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B4126

Sigma-Aldrich

Bilirubin

≥98% (EmM/453 = 60), powder

Sinónimos:
Hemetoidin, Bile pigment
Empirical Formula (Hill Notation):
C33H36N4O6
Número de CAS:
Peso molecular:
584.66
Beilstein:
74376
Número de EC:
Número MDL:
ID de la sustancia en PubChem:

Nivel de calidad

300

descripción

mixed isomers

ensayo

≥98% (EmM/453 = 60)

formulario

powder

solubilidad

aqueous acid: soluble
aqueous base: soluble
benzene: soluble
chloroform: soluble

temp. de almacenamiento

−20°C

SMILES string

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-

InChI key

BPYKTIZUTYGOLE-IFADSCNNSA-N

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Descripción general

Bilirubin, an end product of heme catabolism, forms from the breakdown of erythrocyte hemoglobin in the reticuloendothelial system. Heme oxygenase converts the heme of hemoglobin to biliverdin, and subsequently an NADPH-dependent biliverdin reductase converts biliverdin to bilirubin.

Bilirubin is commonly found bound to serum albumin, when circulating in blood, in its dianion form. Bilirubin is also associated with bile salts, in its monoanion form.

Disorders of hyperbilirubinemia may occur due to increased bilirubin synthesis or decreased bilirubin clearance.

Aplicación

Bilirubin has been used:
  • in phantom preparation
  • in in vitro experiments
  • in the preparation of bilirubin solutions for infusion

Envase

1, 5 g in glass bottle

Acciones bioquímicas o fisiológicas

Well over 99% of total bilirubin is transported as a conjugate with albumin. Abnormally high levels of bilirubin can cause severe neurological damage, but mildly elevated levels are linked to protection from oxidative stress.
Bilirubin has been studied for its properties as an endogenous antioxidant, such as for its capabilities to scavenge reactive oxygen species (ROS) and to inhibit NADPH-oxidase activity. It appears to function as an efficient peroxyl radical scavenger, protecting membrane lipids from oxidation by these radicals. At nanomolar concentrations it has been shown to protect neurons from oxidative damage.

Otras notas

A major component of hemoglobin decomposition. The principal pigment of bile, and the yellow color in jaundice.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. B4126.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Precaución

Protect from light.

Código de clase de almacenamiento

13 - Non Combustible Solids

WGK

WGK 2

Punto de inflamabilidad F

Not applicable

Punto de inflamabilidad C

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

Certificado de Análisis

Introduzca el número de lote para buscar un certificado de análisis (COA).

Certificado de origen

Introduzca el número de lote para buscar un Certificado de origen (COO).

Inherited disorders of bilirubin clearance
Memon N, et al.
Pediatric Research, 79(3), 378-378 (2016)
Bhargavi Kamineni et al.
Journal of tropical pediatrics, 66(6), 630-636 (2020-05-21)
Early diagnosis and appropriate management of neonatal jaundice is crucial in avoiding severe hyperbilirubinemia and brain injury. A low-cost, minimally invasive, point-of-care (PoC) tool for total bilirubin (TB) estimation which can be useful across all ranges of bilirubin values and
Photoacoustic microscopy of bilirubin in tissue phantoms
Zhou y, et al.
Journal of Biomedical Optics, 17(12), 126019-126019 (2012)
Sem J Aronson et al.
Molecular therapy. Methods & clinical development, 18, 250-258 (2020-07-09)
Potency assessment of clinical-grade vector lots is crucial to support adeno-associated virus (AAV) vector release and is required for future marketing authorization. We have developed and validated a cell-based, quantitative potency assay that detects both transgenic expression and activity of
Changes in the auditory brainstem response associated with intravenous infusion of unconjugated bilirubin into infant rhesus monkeys
Ahlfors C E, et al.
Pediatric Research, 20(6), 511-511 (1986)

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