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B4126

Sigma-Aldrich

Bilirubin

≥98% (EmM/453 = 60), powder

Synonym(s):

Bile pigment, Hemetoidin

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About This Item

Empirical Formula (Hill Notation):
C33H36N4O6
CAS Number:
Molecular Weight:
584.66
Beilstein:
74376
EC Number:
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77

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

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 Code

11 - 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
Inherited disorders of bilirubin clearance
Memon N, et al.
Pediatric Research, 79(3), 378-378 (2016)
Brain bilirubin content is increased in P-glycoprotein-deficient transgenic null mutant mice
Watchko J F, et al.
Pediatric Research, 44(5), 763-763 (1998)

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