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635-65-4 Usage

Description

Bilirubin is a yellow breakdown product of heme catabolism, formed when heme is cleaved by heme oxygenase. This reaction produces carbon monoxide and biliverdin, which is rapidly reduced to bilirubin by biliverdin reductase. Bilirubin has key roles as a free radical scavenger with antioxidant and anti-inflammatory actions. Free and albumin-bound bilirubin can also scavenge nitric oxide (NO) and NO-related species. Unconjugated bilirubin is highly water-insoluble and must be conjugated with glucuronides to become water soluble and subsequently excreted by the liver and kidney.

Chemical Properties

Light Orange to Deep Redish-Brown Crystalline Solid

Uses

Different sources of media describe the Uses of 635-65-4 differently. You can refer to the following data:
1. Principal pigment of bile and constituent of many biliary calculi
2. Bilirubin is widely utilized to monitor the liver function and their disease, such as hepatitis or cirrhosis; or the effects of medicines which are damage the liver. It acts as a pigment in certain algae to capture light energy. Its double bonds are isomerizes in the presence of light, which is employed in phototherapy of jaundiced newborns babies. It is used to detect the blocking in bile ducts.
3. Bilirubin has been used:in phantom preparationin in vitro experimentsin the preparation of bilirubin solutions for infusion

Definition

Red coloring matter of bile. Also occurs in blood serum as decomposition product of hemoglobin.

General Description

Bilirubin, a heme catabolism end-product is produced by the reduction of its metabolic precursor biliverdin by the action of enzyme biliverdin reductase.

Biochem/physiol Actions

Bilirubin is an active oxidative DNA cleaving agent as well as an effective antioxidant agent, a hydroxyl radical quencher. This bile pigment has both antioxidant and toxic properties. It is a natural inhibitor of vascular smooth muscle cell proliferation (VSMCs). It displays anti-inflammatory and anti-proliferative properties when used as a therapeutic agent in lung/vascular diseases. Serum bilirubin concentration slightly above the normal levels have shown a lesser incidence of heart disease. It is a potential therapeutic agent in heart transplantation and T-cell mediated immune disorders.

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.]

Check Digit Verification of cas no

The CAS Registry Mumber 635-65-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,3 and 5 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 635-65:
(5*6)+(4*3)+(3*5)+(2*6)+(1*5)=74
74 % 10 = 4
So 635-65-4 is a valid CAS Registry Number.
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
  • TCI America

  • (B0460)  Bilirubin  

  • 635-65-4

  • 100mg

  • 265.00CNY

  • Detail
  • TCI America

  • (B0460)  Bilirubin  

  • 635-65-4

  • 1g

  • 940.00CNY

  • Detail
  • Alfa Aesar

  • (A17522)  Bilirubin 97%   

  • 635-65-4

  • 1g

  • 1315.0CNY

  • Detail
  • Alfa Aesar

  • (A17522)  Bilirubin 97%   

  • 635-65-4

  • 5g

  • 5089.0CNY

  • Detail
  • Alfa Aesar

  • (A17522)  Bilirubin 97%   

  • 635-65-4

  • 25g

  • 19313.0CNY

  • 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;

635-65-4Relevant articles and documents

A method for preparing high-content bilirubin IX[alpha] from bilirubin IX[alpha] diester

-

Paragraph 0028; 0041-0043; 0050-0055, (2019/04/10)

A method for preparing high-content bilirubin IX[alpha] from bilirubin IX[alpha] diester is disclosed, belonging to the field of bilirubin IX[alpha] preparation. The method includes following steps (aroute including firstly hydrolysis and then reduction): a step of adding dropwise a methanol solution of sodium hydroxide into an alcohol solution of bilirubin IX[alpha] diester, adding water, then performing hydrolysis, adjusting pH to 4-5 with a weak acid, performing rotary evaporation to remove a solvent, washing a product with water to remove inorganic salt, and performing vacuum drying to obtain bilirubin IX[alpha]; and a step of adding a free radical scavenger (stabilizer) into an alcohol solution of the bilirubin IX[alpha], adding a reductant that is borohydride, adding an acetone immediately after reduction is finished to decompose the excessive reductant, then adjusting pH to 4-5 with weak acid, performing rotary evaporation to remove a solvent, performing water washing, and performing purification with methanol and chloroform to obtain bilirubin IX[alpha] the purity of which is more than 97%. The method has characteristics of no need of chromatographic separation, mild reaction conditions, low cost, and convenient operation, and is suitable for industrial large-scale production.

PRODUCTION OF RED BLOOD CELLS AND PLATELETS FROM STEM CELLS

-

, (2014/03/24)

This disclosure provides methods of making a megakaryocyte-erythroid progenitor cell (MEP), comprising differentiating a stem cell into a MEP in culture in the presence of an aryl hydrocarbon receptor (AhR) agonist. In some embodiments the stem cell is a pluripotent stem cell. In some embodiments the MEP co-expresses CD41 and CD235. In some embodiments the number of MEPs produced in the culture increases exponentially. Methods of making a red blood cell (RBC) by culturing a MEP in the presence of an AhR agonist are also provided. Methods of making a megakaryocyte and/or a platelet, comprising culturing a MEP in the presence of an AhR modulator are also provided. In some embodiments the AhR modulator is an AhR antagonist. This disclosure also provides compositions comprising at least 1 million MEPs per ml and compositions in which at least 50% of the cells are MEPs.

Solvent effects on the photoisomerization of bilirubin

Sailofsky,Brown

, p. 1908 - 1916 (2007/10/02)

-

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