Tyrian Purple: 6,6’-Dibromoindigo and Related Compounds

作者: Christopher Cooksey

DOI: 10.3390/60900736

关键词: BiologyAncient historyTyrindoleninoneMuricidaeStereochemistryHypobranchial gland

摘要: Abstract: The genesis of the purple dye from shellfish, its composition, origin,intermediates, analysis and synthesis components, 6,6’-dibromoindigo, 6-bromoindigo 6,6’-dibromoindirubin are reviewed Keywords: 6-bromoindigo, 6,6’-dibromoindirubin, tyrindoxyl,tyriverdin, tyrindoleninone, tyrindolinone, synthesis, structure, properties Introduction 6,6’-Dibromoindigo is a major component historic pigment Tyrian purple, also known asRoyal shellfish Purple Ancients. Arguably, it oldest pigment,the longest lasting, subject first chemical industry, most expensive best known.The colour derived exclusively marine Muricidae Thaisidae families. Thelong history, stretching back well into pre-chemical era, embracing chemistry, biology andsociology, contains not few misconceptions erroneous conclusions. This review attempts to setthe record straight.This molluscan has been since pre-Roman times in Mediterranean region thereis evidence for industry around 13th century B.C. [1] at Sarepta, now Sarafand, Lebanon. Theancient was distributed world-wide [2]. Surviving details ancient process areinsufficient explain chemistry involved this continuing speculation. But isclear that does exist mollusc generated precursors, sometimes termed

参考文章(75)
Jorge Juan y Santacilia, Relación histórica del viaje a la América meridional Fundación Universitaria Española. ,(1978)
Kirsten Benkendorff, John B. Bremner, Andrew R. Davis, TYRIAN PURPLE PRECURSORS IN THE EGG MASSES OF THE AUSTRALIAN MURICID, Dicathais orbita: A POSSIBLE DEFENSIVE ROLE Journal of Chemical Ecology. ,vol. 26, pp. 1037- 1050 ,(2000) , 10.1023/A:1005441116095
M. Klessinger, W. Lüttke, Theoretische und spektroskopische untersuchungen an indigo-farbstoffen — II Tetrahedron. ,vol. 19, pp. 315- 335 ,(1963) , 10.1016/S0040-4020(63)80023-X
C. Christophersen, F. Wätjen, O. Buchardt, U. Anthoni, A revised structure of tyriverdin Tetrahedron. ,vol. 34, pp. 2779- 2781 ,(1978) , 10.1016/0040-4020(78)88419-1
Gundula Voss, Willfried Schramm, Selectively C‐Deuterated Indigotins Helvetica Chimica Acta. ,vol. 83, pp. 2884- 2892 ,(2000) , 10.1002/1522-2675(20001108)83:11<2884::AID-HLCA2884>3.0.CO;2-C
P. S�sse, C. Krampe, 6,6'-Dibromo-indigo, a main component of tyrian Purple Naturwissenschaften. ,vol. 66, pp. 110- 110 ,(1979) , 10.1007/BF00373504
A. Nikki Padden, Vivian M. Dillon, Philip John, John Edmonds, M. David Collins, Nerea Alvarez, Clostridium used in mediaeval dyeing Nature. ,vol. 396, pp. 225- 225 ,(1998) , 10.1038/24290
R. KLEBER, L. MASSCHELEIN-KLEINER, J. THISSEN, Étude et Identification du ‘Bleu Maya’ Studies in Conservation. ,vol. 12, pp. 41- 56 ,(1967) , 10.1179/SIC.1967.006
P. Friedländer, Über die Farbstoffe aus Purpura aperta und Purpura lapillus European Journal of Inorganic Chemistry. ,vol. 55, pp. 1655- 1658 ,(1922) , 10.1002/CBER.19220550619