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B4126

Sigma-Aldrich

Bilirubin

≥98% (EmM/453 = 60), powder

Synonym(s):
Bile pigment, Hemetoidin
Empirical Formula (Hill Notation):
C33H36N4O6
CAS Number:
Molecular Weight:
584.66
Beilstein:
74376
EC Number:
MDL number:
PubChem Substance ID:

description

mixed isomers

Quality Level

assay

≥98% (EmM/453 = 60)

form

powder

solubility

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

storage temp.

−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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General description

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.

Application

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

Packaging

1, 5 g in glass bottle

Biochem/physiol Actions

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.

Other Notes

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.

Caution

Protect from light.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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