An alkaloid with insecticidal activity
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(S)-Canadine

Item No. 33805

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5,8,13,13aS-tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine
CAS Number
5096-57-1
Synonyms
  • (–)-Canadine
  • (S)-Tetrahydroberberine
Molecular Formula
C20H21NO4
Formula Weight
339.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: slightly solubleMethanol: very slightly, heated
SMILES
COC1=C2CN3[C@](CC2=CC=C1OC)([H])C4=CC(OCO5)=C5C=C4CC3
InChi Code
InChI=1S/C20H21NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,8-9,16H,5-7,10-11H2,1-2H3/t16-/m0/s1
InChi Key
VZTUIEROBZXUFA-INIZCTEOSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $29

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    5 mg

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    10 mg

    $212

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    Cayman Chemical
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    Product Description

    (S)-Canadine is an alkaloid and intermediate in the biosynthesis of berberine (Item No. 10006427) that has been found in H. canadensis.1,2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Malhotra, S., Taneja, S.C., and Dhar, K.L. Minor alkaloid from Coscinium fenestratum. Phytochem. 28(7), 1998-1999 (1989).

    2. Galanie, S., and Smolke, C.D. Optimization of yeast-based production of medicinal protoberberine alkaloids. Microb. Cell Fact. 14, 144 (2015).

    3. Leyte-Lugo, M., Britton, E.R., Foil, D.H., et al. Secondary metabolites from the leaves of the medicinal plant goldenseal (Hydrastis canadensis). Phytochem. Lett. 20, 54-60 (2017).