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14370

Sigma-Aldrich

Bilirubine

purum, ≥95.0% (UV)

Synonyme(s) :

Bile pigment, Hemetoidin

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About This Item

Formule empirique (notation de Hill):
C33H36N4O6
Numéro CAS:
635-65-4
Poids moléculaire :
584.66
Numéro Beilstein :
74376
Numéro CE :
211-239-7
Numéro MDL:
MFCD00005499
Code UNSPSC :
12352202
ID de substance PubChem :
57647150
Nomenclature NACRES :
NA.25

Qualité

purum

Pureté

≥95.0% (UV)

Forme

powder

Résidus de calcination

≤0.5%

Chaîne SMILES 

CC1=C(C=C)\C(NC1=O)=C\c2[nH]c(Cc3[nH]c(\C=C4/NC(=O)C(C=C)=C4C)c(C)c3CCC(O)=O)c(CCC(O)=O)c2C

InChI

1S/C33H36N4O6/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/h7-8,13-14,34-35H,1-2,9-12,15H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13-,27-14-

Clé InChI

BPYKTIZUTYGOLE-IFADSCNNSA-N

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Catégories apparentées

Description générale

Bilirubin, a heme catabolism end-product is produced by the reduction of its metabolic precursor biliverdin by the action of enzyme biliverdin reductase.

Application

Bilirubin has been used as an interfering substance for in vitro interference and stability tests for myoglobin, creatine kinase-MB (CK-MB), and troponin-I. It has also been used as an interfering agent to test the effectiveness of the Heparin Red kit in the detection of various heparins.

Actions biochimiques/physiologiques

Plus de 99 % de la bilirubine totale est transportée sous forme conjuguée à l′albumine. Des taux anormalement élevés de bilirubine peuvent provoquer des dommages neurologiques graves, mais des niveaux légèrement élevés sont associés à une protection contre le stress oxydant.
Bilirubin is an active oxidative DNA cleaving agent as well as an effective antioxidant agent, a hydroxyl radical quencher. This bile pigment has both antioxidant and toxic properties. It is a natural inhibitor of vascular smooth muscle cell proliferation (VSMCs). It displays anti-inflammatory and anti-proliferative properties when used as a therapeutic agent in lung/vascular diseases. Serum bilirubin concentration slightly above the normal levels have shown a lesser incidence of heart disease. It is a potential therapeutic agent in heart transplantation and T-cell mediated immune disorders.

Remarque sur l'analyse

λmax. ∼453 nm, mol. absorption >56100 (chloroform)

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Kenichiro Yamashita et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 18(6), 765-767 (2004-02-24)
Biliverdin, a product of heme oxygenase-1 (HO-1) enzymatic action, is converted into bilirubin, which has been considered a waste product in the past. We now show that administration of biliverdin has a salutary effect in organ transplantation. A brief course
Yen-Wen Wu et al.
Acta Cardiologica Sinica, 36(6), 649-659 (2020-11-26)
The rapid diagnosis of acute myocardial infarction (AMI) is a clinical and operational priority in emergency departments. Serial serum levels of cardiac biomarkers play a crucial role in the evaluation of patients presenting with acute chest pain, so that an
Stefan W Ryter et al.
American journal of respiratory cell and molecular biology, 36(2), 175-182 (2006-09-19)
Heme oxygenase (HO)-1, an inducible, low-molecular-weight stress protein, confers cellular and tissue protection in multiple models of injury and disease, including oxidative or inflammatory lung injury, ischemia/reperfusion (I/R) injuries, and vascular injury/disease. The tissue protection provided by HO-1 potentially relates
Robert Ollinger et al.
Cell cycle (Georgetown, Tex.), 6(1), 39-43 (2007-01-25)
We have recently shown that the natural bile pigment bilirubin has antiproliferative effects on vascular smooth muscle cells (VSMCs). Bilirubin is the end product of heme catabolism mediated by heme oxygenases and has for decades been considered a toxic waste
S F Asad et al.
Chemico-biological interactions, 137(1), 59-74 (2001-08-24)
Bilirubin, which is derived from its metabolic precursor biliverdin, is the end product of heme catabolism. It has been proposed as a physiological antioxidant present in human extracellular fluids. We have earlier shown that bilirubin in the presence of the
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