Padimate A

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 checkY☒N ?)
Infobox references

Padimate A is an organic compound that is an ingredient in some sunscreens. It is a dimethyl 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its chemical structure and behaviour is similar to an industrial free radical generator.[1] In Europe this chemical was withdrawn in 1989 for unstated reasons.[1] In the US it was never approved for use in sunscreens.

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. 1 2 3 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. Bibcode:1993FEBSL.324..309K. doi:10.1016/0014-5793(93)80141-G. PMID 8405372. S2CID 23853321.


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