A kavalactone with affinity for the CB1 receptor
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Analytical Standard(s)
33883Yangonin41211Yangonin (CRM)
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Yangonin

Item No. 14351

Product Insert (PDF)GC-MS (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-methoxy-6-[(1E)-2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one
CAS Number
500-62-9
Molecular Formula
C15H14O4
Formula Weight
258.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 5 mg/mlDMSO:PBS (pH 7.2) (1:2): 0.3 mg/ml
λmax
218, 267, 357 nm
SMILES
COC1=CC=C(/C=C/C(O2)=CC(OC)=CC2=O)C=C1
InChi Code
InChI=1S/C15H14O4/c1-17-12-6-3-11(4-7-12)5-8-13-9-14(18-2)10-15(16)19-13/h3-10H,1-2H3/b8-5+
InChi Key
XLHIYUYCSMZCCC-VMPITWQZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

    $69

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    5 mg

    $198

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    10 mg

    $297

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    25 mg

    $655

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    Cayman Chemical
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    Product Description

    Yangonin is a natural kavalactone from the kava plant, P. methysticum1. It enhances the binding of bicuculline at the γ-amino butyric acid (GABA) receptor GABAA at 1.0 µM. Yangonin also binds the central cannabinoid (CB1) receptor with a Ki value of 0.72 µM.2 Yangonin blocks the activation of NF-κB by TNF-α.3 It also inhibits anchorage-dependent and independent growth of bladder cancer cell lines through induction of autophagic cell death (IC50s = 15-59 mg/ml).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Boonen, G., and Häberlein, H. Influence of genuine kavapyrone enantiomers on the GABAA binding site. Planta Med. 64(6), 504-506 (1998).

    2. Ligresti, A., Villano, R., Allará, M., et al. Kavalactones and the endocannabinoid system: The plant-derived yangonin is a novel CB1 receptor ligand. Pharmacol. Res. 66(2), 163-169 (2012).

    3. Ma, J., Liang, H., Jin, H.R., et al. Yangonin blocks tumor necrosis factor-α-induced nuclear factor-κB-dependent transcription by inhibiting the transactivation potential of the RelA/p65 subunit. J. Pharmacol. Sci. 118(4), 447-454 (2012).

    4. Zhongbo, L., U-Syn, H., Ke, Y., et al. Kavalactone yangonin induces autophagy and sensitizes bladder cancer cells to flavokawain A and docetaxel via inhibition of the mTOR pathway. J. Biomed. Res. 31(5), 408-418 (2017).