Padimate O
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| Names | |
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| IUPAC name
2-ethylhexyl 4-(dimethylamino)benzoate
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| Other names
2-ethylhexyl dimethyl PABA
Escalol 507 Sundown | |
| Identifiers | |
3D model (JSmol)
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| ECHA InfoCard | 100.040.248 |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C17H27NO2 | |
| Molar mass | 277.402 |
| Density | 0.99 g/cm³ |
| Melting point | <25 °C |
| Boiling point | 362 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Padimate O is an organic compound that is an ingredient in some sunscreens. It is a derivative of PABA, an ester formed by the condensation of 2-ethylhexanol and dimethylaminobenzoic acid. It is a yellowish oily liquid that is insoluble in water. It absorbs ultraviolet rays, thereby preventing direct DNA damage by UV-B. Unfortunately the excited padimate O molecule reacts bimolecularly with DNA and produces indirect DNA damages, that are similar to those done by ionizing radiation. Therefore padimate O is presumably photocarcinogenic.[1]
Other names for padimate-O are: 2-ethylhexyl 4-dimethylaminobenzoate, Escalol 507, oxtyldimethyl PABA, or OD-PABA.
This compound does not dissipate energy as fast as melanin, and therefore it is unsuitable as a sunscreen ingredient (see photoprotection).[citation needed]
Photobiology
The photobiological properties of padimate O resemble that of Michler's ketone. The compound has been shown to increase the lethal effects of UV-radiation.[2] Michler's ketone is known to be photocarcinogenic in rats and mice, therefore padimate O is implicated in the sunscreen controversy.
References
- ^ Melanie Gulston, John Knowland (1999). "Illumination of human keratinocytes in the presence of sunscreen ingredient padimat-O .... increases strand breaks". Mutation Research. 1999 (444): 49–60.
{{cite journal}}: Unknown parameter|coauthors=ignored (|author=suggested) (help) - ^ 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.
{{cite journal}}: CS1 maint: multiple names: authors list (link)
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