Oxybenzone
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MedKoo CAT#: 318403

CAS#: 131-57-7

Description: Oxybenzone pale-yellow solid organic compound that is readily soluble in most organic solvents. Oxybenzone belongs to the class of aromatic ketones known as benzophenones. It is a component of many sunscreen lotions.

Chemical Structure

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Oxybenzone
CAS# 131-57-7
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318403
Name: Oxybenzone
CAS#: 131-57-7
Chemical Formula: C14H12O3
Exact Mass: 228.08
Molecular Weight: 228.243
Elemental Analysis: C, 73.67; H, 5.30; O, 21.03

Price and Availability

Size Price Availability Quantity
1kg USD -1
2kg USD -1
100mg USD 180
200mg USD 200
500mg USD 220
1g USD 250
2g USD 280
5g USD 300
10g USD 350
20g USD 380
50g USD 400
100g USD 420
200g USD 450
500g USD 550
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Synonym: Oxybenzone, Benzophenone-3, 2-hydroxy-4-methoxybenzone, Eusolex-4360

IUPAC/Chemical Name: (2-hydroxy-4-methoxyphenyl)-phenylmethanone

InChi Key: DXGLGDHPHMLXJC-UHFFFAOYSA-N

InChi Code: InChI=1S/C14H12O3/c1-17-11-7-8-12(13(15)9-11)14(16)10-5-3-2-4-6-10/h2-9,15H,1H3

SMILES Code: O=C(C1=CC=C(OC)C=C1O)C2=CC=CC=C2

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
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Biological target: Oxybenzone act as endocrine disrupting chemicals (EDCs) and can pass through the placental and blood-brain barriers.
In vitro activity: 50 μg L-1 of oxybenzone significantly impacted the cell density of C. goreaui, causing a 36.73% decrease. When oxybenzone concentration increased to 500 μg L-1 and 5000 μg L-1, cell division was completely suppressed; meanwhile, chl-a content declined to zero. As revealed by KEGG pathway analysis, oxybenzone affected energy metabolism and inhibited the metabolism of cofactors and vitamins in C. goreaui, while 5000 μg L-1 of oxybenzone significantly altered the carbohydrate metabolism, membrane transport and amino acid metabolism in E. voratum. Reference: Environ Pollut. 2023 Jan 15;317:120807. https://pubmed.ncbi.nlm.nih.gov/36464119/
In vivo activity: This study investigated mammary stromal changes in BALB/c animals exposed during gestation and perinatal development to 0, 30, or 3000 μg oxybenzone/kg/day. In mice exposed to 30 μg/kg/day, this study observed morphological changes in adulthood (e.g., a thicker periductal stroma and adipocytes that were considerably larger). This study also observed an increased number of mast cells in the mammary stroma at puberty which may represent a transient influence of oxybenzone exposure. These results provide additional evidence that even low doses of oxybenzone can disrupt hormone sensitive outcomes in the mammary gland when exposures occur during critical windows of development, and some of these effects manifest in later life. Reference: Front Toxicol. 2022 May 20;4:910230. https://pubmed.ncbi.nlm.nih.gov/35669359/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 72.5 317.64
Ethanol 45.0 197.16
Water 1.0 4.38

Preparing Stock Solutions

The following data is based on the product molecular weight 228.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Yang F, Wei Z, Long C, Long L. Toxicological effects of oxybenzone on the growth and bacterial composition of Symbiodiniaceae. Environ Pollut. 2023 Jan 15;317:120807. doi: 10.1016/j.envpol.2022.120807. Epub 2022 Dec 1. PMID: 36464119. 2. Chang KY, Yang CH, Chou HY, Chen KC, Huang YC. Organic ultraviolet filters regulate hyaluronan metabolism in human epidermal keratinocytes through the phosphatidylinositol 3-kinase pathway. Toxicol In Vitro. 2023 Feb;86:105511. doi: 10.1016/j.tiv.2022.105511. Epub 2022 Nov 4. PMID: 36336209. 3. Matouskova K, Bugos J, Schneider SS, Vandenberg LN. Exposure to Low Doses of Oxybenzone During Perinatal Development Alters Mammary Gland Stroma in Female Mice. Front Toxicol. 2022 May 20;4:910230. doi: 10.3389/ftox.2022.910230. PMID: 35669359; PMCID: PMC9163781. 4. LaPlante CD, Bansal R, Dunphy KA, Jerry DJ, Vandenberg LN. Oxybenzone Alters Mammary Gland Morphology in Mice Exposed During Pregnancy and Lactation. J Endocr Soc. 2018 May 22;2(8):903-921. doi: 10.1210/js.2018-00024. PMID: 30057971; PMCID: PMC6057512.
In vitro protocol: 1. Yang F, Wei Z, Long C, Long L. Toxicological effects of oxybenzone on the growth and bacterial composition of Symbiodiniaceae. Environ Pollut. 2023 Jan 15;317:120807. doi: 10.1016/j.envpol.2022.120807. Epub 2022 Dec 1. PMID: 36464119. 2. Chang KY, Yang CH, Chou HY, Chen KC, Huang YC. Organic ultraviolet filters regulate hyaluronan metabolism in human epidermal keratinocytes through the phosphatidylinositol 3-kinase pathway. Toxicol In Vitro. 2023 Feb;86:105511. doi: 10.1016/j.tiv.2022.105511. Epub 2022 Nov 4. PMID: 36336209.
In vivo protocol: 1. Matouskova K, Bugos J, Schneider SS, Vandenberg LN. Exposure to Low Doses of Oxybenzone During Perinatal Development Alters Mammary Gland Stroma in Female Mice. Front Toxicol. 2022 May 20;4:910230. doi: 10.3389/ftox.2022.910230. PMID: 35669359; PMCID: PMC9163781. 2. LaPlante CD, Bansal R, Dunphy KA, Jerry DJ, Vandenberg LN. Oxybenzone Alters Mammary Gland Morphology in Mice Exposed During Pregnancy and Lactation. J Endocr Soc. 2018 May 22;2(8):903-921. doi: 10.1210/js.2018-00024. PMID: 30057971; PMCID: PMC6057512.

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1: Zhang S, Wang X, Yang H, Xie YF. Chlorination of oxybenzone: Kinetics, transformation, disinfection byproducts formation, and genotoxicity changes. Chemosphere. 2016 Jul;154:521-7. doi: 10.1016/j.chemosphere.2016.03.116. Epub 2016 Apr 14. PubMed PMID: 27085067.

2: Downs CA, Kramarsky-Winter E, Segal R, Fauth J, Knutson S, Bronstein O, Ciner FR, Jeger R, Lichtenfeld Y, Woodley CM, Pennington P, Cadenas K, Kushmaro A, Loya Y. Toxicopathological Effects of the Sunscreen UV Filter, Oxybenzone (Benzophenone-3), on Coral Planulae and Cultured Primary Cells and Its Environmental Contamination in Hawaii and the U.S. Virgin Islands. Arch Environ Contam Toxicol. 2016 Feb;70(2):265-88. doi: 10.1007/s00244-015-0227-7. PubMed PMID: 26487337.

3: Chen F, Huber C, May R, Schröder P. Metabolism of oxybenzone in a hairy root culture: Perspectives for phytoremediation of a widely used sunscreen agent. J Hazard Mater. 2016 Apr 5;306:230-6. doi: 10.1016/j.jhazmat.2015.12.022. Epub 2015 Dec 18. PubMed PMID: 26736174.

4: Abdel-Ghany MF, Abdel-Aziz O, Ayad MF, Mikawy NN. Simultaneous Determination of Octinoxate, Oxybenzone, and Octocrylene in a Sunscreen Formulation Using Validated Spectrophotometric and Chemometric Methods. J AOAC Int. 2015 Sep-Oct;98(5):1215-25. doi: 10.5740/jaoacint.14-229. PubMed PMID: 26525239.

5: Baker LA, Horbury MD, Greenough SE, Ashfold MN, Stavros VG. Broadband ultrafast photoprotection by oxybenzone across the UVB and UVC spectral regions. Photochem Photobiol Sci. 2015 Oct;14(10):1814-20. doi: 10.1039/c5pp00217f. PubMed PMID: 26295590.

6: Yılmazcan Ö, Kanakaki C, Izgi B, Rosenberg E. Fast determination of octinoxate and oxybenzone uv filters in swimming pool waters by gas chromatography/mass spectrometry after solid-phase microextraction. J Sep Sci. 2015 Jul;38(13):2286-97. doi: 10.1002/jssc.201401250. Epub 2015 Jun 3. PubMed PMID: 25931007.

7: Baker LA, Horbury MD, Greenough SE, Coulter PM, Karsili TN, Roberts GM, Orr-Ewing AJ, Ashfold MN, Stavros VG. Probing the Ultrafast Energy Dissipation Mechanism of the Sunscreen Oxybenzone after UVA Irradiation. J Phys Chem Lett. 2015 Apr 16;6(8):1363-8. doi: 10.1021/acs.jpclett.5b00417. Epub 2015 Mar 30. PubMed PMID: 26263136.

8: Yiin LM, Tian JN, Hung CC. Assessment of dermal absorption of DEET-containing insect repellent and oxybenzone-containing sunscreen using human urinary metabolites. Environ Sci Pollut Res Int. 2015 May;22(9):7062-70. doi: 10.1007/s11356-014-3915-3. Epub 2014 Dec 11. PubMed PMID: 25491253.

9: Pawar AP, Gholap AP, Kuchekar AB, Bothiraja C, Mali AJ. Formulation and evaluation of optimized oxybenzone microsponge gel for topical delivery. J Drug Deliv. 2015;2015:261068. doi: 10.1155/2015/261068. Epub 2015 Feb 18. PubMed PMID: 25789176; PubMed Central PMCID: PMC4348582.

10: Karsili TN, Marchetti B, Ashfold MN, Domcke W. Ab initio study of potential ultrafast internal conversion routes in oxybenzone, caffeic acid, and ferulic acid: implications for sunscreens. J Phys Chem A. 2014 Dec 26;118(51):11999-2010. doi: 10.1021/jp507282d. Epub 2014 Aug 25. PubMed PMID: 25137024.

11: Wang T, Miller D, Burczynski F, Gu X. Evaluation of percutaneous permeation of repellent DEET and sunscreen oxybenzone from emulsion-based formulations in artificial membrane and human skin. Acta Pharm Sin B. 2014 Feb;4(1):43-51. doi: 10.1016/j.apsb.2013.11.002. Epub 2014 Jan 13. PubMed PMID: 26579363; PubMed Central PMCID: PMC4590294.

12: Blüthgen N, Zucchi S, Fent K. Effects of the UV filter benzophenone-3 (oxybenzone) at low concentrations in zebrafish (Danio rerio). Toxicol Appl Pharmacol. 2012 Sep 1;263(2):184-94. doi: 10.1016/j.taap.2012.06.008. Epub 2012 Jun 18. PubMed PMID: 22721600.

13: Fediuk DJ, Wang T, Chen Y, Parkinson FE, Namaka MP, Simons KJ, Burczynski FJ, Gu X. Metabolic disposition of the insect repellent DEET and the sunscreen oxybenzone following intravenous and skin administration in rats. Int J Toxicol. 2012 Sep-Oct;31(5):467-76. doi: 10.1177/1091581812459893. PubMed PMID: 23064701.

14: Fediuk DJ, Wang T, Chen Y, Parkinson FE, Namaka MP, Simons KJ, Burczynski FJ, Gu X. Tissue disposition of the insect repellent DEET and the sunscreen oxybenzone following intravenous and topical administration in rats. Biopharm Drug Dispos. 2011 Oct;32(7):369-79. doi: 10.1002/bdd.765. Epub 2011 Aug 2. PubMed PMID: 21812003.

15: Wang SQ, Burnett ME, Lim HW. Safety of oxybenzone: putting numbers into perspective. Arch Dermatol. 2011 Jul;147(7):865-6. doi: 10.1001/archdermatol.2011.173. PubMed PMID: 21768493.

16: Garcia HA, Hoffman CM, Kinney KA, Lawler DF. Laccase-catalyzed oxidation of oxybenzone in municipal wastewater primary effluent. Water Res. 2011 Feb;45(5):1921-32. doi: 10.1016/j.watres.2010.12.027. Epub 2010 Dec 28. PubMed PMID: 21237478.

17: Chen T, Burczynski FJ, Miller DW, Gu X. Percutaneous permeation comparison of repellents picaridin and DEET in concurrent use with sunscreen oxybenzone from commercially available preparations. Pharmazie. 2010 Nov;65(11):835-9. PubMed PMID: 21155391.

18: Sanad RA, Abdel Malak NS, El-Bayoomy TS, Badawi AA. Preparation and characterization of oxybenzone-loaded solid lipid nanoparticles (SLNs) with enhanced safety and sunscreening efficacy: SPF and UVA-PF. Drug Discov Ther. 2010 Dec;4(6):472-83. PubMed PMID: 22491313.

19: Sanad RA, Abdelmalak NS, Elbayoomy TS, Badawi AA. Formulation of a novel oxybenzone-loaded nanostructured lipid carriers (NLCs). AAPS PharmSciTech. 2010 Dec;11(4):1684-94. doi: 10.1208/s12249-010-9553-2. Epub 2010 Nov 24. PubMed PMID: 21107771; PubMed Central PMCID: PMC3011069.

20: Fediuk DJ, Wang T, Raizman JE, Parkinson FE, Gu X. Tissue deposition of the insect repellent DEET and the sunscreen oxybenzone from repeated topical skin applications in rats. Int J Toxicol. 2010 Dec;29(6):594-603. doi: 10.1177/1091581810380147. Epub 2010 Oct 19. PubMed PMID: 20959613.