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• W2019966750 abstract "[10]-Semirubin (1) and [20]-semirubin (2), with dipyrrinones covalently linked to C10 and C20 fatty acid chains, were synthesized following Friedel–Crafts acylation of the parent 9-H dipyrrinone, (4Z)-2,3,7,8-tetramethyl-(10H)-dipyrrin-1-one, with the diacid chlorides of decanedioic acid and eicosanedioic acid, respectively. Both of these bright yellow pigments are monomeric in CHCl3 solvent: MWobs=394±20 for 1 (formula weight 386), and 533±20 for 2 (formula weight 526) as determined by vapor pressure osmometry (VPO) measurements. In contrast, their methyl esters are dimeric in CHCl3. 1H{1H}-Nuclear Overhauser effects are found between the lactam NH and carboxylic acid OH of 1 and 2, consistent with the type of intramolecular hydrogen bonding found in bilirubin (the yellow pigment of jaundice) and its analogs." @default.
• W2019966750 created "2016-06-24" @default.
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• W2019966750 date "2001-03-01" @default.
• W2019966750 modified "2023-09-27" @default.
• W2019966750 title "Intramolecular hydrogen bonding between remote termini" @default.
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• W2019966750 doi "https://doi.org/10.1016/s0040-4020(01)00109-0" @default.
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