Skip to Content
Merck
All Photos(1)

Documents

30891

Sigma-Aldrich

Biliverdin hydrochloride

≥97.0% (TLC)

Synonym(s):

Biliverdin

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C33H34N4O6 · HCl
CAS Number:
Molecular Weight:
619.11
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.32

Quality Level

Assay

≥97.0% (TLC)

form

powder or crystals

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

Cl.CC1=C(C=C)C(\NC1=O)=C\c2[nH]c(/C=C3\N=C(\C=C4/NC(=O)C(C=C)=C4C)C(C)=C3CCC(O)=O)c(CCC(O)=O)c2C

InChI

1S/C33H34N4O6.ClH/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;/h7-8,13-15,35H,1-2,9-12H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41);1H/b26-13-,27-14-,28-15-;

InChI key

KTRFJVRKVQROKS-UJCZHUFNSA-N

General description

Biliverdin (BV) is considered as a near-infrared (NIR)-absorbing pigment, that is endogenic. It is a linear tetrapyrrolic intermediate of heme degradation (heme catabolism) to bilirubin. The bile of amphibia and birds contains only biliverdine, no bilirubin.

Application

Biliverdin hydrochloride has been used:
  • as a treatment to J774A.1 cells to study its role in alternation of beta (β)-endorphins level
  • as a commercial standard for the detection of biliverdin in mouse unstable and stable plaques tissues using liquid chromatography-tandem mass spectrometry (LC-MS-MS)
  • to add to Fucci-containing cells to improve the mIFP signal
  • to examine its impact on infrared fluorescent protein (iRFP) in some retinal preparations

Biochem/physiol Actions

Biliverdin (BV) is an excellent anti-inflammatory agent that protects against lipopolysaccharides (LPS)-induced lung injury in mouse endothelial cells. It aids protection in polymicrobial sepsis. Biliverdin has cytoprotective effects on rat livers and protects from prolonged ischemia and reperfusion injury. It also shows antioxidant activities.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

T Yoshida et al.
Journal of inorganic biochemistry, 82(1-4), 33-41 (2001-01-02)
Heme oxygenase catalyzes the three step-wise oxidation of hemin to alpha-biliverdin, via alpha-meso-hydroxyhemin, verdoheme, and ferric iron-biliverdin complex. This enzyme is a simple protein which does not have any prosthetic groups. However, heme and its two metabolites, alpha-meso-hydroxyhemin and verdoheme
Marcus Overhaus et al.
American journal of physiology. Gastrointestinal and liver physiology, 290(4), G695-G703 (2006-03-16)
Highly inducible heme oxygenase (HO)-1 is protective against acute and chronic inflammation. HO-1 generates carbon monoxide (CO), ferrous iron, and biliverdin. The aim of this study was to investigate the protective effects of biliverdin against sepsis-induced inflammation and intestinal dysmotility.
Marking cells with infrared fluorescent proteins to preserve photoresponsiveness in the retina
Fyk-Kolodziej B, et al.
Biotechniques, 57(5), 245-253 (2014)
Elin Claesson et al.
eLife, 9 (2020-04-02)
Phytochrome proteins control the growth, reproduction, and photosynthesis of plants, fungi, and bacteria. Light is detected by a bilin cofactor, but it remains elusive how this leads to activation of the protein through structural changes. We present serial femtosecond X-ray
Biological implications of heme metabolism.
Sassa, S.
Journal of Clinical Biochemistry and Nutrition, 38, 138-155 (2006)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service