| Avobenzone |
 |
| IUPAC name | 1-(4-Methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione |
| Identifiers |
| CAS number | 70356-09-1  Y |
| PubChem | 51040 |
| EC number | 274-581-6 |
| SMILES | O=C(c1ccc(cc1)C(C)(C)C)CC(=O)c2ccc(OC)cc2 |
| 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 |
| InChI key | XNEFYCZVKIDDMS-UHFFFAOYAG |
| ChemSpider ID | 46261 |
| Properties |
| Molecular formula | C20H22O3 |
| Molar mass | 310.39 g mol−1 |
| Supplementary data page |
Structure and
properties | n, εr, etc. |
Thermodynamic
data | Phase behaviour
Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
 Y (what is this?) (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
| Infobox references |
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.[1]
[edit] 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.[2][3][4] The UV-A light in a day of sunlight in a temperate climate is sufficient to break down most of the compound. Data presented to the Food and Drug Administration by the Cosmetic, Toiletry and Fragrance Association indicates a -36% change in avobenzone's UV absorbance following one hour of exposure to sunlight.[5] 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 (Tradename HallBrite BHB - [1])
- Hexadecyl Benzoate
- Butyloctyl Benzoate
- Mexoryl SX (USAN Ecamsule, INCI Terephthalylidene Dicamphor Sulfonic Acid)
- Corapan TQ (INCI Diethylhexyl 2,6-Naphthalate)[6]
- Parsol SLX (INCI Polysilicone-15)[7]
- Oxynex ST (INCI Diethylhexyl Syringylidene Malonate)[8]
- Polycrylene (INCI Polyester-8)[9]
Complexing avobenzone with cyclodextrins may also increase its photostability.[10]
According to some studies, "the most effective sunscreens contain avobenzone and titanium dioxide." [11]
[12] 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.[13] A manganese doped titanium dioxide may be better than undoped titanium dioxide to improve avobenzone's stability.[14]
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.
[edit] See also
- ^ Vielhaber G, Grether-Beck S, Koch O, Johncock W, Krutmann J (March 2006). "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". Photochem Photobiol Sci 5(3): 275–82. doi:10.1039/b516702g. PMID 16520862.
- ^ Chatelain E, Gabard B. (September 2001). "Photostabilization of Butyl methoxydibenzoylmethane (Avobenzone) and Ethylhexyl methoxycinnamate by Bis-ethylhexyloxyphenol methoxyphenyl triazine (Tinosorb S), a new UV broadband filter". Photochem Photobiol 74(3): 401–6. doi:10.1562/0031-8655(2001)074<0401:POBMAA>2.0.CO;2. PMID 11594052.
- ^
Tarras-Wahlberg N, Stenhagen G, Larko O, Rosen A, Wennberg AM, Wennerstrom O (October 1999). "Changes in ultraviolet absorption of sunscreens after ultraviolet irradiation". J Invest Dermatol 113(4): 547–53. doi:10.1046/j.1523-1747.1999.00721.x. PMID 10504439. http://www.nature.com/jid/journal/v113/n4/full/5603262a.html. - ^ Wetz F, Routaboul C, Denis A, Rico-Lattes I (Mar-Apr 2005). "A new long-chain UV absorber derived from 4-tert-butyl-4'-methoxydibenzoylmethane: absorbance stability under solar irradiation". J Cosmet Sci 56(2): 135–48. PMID 15870853.
- ^ CTFA letter re: Tentative Final Monograph for OTC Sunscreen
- ^ Bonda C., Steinberg D. C. (2000). "A new photostabilizer for full spectrum sunscreens". Cosmet. Toiletries 115(6): 37–45.
- ^ http://www.dsm.com/en_US/downloads/dnp/Parsol_SLX_Skin.pdf
- ^ Chaudhuri RK, Lascu Z, Puccetti G, Deshpande AA, Paknikar SK (May-Jun 2006). "Design of a photostabilizer having built-in antioxidant functionality and its utility in obtaining broad-spectrum sunscreen formulations.". Photochem Photobiol 82(3): 823–8. doi:10.1562/2005-07-15-RA-612. PMID 16492073.
- ^ http://www.hallstar.com/techdocs/Polycrylene&CorapanTQAvobenzoneStabilization.pdf
- ^ Scalia S, Simeoni S, Barbieri A, Sostero S (November 2002). "Influence of hydroxypropyl-beta-cyclodextrin on photo-induced free radical production by the sunscreen agent, butyl-methoxydibenzoylmethane.". J Pharm Pharmacol 54(11): 1553–8. doi:10.1211/002235702207. PMID 12495559.
- ^ Warwick L. Morison, M.D. (March 11, 2004.). "Photosensitivity". The New England Journal of Medicine 350: 1111–1117. doi:10.1056/NEJMcp022558. PMID 15014184.
- ^ "Sunscreen Drug Products for Over-the-Counter use; Marketing Status of Products Containing Avobenzone; Enforcement Policy" (PDF). US Food and Drug Administration. 1997-04-30. p. 23354. http://www.fda.gov/cder/otcmonographs/Sunscreen/sunscreen_avobenzone_enforc_policy_19970420.pdf. Retrieved 2007-06-03.
- ^ Stability Study of Avobenzone with Inorganic Sunscreens, Kobo Products Poster, 2001, Online version
- ^ Wakefield G, Lipscomb S, Holland E, Knowland J (July 2004). "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.". Photochem Photobiol Sci 3(7): 648–52. doi:10.1039/b403697b. PMID 15238999.
[edit] External links
| Sunscreening agents approved by the US FDA or other agencies | | | UVA: 400–315 nm • UVB: 315–290 nm • chemical agents unless otherwise noted | | | UVA filters | | | | UVB filters | | | | UVA+UVB filters | | | | | |
