A fecal pigment and metabolite of bilirubin
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Stercobilin (hydrochloride)

Item No. 36509

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R,3R,4S,16S,17R,18R)-3,18-diethyl-1,2,3,4,5,15,16,17,18,19,22,24-dodecahydro-2,7,13,17-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid, hydrochloride
Synonyms
  • (–)-Stercobilin
  • L-Stercobilin
Molecular Formula
C33H46N4O6 • XHCl
Formula Weight
594.8
Purity
≥95% (mixture of isomers)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleNaOH (aq): Soluble
λmax
488 nm
SMILES
OC(CCC1=C(C)C(C[C@@H]2NC([C@H](CC)[C@H]2C)=O)=N/C1=C\C3=C(CCC(O)=O)C(C)=C(C[C@@H]4NC([C@H](C)[C@H]4CC)=O)N3)=O.Cl
InChi Code
InChI=1S/C33H46N4O6.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;/h15-16,19-21,26-27,35H,7-14H2,1-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41);1H/b28-15-;/t16-,19-,20-,21-,26+,27+;/m1./s1
InChi Key
WPZBPYPTZWWARY-JRFVQKEISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $85

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    5 mg

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    Cayman Chemical
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    Product Description

    Stercobilin is a fecal pigment and a metabolite of the heme catabolite bilirubin (Item No. 17161).1 It induces DNA damage in a comet assay in HepG2 cells when used at concentrations ranging from 0.5 to 17 µM.2 Stercobilin (20 and 30 µM) induces activation of NF-κB in a reporter assay and increases the expression of the genes encoding TNF-α, IL-1β, IL-6, inducible nitric oxide synthase (iNOS), and COX-2 in RAW 264.7 macrophages.3 Fecal and plasma levels of stercobilin are increased in ob/ob mice.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Vítek, L., Majer, F., Muchová, L., et al. Identification of bilirubin reduction products formed by Clostridium perfringens isolated from human neonatal fecal flora. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 833(2), 149-157 (2006).

    2. Mölzer, C., Pfleger, B., Putz, E., et al. In vitro DNA-damaging effects of intestinal and related tetrapyrroles in human cancer cells. Exp. Cell Res. 319(4), 536-545 (2013).

    3. Sanada, S., Suzuki, T., Nagata, A., et al. Intestinal microbial metabolite stercobilin involvement in the chronic inflammation of ob/ob mice. Sci. Rep. 10(1), 6479 (2020).