114-25-0

Usage

Uses

Used in Biological Processes:
Biliverdin is used as a precursor of bilirubin for its role in the body's natural metabolic processes. It is formed from hemoglobin and plays a crucial part in the synthesis of bilirubin, which is essential for various physiological functions.
Used in Amphibians and Birds:
In the bile of amphibians and birds, biliverdin is used as the primary pigment, giving these species their unique characteristics. It is the only pigment found in their bile, which is important for their digestive processes.
Used in Antiviral Applications:
Biliverdin is used as an inhibitor for the hepatitis C virus, providing a potential therapeutic application in the treatment and management of this viral infection. Its antiviral properties make it a valuable compound in medical research and pharmaceutical development.

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

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

Downstream Products

• 635-65-4 bilirubin 
• 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 
• 109203-61-4 biliverdin-IXα bis<(S)-phenylalanine t-butyl ester> 
• 97241-10-6 C₅₁H₅₆N₆O₄ 
• 109203-65-8 biliverdin-IXα bis<(S)-proline benzyl ester> 
• 97241-04-8 C₅₃H₅₆N₆O₈ 

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 academic research and scientific papers

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.

Bilirubin oxidase from Magnaporthe oryzae and applications thereof

The present invention relates to a novel bilirubin oxidase from Magnaporthe oryzae, to the method of preparation thereof as well as use thereof notably for assay of bilirubin and for the application of enzymatic biofuel cells.

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.

Reactivity of Pyrrole Pigments, Part 15: On the Oxidation of Bilirubins and Biliverdins

Characteristic oxidation reactions of bilin-1,19-diones (biliverdins) and biladien-ac-1,19-diones (bilirubins) were reinvestigated.These include bromine and iodine oxidation of biliverdin IXα, bilirubin IXα and their Zn(II)complexes, the reaction described by Siedel (1941) of mesobilirubin XIIIα dimethyl ester with nitric acid (Gmelin reaction) and Smith's oxidation (1977) of etiobiliverdin IVγ using Tl triacetate and Pb tetra-acetate.For some of these reaction products new structures were assigned on the basis of their spectrometric data.These structures agreed with the expected reactivity pattern of biliverdins and bilirubins. Keywords: Bilipurpurins; Biliviolins; Electron transfer vs.Electrophilic attack.

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.