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N-(3-Oxohexanoyl)-L-homoserine lactonehomoserine lactone

Cat No.:V49516 Purity: ≥98%
N-(3-Oxohexanoyl)-L-homoserine lactone is a component of quorum sensing.
N-(3-Oxohexanoyl)-L-homoserine lactonehomoserine lactone
N-(3-Oxohexanoyl)-L-homoserine lactonehomoserine lactone Chemical Structure CAS No.: 143537-62-6
Product category: New3
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
N-(3-Oxohexanoyl)-L-homoserine lactone is a component of quorum sensing.
N-(3-Oxohexanoyl)-L-homoserine lactone (3-Oxo-C6-HSL) (CAS#: 143537-62-6) is a small diffusible signaling molecule and a member of the N-acyl-homoserine lactone (AHL) family. It has a molecular formula of C10H15NO4 and a molecular weight of 213.23. This compound is a component of quorum regulatory sensing and is used to study bacterial quorum sensing mechanisms. It has been reported in Azospirillum lipoferum.
Biological Activity I Assay Protocols (From Reference)
Targets
N-(3-Oxohexanoyl)-L-homoserine lactone does not have a specific mammalian target but functions as a bacterial quorum sensing signal molecule. It is an N-acyl-L-homoserine lactone having 3-oxohexanoyl as the acyl substituent. In bacteria, it acts as a diffusible signaling molecule that regulates gene expression in response to cell density, controlling secondary metabolism and virulence factor regulatory pathways.
ln Vitro
In vitro, N-(3-Oxohexanoyl)-L-homoserine lactone is used to study bacterial quorum sensing mechanisms. It regulates secondary metabolism and virulence factor pathways in Erwinia carotovora and Yersinia enterocolitica. Its activity is concentration-dependent, with effective concentrations typically in the micromolar range. It is a valuable tool for understanding bacterial behavior, infection control, and the development of quorum-sensing inhibitors as potential therapeutics.
ln Vivo
In vivo, N-(3-Oxohexanoyl)-L-homoserine lactone is not used as a therapeutic agent but as a research tool for studying bacterial quorum sensing. It is used to investigate the regulation of bacterial virulence and secondary metabolism in the context of infection. The compound's in vivo effects are related to its role as a bacterial signaling molecule.
Enzyme Assay
The in vitro quorum sensing assays for N-(3-Oxohexanoyl)-L-homoserine lactone typically use bacterial reporter strains (e.g., Agrobacterium tumefaciens, Pseudomonas aeruginosa) that produce a detectable signal in response to AHLs. The compound is added to bacterial cultures at varying concentrations (typically 0.1 to 100 µM), and the induction of reporter gene expression is measured by β-galactosidase or luminescence assays.
Cell Assay
For in vitro bacterial assays, cultures of quorum sensing reporter strains are treated with N-(3-Oxohexanoyl)-L-homoserine lactone at concentrations ranging from 0.1 to 100 µM. Reporter gene expression is measured, and the compound's ability to activate quorum sensing pathways is assessed.
Animal Protocol
For in vivo infection studies, animal models of bacterial infection are used to study the role of quorum sensing in virulence. Bacterial strains with mutations in quorum sensing genes are compared to wild-type strains. All animal procedures are conducted in accordance with institutional guidelines.
ADME/Pharmacokinetics
The pharmacokinetic properties of N-(3-Oxohexanoyl)-L-homoserine lactone are not relevant, as it is a bacterial signaling molecule rather than a therapeutic agent. The compound has a molecular weight of 213.23 and is a small, diffusible molecule. It is produced and degraded by bacteria.
Toxicity/Toxicokinetics
Toxicology data for N-(3-Oxohexanoyl)-L-homoserine lactone are limited, as it is a bacterial signaling molecule. At the concentrations used for research, it is not considered toxic to mammalian cells.
References

[1]. N-acyl homoserine lactone binding to the CarR receptor determines quorum-sensing specificity in Erwinia. EMBO J. 2000 Feb 15;19(4):631-41.

Additional Infomation
N-(3-oxohexanoyl)-L-homoserine lactone is an N-acyl-L-homoserine lactone with a 3-oxohexanoyl substituent. It has been reported to exist in Azospirillum lipoferum, and relevant data are available for reference.
N-(3-Oxohexanoyl)-L-homoserine lactone (3-Oxo-C6-HSL) is a small diffusible signaling molecule and a member of the N-acyl-homoserine lactone family. It has a molecular formula of C10H15NO4 and a molecular weight of 213.23. It is used to study bacterial quorum sensing mechanisms. It is not approved for human use and is intended for research purposes only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H15NO4
Molecular Weight
213.2304
Exact Mass
213.1
CAS #
143537-62-6
PubChem CID
688505
Appearance
Off-white to light yellow solid powder
Density
1.2±0.1 g/cm3
Boiling Point
482.9±45.0 °C at 760 mmHg
Flash Point
245.9±28.7 °C
Vapour Pressure
0.0±1.2 mmHg at 25°C
Index of Refraction
1.486
LogP
0.9
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
5
Heavy Atom Count
15
Complexity
275
Defined Atom Stereocenter Count
1
SMILES
O=C1[C@H](CCO1)NC(CCCCC=O)=O
InChi Key
YRYOXRMDHALAFL-QMMMGPOBSA-N
InChi Code
InChI=1S/C10H15NO4/c1-2-3-7(12)6-9(13)11-8-4-5-15-10(8)14/h8H,2-6H2,1H3,(H,11,13)/t8-/m0/s1
Chemical Name
3-oxo-N-[(3S)-2-oxooxolan-3-yl]hexanamide
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~468.98 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (11.72 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (11.72 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (11.72 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.6898 mL 23.4489 mL 46.8977 mL
5 mM 0.9380 mL 4.6898 mL 9.3795 mL
10 mM 0.4690 mL 2.3449 mL 4.6898 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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