An HMG-CoA synthase inhibitor
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.

Hymeglusin

Item No. 11899

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
11-[3R-(hydroxymethyl)-4-oxo-2R-oxetanyl]-3,5,7R-trimethyl-2E,4E-undecadienoic acid
CAS Number
29066-42-0
Synonyms
  • Antibiotic 1233A
  • Antibiotic F 244
  • L 659,699
Molecular Formula
C18H28O5
Formula Weight
324.4
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Chloroform: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
OC[C@@H](C1=O)[C@H](O1)CCCC[C@@H](C)C/C(C)=C/C(C)=C/C(O)=O
InChi Code
InChI=1S/C18H28O5/c1-12(8-13(2)9-14(3)10-17(20)21)6-4-5-7-16-15(11-19)18(22)23-16/h9-10,12,15-16,19H,4-8,11H2,1-3H3,(H,20,21)/b13-9+,14-10+/t12-,15-,16-/m1/s1
InChi Key
ODCZJZWSXPVLAW-KXCGKLMDSA-N
Origin
Fungus/Scopulariopsis sp. F-244
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

    $137

    Add

    1 mg

    $233

    Add

    2.5 mg

    $546

    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

    Hymeglusin is a fungal β-lactone antibiotic that inhibits HMG-CoA synthase (IC50 = 0.12 μM) by covalently modifying the active Cys129 residue of the enzyme.1,2 At a dose of 25 mg/kg, hymeglusin inhibits cholesterol biosynthesis in rats by 45%.1 Chiral studies indicate that the (2R,3R)-β-lactone moiety of hymeglusin is important for eliciting the specific inhibition of HMG-CoA synthase.3 As a cell-wall targeting antibiotic, hymeglusin has been used to investigate the role of a gene important for controlling S. aureus virulence in a mouse sepsis model of infection.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Greenspan, M.D., Yudkovitz, J.B., Lo, C.Y., et al. Inhibition of hydroxymethylglutaryl-coenzyme A synthase by L-659,699. Proc. Natl. Acad. Sci. USA 84(21), 7488-7492 (1987).

    2. Tomoda, H., Ohbayashi, N., Morikawa, Y., et al. Binding site for fungal β-lactone hymeglusin on cytosolic 3- hydroxy-3-methylglutaryl coenzyme A synthase. Biochim. Biophys. Acta 1636(1), 22-28 (2004).

    3. Tomoda, H., Ohbayashi, N., Kumagai, H., et al. Differential inhibition of HMG-CoA synthase and pancreatic lipase by the specific chiral isomers of β-lactone DU-6622. Biochem. Bioph. Res. Commun. 265(2), 536-540 (1999).

    4. Balibar, C.J., Shen, X., McGuire, D., et al. cwrA, a gene that specifically responds to cell wall damage in Staphylococcus aureus. Microbiology 156(Pt 5), 1372-1383 (2010).