Bilirubin

• CAS: 635-65-4
• Catalog Number: ACM635654
• Category: Other Products
• Molecular Weight: 584.66
• Molecular Formula: C33H36N4O6
• 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
• 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
• 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 Codes: Xn
• 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
• LogP: 5.18880
• Monoisotopic Mass: 584.26348488
• Physical State: Powder
• pKa: 4.62±0.10(Predicted)
• PSA: 164.38
• Refractive Index: 1.6000
• Rotatable Bond Count: 12
• Safety Description: 22-24/25-36-26
• Stability: Stable. Refrigerate.
• Storage Conditions: -20ºC
• Topological Polar Surface Area: 164 Ų
• WGK Germany: 2

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.

Synthetic Use

Upstream Synthesis Route 1

• 35677-91-9

• 635-65-4

Reference: [1] Gazzetta Chimica Italiana, 1982, vol. 112, # 9/10, p. 361 - 366

Upstream Synthesis Route 2

• 19792-68-8

• 635-65-4

Reference: [1] Monatshefte fur Chemie, 2014, vol. 145, # 3, p. 465 - 482

Upstream Synthesis Route 3

• 66735-42-0

• 635-65-4

Reference: [1] Gazzetta Chimica Italiana, 1982, vol. 112, # 9/10, p. 361 - 366

Upstream Synthesis Route 4

• 114-25-0

• 635-65-4

Reference: [1]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1941,vol. 268,p. 197,222

Upstream Synthesis Route 5

• 35677-91-9

• 635-65-4

Reference: [1]Justus Liebigs Annalen der Chemie,1932,vol. 499,p. 25,33, 36

Downstream Synthesis Route 1

• 186581-53-3
• 635-65-4

• 19792-68-8

Reference: [1]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1941,vol. 268,p. 197,222
[2]Liebigs Annalen der Chemie,1982,p. 1759 - 1765
[3]Monatshefte fur Chemie,1982,vol. 113,p. 1421 - 1432
[4],1959,vol. 71,p. 7065
Chem.Abstr.,1960,p. 24970

* For details of the synthesis route, please refer to the original source to ensure accuracy.