octocrylene
{{Short description|Organic compound}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 402511143
| Name = Octocrylene
| ImageFile = Octocrylene Structural Formula V1.svg
| ImageSize = 220
| ImageAlt = Structural formula of octocrylene
| ImageFile1 = Octocrylene 3D spacefill.png
| ImageSize1 = 220
| ImageAlt1 = Space-filling model of octocrylene
| PIN = 2-Ethylhexyl 2-cyano-3,3-diphenylprop-2-enoate
| OtherNames = Octocrylene
Octocrilene
Uvinul N-539
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21165
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1201147
| PubChem = 22571
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5A68WGF6WM
| InChI = 1/C24H27NO2/c1-3-5-12-19(4-2)18-27-24(26)22(17-25)23(20-13-8-6-9-14-20)21-15-10-7-11-16-21/h6-11,13-16,19H,3-5,12,18H2,1-2H3
| InChIKey = FMJSMJQBSVNSBF-UHFFFAOYAD
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C24H27NO2/c1-3-5-12-19(4-2)18-27-24(26)22(17-25)23(20-13-8-6-9-14-20)21-15-10-7-11-16-21/h6-11,13-16,19H,3-5,12,18H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FMJSMJQBSVNSBF-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 6197-30-4
| SMILES = N#C/C(C(=O)OCC(CC)CCCC)=C(/c1ccccc1)c2ccccc2
}}
|Section2={{Chembox Properties
| Formula = C24H27NO2
| MolarMass = 361.48 g/mol
| Density = 1.05 g/cm3
| MeltingPtC = 14
| BoilingPtC = 218
| BoilingPt_notes = at 1.5 mmHg
}}
}}
Octocrylene is an organic compound used as an ingredient in sunscreens and cosmetics. It is an ester formed by the Knoevenagel condensation of 2-ethylhexyl cyanoacetate with benzophenone. It is a viscous, oily liquid that is clear and colorless.
The extended conjugation of the acrylate portion of the molecule absorbs UVB and short-wave UVA (ultraviolet) rays with wavelengths from 280 to 320 nm,{{Cite web|url=http://www.smartskincare.com/skinprotection/sunblocks/sunblock_octocylene.html|title=Octocrylene - Chemical UVB+UVA sunscreen/sunblock agent|website=www.smartskincare.com}} protecting the skin from direct DNA damage. The ethylhexanol portion is a fatty alcohol, adding emollient and oil-like (water resistant) properties.
Safety
Octocrylene can penetrate into the skin where it acts as a photosensitizer, resulting in an increased production of free radicals under illumination.{{cite journal |author1=Hanson Kerry M. |author2=Gratton Enrico |author3=Bardeen Christopher J. |title=Sunscreen enhancement of UV-induced reactive oxygen species in the skin |doi=10.1016/j.freeradbiomed.2006.06.011| journal=Free Radical Biology and Medicine |volume=41 |issue=8 |pages=1205–1212 |year=2006 |pmid=17015167 |s2cid=13999532 |url=http://www.escholarship.org/uc/item/9f14s2dd }} It may also pass through the skin, into the blood stream, eventually being metabolized and excreted in urine in form of its metabolites.{{cite journal |last1=Bury |first1=Daniel |last2=Belov |first2=Vladimir N. |last3=Qi |first3=Yulin |last4=Hayen |first4=Heiko |last5=Volmer |first5=Dietrich A. |last6=Brüning |first6=Thomas |last7=Koch |first7=Holger M. |title=Determination of urinary metabolites of the emerging UV filter octocrylene by online-SPE-LC-MS/MS |journal=Analytical Chemistry |date=2018 |volume=90 |issue=1 |pages=944–951 |doi=10.1021/acs.analchem.7b03996|pmid=29188988 |hdl=21.11116/0000-0000-3212-3 |hdl-access=free }}{{cite journal |last1=Bury |first1=Daniel |last2=Modick-Biermann |first2=Hendrik |last3=Leibold |first3=Edgar |last4=Brüning |first4=Thomas |last5=Koch |first5=Holger M. |title=Urinary metabolites of the UV filter octocrylene in humans as biomarkers of exposure |journal=Archives of Toxicology |date=2019 |volume=93 |issue=5 |pages=1227–1238 |doi=10.1007/s00204-019-02408-7|pmid=30739143 |bibcode=2019ArTox..93.1227B |s2cid=59622082 }} Octocrylene can convert to benzophenone through a retro-aldol condensation.{{cite journal |last1=Downs |first1=C. A. |last2=DiNardo |first2=Joseph C. |last3=Stien |first3=Didier |last4=Rodrigues |first4=Alice M. S. |last5=Lebaron |first5=Philippe |title=Benzophenone Accumulates over Time from the Degradation of Octocrylene in Commercial Sunscreen Products |journal=Chemical Research in Toxicology |date=7 March 2021 |volume=34 |issue=4 |pages=1046–1054 |doi=10.1021/acs.chemrestox.0c00461|pmid=33682414 |doi-access=free }} The reaction occurs slowly over time, yielding significant concentration of benzophenone in all commercial cosmetics tested formulated with octocrylene.
In coral, octocrylene has been shown to accumulate in the form of fatty acid conjugates and trigger mitochondrial dysfunction.{{cite journal |last1=Stien |first1=Didier |last2=Clergeaud |first2=Fanny |last3=Rodrigues |first3=Alice M.S. |last4=Lebaron |first4=Karine |last5=Pillot |first5=Rémi |last6=Romans |first6=Pascal |last7=Fagervold |first7=Sonja |last8=Lebaron |first8=Philippe |title=Metabolomics reveal that octocrylene accumulates in Pocillopora damicornis tissues as fatty acid conjugates and triggers coral cell mitochondrial dysfunction |journal=Analytical Chemistry |date=2019 |volume=91 |issue=1 |pages=990–995 |doi=10.1021/acs.analchem.8b04187|pmid=30516955 |s2cid=54567139 |url=https://hal.sorbonne-universite.fr/hal-01973836/file/Manuscript%20File.pdf }}
=Regulation=
Palau has banned the sale and use of three reef-toxic UV filters including octocrylene in its Responsible Tourism Education Act of 2018.{{cite web |last1=Republic of Palau |title=RPPL No. 10-30: The Responsible Tourism Education Act of 2018 – PalauGov.pw |url=https://www.palaugov.pw/documents/rppl-no-10-30-the-responsible-tourism-education-act-of-2018/ |website=PalauGov.pw Your guide to finding and using Palau National Government services |access-date=16 October 2019}} The United States Virgin Islands has also banned the use of sunscreens containing octocrylene, requiring that all visitors use "non-nano mineral sunscreen" containing zinc oxide and titanium dioxide.{{cite web |title=Sustainable Travel in USVI |url=https://www.visitusvi.com/travel-information/sustainable |website=United States Virgin Islands |access-date=17 February 2024 |archive-url=https://web.archive.org/web/20240114080831/https://www.visitusvi.com/travel-information/sustainable |archive-date=14 January 2024 |language=en |quote=Avoid sunscreens that contain the “Toxic 3 Os” of oxybenzone, octinoxate and octocrylene – they are prohibited in the United States Virgin Islands. Wear rashguards, hats and use only non-nano mineral sunscreen containing zinc oxide and titanium dioxide, the only sunscreen ingredients deemed safe and effective by the FDA.}}
References
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{{Sunscreening agents}}