6,6'-Dibromoindigo is an organic compound with the formula (BrC6H3C(O)CNH)2. A deep purple solid, the compound is also known as Tyrian purple, a dye of historic significance. Presently, it is only a curiosity, although the related derivative indigo is of industrial significance. The molecule consists of a pair of monobrominated indole rings linked by a carbon-carbon double bond. It is produced by molluscs of the Muricidae species.[1]
The pure compound has semiconductor properties in the thin film phase, which is potentially useful for wearable electronics, and has better performance than the parent indigo in this context.[2][3]
Biosynthesisedit
The biosynthesis proceeds by the intermediacy of tyrindoxyl sulphate.[4]
6BrIG can also be produced enzymatically in vitro from the amino acidtryptophan. The sequence begins with bromination of the benzo ring followed by conversion to 6-bromoindole. Flavin-containing monooxygenase then couples two of these indole units to give the dye.
Chemical synthesisedit
The main chemical constituent of the Tyrian dye was discovered by Paul Friedländer in 1909 to be 6,6′-dibromoindigo, derivative of indigo dye, which had been synthesized in 1903.[5][6] Although the first chemical synthesis was reported in 1914, unlike indigo, it has never been synthesized at commercial level.[7][8] An efficient protocol for laboratory synthesis of dibromoindigo was developed in 2010.[9]
Referencesedit
^McGovern, Patrick E.; Michel, R. H. (1990). "Royal Purple dye: The chemical reconstruction of the ancient Mediterranean industry". Accounts of Chemical Research. 23 (5): 152–158. doi:10.1021/ar00173a006.
^Pandolfi, Lorenzo; Rivalta, Arianna; Salzillo, Tommaso; Giunchi, Andrea; D’Agostino, Simone; Della Valle, Raffaele G.; Brillante, Aldo; Venuti, Elisabetta (13 August 2020). "In Search of Surface-Induced Crystal Structures: The Case of Tyrian Purple". The Journal of Physical Chemistry C. 124 (32): 17702–17710. doi:10.1021/acs.jpcc.0c05186. hdl:11585/786088.
^"Tyrian purple: The lost ancient pigment that was more valuable than gold". www.bbc.com.
^Valles-Regino, Roselyn; Mouatt, Peter; Rudd, David; Yee, Lachlan; Benkendorff, Kirsten (2016). "Extraction and Quantification of Bioactive Tyrian Purple Precursors: A Comparative and Validation Study from the Hypobranchial Gland of a Muricid Dicathais orbita". Molecules. 21 (12): 1672. doi:10.3390/molecules21121672. PMC6273837. PMID 27929402.
^Friedlaender, P. (1909). "Zur Kenntnis des Farbstoffes des antiken Purpurs aus Murex brandaris" [Towards understanding the ancient purple dye from Murex brandaris]. Monatshefte für Chemie. 30 (3): 247–253. doi:10.1007/BF01519682. S2CID 97865025.
^Sachs, Franz; Kempf, Richard (1903). "Über p-Halogen-o-nitrobenzaldehyde". Berichte der Deutschen Chemischen Gesellschaft. 36 (3): 3299–3303. doi:10.1002/cber.190303603113.
^"Indigo". Encyclopædia Britannica. Vol. V (15th ed.). Chicago, IL: Encyclopædia Britannica, Inc. 1981. p. 338. ISBN0-85229-378-X.
^Cooksey, C.J. (2001). "Tyrian purple: 6,6'-dibromoindigo and related compounds" (PDF). Molecules. 6 (9): 736–769. doi:10.3390/60900736. S2CID 5592747.
^Wolk JL, Frimer AA (August 2010). "A simple, safe and efficient synthesis of Tyrian purple (6,6'-dibromoindigo)". Molecules. 15 (8): 5561–5580. doi:10.3390/molecules15085561. PMC6257764. PMID 20714313.
January 01, 1970
dibromoindigo, organic, compound, with, formula, brc6h3c, deep, purple, solid, compound, also, known, tyrian, purple, historic, significance, presently, only, curiosity, although, related, derivative, indigo, industrial, significance, molecule, consists, pair,. 6 6 Dibromoindigo is an organic compound with the formula BrC6H3C O CNH 2 A deep purple solid the compound is also known as Tyrian purple a dye of historic significance Presently it is only a curiosity although the related derivative indigo is of industrial significance The molecule consists of a pair of monobrominated indole rings linked by a carbon carbon double bond It is produced by molluscs of the Muricidae species 1 6 6 Dibromoindigo Names Other names 6BrIG Tyrian purple Identifiers CAS Number 1277170 99 6 3D model JSmol Interactive image ChEBI CHEBI 80914 ChemSpider 4590500 KEGG C17084 PubChem CID 177057 UNII 2O3DDL8TAF InChI InChI 1S C16H8Br2N2O2 c17 7 1 3 9 11 5 7 19 13 15 9 21 14 16 22 10 4 2 8 18 6 12 10 20 14 h1 6 19 21HKey UOZOCOQLYQNHII UHFFFAOYSA N SMILES C1 CC2 C C C1Br NC C2O C3 NC4 C C3 O C CC C4 Br Properties Chemical formula C 16H 8Br 2N 2O 2 Molar mass 420 060 g mol 1 Appearance purple solid Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references The pure compound has semiconductor properties in the thin film phase which is potentially useful for wearable electronics and has better performance than the parent indigo in this context 2 3 Biosynthesis editThe biosynthesis proceeds by the intermediacy of tyrindoxyl sulphate 4 6BrIG can also be produced enzymatically in vitro from the amino acid tryptophan The sequence begins with bromination of the benzo ring followed by conversion to 6 bromoindole Flavin containing monooxygenase then couples two of these indole units to give the dye Chemical synthesis editThe main chemical constituent of the Tyrian dye was discovered by Paul Friedlander in 1909 to be 6 6 dibromoindigo derivative of indigo dye which had been synthesized in 1903 5 6 Although the first chemical synthesis was reported in 1914 unlike indigo it has never been synthesized at commercial level 7 8 An efficient protocol for laboratory synthesis of dibromoindigo was developed in 2010 9 References edit McGovern Patrick E Michel R H 1990 Royal Purple dye The chemical reconstruction of the ancient Mediterranean industry Accounts of Chemical Research 23 5 152 158 doi 10 1021 ar00173a006 Pandolfi Lorenzo Rivalta Arianna Salzillo Tommaso Giunchi Andrea D Agostino Simone Della Valle Raffaele G Brillante Aldo Venuti Elisabetta 13 August 2020 In Search of Surface Induced Crystal Structures The Case of Tyrian Purple The Journal of Physical Chemistry C 124 32 17702 17710 doi 10 1021 acs jpcc 0c05186 hdl 11585 786088 Tyrian purple The lost ancient pigment that was more valuable than gold www bbc com Valles Regino Roselyn Mouatt Peter Rudd David Yee Lachlan Benkendorff Kirsten 2016 Extraction and Quantification of Bioactive Tyrian Purple Precursors A Comparative and Validation Study from the Hypobranchial Gland of a Muricid Dicathais orbita Molecules 21 12 1672 doi 10 3390 molecules21121672 PMC 6273837 PMID 27929402 Friedlaender P 1909 Zur Kenntnis des Farbstoffes des antiken Purpurs aus Murex brandaris Towards understanding the ancient purple dye from Murex brandaris Monatshefte fur Chemie 30 3 247 253 doi 10 1007 BF01519682 S2CID 97865025 Sachs Franz Kempf Richard 1903 Uber p Halogen o nitrobenzaldehyde Berichte der Deutschen Chemischen Gesellschaft 36 3 3299 3303 doi 10 1002 cber 190303603113 Indigo Encyclopaedia Britannica Vol V 15th ed Chicago IL Encyclopaedia Britannica Inc 1981 p 338 ISBN 0 85229 378 X Cooksey C J 2001 Tyrian purple 6 6 dibromoindigo and related compounds PDF Molecules 6 9 736 769 doi 10 3390 60900736 S2CID 5592747 Wolk JL Frimer AA August 2010 A simple safe and efficient synthesis of Tyrian purple 6 6 dibromoindigo Molecules 15 8 5561 5580 doi 10 3390 molecules15085561 PMC 6257764 PMID 20714313 Retrieved from https en wikipedia org w index php title 6 6 27 Dibromoindigo amp oldid 1209073042, wikipedia, wiki, book, books, library,
