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Bilirubin

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Name

Bilirubin

EINECS 211-239-7
CAS No. 635-65-4 Density 1.374 g/cm3
PSA 164.38000 LogP 5.18880
Solubility practically insoluble in water Melting Point 192 °C
Formula C33H36N4O6 Boiling Point 925.157 °C at 760 mmHg
Molecular Weight 584.73 Flash Point 513.317 °C
Transport Information Appearance Light orange to deep redish-brown crystalline solid
Safety 22-24/25-36-26 Risk Codes 62-36/37/38-20/21/22
Molecular Structure Molecular Structure of 635-65-4 (21H-Biline-8,12-dipropanoicacid,2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-) Hazard Symbols HarmfulXn
Synonyms

Hematoidin (6CI);(4Z,15Z)-Bilirubin IXa;(Z,Z)-Bilirubin IXa;Bilirubin;Bilirubin IXa;Cholerythrin;NSC 26685;

 

Bilirubin Synthetic route

35677-91-9

18-devinyl-18-(1-methoxyethyl)bilirubin

635-65-4

bilirubin

Conditions
ConditionsYield
With toluene-4-sulfonic acid In chloroform for 0.583333h; Ambient temperature;85%
114-25-0

3,18-diethenyl-1,19,22,24-tetrahydro-2,7,13,17-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid

635-65-4

bilirubin

Conditions
ConditionsYield
With acetic acid; zinc
80575-27-5

18-Devinyl-18-(1-carboxymethylthio)ethyl-bilirubin-IXα

A

35991-50-5

4Z,15Z-bilirubin

B

80575-28-6

2,18-Bis-devinyl-2,18-bis-(1-carboxymethylthio)ethyl-bilirubin-IIIα

C

635-65-4

bilirubin

Conditions
ConditionsYield
With hydrogenchloride In dimethyl sulfoxide for 0.0166667h; Product distribution; Ambient temperature;
10035-62-8

α-biliverdin-IX dimethyl ester

635-65-4

bilirubin

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; ethylenediaminetetraacetic acid; sodium cyanoborohydride 1.) CH3OH, 37 deg C, 30 min, 2.) CH3OH, ethanol, 5-10 deg C, 30 min; Yield given. Multistep reaction;
92735-37-0

2,17-bis-(2-chloroethyl)-21,24-dihydro-8,12-bis-(2-methoxycarbonylethyl)-3,7,13,18-tetramethylbilin-1,19-dione

635-65-4

bilirubin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 44 percent / pyridinr, 3percent aq. NaOH / 2 h / Heating
2: 1.) 1 M NaOH, EDTA, 2.) 0.4 M aq. HCl, NaBH3CN / 1.) CH3OH, 37 deg C, 30 min, 2.) CH3OH, ethanol, 5-10 deg C, 30 min
View Scheme

3,18-bis-(2-chloroethyl)-8,12-bis-(2-methoxycarbonylethyl)-2,7,13,17-tetramethyl-b-bilene-1,19-dicarboxylic acid hydrobromide

635-65-4

bilirubin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 54 percent / trifluoroacetic acid, Br2 / 1.5 h / 0 - 5 °C
2: 44 percent / pyridinr, 3percent aq. NaOH / 2 h / Heating
3: 1.) 1 M NaOH, EDTA, 2.) 0.4 M aq. HCl, NaBH3CN / 1.) CH3OH, 37 deg C, 30 min, 2.) CH3OH, ethanol, 5-10 deg C, 30 min
View Scheme
66735-42-0

3,3'-[2-(1-mercapto-ethyl)-3,7,13,18-tetramethyl-1,19-dioxo-17-vinyl-1,10,19,22,23,24-hexahydro-21H-biline-8,12-diyl]-bis-propionic acid

635-65-4

bilirubin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 0.1M aq. NaOH, ClHgCH3 / Ambient temperature
2: 85 percent / p-TsOH / CHCl3 / 0.58 h / Ambient temperature
View Scheme
59614-72-1

18-devinyl-18-<1-(acetylthio)ethyl>bilirubin

635-65-4

bilirubin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 79 percent / 0.1M aq. NaOH, p-ClHgC6H4COONa / H2O / 0.12 h / 50 °C
2: 85 percent / p-TsOH / CHCl3 / 0.58 h / Ambient temperature
View Scheme
19792-68-8

bilirubin dimethylester

635-65-4

bilirubin

Conditions
ConditionsYield
With ammonium hydroxide; trifluoroacetic acid In methanol UV-irradiation;
68-11-1

mercaptoacetic acid

635-65-4

bilirubin

80575-27-5

18-Devinyl-18-(1-carboxymethylthio)ethyl-bilirubin-IXα

Conditions
ConditionsYield
With toluene-4-sulfonic acid In chloroform Ambient temperature; Overnight;95%
With toluene-4-sulfonic acid In chloroform at 40℃; for 18h;77%
106-95-6

allyl bromide

635-65-4

bilirubin

354819-53-7

bilirubin diallyl ester

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 60℃; for 4h;95%
635-65-4

bilirubin

16568-56-2

mesobilirubin

Conditions
ConditionsYield
With sodium hydroxide; sodium hypophosphite; nickel In ethanol Ambient temperature;90%
With ammonia; palladium Hydrogenation;
With potassium hydroxide Hydrogenation;
With sodium hydroxide Hydrogenation;
635-65-4

bilirubin

39923-99-4

p-Nitrothiobenzoic S-acid

C40H41N5O9S

Conditions
ConditionsYield
With toluene-4-sulfonic acid In chloroform79%
98-91-9

thiobenzoic acid

635-65-4

bilirubin

3-(5-[4-(1-Benzoylsulfanyl-ethyl)-3-methyl-5-oxo-1,5-dihydro-pyrrol-(2Z)-ylidenemethyl]-2-{3-(2-carboxy-ethyl)-4-methyl-5-[4-methyl-5-oxo-3-vinyl-1,5-dihydro-pyrrol-(2Z)-ylidenemethyl]-1H-pyrrol-2-ylmethyl}-4-methyl-1H-pyrrol-3-yl)-propionic acid

Conditions
ConditionsYield
With toluene-4-sulfonic acid In chloroform75%
371-42-6

4-Fluorothiophenol

635-65-4

bilirubin

3,18-didevinyl-3,18-bis[2-(pfluorothiophenyl)ethyl]bilirubin

Conditions
ConditionsYield
With toluene-4-sulfonic acid In chloroform for 24h; Ambient temperature;73%
403-44-1

4-fluorobenzenecarbothioic S-acid

635-65-4

bilirubin

C40H41FN4O7S

Conditions
ConditionsYield
With toluene-4-sulfonic acid In chloroform62%
635-65-4

bilirubin

A

35991-50-5

4Z,15Z-bilirubin

B

36284-06-7

bilirubin

Conditions
ConditionsYield
In hydrogenchloride; dimethyl sulfoxideA 29%
B 18%
With hydrogenchloride In dimethyl sulfoxide for 0.0166667h; Product distribution;
Conditions
ConditionsYield
With human serum albumin In water for 4h; Irradiation; pH 7.4 (phosphate buffer);20%
With disodium ethylenediaminetetraacetic acid In dimethyl sulfoxide Irradiation;
635-65-4

bilirubin

19792-68-8

bilirubin dimethylester

67-56-1

methanol

635-65-4

bilirubin

10035-62-8

α-biliverdin-IX dimethyl ester

Conditions
ConditionsYield
With hydrogenchloride; water; iron(III) chloride
67-66-3

chloroform

635-65-4

bilirubin

31,32,181,182-tetrabromo-mesobiliverdin; hydrobromide

Conditions
ConditionsYield
With bromine
635-65-4

bilirubin

108-46-3

recorcinol

54620-18-7

4,3'-Dimethyl-3-vinyl-5(1H)-pyrromethenon-4'-propionsaeure

635-65-4

bilirubin

600-28-2

2,3-dimethyl-1H-pyrrole

Conditions
ConditionsYield
With potassium hydroxide; water at 370℃;
635-65-4

bilirubin

3855-78-5

2,3,4-trimethyl-1H-pyrrole

Conditions
ConditionsYield
With potassium hydroxide; water at 370℃;
635-65-4

bilirubin

517-22-6

2,4-dimethyl-3-ethyl-pyrrole

Conditions
ConditionsYield
With hydrogen iodide; acetic acid
635-65-4

bilirubin

21494-57-5

2-Methyl-3-vinylmaleimide

Conditions
ConditionsYield
With chromium(VI) oxide; sulfuric acid; acetone
With acetic acid; sodium nitrite
635-65-4

bilirubin

20189-42-8

3-ethyl-4-methyl-pyrrole-2,5-dione

Conditions
ConditionsYield
With sodium amalgam nachfolgende Oxidation mit Natriumnitrit und Salzsaeure;
With hydrogen; palladium nachfolgende Oxidation mit Bleidioxyd und Schwefelsaeure;
Multi-step reaction with 2 steps
1: acetic acid; sodium nitrite
2: methanol; palladium / Hydrogenation
View Scheme
635-65-4

bilirubin

54474-50-9

2,4-dimethyl-3-pyrrolepropanoic acid

Conditions
ConditionsYield
With phosphonium iodide; hydrogen iodide; acetic acid
635-65-4

bilirubin

100132-26-1

3-(2-carboxyethyl)-2,4,5-trimethylpyrrole

Conditions
ConditionsYield
With sodium methylate
With potassium ethoxide
635-65-4

bilirubin

487-66-1

2-propionic-3-methylmaleic anhydride

Conditions
ConditionsYield
With sodium dichromate; acetic acid
With sulfuric acid; chromic acid
With dihydrogen peroxide Behandlung mit Kaliumpermanganat und Ansaeuern der Loesung;
635-65-4

bilirubin

487-65-0

3-(4-methyl-2,5-dioxo-2,5-dihydro-pyrrol-3-yl)-propionic acid

Conditions
ConditionsYield
With sodium dichromate; acetic acid
With sulfuric acid; lead dioxide
635-65-4

bilirubin

28098-80-8

ethyl-methyl-maleic acid

Conditions
ConditionsYield
bei der Oxidation ensteht als Anhydrid oder Imid;
635-65-4

bilirubin

3-[5-(3-ethyl-4-methyl-5-oxo-4,5-dihydro-pyrrol-2-ylmethyl)-2,4-dimethyl-pyrrol-3-yl]-propionic acid

Conditions
ConditionsYield
With hydrogen iodide; acetic acid
635-65-4

bilirubin

15770-19-1, 113275-42-6

xanthobilirubic acid

Conditions
ConditionsYield
With sodium methylate at 220 - 230℃;
635-65-4

bilirubin

10035-62-8

α-biliverdin-IX dimethyl ester

Conditions
ConditionsYield
With acetic acid; dimethyl sulfoxide; p-benzoquinone anschliessenden Verestern mit Methanol-BF3;
635-65-4

bilirubin

A

99276-19-4

181,182-Dihydro-bilirubin

B

16568-56-2

mesobilirubin

Conditions
ConditionsYield
With sodium hydroxide; palladium Hydrogenation;
635-65-4

bilirubin

31,32-Didehydro-(R,R)-urobilin

Conditions
ConditionsYield
mit Hilfe von Darmbakterien;

Bilirubin Chemical Properties

Molecule structure of Bilirubin (CAS NO.635-65-4) :

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: 584.66214 g/mol
Molecular Formula: C33H36N4O6
Density: 1.374 g/cm3 
Melting Point: 192 °C
Boiling Point: 925.2 °C at 760 mmHg 
Flash Point: 513.3 °C
Molar Volume: 425.3 cm3
Polarizability: 66.74*10-24 cm3
Surface Tension: 74.5 dyne/cm 
Enthalpy of Vaporization: 140.96 kJ/mol 
Storage temp.: −20 °C
Appreance: light orange to deep redish-brown crystalline solid
Merck: 14.1218
XLogP3-AA: 2.9
H-Bond Donor: 6
H-Bond Acceptor: 6
Rotatable Bond Count: 12
Tautomer Count: 25
Exact Mass: 584.263485
MonoIsotopic Mass: 584.263485
Topological Polar Surface Area: 164
Heavy Atom Count: 43
Complexity: 1340
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
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
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-
InChIKey: BPYKTIZUTYGOLE-IFADSCNNSA-N
EINECS: 211-239-7
Product Categories: Colours, Dyes, Indicators & Pigments; Bile Pigments; Porphyrins; Antioxidant; Biochemistry; Intermediates & Fine Chemicals; Pharmaceuticals; Antioxidants and CytoprotectantsPlasma&Blood Proteins; BilirubinResearch Essentials; Enzyme InhibitorsApplication Index; Cell Stress; Core Bioreagents; Nitric Oxide and Cell Stress; Plasma, Blood, and Related Proteins and Reagents; Serum Proteins; Serum Proteins and Related Enzymes
 

Bilirubin Uses

 Bilirubin (CAS NO.635-65-4) is used as principal pigment of bile and constituent of many biliary calculi. And also used to be artificial bezoar for the determination of bilirubin in artificial calculus bovis preparation and biochemistry. Bilirubin (CAS NO.635-65-4) has a variety of pharmacological effects, is to create artificial bezoar of the main raw material.

Bilirubin Production

 Bilirubin (CAS NO.635-65-4) is mainly extracted from the bile. Bilirubin is made from fresh cow or pig bile through the bile quicklime role in generating bilirubin calcium, and then hydrochloric acid, chloroform solvent extraction.

Bilirubin Toxicity Data With Reference

mouse LD50 intraperitoneal > 2gm/kg (2000mg/kg) GASTROINTESTINAL: OTHER CHANGES Eisei Shikenjo Hokoku. Bulletin of the Institute of Hygienic Sciences. Vol. (103), Pg. 29, 1985.
 
mouse LD50 oral > 15gm/kg (15000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Eisei Shikenjo Hokoku. Bulletin of the Institute of Hygienic Sciences. Vol. (103), Pg. 29, 1985.
 

Bilirubin Safety Profile

Hazard Codes: HarmfulXn
Risk Statements: 62-36/37/38-20/21/22 
R62:Risk of impaired fertility. 
R36/37/38: Irritating to eyes, respiratory system and skin 
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed
Safety Statements: 22-24/25-36-26 
S22: Do not breathe dust
S24/25: Avoid contact with skin and eyes
S36: Wear suitable protective clothing 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany: 2
RTECS: DU3038000
F: 8
HS Code: 29339990

Bilirubin Specification

 Bilirubin (CAS NO.635-65-4) is also called Hematoidin;bilirubin (ex pig) ; 21H-Biline-8,12-dipropanoic acid,2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo- ; 2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid ; 13,18-Tetramethyl-1,19-dioxo- ; 1,10,19,22,23,24-hexahydro-2,7,13,17-tetramethyl-biline-12-dipropionicacid . Bilirubin (CAS NO.635-65-4) is soluble in benzene, chloroform and carbon disulfide and other organic solvents; also soluble in hot ethanol and chloroform mixture; salt soluble in water, but calcium, magnesium and barium salts do not dissolve in water. Bilirubin is created by the activity of biliverdin reductase on biliverdin. Bilirubin, when oxidized, reverts to become biliverdin once again. This cycle, in addition to the demonstration of the potent antioxidant activity of bilirubin, has led to the hypothesis that bilirubin's main physiologic role is as a cellular antioxidant.

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