Editing Bilirubin (section)

{{Short description|Red pigment of the bile}}
{{redirect|Billy Rubin|the American art scholar|William Rubin}}
{{Use dmy dates|date=March 2020}}
{{chembox
| Watchedfields  = changed
| verifiedrevid  = 443422624
| Name           =
| ImageFile      = Bilirubin (CAS 635-65-4).svg
| ImageSize      =
| ImageFile1     = bilirubin-from-xtal-1978-3D-balls.png
| IUPACName      = 3,3′-(2,17-Diethenyl-3,7,13,18-tetramethyl-1,19-dioxo-10,19,21,22,23,24-hexahydro-1''H''-biline-8,12-diyl)dipropanoic acid
| SystematicName = 3,3′-([1<sup>2</sup>(2)''Z'',6(7<sup>2</sup>)''Z'']-1<sup>3</sup>,7<sup>4</sup>-Diethenyl-1<sup>4</sup>,3<sup>3</sup>,5<sup>4</sup>,7<sup>3</sup>-tetramethyl-1<sup>5</sup>,7<sup>5</sup>-dioxo-1<sup>1</sup>,1<sup>5</sup>,7<sup>1</sup>,7<sup>5</sup>-tetrahydro-3<sup>1</sup>''H'',5<sup>1</sup>''H''-1,7(2),3,5(2,5)-tetrapyrrolaheptaphane-1<sup>2</sup>(2),6(7<sup>2</sup>)-diene-3<sup>4</sup>,5<sup>3</sup>-diyl)dipropanoic acid
| OtherNames     = Bilirubin IXα
| Section1       = {{Chembox Identifiers
| IUPHAR_ligand = 4577
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4444055
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = RFM9X3LJ49
| InChIKey = BPYKTIZUTYGOLE-IFADSCNNBS
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 501680
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=635-65-4
| PubChem = 5280352
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 16990
| SMILES = CC1=C(/C=C2C(C)=C(C=C)C(N/2)=O)NC(CC3=C(CCC(O)=O)C(C)=C(/C=C4C(C=C)=C(C)C(N/4)=O)N3)=C1CCC(O)=O
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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-
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BPYKTIZUTYGOLE-IFADSCNNSA-N
| SMILES1 = Cc1c(c([nH]c1/C=C\2/C(=C(C(=O)N2)C=C)C)Cc3c(c(c([nH]3)/C=C\4/C(=C(C(=O)N4)C)C=C)C)CCC(=O)O)CCC(=O)O
}}
| Section2       = {{Chembox Properties
| C=33 | H=36 | N=4 | O=6
| Appearance=
| Density= 1.31 g·cm-3<ref name="Reaxys">{{cite journal |last1=Bonnett |first1=Raymond |last2=Davies |first2=John E. |last3=Hursthouse |first3=Michael B. |title=Structure of bilirubin |journal=Nature |date=July 1976 |volume=262 |issue=5566 |pages=326–328 |doi=10.1038/262326a0|pmid=958385 |bibcode=1976Natur.262..326B |s2cid=4278361 }}</ref>
| MeltingPt= 235°C<ref name="Reaxysb">{{cite journal |last1=Sturrock |first1=E. D. |last2=Bull |first2=J. R. |last3=Kirsch |first3=R. E. |title=The synthesis of [10-13C]bilirubin IXα |journal=Journal of Labelled Compounds and Radiopharmaceuticals |date=March 1994 |volume=34 |issue=3 |pages=263–274 |doi=10.1002/jlcr.2580340309}}</ref>
| BoilingPt=
| Solubility=
  }}
| Section3       = {{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
  }}
| Section4       =
| Section5       =
| Section6       =
}}

'''Bilirubin''' ('''BR''') (adopted from German, originally bili—bile—plus ruber—red—from [[Latin]]) is a red-orange compound that occurs in the normcomponent of the straw-yellow color in urine.<ref>{{Citation |last1=Chew |first1=Dennis J. |title=Chapter 1 - Urinalysis |date=2011-01-01 |url=https://www.sciencedirect.com/science/article/pii/B9780721681788100016 |work=Canine and Feline Nephrology and Urology (Second Edition) |pages=1–31 |editor-last=Chew |editor-first=Dennis J. |access-date=2023-11-01 |place=Saint Louis |publisher=W.B. Saunders |isbn=978-0-7216-8178-8 |last2=DiBartola |first2=Stephen P. |last3=Schenck |first3=Patricia A. |editor2-last=DiBartola |editor2-first=Stephen P. |editor3-last=Schenck |editor3-first=Patricia A.}}</ref> Another breakdown product, [[stercobilin]], causes the brown color of feces.

Although bilirubin is usually found in animals rather than plants, at least one plant species, ''[[Strelitzia nicolai]]'', is known to contain the pigment.<ref name="pmid19206232">{{cite journal | vauthors = Pirone C, Quirke JM, Priestap HA, Lee DW | title = Animal pigment bilirubin discovered in plants | journal = Journal of the American Chemical Society | volume = 131 | issue = 8 | page = 2830 | date = March 2009 | pmid = 19206232 | pmc = 2880647 | doi = 10.1021/ja809065g }}</ref>