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About This Item
Empirical Formula (Hill Notation):
C33H36N4O6
CAS Number:
Molecular Weight:
584.66
UNSPSC Code:
12352202
NACRES:
NA.77
PubChem Substance ID:
EC Number:
211-239-7
Beilstein/REAXYS Number:
74376
MDL number:
description
mixed isomers
Quality Level
assay
≥98% (EmM/453 = 60)
form
powder
solubility
aqueous acid: soluble, aqueous base: soluble, benzene: soluble, chloroform: soluble
storage temp.
−20°C
SMILES string
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
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-
InChI key
BPYKTIZUTYGOLE-IFADSCNNSA-N
General description
Bilirubin, an end product of heme catabolism, forms from the breakdown of erythrocyte hemoglobin in the reticuloendothelial system. Heme oxygenase converts the heme of hemoglobin to biliverdin, and subsequently an NADPH-dependent biliverdin reductase converts biliverdin to bilirubin.
Bilirubin is commonly found bound to serum albumin, when circulating in blood, in its dianion form. Bilirubin is also associated with bile salts, in its monoanion form.
Disorders of hyperbilirubinemia may occur due to increased bilirubin synthesis or decreased bilirubin clearance.
Bilirubin is commonly found bound to serum albumin, when circulating in blood, in its dianion form. Bilirubin is also associated with bile salts, in its monoanion form.
Disorders of hyperbilirubinemia may occur due to increased bilirubin synthesis or decreased bilirubin clearance.
Application
Bilirubin has been used:
- in phantom preparation
- in in vitro experiments
- in the preparation of bilirubin solutions for infusion
Biochem/physiol Actions
Bilirubin has been studied for its properties as an endogenous antioxidant, such as for its capabilities to scavenge reactive oxygen species (ROS) and to inhibit NADPH-oxidase activity. It appears to function as an efficient peroxyl radical scavenger, protecting membrane lipids from oxidation by these radicals. At nanomolar concentrations it has been shown to protect neurons from oxidative damage.
Well over 99% of total bilirubin is transported as a conjugate with albumin. Abnormally high levels of bilirubin can cause severe neurological damage, but mildly elevated levels are linked to protection from oxidative stress.
Other Notes
A major component of hemoglobin decomposition. The principal pigment of bile, and the yellow color in jaundice.
Disclaimer
Protect from light.
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Storage Class
11 - Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Related Content
Changes in the auditory brainstem response associated with intravenous infusion of unconjugated bilirubin into infant rhesus monkeys
Ahlfors C E, et al.
Pediatric Research, 20(6), 511-511 (1986)
Photoacoustic microscopy of bilirubin in tissue phantoms
Zhou y, et al.
Journal of Biomedical Optics, 17(12), 126019-126019 (2012)
Bhargavi Kamineni et al.
Journal of tropical pediatrics, 66(6), 630-636 (2020-05-21)
Early diagnosis and appropriate management of neonatal jaundice is crucial in avoiding severe hyperbilirubinemia and brain injury. A low-cost, minimally invasive, point-of-care (PoC) tool for total bilirubin (TB) estimation which can be useful across all ranges of bilirubin values and
Global Trade Item Number
| SKU | GTIN |
|---|---|
| B4126-1G | 04061833429198 |
| B4126-5G | 04061833429204 |