Bilirubin

Title: Bilirubin
CAS Registry Number: 635-65-4
CAS Name: 2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid
Additional Names: 1,10,19,22,23,24-hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinylbiline-8,12-dipropionic acid; 1,3,6,7-tetramethyl-4,5-dicarboxyethyl-2,8-divinyl-(b-13)-dihydrobilenone; bilirubin IXa
Molecular Formula: C33H36N4O6
Molecular Weight: 584.66
Percent Composition: C 67.79%, H 6.21%, N 9.58%, O 16.42%
Literature References: Principal pigment of bile and constituent of many biliary calculi. Major end-product of the biological breakdown of heme, q.v. Bilirubin is the chromophore responsible for coloration in various forms of jaundice. Also found in blood serum, where it exists in four major forms: unconjugated bilirubin, the monoglucuronide, the diglucuronide, and albumin-bound bilirubin. Most easily obtained from ox gallstones which are largely calcium bilirubinate: Städeler, Ann. 132, 323 (1864); Küster, Z. Physiol. Chem. 94, 136 (1915); 99, 86 (1917); 121, 80 (1922); Küster, Haas, ibid. 141, 279 (1924); Fischer, ibid. 3, 204 (1911); Fischer, Hess, ibid. 194, 193 (1931). Isoln from pig bile: Gibson, Lowe, J. Biol. Chem. 123, XLI (1938); Gray et al., J. Chem. Soc. 1961, 2264, 2268; from ox bile: Libowitzky, Z. Physiol. Chem. 263, 267 (1940). Industrial isoln from ox bile using chlorobenzene as extractant: US 2166073; US 2331574; US 2363471; US 2386716. Structure and synthesis: Fischer, Plieninger, Naturwissenschaften 30, 382 (1942); Z. Physiol. Chem. 274, 231 (1942); cf. Fischer-Orth, Die Chemie des Pyrrols II, 1, 621 (Leipzig, 1937); Gray et al., Nature 181, 183 (1958); eidem, J. Chem. Soc. 1961, 2276. Structure: Fog, Jellum, Nature 198, 88 (1963). Configuration: Kuenzle et al., Biochem. J. 133, 364 (1973). X-ray analysis and structure: Bonnett et al., J. Chem. Soc. Perkin Trans. 2 1972, 902, 1335; Nature 262, 326 (1976). NMR conformation studies: D. Kaplan, G. Navon, J. Chem. Soc. Perkin Trans. 2 1981, 1374. Separation of bilirubin species in serum and bile by reversed-phase HPLC: J. J. Lauff et al., J. Chromatogr. 226, 391 (1981); eidem, Clin. Chem. 29, 800 (1983). Clinical importance of albumin-bound bilirubin: J. S. Weiss et al., N. Engl. J. Med. 309, 148 (1983). Comprehensive reviews: Lemberg, Legge, Hematin Compounds and Bile Pigments (New York, 1949); With, Bile Pigments (Academic Press, New York, 1968). Reviews of toxicity: D. Bratlid, N. Y. State J. Med. 91, 489-493 (1991); R. P. Wennberg, ibid. 493-496.
Properties: Light orange to deep reddish-brown monoclinic rhomboid, prisms, plates from chloroform. Gradually blackens on heating and does not melt. The greenish solns show a red fluorescence in ultraviolet light. A 0.001% soln in chloroform shows selective abs from 490 to 400 nm with a max at 453 nm; e mM 60.7 ± 0.8. Practically insol in water. Sol in benzene, chloroform, chlorobenzene, carbon disulfide, acids, alkalies; slightly sol in alcohol, ether. Spreads on water. Penetrates into cholesterol, octadecylamine, and protein monolayers: Stenhagen, Rideal, Biochem. J. 33, 1591 (1939).
Biliverdine Bimosiamose Binapacryl Binedaline Binifibrate

Bilirubin
Identifiers
CAS number 635-65-4 YesY
PubChem 5280352
ChemSpider 4444055 YesY
UNII RFM9X3LJ49 YesY
ChEBI CHEBI:16990 YesY
ChEMBL CHEMBL501680 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C33H36N4O6
Molar mass 584.66 g mol−1
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Bilirubin (formerly referred to as haematoidin) is the yellow breakdown product of normal haeme catabolism. Haeme is found in haemoglobin, a principal component of red blood cells. Bilirubin is excreted in bile and urine, and elevated levels may indicate certain diseases. It is responsible for the yellow color of bruises, the background straw-yellow color of urine (via its reduced breakdown product, urobilin – the more obvious but variable bright yellow colour of urine is due to thiochrome, a breakdown product of thiamine), the brown color of feces (via its conversion to stercobilin), and the yellow discoloration in jaundice.

It has also been found in plants.[1]