ChemicalBook CAS DataBase List 635-65-4

635-65-4

Name	Bilirubin
CAS	635-65-4
EINECS(EC#)	211-239-7
Molecular Formula	C33H36N4O6
MDL Number	MFCD00005499
Molecular Weight	584.66
MOL File	635-65-4.mol

Synonyms

BILIRUBIN filirubin Bilibubin Biliyubin HEMATOIDIN hemetoidin 1,19-dioxo- BilirubinGr Cholerythrin Bilirubin,99% Bilirubin,97% Bilirubin IXa (Z,Z)-Bilirubin Obeticholic Acid2 bilirubinix-alpha BILIRUBIN (ALPHA) BILIRUBIN (EX PIG) BILIRUBIN STANDARD Bilirubin, 99% 1GR Bilirubin, 99% 500MG principalbilepigment 18-divinyl-19-dioxo-3 BILIRUBIN extrapure AR Bilirubin from Porcine BILIRUBIN REAGENT-GRADE BILIRUBIN MIXED ISOMERS Bilirubin, synthesis grade ,13,18-tetramethyl-1,19-dioxo- BILIRUBIN LIN-TROL TOTAL & DIRECT BILIRUBIN LIN-TROL PREDILUTED SET D-BiotinForBiochemistry(VitaminH) BILIRUBIN CALIBRATOR, TOTAL & DIRECT BILIRUBIN CONTROL, TOTAL AND DIRECT*NORMAL BILIRUBIN CONTROL, TOTAL AND DIRECT*ELEVATED 21H-Biline-8,12-dipropanoicacid,2,17-diethenyl- 1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl- 1,10,19,22,23,24-hexahydro-2,7,13,17-tetramethyl-biline-12-dipropionicacid 21h-biline-8,12-dipropanoicacid,2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7 3-{2-({3-(2-Carboxyethyl)-4-methyl-5-[(Z)-(3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylid Biline-8,12-dipropionic acid, 1,10,19,22,23,24-hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl- 1，10，19，22，23，24-hexahydro-2，7，13，17-tetramethyl-1，19-dioxo-3，18-divinylbilidiene-8，12-dipropionic acid 2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetrametyl-1,19-dioxo-21H-biline-8,12-dipropanoic Acid 12-dipropanoicacid,2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-Biline-8 2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid 21H-BILINE-8,12-DIPROPANOIC ACID,2,17-DIETHENYL-1,10,19,22,23,24-HEXAHYDRO-3,7,13,18-TETRAMETHYL-1,19-DIOXO- 12-dipropanoic acid, 2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-Biline-8 21H-Biline-8,12-dipropanoic acid, 2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo- BILIRUBIN: 21H-BILINE-8,12-DIPROPANOICACID,2,17-DIETHENYL-1,10,19,22,23,24-HEXAHYDRO-3,7,13,18-TETRAMETHYL-1,19-DIOXO-, 3-[2-[[3-(2-carboxyethyl)-5-[(Z)-(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid

Chemical Properties

Definition	Red coloring matter of bile. Also occurs in blood serum as decomposition product of hemoglobin.
Appearance	Light Orange to Deep Redish-Brown Crystalline Solid
Melting point	192 °C
Boiling point	641.7°C (rough estimate)
density	1.2163 (rough estimate)
refractive index	1.6000 (estimate)
storage temp.	−20°C
solubility	aqueous acid: soluble
form	powder
pka	4.62±0.10(Predicted)
color	orange
Stability:	Stable. Refrigerate.
Water Solubility	practically insoluble
Sensitive	Light Sensitive
Merck	14,1218
BRN	74376
Cosmetics Ingredients Functions	CHELATING REDUCING ANTIOXIDANT
InChIKey	BPYKTIZUTYGOLE-IFADSCNNSA-N
SMILES	CC1=C(C=C)\C(NC1=O)=C\c2[nH]c(Cc3[nH]c(\C=C4/NC(=O)C(C=C)=C4C)c(C)c3CCC(O)=O)c(CCC(O)=O)c2C
EPA Substance Registry System	21H-Biline-8,12- dipropanoic acid, 2,17-diethenyl-1,10,19,22, 23,24-hexahydro-3,7,13,18- tetramethyl-1,19-dioxo-(635-65-4)

Safety Data

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H302-H315-H319-H335
Precautionary statements	P261-P305+P351+P338
Hazard Codes	Xn
Risk Statements	62-36/37/38-20/21/22 less more
Safety Statements	22-24/25-36-26 less more
WGK Germany	2
RTECS	DU3038000
F	8
TSCA	Yes
HS Code	29339990
Storage Class	11 - Combustible Solids

Raw materials And Preparation Products

Hazard Information

Chemical Properties

Light Orange to Deep Redish-Brown Crystalline Solid

Uses

Principal pigment of bile and constituent of many biliary calculi

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.

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.]

References

[1] DAVID G LEVITT Michael D L. Quantitative assessment of the multiple processes responsible for bilirubin homeostasis in health and disease.[J]. Clinical and Experimental Gastroenterology, 2014, 7: 307-328. DOI: 10.2147/ceg.s64283

Material Safety Data Sheet(MSDS)

Spectrum Detail

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