Avobenzone | CAS#70356-09-1 | Broad Range UV Protector

Avobenzone
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 531005

CAS#: 70356-09-1

Description: Avobenzone is a dibenzoylmethane compound commonly found in sunscreens and can photoisomerize after exposure to near-ultraviolet light. At equilibrium, Avobenzone exists as a chelated enol characterized by a strong intramolecular hydrogen bond. The photochemistry of Avobenzone includes keto-enol tautomerization, cis-trans isomerization, rotation about the single bond and α bond cleavages of carbonyl groups. Findings suggest that torsion around the double C2-C3 bond of photoexcited chelated enol leads to internal conversion to the ground state and formation of rotamer E. In addition, opening of the chelated hydrogen ring by torsion of the hydroxyl group creates non-chelated enol. The possible mechanisms of rotamer Z formation are discussed.

Chemical Structure

Avobenzone

CAS# 70356-09-1

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 531005
Name: Avobenzone
CAS#: 70356-09-1
Chemical Formula: C20H22O3
Exact Mass: 310.16
Molecular Weight: 310.393
Elemental Analysis: C, 77.39; H, 7.14; O, 15.46

Price and Availability

Size	Price	Availability
5g	USD 250	2 Weeks
25g	USD 550	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Avobenzone, Avobenzonum, Parsol 1789, Parsol1789, Parsol-1789, HSDB 7423, HSDB-7423, HSDB7423

IUPAC/Chemical Name: 1-(4-(tert-butyl)phenyl)-3-(4-methoxyphenyl)propane-1,3-dione

InChi Key: XNEFYCZVKIDDMS-UHFFFAOYSA-N

InChi Code: 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

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

Appearance: White to light yellow crystalline 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

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:	Avobenzone is an endocrine disruptor that directly binds to estrogen receptor β and acts as an estrogen agonist
In vitro activity:	HTR8/SVneo cells were treated with various concentrations (0, 1, 2, 5, 10, 20, and 50 μM) of avobenzone with 50 μM being the maximum concentration. A significant decrease in cell proliferation was observed at 5 μM (Fig. 1A). Avobenzone at 10 μM produced more than 50% inhibition of cell proliferation and 74.6% (P <  0.001) and 77.2% (P <  0.001) cell proliferation were observed at 20 and 50 μM, respectively. Reference: Reprod Toxicol. 2018 Oct;81:50-57. https://pubmed.ncbi.nlm.nih.gov/29981360/
In vivo activity:	TBD

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO:PBS (pH 7.2) (1:2)	0.3	1.06
	DMF	30.0	96.65
	Ethanol	5.0	16.11

Preparing Stock Solutions

The following data is based on the product molecular weight 310.39 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.

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. Ahn S, An S, Lee M, Lee E, Pyo JJ, Kim JH, Ki MW, Jin SH, Ha J, Noh M. A long-wave UVA filter avobenzone induces obesogenic phenotypes in normal human epidermal keratinocytes and mesenchymal stem cells. Arch Toxicol. 2019 Jul;93(7):1903-1915. doi: 10.1007/s00204-019-02462-1. Epub 2019 Apr 23. PMID: 31016361. 2. Yang C, Lim W, Bazer FW, Song G. Avobenzone suppresses proliferative activity of human trophoblast cells and induces apoptosis mediated by mitochondrial disruption. Reprod Toxicol. 2018 Oct;81:50-57. doi: 10.1016/j.reprotox.2018.07.003. Epub 2018 Jul 4. PMID: 29981360
In vitro protocol:	1. Ahn S, An S, Lee M, Lee E, Pyo JJ, Kim JH, Ki MW, Jin SH, Ha J, Noh M. A long-wave UVA filter avobenzone induces obesogenic phenotypes in normal human epidermal keratinocytes and mesenchymal stem cells. Arch Toxicol. 2019 Jul;93(7):1903-1915. doi: 10.1007/s00204-019-02462-1. Epub 2019 Apr 23. PMID: 31016361. 2. Yang C, Lim W, Bazer FW, Song G. Avobenzone suppresses proliferative activity of human trophoblast cells and induces apoptosis mediated by mitochondrial disruption. Reprod Toxicol. 2018 Oct;81:50-57. doi: 10.1016/j.reprotox.2018.07.003. Epub 2018 Jul 4. PMID: 29981360
In vivo protocol:	TBD

Molarity Calculator

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*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

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1: Dunkelberger AD, Kieda RD, Marsh BM, Crim FF. Picosecond Dynamics of Avobenzone in Solution. J Phys Chem A. 2015 Jun 18;119(24):6155-61. doi: 10.1021/acs.jpca.5b01641. Epub 2015 Jun 2. PubMed PMID: 25978304.

2: Afonso S, Horita K, Sousa e Silva JP, Almeida IF, Amaral MH, Lobão PA, Costa PC, Miranda MS, Esteves da Silva JC, Sousa Lobo JM. Photodegradation of avobenzone: stabilization effect of antioxidants. J Photochem Photobiol B. 2014 Nov;140:36-40. doi: 10.1016/j.jphotobiol.2014.07.004. Epub 2014 Jul 15. PubMed PMID: 25086322.

3: Kumar P, Deshpande A. Patent review on photostability enhancement of avobenzone and its formulations. Recent Pat Drug Deliv Formul. 2015;9(2):121-8. Review. PubMed PMID: 25643262.

4: Kim MG, Kim TH, Shin BS, Kim MG, Seok SH, Kim KB, Lee JB, Choi HG, Lee YS, Yoo SD. A sensitive LC-ESI-MS/MS method for the quantification of avobenzone in rat plasma and skin layers: Application to a topical administration study. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Oct 15;1003:41-6. doi: 10.1016/j.jchromb.2015.09.014. Epub 2015 Sep 15. PubMed PMID: 26409261.

5: Trossini GH, Maltarollo VG, Garcia RD, Pinto CA, Velasco MV, Honorio KM, Baby AR. Theoretical study of tautomers and photoisomers of avobenzone by DFT methods. J Mol Model. 2015 Dec;21(12):319. doi: 10.1007/s00894-015-2863-2. Epub 2015 Dec 2. PubMed PMID: 26631072.

6: Kim EJ, Kim MJ, Im NR, Park SN. Photolysis of the organic UV filter, avobenzone, combined with octyl methoxycinnamate by nano-TiO2 composites. J Photochem Photobiol B. 2015 Aug;149:196-203. doi: 10.1016/j.jphotobiol.2015.05.011. Epub 2015 Jun 2. PubMed PMID: 26093231.

7: Ceresole R, Han YK, Rosasco MA, Orelli LR, Segall A. Drug-excipient compatibility studies in binary mixtures of avobenzone. J Cosmet Sci. 2013 Sep-Oct;64(5):317-28. PubMed PMID: 24139431.

8: Kawakami CM, Gaspar LR. Mangiferin and naringenin affect the photostability and phototoxicity of sunscreens containing avobenzone. J Photochem Photobiol B. 2015 Oct;151:239-47. doi: 10.1016/j.jphotobiol.2015.08.014. Epub 2015 Aug 15. PubMed PMID: 26318281.

9: Liu JJ, Nazzal S, Chang TS, Tsai T. Preparation and characterization of cosmeceutical liposomes loaded with avobenzone and arbutin. J Cosmet Sci. 2013 Jan-Feb;64(1):9-17. PubMed PMID: 23449127.

10: Chisholm MH, Gustafson TL, Kender WT, Spilker TF, Young PJ. Electronic and spectroscopic properties of avobenzone derivatives attached to ditungsten quadruple bonds. Inorg Chem. 2015 Oct 5;54(19):9438-46. doi: 10.1021/acs.inorgchem.5b01221. Epub 2015 Sep 21. PubMed PMID: 26389702.

11: Trebše P, Polyakova OV, Baranova M, Kralj MB, Dolenc D, Sarakha M, Kutin A, Lebedev AT. Transformation of avobenzone in conditions of aquatic chlorination and UV-irradiation. Water Res. 2016 Sep 15;101:95-102. doi: 10.1016/j.watres.2016.05.067. Epub 2016 May 26. PubMed PMID: 27258620.

12: Chisholm MH, Durr CB, Gustafson TL, Kender WT, Spilker TF, Young PJ. Electronic and Spectroscopic Properties of Avobenzone Derivatives Attached to Mo₂ Quadruple Bonds: Suppression of the Photochemical Enol-to-Keto Transformation. J Am Chem Soc. 2015 Apr 22;137(15):5155-62. doi: 10.1021/jacs.5b01495. Epub 2015 Apr 9. PubMed PMID: 25856290.

13: Yang J, Wiley CJ, Godwin DA, Felton LA. Influence of hydroxypropyl-beta-cyclodextrin on transdermal penetration and photostability of avobenzone. Eur J Pharm Biopharm. 2008 Jun;69(2):605-12. doi: 10.1016/j.ejpb.2007.12.015. Epub 2007 Dec 25. PubMed PMID: 18226883.

14: Paris C, Lhiaubet-Vallet V, Jiménez O, Trullas C, Miranda MA. A blocked diketo form of avobenzone: photostability, photosensitizing properties and triplet quenching by a triazine-derived UVB-filter. Photochem Photobiol. 2009 Jan-Feb;85(1):178-84. doi: 10.1111/j.1751-1097.2008.00414.x. Epub 2008 Jul 30. PubMed PMID: 18673327.

15: Beasley DG, Meyer TA. Characterization of the UVA protection provided by avobenzone, zinc oxide, and titanium dioxide in broad-spectrum sunscreen products. Am J Clin Dermatol. 2010 Dec 1;11(6):413-21. doi: 10.2165/11537050-000000000-00000. PubMed PMID: 20806994.

16: Kojić M, Petković M, Etinski M. A new insight into the photochemistry of avobenzone in gas phase and acetonitrile from ab initio calculations. Phys Chem Chem Phys. 2016 Aug 10;18(32):22168-78. doi: 10.1039/c6cp03533g. PubMed PMID: 27443629.

17: Mbah CJ. Degradation kinetics of butylmethoxydibenzoylmethane (avobenzone) in aqueous solution. Pharmazie. 2007 Oct;62(10):747-9. PubMed PMID: 18236778.

18: Albertini B, Mezzena M, Passerini N, Rodriguez L, Scalia S. Evaluation of spray congealing as technique for the preparation of highly loaded solid lipid microparticles containing the sunscreen agent, avobenzone. J Pharm Sci. 2009 Aug;98(8):2759-69. doi: 10.1002/jps.21636. PubMed PMID: 19067396.

19: Galimany-Rovira F, Miñarro-Carmona M, Pérez-Lozano P, García-Montoya E, Ticó-Grau JR, Suñé-Negre JM. Optimization and Validation of a Fast UPLC Method for Simultaneous Determination of Hydroquinone, Kojic Acid, Octinoxate, Avobenzone, BHA, and BHT. J AOAC Int. 2016 Sep 29. [Epub ahead of print] PubMed PMID: 27874826.

20: Wang C, Bavcon Kralj M, Košmrlj B, Yao J, Košenina S, Polyakova OV, Artaev VB, Lebedev AT, Trebše P. Stability and removal of selected avobenzone's chlorination products. Chemosphere. 2017 May 6;182:238-244. doi: 10.1016/j.chemosphere.2017.04.125. [Epub ahead of print] PubMed PMID: 28500968.

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