Padimate A

Padimate A is an organic compound that is an ingredient in some sunscreens. It is an ester derivative of PABA. This aromatic chemical absorbs ultraviolet rays thereby preventing sunburn. However, its chemical structure and behaviour is similar to an industrial free radical generator.[1] In Europe this chemical was withdrawn in 1989 for unstated reasons.[1] In the US it was never approved for use in sunscreens.

Padimate A
Names
Preferred IUPAC name
3-Methylbutyl 4-(dimethylamino)benzoate
Other names
isoamyl dimethyl PABA
Escalol 506, 4-dimethylaminobenzoic acid isopentyl ester
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.040.247
PubChem CID
UNII
InChI
  • InChI=1S/C14H21NO2/c1-11(2)9-10-17-14(16)12-5-7-13(8-6-12)15(3)4/h5-8,11H,9-10H2,1-4H3 N
    Key: OFSAUHSCHWRZKM-UHFFFAOYSA-N N
  • InChI=1/C14H21NO2/c1-11(2)9-10-17-14(16)12-5-7-13(8-6-12)15(3)4/h5-8,11H,9-10H2,1-4H3
    Key: OFSAUHSCHWRZKM-UHFFFAOYAM
SMILES
  • CC(C)CCOC(=O)c1ccc(cc1)N(C)C
Properties
Chemical formula
 C14H21NO2
Molar mass 235.322
Melting point <25 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Photobiology

The photobiological properties of padimate O and padimate A resemble that of Michler's ketone. These compounds have been shown to increase the lethal effects of UV-radiation on cells.[1] This photochemistry is relevant to the sunscreen controversy.

See also

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. PMID 8405372. S2CID 23853321.


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