A phthalide antibacterial agent
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.

Spirolaxine

Item No. 22063

Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-hydroxy-7-methoxy-3R-[5-[(2R,5R,7R)-2-methyl-1,6-dioxaspiro[4.5]dec-7-yl]pentyl]-1(3H)-isobenzofuranone
CAS Number
126382-01-2
Molecular Formula
C23H32O6
Formula Weight
404.5
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Methanol: Slightly Soluble: 0.1-1 mg/ml
SMILES
OC1=CC(OC)=C(C(O[C@@H]2CCCCC[C@@H]3CCC[C@]4(CC[C@@H](C)O4)O3)=O)C2=C1
InChi Code
InChI=1S/C23H32O6/c1-15-10-12-23(28-15)11-6-8-17(29-23)7-4-3-5-9-19-18-13-16(24)14-20(26-2)21(18)22(25)27-19/h13-15,17,19,24H,3-12H2,1-2H3/t15-,17-,19-,23-/m1/s1
InChi Key
CZIMFHQXGMXDMO-DGROVODQSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice 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

    500 µg

    $160

    Add

    2.5 mg

    $758

    Add
    Cayman Chemical
    Visit Our Cancer Resource Center
    Find Tools & Resources to Study the Hallmarks of Cancer
    • Cancer cell signaling & regulation
    • Cancer metabolism
    • Tumor microenvironment
    EXPLORE NOW
    Product Description

    Spirolaxine is a long-chain phthalide produced by the fungus S. laxum that has antibacterial properties.1,2 Spirolaxine is a potent anti-H. pylori agent (MIC = 0.2 µg/cm3) with weak activity against E. coli.2,3 Spirolaxine (1-40 µM) inhibits proliferation of endothelial (BMEC, HUVEC) and tumor (LoVo, HL-60) cells in culture.4 B. megaterium and C. echinulate produce hydroxylated metabolites of spirolaxine when given spirolaxine as a substrate.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Arnone, A., Assante, G., Nasini, G., et al. Spirolaxine and sporotricale: Two long-chain phthalides produced by Sporotrichum laxum. Phytochemistry 29(2), 613-616 (1990).

    2. Guadliana, M.A., Huang, L.H., and Kaneko, T. Process for preparing spirolaxine and spirolaxine methyl ether. (2000).

    3. León, A., Del-Ángel, M., Ávila, J.L., et al. Phthalides: Distribution in nature, chemical reactivity, synthesis, and biological activity. Prog. Chem. Org. Nat. Prod. 104, 127-246 (2017).

    4. Giannini, G., Pisano, C., Riccioni, T., et al. Spirolaxine, a fungal metabolite from Sporotrichum laxum: Determination of relative stereochemistry and biological activity in vitro. Proc. Amer. Assoc. Cancer Res. 64(7), (2004).

    5. Nasini, G., Bava, A., Fronza, G., et al. Microbial transformation of spirolaxine, a bioactive undecaketide fungal metabolite from the basidiomycete Sporotrichum laxum. Chem. Biodivers. 4(12), 2772-2779 (2007).