N-[(3S)-2-Oxotetrahydro-3-furanyl]octadecanamide
Modify Date: 2024-01-30 18:12:25
![N-[(3S)-2-Oxotetrahydro-3-furanyl]octadecanamide Structure](https://www.chemsrc.com/caspic/293/479050-96-9.png)
N-[(3S)-2-Oxotetrahydro-3-furanyl]octadecanamide structure
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Common Name | N-[(3S)-2-Oxotetrahydro-3-furanyl]octadecanamide | ||
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| CAS Number | 479050-96-9 | Molecular Weight | 367.566 | |
| Density | 1.0±0.1 g/cm3 | Boiling Point | 548.6±39.0 °C at 760 mmHg | |
| Molecular Formula | C22H41NO3 | Melting Point | N/A | |
| MSDS | N/A | Flash Point | 285.6±27.1 °C | |
Use of N-[(3S)-2-Oxotetrahydro-3-furanyl]octadecanamideQuorum sensing is a regulatory system used by bacteria to control gene expression in response to increased cell density. This regulatory process manifests itself in a variety of phenotypes, including biofilm formation and virulence factor production. Coordinated gene expression is achieved through the production, release and detection of small diffusible signaling molecules called autoinducers. N-acylated homoserine lactones (AHLs) comprise a class of such autoinducers, each of which generally consists of a fatty acid coupled to a homoserine lactone (HSL). Modulation of bacterial quorum-sensing signaling systems to suppress pathogenesis represents a new approach to antimicrobial therapy for infectious diseases. AHLs differ in acyl length (C4-C18), C3 substitution (hydrogen, hydroxyl, or oxo group), and the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signaling specificity through the affinity of the LuxR family of transcriptional regulators. C18-HSL, one of four lipophilic long acyl side chain AHLs produced by the LuxI AHL synthase homolog SinI, is involved in quorum-sensing signaling in strains of Rhizobium meliloti (a nitrogen-fixing bacterial symbiont of the legume M. sativa) . C18-HSL and other hydrophobic AHLs tend to localize in the relatively lipophilic environment of bacterial cells and cannot diffuse freely across the cell membrane. Long-chain N-acyl homoserine lactones can be exported from cells by efflux pumps, or can be transported between communicating cells by extracellular outer membrane vesicles. |
| Name | N-(2-oxooxolan-3-yl)octadecanamide |
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| Synonym | More Synonyms |
| Description | Quorum sensing is a regulatory system used by bacteria to control gene expression in response to increased cell density. This regulatory process manifests itself in a variety of phenotypes, including biofilm formation and virulence factor production. Coordinated gene expression is achieved through the production, release and detection of small diffusible signaling molecules called autoinducers. N-acylated homoserine lactones (AHLs) comprise a class of such autoinducers, each of which generally consists of a fatty acid coupled to a homoserine lactone (HSL). Modulation of bacterial quorum-sensing signaling systems to suppress pathogenesis represents a new approach to antimicrobial therapy for infectious diseases. AHLs differ in acyl length (C4-C18), C3 substitution (hydrogen, hydroxyl, or oxo group), and the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signaling specificity through the affinity of the LuxR family of transcriptional regulators. C18-HSL, one of four lipophilic long acyl side chain AHLs produced by the LuxI AHL synthase homolog SinI, is involved in quorum-sensing signaling in strains of Rhizobium meliloti (a nitrogen-fixing bacterial symbiont of the legume M. sativa) . C18-HSL and other hydrophobic AHLs tend to localize in the relatively lipophilic environment of bacterial cells and cannot diffuse freely across the cell membrane. Long-chain N-acyl homoserine lactones can be exported from cells by efflux pumps, or can be transported between communicating cells by extracellular outer membrane vesicles. |
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| Related Catalog |
| Density | 1.0±0.1 g/cm3 |
|---|---|
| Boiling Point | 548.6±39.0 °C at 760 mmHg |
| Molecular Formula | C22H41NO3 |
| Molecular Weight | 367.566 |
| Flash Point | 285.6±27.1 °C |
| Exact Mass | 367.308655 |
| PSA | 55.40000 |
| LogP | 6.34 |
| Vapour Pressure | 0.0±1.5 mmHg at 25°C |
| Index of Refraction | 1.479 |
| N-octadecanoyl-L-Homoserine lactone |
| Octadecanamide, N-[(3S)-tetrahydro-2-oxo-3-furanyl]- |
| N-[(3S)-2-Oxotetrahydro-3-furanyl]octadecanamide |