Padimate O
IUPAC name	2-ethylhexyl 4-(dimethylamino)benzoate
Other names	2-ethylhexyl dimethyl PABA Escalol 507 Sundown
Identifiers
CAS number	21245-02-3 Y
PubChem	30541
SMILES	CCCCC(CC)COC(=O)C1=CC=C(C=C1)N(C)C
Properties
Molecular formula	C17H27NO2
Molar mass	277.402
Density	0.99 g/cm³
Melting point	<25 °C
Boiling point	362 °C
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

Padimate O is an ester organic compound related to the water soluble compound PABA (4-aminobenzoic acid), and used as an ingredient in some sunscreens. This yellowish water-insoluble oily liquid is formed by the condensation of 2-ethylhexanol and dimethylaminobenzoic acid. Other names for padimate-O are: 2-ethylhexyl 4-dimethylaminobenzoate, Escalol 507, oxtyldimethyl PABA, or OD-PABA.

[edit] Photobiology

Padimate O has been implicated in the sunscreen controversy. Padimate O absorbs ultraviolet rays, thereby preventing direct DNA damage by UV-B. However, the thus excited padimate O molecule can then react with DNA and produce indirect DNA damage, similar to the effects of ionizing radiation. A study in 1993 demonstrated the sunlight-induced mutagenicity of Padimate O.^[1] The photobiological properties of padimate O resemble those of Michler's ketone which is considered photocarcinogenic in rats and mice. These findings suggest that padimate O might also be photocarcinogenic.^[2]

[edit] References

1. ^ Knowland, John; McKenzie, Edward A.; McHugh, Peter J.; Cridland, Nigel A. (1993). "Sunlight-induced mutagenicity of a common sunscreen ingredient.". FEBS Letters 324(3): 309–313. doi:10.1016/0014-5793(93)80141-G. http://www.sciencedirect.com/science?_ob=MImg&_imagekey=B6T36-44G8DXC-HB-1&_cdi=4938&_user=10&_orig=search&_coverDate=06%2F21%2F1993&_sk=996759996&view=c&wchp=dGLbVlz-zSkzk&md5=52a598965b8eebd278f34d304b27e2a0&ie=/sdarticle.pdf. 
2. ^ Melanie Gulston, John Knowland; S. H. Moss, D. J. Davies (1999). "Illumination of human keratinocytes in the presence of sunscreen ingredient padimat-O .... increases strand breaks.". Mutation Research 1999 (444): 49–60. http://www.ncbi.nlm.nih.gov/pubmed/10477339. 

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