 1): non-ionic emulsion plate with the formulation 1 (base) was used as blank. The spectral
without avobenzone (base) and without antioxidants (1), with avo- data were processed with a personal computer and the SPF
benzone and without antioxidants (2), with avobenzone associated calculated according to Eq. (3):
to vitamin C (3), vitamin E (4) and ubiquinone (5). The creams were R k¼400 nm
prepared by the conventional hot emulsification process with nm
EðkÞ  IðkÞ  dk
FPS in v itro ¼ R k¼400k¼290
nm
ð3Þ
phase inversion. The antioxidants were added after the cooling k¼290 nm
EðkÞ  IðkÞ  10A0 ðkÞ  dk
phase. Vitamin C was previously dissolved in water, vitamin E
was directly incorporated into the cream and ubiquinone was where E(k) is the spectral irradiance of terrestrial sunlight under
previously dissolved in isopropyl myristate. These formulations defined conditions at wavelength k, I(k) is the erythemal action
spectrum at wavelength k and A(k) is the monochromatic absor-
bance of the sample.
Table 1 AUC ratio and photostability increase (PI) were also calculated
Composition of sunscreen formulations under study (wt%).
as described previously in triplicate.
Ingredients 1 2 3 4 5
Cetostearyl alcohol 6 5 5 5 5 2.6. Statistical analysis
Isopropyl myristate 17 14 14 14 14
TweenÒ 60 4.5 4.5 4.5 4.5 4.5 Statistical analysis of the experimental data (AUC ratio) of sun-
SpanÒ 60 2 2 2 2 2
screens was performed by Anova followed by Tukey HDS tests
Liquid paraffin 2 2 2 2 2
Glycerin 2 2 2 2 2 using SPSS 20.0 (SPSS Inc., software). Differences were accepted
EDTA 0.1 0.1 0.1 0.1 0.1 as statistically significant when p < 0.05.
Sodium benzoate 0.1 0.1 0.1 0.1 0.1
NipaginÒ 0.1 0.1 0.1 0.1 0.1
Water q.s. 100 100 100 100 100 3. Results and discussion
Avobenzone – 4 4 4 4
Vitamin C – – 2 – – Photostability is an important property that impact UV-filters
Vitamin E – – – 8 –
effectiveness and can be evaluated by measuring the decrease in
Ubiquinone – – – – 2
absorption after irradiation.
38 S. Afonso et al. / Journal of Photochemistry and Photobiology B: Biology 140 (2014) 36–40

Table 2 this filter. Antioxidants contain free electrons that can be donated
Photostability increase (%) of different concentrations of vitamin E, vitamin C and to unpaired electrons present in free radicals [23] and thus, the
ubiquinone.
antioxidants used in this study could photostabilize avobenzone
Concentration of Vitamin E Vitamin C Ubiquinone by quenching reactive species by physical or chemical processes
antioxidants photostability photostability photostability [2]. The use of antioxidants as UV-filter stabilizers has been previ-
(lg/mL) increase (%) increase (%) increase (%)
ously reported. Scalia and Mezzena [24] studied the photostabili-
1.25 (1:0.25) 0 33.3 5.6 zation effect of quercetin, a natural flavonoid with high
2.5 (1:0.5) 10.5 83.3 16.7
3.75 (1:0.75) 14.3 22.2 8.3
antioxidant activity, on an avobenzone–octylmethoxycinnamate
5 (1:1) 0 22.2 33.3 association and found an increment on photostability.
10 (1:2) 33.3 16.7 4.2 For this study three well known antioxidants were chosen: vita-
mins C and E and ubiquinone, which belong to the endogenous
skin antioxidant network. Vitamin C (ascorbic acid) is a water-sol-
3.1. Irradiation of avobenzone in DMSO uble substance and it is the most important antioxidant present in
the skin. Furthermore, it plays an important role in regenerating
Fig. 1 shows the UV spectrum of avobenzone in DMSO before oxidized vitamin E and it is also a cofactor for critical enzymes in
and two hours after irradiation. The spectra obtained confirmed a collagen synthesis. Its stability in topical formulations is trouble-
decrease in avobenzone absorbance in the UVA range (320– some and is pH-dependent [25,26]. Vitamin E is a lipid–soluble
400 nm) and a concomitant increase of the absorption in the UVC antioxidant and exists as 8 major compounds, including a-tocofer-
range. This observation is well documented and has been attrib- ol which is the most abundant. It protects the cell membranes from
uted to enol–keto isomerization induced by irradiation. After irra- oxidative stress [25]. Ubiquinone (Coenzyme Q10) is an important
diation the enol form photoisomerizes in the keto form which lipophilic antioxidant synthesized by the body and critical for pro-
absorbs in the UVC range from 260 to 280 nm [7,9]. This photoiso- tection of mitochondrial membranes [27].
merization process is oxygen-dependent and according to some The results regarding the photostabilizing effect of the antioxi-
authors [7,22], it occurs through a triplet excited state which could dants towards avobenzone solutions (5 lg/mL) in DMSO are pre-
be a rational explanation for its stabilization with triplet-state sented in Table 2. The stabilization effect is dependent on the
quenchers like octocrylene. Mturi and Martincigh [7] proved on antioxidant concentration and a linear relationship was not
their investigation that avobenzone photoinstability mechanisms observed. Ubiquinone has shown a photostability increase in all
are solvent-dependent. The authors studied avobenzone photosta- concentrations but 5 lg/mL (1:1). For the other antioxidants, only
bility on four solvents of different polarity and proticity and con- one concentration was effective. Higher antioxidant concentrations
cluded that avobenzone, when irradiated, is photostable in polar do not seem to increase the photostabilization effect except in the
protic solvents like methanol but unstable in DMSO, a polar aprotic case of vitamin E.
solvent. This fact led us to select DMSO in order to study the use of Vitamin E (1:2), vitamin C (1:0.5) and ubiquinone (1:0.5) were
antioxidants in the stabilization of avobenzone. During this the more effective concentrations regarding the improvement of
research we also observed that keto form can revert to enol form, avobenzone photostability and were the concentrations selected
which was already reported in the literature. for the next phase of the study.
Fig. 2 shows the UV spectra before and after irradiation of the
DMSO solutions of antioxidants used in this study, in which it is
3.2. Antioxidants photostabilization effect in avobenzone solutions
possible to observe that the three compounds do not notably affect
the determination of AUC ratio of avobenzone spectrum in the UVA
The ideal photostabilizer should prevent or quench all the haz-
range.
ardous mechanisms produced by avobenzone keto form, and it
should not degrade nor interact with avobenzone [2]. Since the
3.3. Photostabilization effect of antioxidants in sunscreens
light induced photodegradation mechanism of avobenzone under-
goes the initial formation of reactive species such as singlet oxygen
The study of avobenzone photostability in sunscreen formula-
[2,17], incorporation of antioxidants into sunscreen formulations
tions was carried out based on the preliminary studies held in
seems to be a logical and a reasonable strategy to photostabilize
DMSO. By evaluating the spectra of all sunscreen formulations
after irradiation we can see an absorption decrease in UVA region
(Fig. 3), and consequently there is a decrease in photoprotection
effectiveness. However this decrease is attenuated in avobenz-
one-containing formulations with antioxidants (Fig. 3 and Table 3).
Thus, we can deduce that antioxidants improve avobenzone photo-
stability. Vitamin C was not included in this phase of the study
since the formulation exhibited great instability. Interestingly,
the results obtained with ubiquinone sunscreen (formulation 5)
showed a greater photostabilty unlike the studies conducted in
solution where vitamin E was more effective. The AUC ratio
observed (Table 3) for ubiquinone was significantly higher than
formulation 2 (p < 0.001) which was not the case with vitamin E
(p = 0.157). One explanation for this discrepancy is the differences
in the vehicle. Sunscreens are complex mixtures of lipophilic liq-
uids and water and the photodegradation of avobenzone in such
an environment is difficult to predict and not directly comparable
to degradation in DMSO. In this solvent, the avobenzone photo-
chemistry is well defined which justifies the use of this approach
Fig. 1. UV spectra of avobenzone solution (5 lg/mL) in DMSO before (dotted line) in a preliminary study. Nevertheless, the study conducted in
and 2 h after irradiation (solid line). sunscreens is more relevant from the consumer point of view.
 S. Afonso et al. / Journal of Photochemistry and Photobiology B: Biology 140 (2014) 36–40 39

Fig. 2. UV spectra of antioxidants solutions in DMSO (10 lg/mL) before (dotted line) and 2 h after (solid line) irradiation: (a) ubiquinone, (b) vitamin E and (c) vitamin C.

1.8
a 1
b
1.5
0.8

0.6
1
Abs Abs
0.4
0.5
0.2

0 0
290 300 350 400 290 300 350 400
Wavelength [nm] Wavelength [nm]

c 1.3

Abs
0.5

0
290 300 350 400
Wavelength [nm]

Fig. 3. UV spectra of the sunscreen formulations before (solid line) and after (dotted line) irradiation: (a) formulation containing avobenzone (formulation 2), (b) formulation
containing avobenzone and ubiquinone (formulation 5) and (c) formulation containing avobenzone and vitamin E (formulation 4).
40 S. Afonso et al. / Journal of Photochemistry and Photobiology B: Biology 140 (2014) 36–40

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