Avobenzone

chembox new
ImageFile = Avobenzone.png ImageSize = 200px
IUPACName = 1-(4-Methoxyphenyl)-3-(4-"tert"-butylphenyl)propane-1,3-dione
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CASNo = 70356-09-1
EINECS = 274-581-6
PubChem = 51040
SMILES = CC(C)(C)C1=CC=C(C=C1)C(=O)CC(=O)C2=CC=C(C=C2)OC
InChI = 1/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
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C=20 | H=22 | O=3
MolarMass =310.387
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Avobenzone (trade names Parsol 1789, Eusolex 9020, Escalol 517 and others, INCI Butyl Methoxydibenzoylmethane) is an oil soluble ingredient used in sunscreen products to absorb the full spectrum of UVA rays. It is a dibenzoylmethane derivative. Its ability to absorb ultraviolet light over a wider range of wavelengths than many organic sunscreen agents has led to its use in many commercial preparations marketed as "broad spectrum" sunscreens. Avobenzone has an absorption maximum of 357 nm. [cite journal
title=Sunscreens with an absorption maximum of > or =360 nm provide optimal protection against UVA1-induced expression of matrix metalloproteinase-1, interleukin-1, and interleukin-6 in human dermal fibroblasts
year=2006| month=Mar| pmid=16520862
author=Vielhaber G, Grether-Beck S, Koch O, Johncock W, Krutmann J
journal= Photochem Photobiol Sci| volume=5(3)| pages=275–82]

History

Avobenzone was patented in 1973 and was approved in the EU in 1978. It was approved by the FDA in 1988. Its use is approved world wide.

Avobenzone has been shown to degrade significantly in light, resulting in less protection over time. [cite journal
title=Photostabilization of Butyl methoxydibenzoylmethane (Avobenzone) and Ethylhexyl methoxycinnamate by Bis-ethylhexyloxyphenol methoxyphenyl triazine (Tinosorb S), a new UV broadband filter
year=2001| month=Sep| pmid=11594052
author=Chatelain E, Gabard B.
journal=Photochem Photobiol| volume=74(3)| pages=401–6
doi=10.1562/0031-8655(2001)074<0401:POBMAA>2.0.CO;2] [ cite journal
title=Changes in ultraviolet absorption of sunscreens after ultraviolet irradiation
year=1999| url=http://www.nature.com/jid/journal/v113/n4/full/5603262a.html|month=Oct| pmid=10504439
author=Tarras-Wahlberg N, Stenhagen G, Larko O, Rosen A, Wennberg AM, Wennerstrom O
journal=J Invest Dermatol| volume=113(4)| pages=547–53
doi=10.1046/j.1523-1747.1999.00721.x] [cite journal
title=A new long-chain UV absorber derived from 4-tert-butyl-4'-methoxydibenzoylmethane: absorbance stability under solar irradiation
year=2005| month=Mar-Apr| pmid=15870853
author=Wetz F, Routaboul C, Denis A, Rico-Lattes I
journal=J Cosmet Sci| volume=56(2)| pages=135–48] The UV-A light in a day of sunlight in a temperate climate is sufficient to break down most of the compound. This degradation can be reduced by using a photostabilizer, like octocrylene. Other photostabilizers include:
* 4-Methylbenzylidene camphor (USAN Enzacamene)
* Tinosorb S (USAN Bemotrizinol, INCI Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine)
* Tinosorb M (USAN Bisoctrizole, INCI Methylene Bis-Benzotriazolyl Tetramethylbutylphenol)
* Butyloctyl Salicylate
* Hexadecyl Benzoate
* Butyloctyl Benzoate
* Mexoryl SX (USAN Ecamsule, INCI Terephthalylidene Dicamphor Sulfonic Acid)
* Corapan TQ (INCI Diethylhexyl 2,6-Naphthalate) [cite journal| title=A new photostabilizer for full spectrum sunscreens| year=2000| author=Bonda C., Steinberg D. C.| journal= Cosmet. Toiletries| volume=115(6)| pages=37–45]
* Parsol SLX (INCI Polysilicone-15) [http://www.dsm.com/en_US/downloads/dnp/Parsol_SLX_Skin.pdf]
* Oxynex ST (INCI Diethylhexyl Syringylidene Malonate) [cite journal
title=Design of a photostabilizer having built-in antioxidant functionality and its utility in obtaining broad-spectrum sunscreen formulations.
year=2006| month=May-Jun| pmid=16492073
author=Chaudhuri RK, Lascu Z, Puccetti G, Deshpande AA, Paknikar SK
journal= Photochem Photobiol| volume=82(3)| pages=823–8
doi=10.1562/2005-07-15-RA-612]
* Polycrylene (INCI Polyester-8) [http://www.hallstar.com/techdocs/Polycrylene&CorapanTQAvobenzoneStabilization.pdf]

Complexing avobenzone with cyclodextrins may also increase its photostability. [cite journal
title=Influence of hydroxypropyl-beta-cyclodextrin on photo-induced free radical production by the sunscreen agent, butyl-methoxydibenzoylmethane.
year=2002| month=Nov| pmid=12495559
author=Scalia S, Simeoni S, Barbieri A, Sostero S
journal=J Pharm Pharmacol| volume=54(11)| pages=1553–8
doi=10.1211/002235702207]

According to some studies, "the most effective sunscreens contain avobenzone and titanium dioxide." [cite journal
author=Warwick L. Morison, M.D.
title=Photosensitivity
journal=The New England Journal of Medicine
date=Mar 11, 2004.
volume=350
pages=1111–1117
doi=10.1056/NEJMcp022558
pmid=15014184] The combination with TiO₂ is approved for use in the EU, but in the US the FDA has yet to approve this, stating (in 1997) that "until complete and adequate data have been submitted, the agency has no basis to allow other avobenzone combinations" (containing titanium dioxide). [NEW-WAVE SUNSCREENS: Active ingredient makers are frustrated by the long list of sunscreens and UV-A testing protocols that are still awaiting FDA decisions, "Chemical & Engineering News", April 11, 2005, Volume 83, Number 15, pp. 18-22. [http://pubs.acs.org/cen/coverstory/83/8315sunscreens.html Online version] ] [cite web
title = Sunscreen Drug Products for Over-the-Counter use; Marketing Status of Products Containing Avobenzone; Enforcement Policy
publisher = US Food and Drug Administration | date = 1997-04-30
url = http://www.fda.gov/cder/otcmonographs/Sunscreen/sunscreen_avobenzone_enforc_policy_19970420.pdf | page=23354 | accessdate = 2007-06-03 ] Avobenzone can degrade faster in light in combination with mineral UV absorbers like zinc oxide and titanium dioxide, though with the right coating of the mineral particles this reaction can be reduced. [Stability Study of Avobenzone with Inorganic Sunscreens, "Kobo Products Poster", 2001, [http://www.koboproductsinc.com/Downloads/NYSCC-Avobenzone.pdf Online version] ] A manganese doped titanium dioxide may be better than undoped titanium dioxide to improve avobenzone's stability. [cite journal| title=The effects of manganese doping on UVA absorption and free radical generation of micronised titanium dioxide and its consequences for the photostability of UVA absorbing organic sunscreen components.| year=2004| month=Jul| pmid=15238999| author=Wakefield G, Lipscomb S, Holland E, Knowland J| journal=Photochem Photobiol Sci| volume=3(7)| pages=648–52| doi=10.1039/b403697b]

Avobenzone reacts with minerals to form colored complexes. Manufacturers of avobenzone, like DSM recommend to include a chelator to prevent this from happening. They also recommend to avoid the inclusion of iron and ferric salts, heavy metals, formaldehyde donors and PABA and PABA esters.

The makers of Coppertone advise that avobenzone binds iron and can cause staining of clothes washed in iron-rich water.

ee also

*Bemotrizinol
*Bisdisulizole disodium
*Bisoctrizole
*Ecamsule
*Sun protection factor
*Sunscreen
*Titanium dioxide
*Ultraviolet
*Zinc oxide

Notes

External links

* [http://www.cosmeticscop.com/learn/art.asp?ID=261 Discussion of Parsol 1789 properties]