Difference between revisions of "Oxybenzone"

Latest revision as of 20:48, 30 June 2020

Oxybenzone is a phenol that may be oxidized, creating a stressful environment for coral reefs.

General Information

IUPAC name: 2-hydroxy-4-methoxyphenyl)-phenylmethanone

Only 4% of ozybenzone in sunscreen is absorbed into the skin, the remaining 96% is washed off and enters various water ways (Dinardo, Joseph and Downs, A Craig 2018).

As a sunscreen additive, oxybenzone is less effective at protecting against UV exposure than avobenzone, titanium dioxide, and/ or zinc oxide (Dinardo, Joseph and Downs, A Craig 2018).

Adverse Effects of Oxybenzone

Several studies have reported that oxybenzone has adverse effects on reproduction and development of algae, the freshwater flea, and plarian (Kim, Sujin and Choi, Kyungho 2014). Oxybenzone is a photoxicant, genotoxicant, and a skeletal endocrine disruptor in coral. Oxybenzone has also been found in the tissue of many fish that humans consume (ex. white fish, perch, and rainbow trout). Oxybenzone inhibits reproduction of coral and fish via embryo toxicity and/or causes male fish to be feminized (DiNardo, Joseph and Downs, A Craig 2018). There is not much information on the long term ecological effects of oxybenzone in our freshwater systems, so further investigation is warranted.

Oxybenzone is also one of the top three most frequent allergens in sunscreens (DiNardo, Joseph and Downs, A Craig 2018).

Physical Properties

Names:

2-Hydroxy-4-methoxybenzophenone
Oxybenzone
Benzophenone-3 (BZ-3) <--trade naming, see other below
Eusolex 4360
Escalol 567

Molecular weight: 228.24 g/mol

Boiling point: 115°C.

Melting point: 65.5°C.

Density: 1.32 g/mL.

pKa: 7.1.

UV max: 288 and 326 nm.

Described as an off-white or light yellow powder.

Other--> Benzophenone-n

Chemical Oxidation

The following link shows an in depth explanation of the chemical oxidation of oxybenzone. This page also contains the data collected from this particular experiment.

Oxybenzone Oxidation

Chlorination of Oxybenzone

Oxybenzone can become chlorinated in swimming pools because of the chlorine in the water. Chlorine also oxidizes oxybenzone quite well. There are three major products of the chlorination of oxybenzone.

Products of chlorination of oxybenzone. Source: Chlorination of oxybenzone: Kinetics, transformation, disinfection byproducts formation, and genotoxicity changes (Chemosphere 154 (2016) 521-527)

Coral Bleaching

Coral bleaching happens when the algae living on the coral are destroyed, leaving the coral to starve. The coral then lose their bright colors, which is why the term is called "bleaching." Oxybenzone reactions can harm these algae, resulting in coral bleaching.

Instrumentation Links

These links explain how to use the HPLC and UV-Vis in these experiments.

HPLC

UV-Vis

Research Paper

This link provides a sample of the senior research paper I am writing on the oxidation of oxybenzone.

Oxybenzone Research Paper

References

Dermatological and environmental toxicological impact of the sunscreen ingredient oxybenzone/benzophenone-3. (review, 2018)

Sunscreens Cause Coral Bleaching by Promoting Viral Infections

Sunscreens: are they beneficial for health? An overview of endocrine disrupting properties of UV-filters (review, 2012, 166 times cited/Sept 2019)

Occurrences, toxicities, and ecological risks of benzophenone-3, a common component of organic sunscreen products: A mini-review (review, 2014)

Fate of Endocrine-Disruptor, Pharmaceutical, and Personal Care Product Chemicals during Simulated Drinking Water Treatment Processes (Environ. Sci. Technol. 2005, 39, 6649-6663)

Chlorination of oxybenzone: Kinetics, transformation, disinfection byproducts formation, and genotoxicity changes (Chemosphere 154 (2016) 521-527)

Development of a Handheld Submersible Chemiluminescent Sensor: Quantification of Superoxide at Coral Surfaces

References for Coral Bleaching

Toxicopathological Effects of the Sunscreen UV Filter,Oxybenzone (Benzophenone-3), on Coral Planulae and CulturedPrimary Cells and Its Environmental Contamination in Hawaiiand the U.S. Virgin Islands, Arch Environ Contam Toxicol (2016) 70:265–288DOI 10.1007/s00244-015-0227-7

@@ Line 1: / Line 1: @@
 Oxybenzone is a phenol that may be oxidized, creating a stressful environment for coral reefs.
-[[File:1000px-Oxybenzone.svg.png|400px]]
+[[File:09728-feature4-graphic.jpg|600px|right]] [[File:Infographic Sunscreen Chemicals and Marine Life.jpg|600px|left]]
+==General Information==
 [https://en.wikipedia.org/wiki/Oxybenzone Oxybenzone - Wikipedia]
-===General Information===
+IUPAC name: 2-hydroxy-4-methoxyphenyl)-phenylmethanone
-===Physical Properties===
+Only 4% of ozybenzone in sunscreen is absorbed into the skin, the remaining 96% is washed off and enters various water ways (Dinardo, Joseph and Downs, A Craig 2018).
-===Chemical Oxidation===
+As a sunscreen additive, oxybenzone is less effective at protecting against UV exposure than avobenzone, titanium dioxide, and/ or zinc oxide (Dinardo, Joseph and Downs, A Craig 2018).
-===References===
+==Adverse Effects of Oxybenzone==
+Several studies have reported that oxybenzone has adverse effects on reproduction and development of algae, the freshwater flea, and plarian (Kim, Sujin and Choi, Kyungho 2014). Oxybenzone is a photoxicant, genotoxicant, and a skeletal endocrine disruptor in coral. Oxybenzone has also been found in the tissue of many fish that humans consume (ex. white fish, perch, and rainbow trout). Oxybenzone inhibits reproduction of coral and fish via embryo toxicity and/or causes male fish to be feminized (DiNardo, Joseph and Downs, A Craig 2018). There is not much information on the long term ecological effects of oxybenzone in our freshwater systems, so further investigation is warranted.
+Oxybenzone is also one of the top three most frequent allergens in sunscreens (DiNardo, Joseph and Downs, A Craig 2018).
+==Physical Properties==
+[[File:1000px-Oxybenzone.svg.png|200px]]
+Names:
+:*2-Hydroxy-4-methoxybenzophenone
+:*Oxybenzone
+:*Benzophenone-3 (BZ-3) <--trade naming, see other below
+:*Eusolex 4360
+:*Escalol 567
+Molecular weight: 228.24 g/mol
+Boiling point: 115°C.
+Melting point: 65.5°C.
+Density: 1.32 g/mL.
+pKa: 7.1.
+UV max: 288 and 326 nm.
+Described as an off-white or light yellow powder.
+Other--> [https://en.wikipedia.org/wiki/Benzophenone-n Benzophenone-n]
+==Chemical Oxidation==
+The following link shows an in depth explanation of the chemical oxidation of oxybenzone. This page also contains the data collected from this particular experiment.
+'''[[Oxybenzone_Oxidation|Oxybenzone Oxidation]]'''
+==Chlorination of Oxybenzone==
+Oxybenzone can become chlorinated in swimming pools because of the chlorine in the water. Chlorine also oxidizes oxybenzone quite well. There are three major products of the chlorination of oxybenzone.
+[[File:2019-10-08 (1).png|400px|thumb|left|Products of chlorination of oxybenzone. Source: Chlorination of oxybenzone: Kinetics, transformation, disinfection byproducts formation, and genotoxicity changes (Chemosphere 154 (2016) 521-527)]]
+==Coral Bleaching==
+Coral bleaching happens when the algae living on the coral are destroyed, leaving the coral to starve. The coral then lose their bright colors, which is why the term is called "bleaching." Oxybenzone reactions can harm these algae, resulting in coral bleaching.
+==Instrumentation Links==
+These links explain how to use the HPLC and UV-Vis in these experiments.
+[[HPLC|HPLC]]
+[[UV_Vis|UV-Vis]]
+==Research Paper==
+This link provides a sample of the senior research paper I am writing on the oxidation of oxybenzone.
+'''[[Oxybenzone_Research_Paper|Oxybenzone Research Paper]]'''
+==References==
 [[Media:Oxybenzone_review.pdf|Dermatological and environmental toxicological impact of the sunscreen ingredient oxybenzone/benzophenone-3. (review, 2018)]]
-[[:File:Sunscreens Cause Coral Bleaching by Promoting Viral Infections.pdf| Sunscreens Cause Coral Bleaching by Promoting Viral Infections]]
+[[Media:Sunscreens Cause Coral Bleaching by Promoting Viral Infections.pdf| Sunscreens Cause Coral Bleaching by Promoting Viral Infections]]
+[[Media:Oxy_01_review.pdf|Sunscreens: are they beneficial for health? An overview of endocrine disrupting properties of UV-filters (review, 2012, 166 times cited/Sept 2019)]]
+[[Media:Oxy_02_review.pdf|Occurrences, toxicities, and ecological risks of benzophenone-3, a common component of organic sunscreen products: A mini-review (review, 2014)]]
+[[Media:es0484799.pdf|Fate of Endocrine-Disruptor, Pharmaceutical, and Personal Care Product Chemicals during Simulated Drinking Water Treatment Processes (Environ. Sci. Technol. 2005, 39, 6649-6663)]]
+[[Media:2016ZhangChemo.pdf|Chlorination of oxybenzone: Kinetics, transformation, disinfection
+byproducts formation, and genotoxicity changes (Chemosphere 154 (2016) 521-527)]]
+[[Media:acs.est.9b04022.pdf|Development of a Handheld Submersible Chemiluminescent Sensor: Quantification of Superoxide at Coral Surfaces]]
+==References for Coral Bleaching==
+[[:File:noaa_13720_DS1.pdf|Toxicopathological Effects of the Sunscreen UV Filter,Oxybenzone (Benzophenone-3), on Coral Planulae and CulturedPrimary Cells and Its Environmental Contamination in Hawaiiand the U.S. Virgin Islands, Arch Environ Contam Toxicol (2016) 70:265–288DOI 10.1007/s00244-015-0227-7]]