| Identification | Back Directory | [Name]
N-cis-octadec-9Z-enoyl-L-Homoserine lactone Exclusive | [CAS]
1400974-23-3 | [Synonyms]
N-cis-octadec-9-enoyl-L-Homoserine lactone
(Z)-N-[(3S)-2-oxooxolan-3-yl]octadec-9-enamide
N-cis-octadec-9Z-enoyl-L-Homoserine lactone Exclusive | [Molecular Formula]
C22H39NO3 | [MOL File]
1400974-23-3.mol | [Molecular Weight]
365.55 |
| Chemical Properties | Back Directory | [Boiling point ]
559.9±49.0 °C(Predicted) | [density ]
0.98±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMF: 20 mg/ml; DMSO: 20 mg/ml; DMSO:PBS(pH7.2) 1:1: 0.5 mg/ml | [form ]
A crystalline solid | [pka]
14.70±0.20(Predicted) |
| Hazard Information | Back Directory | [Description]
Quorum sensing is a regulatory process used by bacteria for controlling gene expression in response to increasing cell density. This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production. Coordinated gene expression is achieved by the production, release, and detection of small diffusible signal molecules called autoinducers. The N-acylated homoserine lactones (AHLs) comprise one such class of autoinducers, each of which generally consists of a fatty acid coupled with homoserine lactone (HSL). AHLs vary in acyl group length (C4-C18), in the substitution of C3 (hydrogen, hydroxyl, or oxo group) and in the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signal specificity through the affinity of transcriptional regulators of the LuxR family. C18:1-Δ9 cis-(L)-HSL is a long-chain AHL that may have antimicrobial activity and thus, might be used to inhibit pathogenesis by regulating bacerial quorum sensing signaling. | [Uses]
N-cis-octadec-9Z-enoyl-L-Homoserine lactone is a potent inhibitor of AhyI. AhyI (expressing acylhomoserine lactone) is responsible for the biosynthesis of autoinducer-1 (AI-1), commonly referred to as a quorum sensing (QS) signaling molecule, which plays an essential role in bacterial communication. N-cis-octadec-9Z-enoyl-L-Homoserine lactone is a competitive inhibitor of AI-1 biosynthesis[1]. | [storage]
Store at -20°C | [References]
[1] Ali F, et al. In silico analysis of AhyI protein and AI-1 inhibition using N-cis-octadec-9z-enoyl-l-homoserine lactone inhibitor in Aeromonas hydrophila. Microb Pathog. 2022;162:105356. DOI:10.1016/j.micpath.2021.105356 |
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