Avobenzone

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Avobenzone

IUPAC name

1-(4-Methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

Identifiers

CAS number

70356-09-1

PubChem

51040

EC number

274-581-6

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

Properties

Molecular formula

C20H22O3

Molar mass

310.39 g mol?1

Supplementary data page

Structure andproperties

n, ?r, etc.

Thermodynamicdata

Phase behaviourSolid, liquid, gas

Spectral data

UV, IR, NMR, MS

Except where noted otherwise, data are given formaterials in their standard state(at 25, 100kPa)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.

Contents

1 History

2 See also

3 Notes

4 External links


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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. 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 (Tradename HallBrite BHB - )

Hexadecyl Benzoate

Butyloctyl Benzoate

Mexoryl SX (USAN Ecamsule, INCI Terephthalylidene Dicamphor Sulfonic Acid)

Corapan TQ (INCI Diethylhexyl 2,6-Naphthalate)

Parsol SLX (INCI Polysilicone-15)

Oxynex ST (INCI Diethylhexyl Syringylidene Malonate)

Polycrylene (INCI Polyester-8)

Complexing avobenzone with cyclodextrins may also increase its photostability.

According to some studies, "the most effective sunscreens contain avobenzone and titanium dioxide."

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. A manganese doped titanium dioxide may be better than undoped titanium dioxide to improve avobenzone's stability.

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.

See also

Sun protection factor

Notes

^ 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): 27582. 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): 4016. 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): 54753. 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): 13548. PMID 15870853.

^ Bonda C., Steinberg D. C. (2000). "A new photostabilizer for full spectrum sunscreens". Cosmet. Toiletries 115(6): 3745.

^ http://www.dsm.com/en_US/downloads/dnp/Parsol_SLX_Skin.pdf

^ Chaudhuri RK, Lascu Z,...(and so on)
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