An alkaloid with diverse biological activities
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Tetrahydroepiberberine

Item No. 36177

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6,6a,11,14-tetrahydro-8,9-dimethoxy-12H-benzo[a]-1,3-benzodioxolo[4,5-g]quinolizine
CAS Number
38853-67-7
Synonyms
  • Sinactine
Molecular Formula
C20H21NO4
Formula Weight
339.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: soluble
SMILES
COC1=C(C=C2C(C3N(CC2)CC4=C5OCOC5=CC=C4C3)=C1)OC
InChi Code
InChI=1S/C20H21NO4/c1-22-18-8-13-5-6-21-10-15-12(3-4-17-20(15)25-11-24-17)7-16(21)14(13)9-19(18)23-2/h3-4,8-9,16H,5-7,10-11H2,1-2H3
InChi Key
UWEHVAXMSWXKRW-UHFFFAOYSA-N
Origin
Plant/Sinomenium acutum
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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    Cayman Chemical
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    Product Description

    Tetrahydroepiberberine is an alkaloid originally isolated from P. rhoeas that has diverse biological activities.1,2 It is active against the fungus C. albicans (MIC = 8 µg/ml), as well as the bacteria E. coli, P. aeruginosa, P. mirabilis, K. pneumoniae, A. baumannii, S. aureus, and B. subtilis (MICs = 32-64 µg/ml, respectively).2 Tetrahydroepiberberine (16 µg/ml) inhibits the cytopathogenic effect of parainfluenza-3 (PI-3) virus in Vero cells. It decreases the viability of HaCaT keratinocytes (IC50 = 150 µM).1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hijazi, M.A., Aboul-Ela, M., Bouhadir, K., et al. Cytotoxic activity of alkaloids from Papaver rhoeas growing in Lebanon. Rec. Nat. Prod. 11(2), 211-216 (2017).

    2. Orhana, I., Ozçelik, B., Karaoğlu, T., et al. Antiviral and antimicrobial profiles of selected isoquinoline alkaloids from Fumaria and Corydalis species. Z. Naturforsch. C. J. Biosci. 62(1-2), 19-26 (2007).