A beta-acid
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Lupulone

Item No. 28481

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-(3-methyl-1-oxobutyl)-2,4-cyclohexadien-1-one
CAS Number
468-28-0
Molecular Formula
C26H38O4
Formula Weight
414.6
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Methanol: slightly soluble
SMILES
O=C1C(C/C=C(C)/C)(C/C=C(C)/C)C(O)=C(C(CC(C)C)=O)C(O)=C1C/C=C(C)/C
InChi Code
InChI=1S/C26H38O4/c1-16(2)9-10-20-23(28)22(21(27)15-19(7)8)25(30)26(24(20)29,13-11-17(3)4)14-12-18(5)6/h9,11-12,19,28,30H,10,13-15H2,1-8H3
InChi Key
WPVSVIXDXMNGGN-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    1 mg

    $49

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    5 mg

    $223

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    10 mg

    $423

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    Cayman Chemical
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    Product Description

    Lupulone is a beta-acid that has been found in the hop plant, H. lupulus, and has diverse biological activities, including antibacterial, antioxidant, and anticarcinogenic properties.1,2,3 Lupulone is active against B. subtilis and S. aureus (MICs = 1 and 1.2 µg/ml, respectively), as well as T. b. brucei and L. m. mexicana (IC50s = 0.9 and 4.7 µg/ml, respectively).1,2 It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) radicals in a cell-free assay and inhibits lipid peroxidation in rat brain homogenates (IC50s = 25 and 39 µM, respectively).4 It reduces proliferation, migration, and capillary tube formation in human umbilical vein endothelial cells (HUVECs) when used at concentrations ranging from 2.5 to 50 µg/ml.5 Lupulone (40 µg/ml) activates the extrinsic apoptotic death pathway in SW480 and SW620 colon cancer cells.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Teuber, M., and Schmalreck, A.F. Membrane leakage in Bacillus subtilis 168 induced by the hop constituents lupulone, humulone, isohumulone and humulinic acid. Arch. Mikrobiol. 94(2), 159-171 (1973).

    2. Bocquet, L., Sahpaz, S., Bonneau, N., et al. Phenolic compounds from Humulus lupulus as natural antimicrobial products: New weapons in the fight against methicillin resistant Staphylococcus aureus, Leishmania mexicana and Trypanosoma brucei strains. Molecules 24(6), 1024 (2019).

    3. Lamy, V., Roussi, S., Chaabi, M., et al. Lupulone, a hop bitter acid, activates different death pathways involving apoptotic TRAIL-receptors, in human colon tumor cells and in their derived metastatic cells. Apoptosis 13(10), 1232-1242 (2008).

    4. Tagashira, M., Watanabe, M., and Uemitsu, N. Antioxidative activity of hop bitter acids and their analogues. Biosci. Biotechnol. Biochem. 59(4), 740-742 (1995).

    5. Siegel, L., Miternique-Grosse, A., Griffon, C., et al. Antiangiogenic properties of lupulone, a bitter acid of hop cones. Anticancer Res. 28(1A), 289-294 (2008).