Bilirubin

Catalog Number	ACM635654
CAS Number	635-65-4
Description	Bilirubin (formerly referred to as haematoidin) 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.
Synonyms	Cholerythrin
IUPAC Name	3-[2-[[3-(2-Carboxyethyl)-5-[(Z)-(3-ethenyl-4-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(4-ethenyl-3-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid
Molecular Weight	584.66
Molecular Formula	C33H36N4O6
Canonical SMILES	CC1=C(NC(=C1CCC(=O)O)CC2=C(C(=C(N2)C=C3C(=C(C(=O)N3)C)C=C)C)CCC(=O)O)C=C4C(=C(C(=O)N4)C=C)C
InChI	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
Boiling Point	641.7 °C
Melting Point	192 °C
Flash Point	513.3 °C
Purity	98%
Density	1.2163 g/cm³
Solubility	Practically insoluble in water
Appearance	Solid
Storage	-20 °C
Complexity	1340
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	0
Exact Mass	584.26348488
Hazard Statements	Xn
Heavy Atom Count	43
HS Code	29339990
Hydrogen Bond Acceptor Count	6
Hydrogen Bond Donor Count	6
Isomeric SMILES	CC1=C(NC(=C1CCC(=O)O)CC2=C(C(=C(N2)/C=C\3/C(=C(C(=O)N3)C)C=C)C)CCC(=O)O)/C=C\4/C(=C(C(=O)N4)C=C)C
Monoisotopic Mass	584.26348488
PhysicalState	Powder
Rotatable Bond Count	12
Topological Polar Surface Area	164 Ų

Custom Q&A

What is the chemical formula for Bilirubin?

The chemical formula for Bilirubin is C33H36N4O6.

What is the melting point of Bilirubin?

The melting point of Bilirubin is 192°C.

How does Bilirubin interact with light?

Bilirubin is sensitive to light and its double bonds can isomerize in the presence of light.

What role does Bilirubin play in the body?

Bilirubin has key roles as a free radical scavenger, with antioxidant and anti-inflammatory actions.

How can Bilirubin be excreted from the body?

Unconjugated bilirubin, which is highly water-insoluble, must be conjugated with glucuronides to become water-soluble and excreted by the liver and kidney.

For what purpose is Bilirubin widely utilized?

Bilirubin is widely used to monitor liver function and diseases such as hepatitis or cirrhosis, as well as to detect blockages in bile ducts.

How is Bilirubin used in phototherapy for jaundiced newborns?

The isomerization of Bilirubin's double bonds in the presence of light is employed in phototherapy for jaundiced newborns.

What are the safety codes associated with Bilirubin?

The hazard code for Bilirubin is Xn, with associated risk and safety statements.

How is Bilirubin purified?

Bilirubin can be purified by successive Soxhlet extraction with diethyl ether and MeOH, and crystallizes as deep red-brown rhombs or plates.

What other products are formed when heme is cleaved in the body?

When heme is cleaved by heme oxygenase, it produces carbon monoxide and biliverdin, which is rapidly reduced to bilirubin by biliverdin reductase.

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