17247
N-Dodecanoyl-DL-homoserine lactone
≥97.0% (HPLC), suitable for ligand binding assays
Synonym(s):
N-Lauroyl-DL-homoserine lactone
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About This Item
Empirical Formula (Hill Notation):
C16H29NO3
CAS Number:
Molecular Weight:
283.41
MDL number:
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.26
Recommended Products
product name
N-Dodecanoyl-DL-homoserine lactone, ≥97.0% (HPLC)
Assay
≥97.0% (HPLC)
form
powder
technique(s)
ligand binding assay: suitable
color
white to faint beige
mp
114-117 °C
storage temp.
2-8°C
SMILES string
CCCCCCCCCCCC(=O)NC1CCOC1=O
InChI
1S/C16H29NO3/c1-2-3-4-5-6-7-8-9-10-11-15(18)17-14-12-13-20-16(14)19/h14H,2-13H2,1H3,(H,17,18)
InChI key
WILLZMOKUUPJSL-UHFFFAOYSA-N
Application
Application test: Induces violacein expression in a Chromobacterium violaceum mutant usually not able to produce homoserine lactones.
Biochem/physiol Actions
N-Dodecanoyl-DL-homoserine lactone (C12-HSL) is among a group of homoserine lactones that includes; N-Heptanoyl-DL-homoserine lactone (C7HSL), N-octanoyl-homoserine lactone (N-C8-HSL), N-Decanoyl-DL-homoserine lactone (N-C10-HSL), N-(3-oxodecanoyl) homoserine-L-lactone (3-oxo-C10 HSL), N-(3-oxododecanoyl)homoserine-L-lactone (3-oxo-C12-HSL), N-(3-Oxotetradecanoyl)-L-homoserine lactone (3-oxo-C14-HSL, N-(3-hydroxydecanoyl)-L-homoserine lactone, and N-(3-hydroxyoctanoyl)-L-homoserine lactone involved in the processes of bacterial quorum sensing. These N-acyl-homoserine lactones are used to study the processes and mechanisms of bacterial quorum sensing.
N-Lauroyl- DL-homoserine lactone is a member of N-acyl-homoserine lactone family. N-acylhomoserine lactones (AHL) regulate gene expression in gram-negative bacteria, such as Echerichia and Salmonella are involved in quorum sensing, cell to cell communication among bacteria. Some AHLs are potent chemoattractants for human immune cells such as neutrophils.
Quorum-sensing signal generation.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Sophie Uzureau et al.
Journal of proteome research, 9(6), 3200-3217 (2010-04-15)
Many pathogenic bacteria use a regulatory process termed quorum sensing (QS) to produce and detect small diffusible molecules to synchronize gene expression within a population. In Gram-negative bacteria, the detection of, and response to, these molecules depends on transcriptional regulators
Kazunori Gomi et al.
Infection and immunity, 74(12), 7029-7031 (2006-09-20)
Chromobacterium violaceum produces autoinducers, including homoserine lactones (HSLs), for genetic regulation. Among the seven HSLs derived from C. violaceum we evaluated, only C(12)-HSL stimulated the production of inflammatory cytokines in mammalian monocytic cell lines through the activation of the NF-kappaB
Deisy G Carneiro et al.
Frontiers in microbiology, 11, 1459-1459 (2020-08-28)
Acyl-homoserine lactones (AHLs) are quorum sensing (QS) signaling molecules that mediate cell-to-cell communication in Gram-negative bacteria. Salmonella does not produce AHL, however, it can recognize AHLs produced by other species through SdiA protein modulating important cellular functions. In this work
Ali E McClean et al.
Phytopathology, 102(2), 195-203 (2012-01-13)
Several members of the bacterial genus Brenneria are pathogenic on different tree species. Cell-free extracts from the bacterial phytopathogens Brenneria rubrifaciens, B. salicis, and B. nigrifluens induced production of the red pigment rubrifacine in the B. rubrifaciens bruI insertional mutant
Miriam Khider et al.
PeerJ, 7, e6845-e6845 (2019-05-21)
Bacterial communication through quorum sensing (QS) systems has been reported to be important in coordinating several traits such as biofilm formation. In Aliivibrio salmonicida two QS systems the LuxI/R and AinS/R, have been shown to be responsible for the production
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