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30891

Sigma-Aldrich

Biliverdin hydrochloride

≥97.0% (TLC)

Synonym(s):

Biliverdin

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¥11,000
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10 MG
¥11,000
50 MG
¥36,600

About This Item

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

¥11,000


Available to ship onApril 14, 2025Details


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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.[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

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


Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

30891-BULK:
30891-VAR:
30891-10MG:
30891-50MG:


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Certificates of Analysis (COA)

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Biological implications of heme metabolism.
Sassa, S.
Journal of Clinical Biochemistry and Nutrition, 38, 138-155 (2006)
Tracking multiple genomic elements using correlative CRISPR imaging and sequential DNA FISH
Guan J, et al.
Biophysical Journal, 112(6), 1077-1084 (2017)
Nader G Abraham et al.
Pharmacological reviews, 60(1), 79-127 (2008-03-08)
This review is intended to stimulate interest in the effect of increased expression of heme oxygenase-1 (HO-1) protein and increased levels of HO activity on normal and pathological states. The HO system includes the heme catabolic pathway, comprising HO and
Constantino Fondevila et al.
Hepatology (Baltimore, Md.), 40(6), 1333-1341 (2004-11-27)
Heme oxygenase (HO-1) provides a cellular defense mechanism during oxidative stress and catalyzes the rate-limiting step in heme metabolism that produces biliverdin (BV). The role of BV and its potential use in preventing ischemia/reperfusion injury (IRI) had never been studied.
Linear tetrapyrroles as functional pigments in chemistry and biology.
Mizutani, T. and Yagi, S.
Journal of Porphyrins and Phthalocyanines, 8, 226-237 (2004)

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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