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B4126

Sigma-Aldrich

Bilirubin

≥98% (EmM/453 = 60), powder

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Synonym(s):
Bile pigment, Hemetoidin
Empirical Formula (Hill Notation):
C33H36N4O6
CAS Number:
Molecular Weight:
584.66
Beilstein/REAXYS Number:
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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1 of 4

This Item
2011NIST916BH9039
vibrant-m

B4126

Bilirubin

vibrant-m

2011

Bilirubin

vibrant-m

NIST916B

Bilirubin

vibrant-m

H9039

Hemin

assay

≥98% (EmM/453 = 60)

assay

-

assay

-

assay

≥90%

Quality Level

300

Quality Level

100

Quality Level

-

Quality Level

200

storage temp.

−20°C

storage temp.

10-30°C

storage temp.

−20°C

storage temp.

2-8°C

solubility

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

solubility

chloroform: 1 mg/mL, alkaline solution: soluble

solubility

-

solubility

1.4 M NH4OH: soluble 25 mg/mL

description

mixed isomers

description

-

description

-

description

-

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

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.

Caution

Protect from light.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Memon N, et al.
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Photoacoustic microscopy of bilirubin in tissue phantoms
Zhou y, et al.
Journal of Biomedical Optics, 17(12), 126019-126019 (2012)
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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