An isoflavone with diverse biological activities
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Isomer(s)
35229Genkwanin
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Calycosin

Item No. 25091

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
7-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
CAS Number
20575-57-9
Molecular Formula
C16H12O5
Formula Weight
284.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 25 mg/ml
λmax
219, 249, 291 nm
SMILES
OC1=CC=C(C(C(C2=CC(O)=C(OC)C=C2)=CO3)=O)C3=C1
InChi Code
InChI=1S/C16H12O5/c1-20-14-5-2-9(6-13(14)18)12-8-21-15-7-10(17)3-4-11(15)16(12)19/h2-8,17-18H,1H3
InChi Key
ZZAJQOPSWWVMBI-UHFFFAOYSA-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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    5 mg

    $90

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    10 mg

    $168

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    25 mg

    $392

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    50 mg

    $653

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    Cayman Chemical
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    Product Description

    Calycosin is an isoflavone and phytoestrogen with diverse biological activities.1,2,3,4,5,6 It is an estrogen receptor (ER) partial agonist that inhibits 17β-estradiol binding to ERα and ERβ (IC50s = 83.14 and 40.38 μM, respectively).1 Calycosin induces tube formation by human umbilical vein endothelial cells (HUVECs) in a Matrigel™ assay and angiogenesis in zebrafish via activation of ERs and ERK1/2. It has antiplasmodial and antiprotozoal activities, reducing the growth of the poW and Dd2 strains of P. falciparum (IC50s = 4.2 and 9.8 μg/ml, respectively) and exhibiting selective toxicity for T. brucei brucei over Vero cells (IC50s = 12.7 and 159 μM, respectively).2,3 Calycosin scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) free radicals in a cell-free assay and inhibits xanthine/xanthine oxidase-induced toxicity in PC12 cells (EC50 = 50 ng/ml).4 In vivo, calycosin (12.5 and 25 mg/kg) reduces alanine aminotransferase (ALT) and aspartate aminotransferase (AST) activity, triglyceride accumulation, and hepatic fibrosis in a mouse model of non-alcoholic steatohepatitis (NASH).5 It also decreases infarct volume and brain edema in a rat model of focal cerebral ischemia and reperfusion injury.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tang, J.Y., Li, S., Li, Z.H., et al. Calycosin promotes angiogenesis involving estrogen receptor and mitogen-activated protein kinase (MAPK) signaling pathway in zebrafish and HUVEC. PLoS One 5(7):e11822, (2010).

    2. Kraft, C., Jenett-Siems, K., Siems, K., et al. Antiplasmodial activity of isoflavones from Andira inermis. J. Ethnopharmacol. 73(1-2), 131-135 (2000).

    3. Salem, M.M., and Werbovetz, K.A. Isoflavonoids and other compounds from Psorothamnus arborescens with antiprotozoal activities. J. Nat. Prod. 69(1), 43-49 (2006).

    4. Yu, D.-H., Bao, Y.-M., Wei, C.-L., et al. Studies of chemical constituents and their antioxidant activities from Astragalus mongholicus Bunge. Biomed. Environ. Sci. 18(5), 297-301 (2005).

    5. Duan, X., Meng, Q., Wang, C., et al. Calycosin attenuates triglyceride accumulation and hepatic fibrosis in murine model of non-alcoholic steatohepatitis via activating farnesoid X receptor. Phytomedicine 25, 83-92 (2017).

    6. Wang, Y., Ren, Q., Zhang, X., et al. Neuroprotective mechanisms of calycosin against focal cerebral ischemia and reperfusion injury in rats. Cell Physiol. Biochem. 45(2), 537-546 (2018).