Identification of indigoid dyes in natural organic pigments used in historical art objects by high-performance liquid chromatography coupled to electrospray ionization spectrometry

Journal of Mass Spectrometry

Volumn 39, Issue 12, 2004, Pages 1441-1449

  Puchalska, Maria ^a   Połeć Pawlak, Kasia ^a   Zadrozna, Irmina ^a   Hryszko, Helena ^b   Jarosz, Maciej ^a  

^a WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

^b Akademia Sztuk Pieknych   (Poland)

Author keywords

Art analysis; Electrospray ionization mass spectrometry; High performance liquid chromatography; Natural indigoid dyestuffs

Indexed keywords

HYDROLYSIS; IONIZATION; ISOMERS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; SPECTROPHOTOMETRY;

ELECTROSPRAY IONIZATION; METHYLENE BLUE;

DYES;

DIMETHYL SULFOXIDE; DYE; INDICAN; INDIGO DYE; INDIRUBIN; INDOXYL ACETATE; ISATIN; ISOINDIGO; ISOINDIRUBIN; METHYLENE BLUE; OXINDOLE; PIGMENT; UNCLASSIFIED DRUG;

ART; CHEMICAL STRUCTURE; COLOR; CONFERENCE PAPER; DEGRADATION; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; PRIORITY JOURNAL; REVERSED PHASE LIQUID CHROMATOGRAPHY; SYNTHESIS; TEXTILE; ULTRAVIOLET SPECTROPHOTOMETRY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COLORING AGENTS; INDOLES; PIGMENTS, BIOLOGICAL; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

ANIMALIA; GRUIDAE; INDIGOFERA; ISATIS; TYRIA;

EID: 10844294162     PISSN: 10765174     EISSN: None     Source Type: Journal    
DOI: 10.1002/jms.728     Document Type: Conference Paper

References (30)

1. Zadrożna I, Połeć-Pawlak K, Głuch I, Ackacha MA, Mojski M, Witowska-Jarosz J, Jarosz M. Old master paintings - a fruitful field of activity for analysts: targets, methods, outlook. J. Sep. Sci. 2003; 26: 996.
2. Halpine SM. An improved dye and lake pigment analysis method for high-performance liquid chromatography and diode-array detector. Stud. Conserv. 1996; 41: 76.
3. Ensley BD, Ratzkin BJ, Osslund TD, Simon MJ, Wackett LP, Gibson DT. Expression of naphthalene oxidation genes in Escherichia coli results in the biosynthesis of indigo. Science 1983; 222: 67.
4. Fitzhugh W. Artist's Pigments, a Handbook of Their History and Characteristics, vol 3. Oxford University Press: Oxford, 1997.
5. Seldes A, Burucúa JE, Maier MS, Abad G, Jáuregui A, Siracusano G. Blue pigments in South American Painting (1610-1780). J. Am. Inst. Conser. 1999; 38: 100.
6. Maugarda T, Enauda E, Choisyb P, Legoya MD. Identification of an indigo precursor from leaves of Isatis tinctoria (woad). Phytochemistry 2001; 58: 897.
7. Von Baeyer A. Synthese des Isoatins und Indigblaus. Chem. Ber. 1878; 11: 1228.
8. Fairbanks VF. Blue gods, blue oil, and blue people. Mayo Clin. Proc. 1994; 69: 889.
9. Son YA, Hong JP, Kim TK. An approach to the dying of polyester fiber using indigo and its extended wash fastness properties. Dyes Pigments 2004; 61: 263.
10. Vautier M, Guillard C, Herrmann J-M. Photocatalytic degradation of dyes in water: case study of indigo and of indigo carmine. J. Catal. 2001; 201: 46.
11. Zollinger H. Color Chemistry: Synthesis, Properties and Applications of Organic Dyes and Pigments. VCH: Weinheim, 1987.
12. Mertz V, Weith W. Mitteilungen aus dem Universitäts-Laboratorium in Zürich; Veber Derivate des Dimethylalanins. Ber. Dtsch. Chem. Gese. 1877; 10: 760.
13. McGovern PE, Michel RH. Royal Purple dye: tracing the chemical origins of the industry. Anal. Chem. 1985; 57: 1514A.
14. Cooksey CJ. Tyrian Purple: 6,6′-dibromoindigo and related compounds. Molecules 2001; 6: 736.
15. Wouters J, Verhecken A. Composition of Murex dyes. J. Soc. Dyers Colour. 1992; 108: 404.
16. Michel RH, Lazar J, McGovern PE. The chemical composition of the indigoid dyes derived from the hypobranchial glandural secretions of Murex mollusks. J. Soc. Dyers Colour. 1992; 108: 145.
17. Sachs F, Kempf R. Uber p-halogen-o-nitrobenzaldehyde. Ber. Dtsch. Chem. Ges. 1903; 36: 3299.
18. Cordy A, Yeh K. Blue dye identification on cellulosic fibers: indigo, logwood, and Prussian blue. J. Am. Instit. Conserv. 1984; 24: 33.
19. Miliani C, Romani A, Favaro G. A spectrophotometric and fluorimetric study of some anthraquinoid and indigoid colorants used in artistic paintings. Spectrochim. Acta, Part A 1998; 54: 581.
20. Vandenabeele P, Moens L. Micro-Raman spectroscopy of natural and synthetic indigo samples. Analyst 2003; 128: 187.
21. Russell GA, Kaupp G. Oxidation of carbanions. IV. Oxidation of indoxyl to indigo in basic solution. J. Am. Chem. Soc. 1969; 91: 3851.
22. Kokubun T, Edmonds J, John P. Indoxyl derivatives in woad in relation to medieval indigo production. Phytochemistry 1998; 49: 79.
23. Wouters J, Rosario-Chirinos N. Dye analysis of pre-Columbian Peruvian textiles with high-performance liquid chromatography and diode array detection. J. Am. Inst. Conserv. 1992; 31: 237.
24. Maugard T, Enaud E, Choisy P, Legoy MD. Identification of an indigo precursor from leaves of Isatis tinctoria (woad). Phytochemistry 2001; 58: 897.
25. Orska-Gawryś J, Surowiec I, Kehl J, Rejniak H, Urbaniak-Walczak K, Trojanowicz M. Identification of natural dyes in archeological Coptic textiles by liquid chromatography with diode array detection. J. Chromatogr. A 2003; 989: 239.
26. Clark RJH, Cooksey CJ. Bromoindirubins: the synthesis and properties of minor components of Tyrian Purple and the composition from Nucella lapillus. J. Soc. Dyers Colour. 1997; 113: 316.
27. McGovern PE, Lazar J, Michel RH. Caveats on the analysis of indigoid dyes by mass spectrometry. J. Soc. Dyers Colour. 1991; 107: 280.
28. Wyplosz N. Laser Desorption Mass Spectrometric Studies of Artists' Organic Pigments. University of Amsterdam: Amsterdam, 2003 (MOLART report ISBN 90-77209-01-6).
29. Szostek B, Orska-Gawryś J, Surowiec I, Trojanowicz M. Investigation of natural dyes occuring in historical Coptic textiles by high-performance liquid chromatography with UV-Vis and mass spectrometric detection. J. Chromatogr. A 2003; 1012: 179.
30. Hoessel R, Leclerc S, Endicott JA, Nobel ME, Lawrie A, Tunnah P, Leost M, Damiens E, Marie D, Marko D, Niedeberger E, Tang W, Eisenbrand G, Meijer L. Indirubin, the active constituent of a Chinese antileukaemia medicine, inhibits cyclin-dependent kinases. Nature Cell Biol. 1999; 1: 60.