A diterpenoid with diverse biological 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.

Kirenol

Item No. 26212

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(α7R,1R,3S,4aS,4bR,7S,10aS)-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-3-hydroxy-α7-(hydroxymethyl)-1,4a,7-trimethyl-1,7-phenanthrenedimethanol
CAS Number
52659-56-0
Molecular Formula
C20H34O4
Formula Weight
338.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlEthanol: 5 mg/ml
SMILES
OC[C@H](O)[C@]1(C)C=C2CC[C@]3([H])[C@@](CO)(C)C[C@@H](O)C[C@@]3(C)[C@]2([H])CC1
InChi Code
InChI=1S/C20H34O4/c1-18(17(24)11-21)7-6-15-13(8-18)4-5-16-19(2,12-22)9-14(23)10-20(15,16)3/h8,14-17,21-24H,4-7,9-12H2,1-3H3/t14-,15-,16-,17+,18+,19+,20+/m1/s1
InChi Key
NRYNTARIOIRWAB-JPDRSCFKSA-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

    5 mg

    $69

    Add

    10 mg

    $120

    Add

    25 mg

    $233

    Add
    Lipid Resource Center
    Discover Products & Resources for Lipid Research
    • High-purity lipid standards
    • Lipid roles in biology
    • Lipids in health & disease
    • Lipids for pharmaceutical development
    • Protocols, advice, & resources
    EXPLORE NOW
    Product Description

    Kirenol is a diterpenoid that has been found in S. orientalis and has diverse biological activities, including anti-arthritic and anti-inflammatory properties.1,2 It inhibits Gram-positive and Gram-negative bacterial growth in disc diffusion assays with MICs ranging from 39 to 156 and 312.5 to 625 μg/ml, respectively.3 Kirenol also reduces K652 chronic myeloid leukemia cell viability with a 48 hour IC50 value of 18.19 μg/ml and induces apoptosis.4 In vivo, kirenol (2 mg/kg, p.o.) reduces motor deficit, delays disease onset by approximately five days, and downregulates inflammatory CD4+IFN-γ+ Th1 cells and CD4+IL-17A+ Th17 cells in a mouse model of experimental autoimmune encephalomyelitis (EAE).5 Intragastric administration of kirenol (1-4 mg/kg) reduces the arthritis index, NF-kB activity, and paw swelling and increases annexin-1 expression without affecting glucocorticoid receptor α (GRα) expression in the synovium in a rat model of collagen-induced arthritis.1 Topical administration of kirenol (0.3-0.5% w/w) reduces edema induced by carrageenan, complete Freund's adjuvant (CFA), and formalin in rats up to 44, 67, and 65%, respectively.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wang, Z.-M., Zhu, S.-G., Wu, Z.-W., et al. Kirenol upregulates nuclear annexin-1 which interacts with NF-κB to attenuate synovial inflammation of collagen-induced arthritis in rats. J. Ethnopharmacol. 137(1), 774-782 (2011).

    2. Wang, J.P., Zhou, Y.-m., Ye, Y.-j., et al. Topical anti-inflammatory and analgesic activity of kirenol isolated from Siegesbeckia orientali. J. Ethnopharmacol. 137(3), 1089-1094 (2011).

    3. Wang, J.-P., Zhou, Y.-M., and Zhang, Y.-H. Kirenol production in hairy root culture of Siegesbeckea orientalis and its antimicrobial activity. Pharmacogn. Mag. 8(30), 149-155 (2012).

    4. Lu, Y., Qian, R., Xiao, J., et al. Kirenol, a compound from Herba Siegesbeckiae, induces apoptosis in human chronic myeloid leukemia K562 cells. Pharmazie 69(2), 148-153 (2014).

    5. Xiao, J., Yang, R., Yang, L., et al. Kirenol attenuates experimental autoimmune encephalomyelitis by inhibiting differentiation of Th1 and Th17 cells and inducing apoptosis of effector T cells. Sci. Rep. 5:9022, (2015).