A negative control for MAPK signaling
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LL-Z 1640-4

Item No. 19159

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3,4,7,8,9,10-hexahydro-7,8,9,16-tetrahydroxy-14-methoxy-3-methyl-1H-2-benzoxacyclotetradecin-1-one
CAS Number
66018-41-5
Synonyms
  • Antibiotic LLZ1640-4
  • (5Z)-Zeaenol
Molecular Formula
C19H24O7
Formula Weight
364.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
OC1C(O)C(O)C/C=C/C2=CC(OC)=CC(O)=C2C(OC(C)C/C=C\1)=O
InChi Code
InChI=1S/C19H24O7/c1-11-5-3-7-14(20)18(23)15(21)8-4-6-12-9-13(25-2)10-16(22)17(12)19(24)26-11/h3-4,6-7,9-11,14-15,18,20-23H,5,8H2,1-2H3/b6-4+,7-3-
InChi Key
BPOLRDGTYHVUAY-KUSYPTLRSA-N
Origin
Fungus/Curvularia sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

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    Product Description

    LL-Z 1640-4 is a cis-enol resorcylic acid lactone that has been shown to exhibit both antiviral and antiprotozoan activity.1 While LL-Z 1640-4 is inactive against JNK/p38 kinase signaling, its companion antibiotic, (5Z)-7-oxo zeaenol (Item No. 17459), has been identified as an irreversible inhibitor of the MAP3K TAK1, blocking T cell activation.2 Thus, LL-Z 1640-4 is useful as negative control to help dissect the selectivity of this MAP3K inhibitor.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ellestad, G.A., Lovell, F.M., Perkinson, N.A., et al. New zearalenone related macrolides and isocoumarins from an unidentified fungus. The Journal of Organic Chemistry 43(12), 2339-2343 (1978).

    2. Sellès, P., and Lett, R. Convergent stereospecific synthesis of LL-Z1640-2 (or C292), hypothemycin and related macrolides. Part 2. Tetrahedron Lett. 43(26), 4627-4631 (2002).