A cyclohexanone
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Ambuic Acid

Item No. 27483

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2E)-4-[(1R,5R,6R)-3-(1E)-1-hepten-1-yl-5-hydroxy-4-(hydroxymethyl)-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-1-yl]-2-methyl-2-butenoic acid
CAS Number
340774-69-8
Synonyms
  • (+)-Ambuic Acid
Molecular Formula
C19H26O6
Formula Weight
350.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: solubleEthanol: solubleMethanol: soluble
SMILES
OCC1=C(/C=C/CCCCC)C([C@@]2(C/C=C(C)/C(O)=O)[C@H](O2)[C@@H]1O)=O
InChi Code
InChI=1S/C19H26O6/c1-3-4-5-6-7-8-13-14(11-20)15(21)17-19(25-17,16(13)22)10-9-12(2)18(23)24/h7-9,15,17,20-21H,3-6,10-11H2,1-2H3,(H,23,24)/b8-7+,12-9+/t15-,17-,19+/m1/s1
InChi Key
UDSQZJMGPSRCEM-HDKVZZTHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Cayman Chemical
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    Product Description

    Ambuic acid is a cyclohexanone originally isolated from Pestalotiopsis and Monochaetia species that has phytopathogenic antifungal, quorum sensing inhibitory, and antibacterial activities.1,2,3 It is active against P. ultimum (MIC = 7.5 µg/ml) and inhibits the growth of a variety of other phytopathogenic fungi, including F. solani, H. sativum, and C. gramineum, but not P. oryzae, R. solani, or B. cinerea. Ambuic acid inhibits the biosynthesis of cyclic peptides involved in quorum sensing, including gelatinase biosynthesis-activating pheromone (GBAP) in E. faecalis, autoinducing peptide I (AIP-I) in S. aureus, and LsrD698 and LsrD826 in L. innocua.2 It suppresses abcess formation in a mouse model of skin infection induced by methicillin-resistant S. aureus (MRSA) when administered at a dose of 5 µg and decreases the activity of the agr quorum sensing system in an in vivo reporter assay.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Li, J.Y., Harper, J.K., Grant, D.M., et al. Ambuic acid, a highly functionalized cyclohexenone with antifungal activity from Pestalotiopsis spp. and Monochaetia sp. Phytochemistry 56(5), 563-468 (2001).

    2. Nakayama, J., Uemura, Y., Nishiguchi, K., et al. Ambuic acid inhibits the biosynthesis of cyclic peptide quormones in gram-positive bacteria. Antimicrob. Agents Chemother. 53(2), 580-586 (2009).

    3. Todd, D.A., Parlet, C.P., Crosby, H.A., et al. Signal biosynthesis inhibition with ambuic acid as a strategy to target antibiotic-resistant infections. Antimicrob. Agents Chemother. 61(8), 1-11 (2017).