28022-06-2

Basic information

• Product Name: biliverdin XIII alpha
• Synonyms: biliverdin XIII alpha;17-Demethyl-17-vinyl-18-devinyl-18-methylbiliverdin;3,17-Divinyl-1,19,23,24-tetrahydro-2,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropionic acid;Biliverdin XIIIα
• CAS NO: 28022-06-2
• Molecular Formula: C₃₃H₃₄N₄O₆
• Molecular Weight: 582.65
• Mol File: 28022-06-2.mol

Chemical Properties

• Boiling Point: 913.2°Cat760mmHg
• Flash Point: 506.1°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.639
• CAS DataBase Reference: biliverdin XIII alpha(CAS DataBase Reference)
• NIST Chemistry Reference: biliverdin XIII alpha(28022-06-2)
• EPA Substance Registry System: biliverdin XIII alpha(28022-06-2)

Safety Data

• Hazardous Substances Data: 28022-06-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C33H34N4O6/c1-7-20-18(5)32(42)36-26(20)13-24-16(3)22(9-11-30(38)39)28(34-24)15-29-23(10-12-31(40)41)17(4)25(35-29)14-27-21(8-2)19(6)33(43)37-27/h7-8,13-15,34H,1-2,9-12H2,3-6H3,(H,36,42)(H,37,43)(H,38,39)(H,40,41)/b26-13-,27-14-,29-15-

Upstream product

• 26458-42-4 Biliverdin-XIIIα-dimethyl ester 
• 19792-68-8 bilirubin dimethylester 

Relevant articles and documents

On the Fate of Biliverdin-IIIα-dimethyl Ester Formed by Scrambling During Syntheses of Biliverdin-IXα-dimethyl Ester from Bilirubin

In the preparations of biliverdin-IXα-dimethyl ester (2b) from bilirubin-IXα (1) the ratio of the XIIIα- and IIIα-isomers 3b and 4b, formed via intermolecular scrambling, should be unity.However, irrespective of the synthetic variant considered, the amount of 4b obtained usually is exceptionally low.This is partly ascribed to a consecutive reaction of 4b in acidic methanol affording the chiral diastereomeric bridged biliverdins 5(a and b) and 6(a and b), respectively. - Keywords: Biliverdin-IIIα; Bridged biliverdins; Bilatrienes

CHIRAL INDUCTION IN BILIVERDIN COVALENTLY BOUND TO AMINO ACIDS

Amidation of the carboxy groups of biliverdin-IXα (2) with the appropiate (S)-amino acid methyl ester yields the optically active derivatives (3)-(8) which exhibit exceedingly strong Cotton effects in their visible and near-u.v. absorption bands.This is due to theinfluence of the chiral centre on the population of helical conformers of the bilatriene moity across five bond lengths.The magnitude of the c.d. observed depends on the steric requirements of the amino acid and the polarity of the solvent.The chiral induction is interpreted in terms of intramolecular interactions of both side chains exerted from different sides of the bilatriene helix by hydrogen bonds.Both the donor and the acceptor sites of the amino acid residues are involved in the chiral association with the bilatriene backbone.