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Bilirubin
Cas No: 635-65-4
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635-65-4 Usage

Chemical Properties

Light Orange to Deep Redish-Brown Crystalline Solid

Uses

Principal pigment of bile and constituent of many biliary calculi

Purification Methods

An acyclic tetrapyrrole bile pigment with impurities which can be eliminated by successive Soxhlet extraction with diethyl ether and MeOH. It crystallises from CHCl3 as deep red-brown rhombs, plates or orange-red prisms from chlorobenzene (m 330o dec) and is dried to constant weight at 80o under vacuum. [Gray et al. J Chem Soc 2264, 2276 1961, Beilstein 26 III/IV 3268.]
InChI:InChI=1/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)/p-2/b26-13-,27-14-

635-65-4 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (A17522)  Bilirubin 97%    635-65-4 25g 19313.0CNY Detail
Alfa Aesar (A17522)  Bilirubin 97%    635-65-4 5g 5089.0CNY Detail
Alfa Aesar (A17522)  Bilirubin 97%    635-65-4 1g 1315.0CNY Detail
TCI America (B0460)  Bilirubin   635-65-4 1g 940.00CNY Detail
TCI America (B0460)  Bilirubin   635-65-4 100mg 265.00CNY Detail

635-65-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name bilirubin

1.2 Other means of identification

Product number -
Other names Cholerythrin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:635-65-4 SDS

635-65-4Synthetic route

18-devinyl-18-(1-methoxyethyl)bilirubin
35677-91-9

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

bilirubin
635-65-4

bilirubin

Conditions
ConditionsYield
With toluene-4-sulfonic acid In chloroform for 0.583333h; Ambient temperature;85%
3,18-diethenyl-1,19,22,24-tetrahydro-2,7,13,17-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid
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

bilirubin
635-65-4

bilirubin

Conditions
ConditionsYield
With acetic acid; zinc
18-Devinyl-18-(1-carboxymethylthio)ethyl-bilirubin-IXα
80575-27-5

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

A

4Z,15Z-bilirubin
35991-50-5

4Z,15Z-bilirubin

B

2,18-Bis-devinyl-2,18-bis-(1-carboxymethylthio)ethyl-bilirubin-IIIα
80575-28-6

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

C

bilirubin
635-65-4

bilirubin

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

α-biliverdin-IX dimethyl ester

bilirubin
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;
2,17-bis-(2-chloroethyl)-21,24-dihydro-8,12-bis-(2-methoxycarbonylethyl)-3,7,13,18-tetramethylbilin-1,19-dione
92735-37-0

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

bilirubin
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

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

bilirubin
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
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
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

bilirubin
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
18-devinyl-18-<1-(acetylthio)ethyl>bilirubin
59614-72-1

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

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
bilirubin dimethylester
19792-68-8

bilirubin dimethylester

bilirubin
635-65-4

bilirubin

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

mercaptoacetic acid

bilirubin
635-65-4

bilirubin

18-Devinyl-18-(1-carboxymethylthio)ethyl-bilirubin-IXα
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%
allyl bromide
106-95-6

allyl bromide

bilirubin
635-65-4

bilirubin

bilirubin diallyl ester
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%
bilirubin
635-65-4

bilirubin

mesobilirubin
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;
bilirubin
635-65-4

bilirubin

p-Nitrothiobenzoic S-acid
39923-99-4

p-Nitrothiobenzoic S-acid

C40H41N5O9S

C40H41N5O9S

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

thiobenzoic acid

bilirubin
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

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%
4-Fluorothiophenol
371-42-6

4-Fluorothiophenol

bilirubin
635-65-4

bilirubin

3,18-didevinyl-3,18-bis[2-(pfluorothiophenyl)ethyl]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%
4-fluorobenzenecarbothioic S-acid
403-44-1

4-fluorobenzenecarbothioic S-acid

bilirubin
635-65-4

bilirubin

C40H41FN4O7S

C40H41FN4O7S

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

bilirubin

A

4Z,15Z-bilirubin
35991-50-5

4Z,15Z-bilirubin

B

bilirubin
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;
bilirubin
635-65-4

bilirubin

bilirubin dimethylester
19792-68-8

bilirubin dimethylester

methanol
67-56-1

methanol

bilirubin
635-65-4

bilirubin

α-biliverdin-IX dimethyl ester
10035-62-8

α-biliverdin-IX dimethyl ester

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

chloroform

bilirubin
635-65-4

bilirubin

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

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

Conditions
ConditionsYield
With bromine
bilirubin
635-65-4

bilirubin

recorcinol
108-46-3

recorcinol

4,3'-Dimethyl-3-vinyl-5(1H)-pyrromethenon-4'-propionsaeure
54620-18-7

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

bilirubin
635-65-4

bilirubin

2,3-dimethyl-1H-pyrrole
600-28-2

2,3-dimethyl-1H-pyrrole

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

bilirubin

2,3,4-trimethyl-1H-pyrrole
3855-78-5

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

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

bilirubin

2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

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

bilirubin

2-Methyl-3-vinylmaleimide
21494-57-5

2-Methyl-3-vinylmaleimide

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

bilirubin

3-ethyl-4-methyl-pyrrole-2,5-dione
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
bilirubin
635-65-4

bilirubin

2,4-dimethyl-3-pyrrolepropanoic acid
54474-50-9

2,4-dimethyl-3-pyrrolepropanoic acid

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

bilirubin

3-(2-carboxyethyl)-2,4,5-trimethylpyrrole
100132-26-1

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

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

bilirubin

2-propionic-3-methylmaleic anhydride
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;
bilirubin
635-65-4

bilirubin

3-(4-methyl-2,5-dioxo-2,5-dihydro-pyrrol-3-yl)-propionic acid
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
bilirubin
635-65-4

bilirubin

ethyl-methyl-maleic acid
28098-80-8

ethyl-methyl-maleic acid

Conditions
ConditionsYield
bei der Oxidation ensteht als Anhydrid oder Imid;
bilirubin
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

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
bilirubin
635-65-4

bilirubin

xanthobilirubic acid
15770-19-1, 113275-42-6

xanthobilirubic acid

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

bilirubin

α-biliverdin-IX dimethyl ester
10035-62-8

α-biliverdin-IX dimethyl ester

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

bilirubin

A

181,182-Dihydro-bilirubin
99276-19-4

181,182-Dihydro-bilirubin

B

mesobilirubin
16568-56-2

mesobilirubin

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

bilirubin

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

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

Conditions
ConditionsYield
mit Hilfe von Darmbakterien;

635-65-4Downstream Products

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