Uteroverdine

Base Information

• Chemical Name: Uteroverdine
• CAS No.: 114-25-0
• Molecular Formula: C33H34 N4 O6
• Molecular Weight: 582.656
• European Community (EC) Number: 204-042-2
• Wikipedia: Biliverdin
• Wikidata: Q104396064
• Mol file: 114-25-0.mol

Synonyms:alpha, Biliverdin IX;Biliverdin;Biliverdin IX;Biliverdin IX alpha;Biliverdine;Dehydrobilirubin;IX alpha, Biliverdin;IX, Biliverdin;Ooecyan;Uteroverdine

Chemical Property of Uteroverdine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: >2000C (dec)
• Refractive Index: 1.6000 (estimate)
• Boiling Point: °Cat760mmHg
• PKA: 4.46±0.10(Predicted)
• Flash Point: °C
• PSA: 160.95000
• Density: 1.3g/cm³
• LogP: 4.89970
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 11
• Exact Mass: 582.24783482
• Heavy Atom Count: 43
• Complexity: 1530

Purity/Quality:

98%,99%, ^*data from raw suppliers

Biliverdine(TechnicalGrade) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=CC2=C(C(=C(N2)C=C3C(=C(C(=O)N3)C)C=C)C)CCC(=O)O)NC1=CC4=NC(=O)C(=C4C)C=C)CCC(=O)O
• General Description: Biliverdin is an open-chain tetrapyrrole of significant biological importance, often serving as an intermediate in heme catabolism and the production of bile pigments. It can be synthesized through the conversion of 1,19-dibromo-a,c-biladienes, with dimethyl sulfoxide (DMSO) playing a key role in facilitating efficient biliverdin formation. The compound is also a precursor to other biologically relevant molecules such as corroles and azaporphyrins.

Technology Process of Uteroverdine

There total 11 articles about Uteroverdine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

α-biliverdin-IX dimethyl ester (10035-62-8) → 3,18-diethenyl-1,19,22,24-tetrahydro-2,7,13,17-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid (114-25-0,493-89-0)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; water; for 4h; Ambient temperature;

Reference yield:

bilirubin dimethylester (19792-68-8) → biliverdin-XIIIα (28022-06-2) + biliverdin-XIIIα (28022-07-3) + 3,18-diethenyl-1,19,22,24-tetrahydro-2,7,13,17-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid (114-25-0,493-89-0)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dimethyl sulfoxide; at 20 ℃; for 0.0166667h; Title compound not separated from byproducts;

DOI:10.1007/BF00810844

Reference yield:

carbonylverdohaemochrome → 3,18-diethenyl-1,19,22,24-tetrahydro-2,7,13,17-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid (114-25-0,493-89-0)

Guidance literature:

Multi-step reaction with 4 steps

2: chloroform

3: oxygen / chloroform

4: acid / chloroform

With oxygen; acid; In chloroform;

upstream raw materials:

α-biliverdin-IX dimethyl ester

bilirubin

bilirubin dimethylester

bilirubin

Downstream raw materials:

bilirubin

C₅₃H₅₆N₆O₈

biliverdin-IXα bis<(S)-proline benzyl ester>

C₅₁H₅₆N₆O₄

Refernces

Stepwise Synthesis of 1,19-Dibromo-a,c-biladienes and Their Conversion into Biliverdins, Corroles and Azaporphyrins

10.1039/c39920000183

The research focuses on the stepwise synthesis of unsymmetrically substituted 1,19-dibromo-a,c-biladienes and their conversion into biliverdins, corroles, and azaporphyrins. The purpose of this study was to develop an efficient route for the synthesis of biliverdins, which are open-chain tetrapyrroles with significant biological importance, and to adapt this methodology for the preparation of symmetrical biliverdins as well as corroles and azaporphyrins. The researchers successfully synthesized 1,19-dibromo-a,c-biladienes via the tripyrrene route and converted them into biliverdins, corroles, and azaporphyrins under appropriate reaction conditions. Key chemicals used in the process included 2-bromo-5-formylpyrrole, dipyrromethanedicarboxylic acid, toluene-p-sulfonic acid, dry HBr gas, and dimethyl sulfoxide (DMSO), among others. The study concluded that the DMSO procedure was unique for efficient biliverdin formation, and further mechanistic studies were ongoing. The research was supported by grants from the National Institutes of Health and Roswell Park Cancer Institute.