Padimate O

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Padimate O
200px
Names
IUPAC name
2-ethylhexyl 4-(dimethylamino)benzoate
Other names
2-ethylhexyl dimethyl PABA
Escalol 507
Sundown
Identifiers
21245-02-3 YesY
ChemSpider 28343 YesY
Jmol 3D model Interactive image
KEGG D05335 YesY
PubChem 30541
UNII Z11006CMUZ YesY
  • InChI=1S/C17H27NO2/c1-5-7-8-14(6-2)13-20-17(19)15-9-11-16(12-10-15)18(3)4/h9-12,14H,5-8,13H2,1-4H3 YesY
    Key: WYWZRNAHINYAEF-UHFFFAOYSA-N YesY
  • InChI=1/C17H27NO2/c1-5-7-8-14(6-2)13-20-17(19)15-9-11-16(12-10-15)18(3)4/h9-12,14H,5-8,13H2,1-4H3
    Key: WYWZRNAHINYAEF-UHFFFAOYAL
  • O=C(OCC(CC)CCCC)c1ccc(N(C)C)cc1
Properties
C17H27NO2
Molar mass 277.41 g·mol−1
Density 0.99 g/cm3
Melting point <25 °C
Boiling point 362 °C (684 °F; 635 K)
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

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

Photobiology

Padimate O absorbs ultraviolet rays, thereby preventing direct DNA damage by UV-B. However, the thus-excited padimate O molecule may then react with DNA to produce indirect DNA damage, similar to the effects of ionizing radiation. An in vitro yeast study conducted 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]

However, multiple in vivo studies conducted in hairless mice following topical application of padimate O have demonstrated no carcinogenic effects and that padimate O reduces the number of and delays the appearance of UV-induced skin tumors.[3][4][5][6]

See also

References

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