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14370

Sigma-Aldrich

Bilirubin

purum, ≥95.0% (UV)

Synonym(s):

Bile pigment, Hemetoidin

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About This Item

Empirical Formula (Hill Notation):
C33H36N4O6
CAS Number:
635-65-4
Molecular Weight:
584.66
Beilstein:
74376
EC Number:
211-239-7
MDL number:
MFCD00005499
UNSPSC Code:
12352202
PubChem Substance ID:
57647150
NACRES:
NA.25
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grade

purum

Assay

≥95.0% (UV)

form

powder

ign. residue

≤0.5%

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

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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.[1]

Application

Bilirubin has been used as an interfering substance for in vitro interference and stability tests for myoglobin, creatine kinase-MB (CK-MB), and troponin-I[2]. It has also been used as an interfering agent to test the effectiveness of the Heparin Red kit in the detection of various heparins.[3]

Biochem/physiol Actions

Bilirubin is an active oxidative DNA cleaving agent as well as an effective antioxidant agent, a hydroxyl radical quencher.[1] This bile pigment has both antioxidant and toxic properties.[1] It is a natural inhibitor of vascular smooth muscle cell proliferation (VSMCs).[4] It displays anti-inflammatory and anti-proliferative properties when used as a therapeutic agent in lung/vascular diseases.[5][6] Serum bilirubin concentration slightly above the normal levels have shown a lesser incidence of heart disease.[7] It is a potential therapeutic agent in heart transplantation and T-cell mediated immune disorders.[7]
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.

Analysis Note

λmax. ∼453 nm, mol. absorption >56100 (chloroform)

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL6435
BCCJ8864
BCCL1458
BCCH1649
BCCF8504

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Yen-Wen Wu et al.
Acta Cardiologica Sinica, 36(6), 649-659 (2020-11-26)
The rapid diagnosis of acute myocardial infarction (AMI) is a clinical and operational priority in emergency departments. Serial serum levels of cardiac biomarkers play a crucial role in the evaluation of patients presenting with acute chest pain, so that an
Stefan W Ryter et al.
American journal of respiratory cell and molecular biology, 36(2), 175-182 (2006-09-19)
Heme oxygenase (HO)-1, an inducible, low-molecular-weight stress protein, confers cellular and tissue protection in multiple models of injury and disease, including oxidative or inflammatory lung injury, ischemia/reperfusion (I/R) injuries, and vascular injury/disease. The tissue protection provided by HO-1 potentially relates
Kenichiro Yamashita et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 18(6), 765-767 (2004-02-24)
Biliverdin, a product of heme oxygenase-1 (HO-1) enzymatic action, is converted into bilirubin, which has been considered a waste product in the past. We now show that administration of biliverdin has a salutary effect in organ transplantation. A brief course
Bruno Hagenbuch et al.
Molecular aspects of medicine, 34(2-3), 396-412 (2013-03-20)
The members of the organic anion transporting polypeptide superfamily (OATPs) are classified within the SLCO solute carrier family. All functionally well characterized members are predicted to have 12 transmembrane domains and are sodium-independent transport systems that mediate the transport of
S F Asad et al.
Chemico-biological interactions, 137(1), 59-74 (2001-08-24)
Bilirubin, which is derived from its metabolic precursor biliverdin, is the end product of heme catabolism. It has been proposed as a physiological antioxidant present in human extracellular fluids. We have earlier shown that bilirubin in the presence of the
View All Related Papers

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
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      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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