54278-11-4Relevant articles and documents
13C-labeled bilirubin: Synthesis of 31(3 2),171(172)-di-[13C]-mesobilirubin- XIIIα
Boiadjiev, Stefan E.,Lightner, David A.
, p. 111 - 119 (2009)
The title compound, labeled with 13C in the ethyl groups was synthesized from K13CN and low-molecular-weight components. The synthetic relay compound was 31(32)[13C]- xanthobilirubinic acid methyl ester in a synthetic route that leads to a label in the ethyl β-substituent of a dipyrrinone model for bilirubin. This labeled dipyrrinone was oxidatively coupled to the dimethyl ester of mesobiliverdin-XIIIα, thereby providing a route to a 13C- labeled mesobiliverdin and mesobilirubin, with one carbon of each ethyl being 98% 13C-enriched.
An efficient route to dipyrrinones: Synthesis of xanthobilirubic acid methyl ester
Shrout,Lightner
, p. 1062 - 1065 (2007/10/02)
Structurally interesting and complicated dipyrrinones, such as xanthobilirubic acid methyl ester (9), can be synthesized on a large scale from simple, inexpensive starting materials like ethyl acetoacetate, 2,4-pentanedione (1) and ethyl acrylate in 8 steps with an average yield of 80% at each step and an overall 17% yield.
Xanthobilirubic Acid and Its Amides. Synthesis, Spectroscopy, and Solution Structures
Lightner, D. A.,Ma, J.-S.,Adams, T. C.,Franklin, R. W.,Landen, G. L.
, p. 139 - 144 (2007/10/02)
Xanthobilirubic acid, 5--2,4-dimethyl-1H-pyrrol-3-propanoic acid, its methyl ester, amide, N-methylamide and dimethylamide, and kryptopyrromethenone have been synthesized and characterized spectroscopically.In d6-DMSO solution all pyrromethenones were monomeric, with lactam and pyrrole N-Hs H-bonded to solvent.In deuteriochloroform, the pyrromethenones preferred a dimeric form, with intramolecular H-bonding between the lactam C=O of one unit and the lactam and pyrrole N-Hs of the second.
