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Padimate O

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(Redirected from 2-ethylhexyl 4-dimethylaminobenzoate) Water-insoluble oily ingredient used in some sunscreens
Padimate O
Names
IUPAC name 2-ethylhexyl 4-(dimethylamino)benzoate
Other names 2-ethylhexyl dimethyl PABA
Escalol 507
Sundown
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.040.248 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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,5-8,13H2,1-4H3Key: WYWZRNAHINYAEF-UHFFFAOYSA-N
  • 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,5-8,13H2,1-4H3Key: WYWZRNAHINYAEF-UHFFFAOYAL
SMILES
  • O=C(OCC(CC)CCCC)c1ccc(N(C)C)cc1
Properties
Chemical formula C17H27NO2
Molar mass 277.408 g·mol
Density 0.99 g/cm
Melting point <25 °C
Boiling point 362 °C (684 °F; 635 K)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1 1 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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. 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.

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.

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): 309–13. Bibcode:1993FEBSL.324..309K. doi:10.1016/0014-5793(93)80141-G. PMID 8405372. S2CID 23853321.
  2. Gulston, Melanie; Knowland, John (1999). "Illumination of human keratinocytes in the presence of the sunscreen ingredient Padimate-O and through an SPF-15 sunscreen reduces direct photodamage to DNA but increases strand breaks". Mutation Research/Genetic Toxicology and Environmental Mutagenesis. 444 (1): 49–60. Bibcode:1999MRGTE.444...49G. doi:10.1016/S1383-5718(99)00091-1. PMID 10477339.
  3. Kligman, Lorraine H.; Akin, Frank J.; Kligman, Albert M. (1980). "Sunscreens prevent ultraviolet photocarcinogenesis". Journal of the American Academy of Dermatology. 3 (1): 30–5. doi:10.1016/S0190-9622(80)80221-0. PMID 6967495.
  4. Bissett, Donald L.; McBride, James F.; Hannon, Daniel P.; Patrick, Larry F. (1991). "Time-dependent decrease in sunscreen protection against chronic photodamage in UVB-irradiated hairless mouse skin". Journal of Photochemistry and Photobiology B: Biology. 9 (3–4): 323–334. Bibcode:1991JPPB....9..323B. doi:10.1016/1011-1344(91)80169-I. PMID 1919875.
  5. Bissett, Donald L; McBride, James F (1996). "Synergistic topical photoprotection by a combination of the iron chelator 2-furildioxime and sunscreen". Journal of the American Academy of Dermatology. 35 (4): 546–9. doi:10.1016/S0190-9622(96)90677-5. PMID 8859281.
  6. Kerr, Caroline (1998). "The effects of two UVB radiation-absorbing sunscreens on UV radiation-induced carcinogenesis, suppression of the contact hypersensitivity response and histological changes in the hairless mouse". Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis. 422 (1): 161–4. Bibcode:1998MRFMM.422..161K. doi:10.1016/S0027-5107(98)00188-2. PMID 9920441.
Sunscreening agents approved by the US FDA or other agencies
  • UVA: 400–315 nm
  • UVB: 315–290 nm
  • Chemical agents unless otherwise noted
UVA filters
UVB filters
UVA+UVB filters
See also: Photoprotection, Sun protective clothing, Sun tanning, and Sunburn
Categories: