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30891

Sigma-Aldrich

Biliverdin hydrochloride

≥97.0% (TLC)

Synonym(s):

Biliverdin

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About This Item

Empirical Formula (Hill Notation):
C33H34N4O6 · HCl
CAS Number:
856699-18-8
Molecular Weight:
619.11
MDL number:
MFCD06245593
UNSPSC Code:
12352204
PubChem Substance ID:
329753599
NACRES:
NA.32
Pricing and availability is not currently available.

Quality Level

100

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

Related Categories

General description

Biliverdin (BV) is considered as a near-infrared (NIR)-absorbing pigment, that is endogenic.[1] It is a linear tetrapyrrolic intermediate of heme degradation (heme catabolism) to bilirubin.[2][3] 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[4]
  • 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)[5]
  • to add to Fucci-containing cells to improve the mIFP signal[6]
  • to examine its impact on infrared fluorescent protein (iRFP) in some retinal preparations[7]

Biochem/physiol Actions

Biliverdin (BV) is an excellent anti-inflammatory agent that protects against lipopolysaccharides (LPS)-induced lung injury in mouse endothelial cells.[8] It aids protection in polymicrobial sepsis.[9] Biliverdin has cytoprotective effects on rat livers and protects from prolonged ischemia and reperfusion injury.[10] It also shows antioxidant activities.[11]

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM5508
BCCL8464
BCCK7496
BCCK0030
BCCH6183

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Marking cells with infrared fluorescent proteins to preserve photoresponsiveness in the retina
Fyk-Kolodziej B, et al.
Biotechniques, 57(5), 245-253 (2014)
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.
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
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
Min-Hyung Ryu et al.
Proceedings of the National Academy of Sciences of the United States of America, 111(28), 10167-10172 (2014-07-02)
Bacteriophytochromes sense light in the near-infrared window, the spectral region where absorption by mammalian tissues is minimal, and their chromophore, biliverdin IXα, is naturally present in animal cells. These properties make bacteriophytochromes particularly attractive for optogenetic applications. However, the lack
View All Related Papers

Questions

1–4 of 4 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    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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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    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.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      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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  3. What is the refractive index and absorption index of Biliverdin Hydrochloride (30891)?

    1 answer

    1. There are no specific quality tests performed on this product to verify refractive or absorption properties. There are some details available in scientific literature for spectral properties with authors at the Chinese Academy of Science describing bilverdin as a NIR absorbing pigment. Please see the citation below for more details and refer specifically to figure 1B on page 2 of the publication.

      R. R. Xing, Q. L. Zou, C. Q. Yuan, L. Y. Zhao, R. Chang, X. H. Yan, Advanced Materials 2019, 31, 1900822. https://doi.org/10.1002/adma.201900822

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  4. Is Biliverdin hydrochloride #30891 suitable for preparing a Biliverdin solution?

    1 answer

    1. Product 30891 is a solid and can be reconstituted to make a solution. Biliverdin (hydrochloride) can be dissolved in organic solvents such as DMSO and dimethyl formamide (DMF) that should be purged with an inert gas, with a solubility of approximately 20 mg/ml. However, it is sparingly soluble in aqueous buffers.

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