An esterase inhibitor
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Ebelactone A

Item No. 19163

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3S,4S)-4-[(1S,3E,5R,7S,8R,9R)-8-hydroxy-1,3,5,7,9-pentamethyl-6-oxo-3-undecen-1-yl]-3-methyl-2-oxetanone
CAS Number
76808-16-7
Synonyms
  • (−)-Ebelactone A
  • NSC 335650
Molecular Formula
C20H34O4
Formula Weight
338.5
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 25 mg/mlEthanol: 20 mg/ml
SMILES
C/C(C[C@H](C)[C@]1([H])OC([C@H]1C)=O)=C\[C@@H](C)C([C@@H](C)[C@H](O)[C@H](C)CC)=O
InChi Code
InChI=1S/C20H34O4/c1-8-12(3)17(21)15(6)18(22)13(4)9-11(2)10-14(5)19-16(7)20(23)24-19/h9,12-17,19,21H,8,10H2,1-7H3/b11-9+/t12-,13-,14+,15+,16+,17-,19+/m1/s1
InChi Key
WOISDAHQBUYEAF-QIQXJRRPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 µg

    $69

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    1 mg

    $106

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    Product Description

    Ebelactone A is a β-lactone enzyme inhibitor that was first isolated from a cultured strain of soil actinomycetes.1 It can inhibit esterases, lipases, and N-formylmethionine aminopeptidases (IC50s = 0.056, 0.003, and 0.08 µg/ml, respectively) found on cell surfaces, which has been shown to stimulate host defense in immune cells.2 Ebelactone A is also reported to inhibit cutinases produced by fungal pathogens, thus demonstrating a plant-protective function.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Uotani, K., Naganawa, H., Kondo, S., et al. Structural studies on ebelactone A and B, esterase inhibitors produced by actinomycetes. J. Antibiot. (Tokyo) 35(11), 1495-1499 (1982).

    2. Umezawa, H., Aoyagi, T., Uotani, K., et al. Ebelactone, an inhibitor of esterase, produced by actinomycetes. J. Antibiot. (Tokyo) 33(12), 1594-1596 (1980).

    3. Köller, W., Trail, F., and Parker, D.M. Ebelactones inhibit cutinases produced by fungal plant pathogens. J. Antibiot. (Tokyo) 43(6), 734-735 (1990).