A natural eNOS 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.

Iromycin A

Item No. 19621

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6-[(2E,5E)-3,7-dimethyl-2,5-octadien-1-yl]-4-hydroxy-3-methyl-5-propyl-2(1H)-pyridinone
CAS Number
213137-53-2
Synonyms
  • NK 26588
Molecular Formula
C19H29NO2
Formula Weight
303.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleMethanol: Slightly Soluble
SMILES
CC1=C(O)C(CCC)=C(C/C=C(C)/C/C=C/C(C)C)NC1=O
InChi Code
InChI=1S/C19H29NO2/c1-6-8-16-17(20-19(22)15(5)18(16)21)12-11-14(4)10-7-9-13(2)3/h7,9,11,13H,6,8,10,12H2,1-5H3,(H2,20,21,22)/b9-7+,14-11+
InChi Key
HVAVEUHAOCVIPN-DTCTWCMCSA-N
Origin
Bacterium/Streptomyces bottropensis
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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

    $248

    Add

    1 mg

    $393

    Add
    Product Description

    Iromycin A is a bacterial pyridone metabolite that inhibits nitric oxide synthase (NOS) activity, with selectivity for NOS III (endothelial NOS) over NOS I (neuronal NOS).1,2 Iromycin metabolites and derivatives block NADH oxidation in beef heart submitochondrial particles (IC50 = 0.461 µM for iromycin A).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Shojaei, H., Li-Böhmer, Z., and von Zezschwitz, P. Iromycins: A new family of pyridone metabolites from Streptomyces sp. II. Convergent total synthesis. The Journal of Organic Chemistry 72(14), 5091-5097 (2007).

    2. Surup, F., Wagner, O., von Frieling, J., et al. The iromycins, a new family of pyridone metabolites from Streptomyces sp. I. Structure, NOS inhibitory activity, and biosynthesis. The Journal of Organic Chemistry 72(14), 5085-5090 (2007).

    3. Surup, F., Shojaei, H., von Zezschwitz, P., et al. Iromycins from Streptomyces sp. and from synthesis: New inhibitors of the mitochondrial electron transport chain. Bioorg. Med. Chem. 16(4), 1738-1746 (2008).