A β-acid with diverse biological activities
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Colupulone

Item No. 34048

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3,5-dihydroxy-2,6,6-tris(3-methyl-2-buten-1-yl)-4-(2-methyl-1-oxopropyl)-2,4-cyclohexadien-1-one
CAS Number
468-27-9
Synonyms
  • NSC 650561
Molecular Formula
C25H36O4
Formula Weight
400.6
Purity
≥95% (mixture of isomers)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: solubleMethanol: soluble
SMILES
O=C(C(C)C)C(C(O)=C1C/C=C(C)\C)=C(O)C(C/C=C(C)\C)(C/C=C(C)\C)C1=O
InChi Code
InChI=1S/C25H36O4/c1-15(2)9-10-19-22(27)20(21(26)18(7)8)24(29)25(23(19)28,13-11-16(3)4)14-12-17(5)6/h9,11-12,18,27,29H,10,13-14H2,1-8H3
InChi Key
GEXOPZHAKQAGLU-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Cayman Chemical
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    Product Description

    Colupulone is a β-acid that has been found in H. lupulus and has diverse biological activities.1,2,3 It activates the pregnane X receptor (PXR) in a reporter assay when used at concentrations of 1, 3, and 10 µM.1 Dietary administration of colupulone (0.18% w/w) induces hepatic cytochrome P450 (CYP) isoform 3A (CYP3A) activity in mice.2 It also decreases serum glucose levels in non-diabetic mice and increases serum glucose levels in db/db mice.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Teotico, D.G., Bischof, J.J., Peng, L., et al. Structural basis of human pregnane X receptor activation by the hops constituent colupulone. Mol. Pharmacol. 74(6), 1512-1520 (2008).

    2. Mannering, G.J., Shoeman, J.A., and Deloria, L.B. Identification of the antibiotic hops component, colupulone, as an inducer of hepatic cytochrome P-4503A in the mouse. Drug Metab. Dispos. 20(2), 142-147 (1992).

    3. Mannering, G.J., Shoeman, J.A., and Shoeman, D.W. Effects of colupulone, a component of hops and brewers yeast, and chromium on glucose tolerance and hepatic cytochrome P450 in nondiabetic and spontaneously diabetic mice. Biochem. Biophys. Res. Commun. 200(3), 1455-1462 (1994).