A pyrrolizidine alkaloid with antibacterial and hepatotoxic activities
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Usaramine

Item No. 34894

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3E,5R,6S,14aR,14bR)-3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-(hydroxymethyl)-5-methyl-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione
CAS Number
15503-87-4
Synonyms
  • Mucronatine
  • trans-Retrorsine
  • (+)-Usaramine
Molecular Formula
C18H25NO6
Formula Weight
351.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: insolDMSO: 1 mg/mlEthanol: insolPBS (pH 7.2): 5 mg/ml
SMILES
O=C1O[C@@]2([H])[C@@]3([H])C(COC([C@](O)([C@@H](C/C1=C\C)C)CO)=O)=CCN3CC2
InChi Code
InChI=1S/C18H25NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/b12-3+/t11-,14-,15-,18-/m1/s1
InChi Key
BCJMNZRQJAVDLD-FXGRWVCYSA-N
Origin
Plant/Crotalaria pallida
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    1 mg

    $69

    Add

    5 mg

    $297

    Add

    10 mg

    $525

    Add

    25 mg

    $1,062

    Add
    Cayman Chemical
    Neutrophil Biology Wall Poster

    Explore how neutrophils shape the immune response in health and disease. This poster highlights neutrophil pathogen defense mechanisms, including phagocytosis, degranulation, and NETosis, as well as neutrophil roles in inflammation and NET-associated pathologies.

    DOWNLOAD NOW
    Product Description

    Usaramine is a pyrrolizidine alkaloid that has been found in C. pallida and has antibacterial and hepatotoxic activities.1,2 It reduces biofilm formation by S. epidermidis but not P. aeruginosa when used at a concentration of 1 mg/ml.1 Usaramine (0.05, 0.1, and 0.2 mmol/kg) induces liver necrosis in rats.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. da Silva Negreiros Neto, T., Gardner, D., Hallwass, F., et al. Activity of pyrrolizidine alkaloids against biofilm formation and Trichomonas vaginalis. Biomed. Pharmacother. 83, 323-329 (2016).

    2. Culvenor, C.C.J., Edgar, J.A., Jago, M.V., et al. Hepato- and pneumotoxicity of pyrrolizidine alkaloids and derivatives in relation to molecular structure. Chem. Biol. Interact. 12(3-4), 299-324 (1976).