title: Photodecomposition of Pigment Yellow 74, a pigment used in tattoo inks.
abstract: Tattooing has become a popular recreational practice among younger adults over the past decade. Although some of the pigments used in tattooing have been described, very little is known concerning the toxicology, phototoxicology or photochemistry of these pigments. Seven yellow tattoo inks were obtained from commercial sources and their pigments extracted, identified and quantitatively analyzed. The monoazo compound Pigment Yellow 74 (PY74; CI 11741) was found to be the major pigment in several of the tattoo inks. Solutions of commercial PY74 in tetrahydrofuran (THF) were deoxygenated using argon gas, and the photochemical reaction products were determined after exposure to simulated solar light generated by a filtered 6.5 kW xenon arc lamp. Spectrophotometric and high-pressure liquid chromatography (HPLC) analyses indicated that PY74 photodecomposed to multiple products that were isolated using a combination of silica chromatography and reversed-phase HPLC. Three of the major photodecomposition products were identified by nuclear magnetic resonance and mass spectrometry as N-(2-methoxyphenyl)-3-oxobutanamide (o-acetoacetanisidide), 2-(hydroxyimine)-N-(2-methoxyphenyl)-3-oxobutanamide and N,N''-bis(2-methoxyphenyl)urea. These results demonstrate that PY74 is not photostable in THF and that photochemical lysis occurs at several sites in PY74 including the hydrazone and amide groups. The data also suggest that the use of PY74 in tattoo inks could potentially result in the formation of photolysis products, resulting in toxicity at the tattoo site after irradiation with sunlight or more intense light sources.
authors.affiliation: Division of Biochemical Toxicology, National Center for Toxicological Research, U.S. Food and Drug Administration, Jefferson, AR 72079, USA.
authors.forename: Yanyan
authors.initials: Y
authors.lastname: Cui
authors.forename: Andrew P
authors.initials: AP
authors.lastname: Spann
authors.forename: Letha H
authors.initials: LH
authors.lastname: Couch
authors.forename: Neera V
authors.initials: NV
authors.lastname: Gopee
authors.forename: Frederick E
authors.initials: FE
authors.lastname: Evans
authors.forename: Mona I
authors.initials: MI
authors.lastname: Churchwell
authors.forename: Lee D
authors.initials: LD
authors.lastname: Williams
authors.forename: Daniel R
authors.initials: DR
authors.lastname: Doerge
authors.forename: Paul C
authors.initials: PC
authors.lastname: Howard
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D004396:Coloring Agents / Q000737:chemistry*; D006835:Hydrazones / Q000737:chemistry*; D007281:Ink; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010782:Photolysis; D013653:Tattooing / Q000295:instrumentation
chemical_list: D000814:Aniline Compounds; D004396:Coloring Agents; D006835:Hydrazones; C509160:pigment yellow 74