Merck
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14370

Sigma-Aldrich

Bilirubin

purum, ≥95.0% (UV)

Empirical Formula (Hill Notation):
C33H36N4O6
CAS Number:
Molecular Weight:
584.66
Beilstein:
74376
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25

grade

purum

Quality Level

assay

≥95.0% (UV)

form

powder

ign. residue

≤0.5%

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, 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.

Biochem/physiol Actions

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.
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.

Analysis Note

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

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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