A chalcone and flavonoid with diverse biological activities
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Isomer(s)
19873Isobavachalcone
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Bavachalcone

Item No. 34673

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2E)-1-[2,4-dihydroxy-5-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one
CAS Number
28448-85-3
Synonyms
  • Broussochalcone B
Molecular Formula
C20H20O4
Formula Weight
324.4
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
λmax
377 nm
SMILES
OC(C=C1)=CC=C1/C=C/C(C2=CC(C/C=C(C)\C)=C(C=C2O)O)=O
InChi Code
InChI=1S/C20H20O4/c1-13(2)3-7-15-11-17(20(24)12-19(15)23)18(22)10-6-14-4-8-16(21)9-5-14/h3-6,8-12,21,23-24H,7H2,1-2H3/b10-6+
InChi Key
BLZGPHNVMRXDCB-UXBLZVDNSA-N
Origin
Plant/Psoralea corylifolia
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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    10 mg

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    25 mg

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    Product Description

    Bavachalcone is a polyketide synthase-derived chalcone and flavonoid that has been found in P. corylifolia and has diverse biological activities.1,2,3,4,5 It inhibits α-glucosidase and the UDP-glucuronosyltransferase (UGT) isoforms UGT1A1 and UGT1A7 (IC50s = 11.1, 11.3, and 3.6 µM, respectively).2,3 Bavachalcone is cytotoxic to K562 chronic myeloid leukemia cells (IC50 = 2.77 µM).4 It inhibits RANKL-induced osteoclastogenesis of isolated mouse bone marrow-derived macrophages (BMDMs) when used at a concentration of 5 µg/ml.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Zhou, K., Yang, S., and Li, S.-M. Naturally occurring prenylated chalcones from plants: Structural diversity, distribution, activities and biosynthesis. Nat. Prod. Rep. (2021).

    2. Ryu, H.W., Lee, B.W., Curtis-Long, M.J., et al. Polyphenols from Broussonetia papyrifera displaying potent α-glucosidase inhibition. J. Agric. Food Chem. 58(1), 202-208 (2010).

    3. Shan, L., Yang, S., Zhang, G., et al. Comparison of the inhibitory potential of bavachalcone and corylin against UDP-glucuronosyltransferases. Evid. Based Complement. Alternat. Med. 958937 (2014).

    4. Wang, H.-M., Zhang, L., Liu, J., et al. Synthesis and anti-cancer activity evaluation of novel prenylated and geranylated chalcone natural products and their analogs. Eur. J. Med. Chem. 92, 439-448 (2015).

    5. Park, C.K., Lee, Y., Chang, E.-J., et al. Bavachalcone inhibits osteoclast differentiation through suppression of NFATc1 induction by RANKL. Biochem. Pharmacol. 75(11), 2175-2182 (2008).