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Bilirubin

Bilirubin
Bilirubin ZZ.png
Bilirubin-from-xtal-1978-3D-balls.png
Names
Other names
Pheophytin
Identifiers
635-65-4 YesY
3D model (Jmol) Interactive image
Interactive image
ChEBI CHEBI:16990 YesY
ChEMBL ChEMBL501680 YesY
ChemSpider 4444055 YesY
ECHA InfoCard 100.010.218
4577
PubChem 5280352
UNII RFM9X3LJ49 YesY
Properties
C33H36N4O6
Molar mass 584.67 g·mol−1
Supplementary data page
Refractive index (n),
Dielectric constantr), etc.
Thermodynamic
data
Phase behaviour
solid–liquid–gas
UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Bilirubin (formerly referred to as haematoidin and discovered by Rudolf Virchow in 1847) is a yellow compound that occurs in the normal catabolic pathway that breaks down heme in vertebrates. This catabolism is a necessary process in the body's clearance of waste products that arise from the destruction of aged red blood cells. First the hemoglobin gets stripped of the heme molecule which thereafter passes through various processes of porphyrin catabolism, depending on the part of the body in which the breakdown occurs. For example, the molecules excreted in the urine differ from those in the feces. The production of biliverdin from heme is the first major step in the catabolic pathway, after which the enzyme biliverdin reductase performs the second step, producing bilirubin from biliverdin.

Bilirubin is excreted in bile and urine, and elevated levels may indicate certain diseases. It is responsible for the yellow color of bruises and the yellow discoloration in jaundice. Its subsequent breakdown products, such as stercobilin, cause the brown color of feces. A different breakdown product, urobilin, is the main component of the straw-yellow color in urine.

It has also been found in plants.

Bilirubin consists of an open chain of four pyrrole-like rings (tetrapyrrole). In heme, these four rings are connected into a larger ring, called a porphyrin ring.

Bilirubin can be "conjugated" with a molecule of glucuronic acid which makes it soluble in water (see below). This is an example of glucuronidation.


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Wikipedia

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