114-25-0

Basic information

• Product Name: biliverdin
• Synonyms: 3-[2-[(Z)-[(5E)-3-(2-carboxyethyl)-5-[(4-ethenyl-3-methyl-5-oxo-pyrrol-2-yl)methylidene]-4-methyl-pyrrol-2-ylidene]methyl]-5-[(Z)-(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid;biliverdin;Biliverdine;3,18-Diethenyl-1,19,22,24-tetrahydro-2,7,13,17-tetrametyl-1,19-dioxo-21H-biline-8,12-dipropanoic Acid;Dehydrobilirubin;Uteroverdine;3-[2-[(E)-[(5E)-3-(2-carboxyethyl)-5-[(4-ethenyl-3-methyl-5-oxo-pyrrol-2-yl)methylidene]-4-methyl-pyrrol-2-ylidene]methyl]-5-[(E)-(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid;Protobiliverdin IXa
• CAS NO: 114-25-0
• Molecular Formula: C₃₃H₃₄N₄O₆
• Molecular Weight: 582.65
• EINECS: 204-042-2
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Amines;Heterocycles;Amines, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 114-25-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: >2000C (dec)
• Boiling Point: 640.55°C (rough estimate)
• Flash Point: °C
• Appearance: /
• Density: 1.2293 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.46±0.10(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: biliverdin(CAS DataBase Reference)
• NIST Chemistry Reference: biliverdin(114-25-0)
• EPA Substance Registry System: biliverdin(114-25-0)

Safety Data

• Hazardous Substances Data: 114-25-0(Hazardous Substances Data)

Usage

Chemical Properties

Dark Green Crystalline Solid

Uses

Different sources of media describe the Uses of 114-25-0 differently. You can refer to the following data:
1. Precursor of Bilirubin. Formed in the body from hemoglobin
2. Biliverdineis a precursor of Bilirubin. Biliverdine is formed in the body from hemoglobin. The bile of amphibia and of birds contains Biliverdine only.
3. Biliverdine is a precursor of Bilirubin. Biliverdine is formed in the body from hemoglobin. The bile of amphibians and of birds contains Biliverdine only. It is also an inhibitor for hepatitis C virus.

Definition

ChEBI: A linear tetrapyrrole produced in the reticuloendothelial system by the first step of heme degradation, catalysed by heme oxygenase.

Purification Methods

This is the precursor of bilirubin (above) and forms dark green plates or prisms, with a violet reflection, from MeOH. The dimethyl ester, when crystallised from MeOH has m 215o(209o), and when crystallised from CHCl3/Pet ether gives blue-green crystals with m 202o. [Gray et al. J Chem Soc 2264 1961, Sheldrick J Chem Soc, Perkin Trans 2 1457 1976, Beilstein 26 III/V 3272.]

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

Upstream product

• 134733-79-2 bilirubin 
• 69853-44-7 bilirubin 
• 19792-68-8 bilirubin dimethylester 
• 635-65-4 bilirubin 
• 10035-62-8 α-biliverdin-IX dimethyl ester 

Downstream Products

• 97241-04-8 C₅₃H₅₆N₆O₈ 
• 109203-65-8 biliverdin-IXα bis<(S)-proline benzyl ester> 
• 97241-10-6 C₅₁H₅₆N₆O₄ 
• 109203-61-4 biliverdin-IXα bis<(S)-phenylalanine t-butyl ester> 
• 10035-62-8 α-biliverdin-IX dimethyl ester 
• 16568-56-2 mesobilirubin 
• 19792-68-8 bilirubin dimethylester 
• 20189-42-8 3-ethyl-4-methyl-pyrrole-2,5-dione 
• 21494-57-5 2-Methyl-3-vinylmaleimide 
• 635-65-4 bilirubin 

Related news

Singlet oxygen oxidation products of biliverdin (cas 114-25-0) IXα dimethyl ester08/30/2019

Biliverdin IXα is a naturally occurring linear tetrapyrrolic product of the enzymatic oxidative ring cleavage of heme. Evidence is mounting that biliverdin possesses antioxidant properties in mammals but its mode of action is unclear. We present the single crystal X-ray structure analysis of tw...detailed

Chiral recognition of bilirubin and biliverdin (cas 114-25-0) in liposomes and micelles08/29/2019

The structural formula of biologically important chiral pigments bilirubin and biliverdin differs only by one double bond. We showed that this results in dissimilar interactions with two models of membranes: cationic liposomes composed of 3β-[N-(N′,N′-dimethylaminoethane)-carbamoyl]cholestero...detailed

Stabilization of structure in near-infrared fluorescent proteins by binding of biliverdin (cas 114-25-0) chromophore08/28/2019

Near-infrared fluorescent proteins (NIR FPs) engineered from bacterial phytochromes and their mutants with different location of Cys residues, which able to bind a biliverdin chromophore, or without these Cys residues were studied using intrinsic tryptophan fluorescence, NIR fluorescence and cir...detailed

Reduced biliverdin (cas 114-25-0) reductase-A levels are associated with early alterations of insulin signaling in obesity08/27/2019

Biliverdin reductase-A (BVR-A) is a serine/threonine/tyrosine kinase involved in the regulation of insulin signaling. In vitro studies have demonstrated that BVR-A is a substrate of the insulin receptor and regulates IRS1 by avoiding its aberrant activation, and in animal model of obesity the lo...detailed

ReviewRedox Functions of Heme Oxygenase-1 and biliverdin (cas 114-25-0) Reductase in Diabetes08/24/2019

In patients with diabetes, the hyperglycemia-driven excess generation of reactive oxygen species (ROS) induces oxidative stress (OS) in a variety of tissues. OS is closely associated with chronic inflammation and has a key role in the pathogenesis of vascular complications. The enzymes that gene...detailed

Is it worth expending energy to convert biliverdin (cas 114-25-0) into bilirubin?08/22/2019

Bilirubin (BR) is generated by the reduction of biliverdin (BV), a metabolite that results from the catalytic degradation of heme by the isoforms of heme oxygenase (HO). BV is nontoxic and water-soluble but BR is potentially toxic and lipophilic. Therefore, a further metabolic step is required f...detailed

Relevant articles and documents

Pyrolyzed photoresist carbon electrodes in aprotic solvent: Bilirubin electrochemistry and interaction with electrogenerated superoxide

Pyrolyzed photoresist carbon electrodes (PPCEs) are fabricated by the photopatterning of a negative tone epoxy-based photoresist, SU-8, through optimized standard UV photolithography. The electrochemical characteristics of PPCEs are investigated in dimethyl sulfoxide (DMSO), observing a wider accessible potential window and a smaller capacitance with respect to glassy carbon electrodes. PPCEs are used to study the cyclic voltammetric behavior of bilirubin (BR) in DMSO. Detailed information is obtained on the multiple steps involved both in the electrochemical oxidation and reduction of BR. Interesting points concerning the electrochemical oxidation of BR to biliverdin are clarified, identifying the formation of an intermediate whose fate depends on the time scale of the electrochemical experiment. PPCEs are also used to electrogenerate the superoxide anion O2-? in DMSO for studying possible reactions between BR and O2-?. The results obtained demonstrate that BR is an efficient superoxide scavenger and that a concentration 2 mM of BR is high enough to consume all the O2-? generated by oxygen reduction at the PPCE/DMSO interface.

Urinary excretion of α- and β-isomers of biliverdin-IX in humans

The distribution and relative proportions of the four isomers of α-, β-, γ- and δ-biliverdin-IX were investigated using urinary samples from seven healthy adults. The biliverdins from samples were adsorbed on talc, and the adsorbed biliverdins were then soaked in a solution of methanol and concentrated sulfuric acid for derivation to the dimethyl esters. The esters were passed to a reversed-phase cartridge for clean-up, then quantitated by HPLC on a reversed-phase column. The analyses revealed that the biliverdins in 24-h urine were comprised of 6.4 ± 2.5 nmol α- and 9.3 ± 5.4 nmol β-isomers. The HPLC analyses suggested the presence of a δ-isomer in a much smaller amount, but no γ-isomer was detected. The identifications of α- and β-isomers were performed with co-chromatography and absorption spectra.

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