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N-Dodecanoyl-DL-homoserine lactone

Cat No.:V68144 Purity: ≥98%
N-Dodecanoyl-DL-homoserine lactone is a serine analogue.
N-Dodecanoyl-DL-homoserine lactone
N-Dodecanoyl-DL-homoserine lactone Chemical Structure CAS No.: 18627-38-8
Product category: Amino Acid Derivatives
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
N-Dodecanoyl-DL-homoserine lactone is a serine analogue.
N-Dodecanoyl-DL-homoserine lactone (CAS 18627-38-8), also known as C12-HSL or N-dodecanoyl-DL-homoserine lactone, is a quorum sensing signaling molecule belonging to the class of N-acyl homoserine lactones (AHLs). With a molecular formula of C₁₆H₂₉NO₃ and a molecular weight of 283.41 g/mol, it appears as a solid. This compound is a homoserine derivative and features a dodecanoyl (C12) acyl chain attached to the amino group of homoserine lactone. N-Dodecanoyl-DL-homoserine lactone is a bacterial quorum sensing molecule used in research to study bacterial communication and biofilm formation. The compound is a racemic mixture of D- and L-enantiomers. Quorum sensing molecules are used by Gram-negative bacteria to regulate gene expression in response to cell density. The compound is intended for research use only and is typically stored at -20°C or at 4°C.
Biological Activity I Assay Protocols (From Reference)
Targets
As a quorum sensing molecule, N-Dodecanoyl-DL-homoserine lactone targets bacterial quorum sensing receptors such as LuxR-type transcriptional regulators. In Gram-negative bacteria, AHLs bind to LuxR-type receptors, which then activate transcription of target genes involved in virulence, biofilm formation, and other population-dependent behaviors. The compound's biological target is the bacterial quorum sensing system, making it a valuable tool for studying bacterial communication and for developing quorum sensing inhibitors. The compound does not target mammalian receptors in the classical pharmacological sense.
ln Vitro
Commercial ergot supplements have been made from amino acids and their derivatives. They affect the release of anabolic hormones, the availability of fuel for activity, the ability to think clearly under pressure, and the prevention of muscular damage brought on by exertion. They are regarded as advantageous synergistic food ingredients [1].
The in vitro activity of N-Dodecanoyl-DL-homoserine lactone is evaluated through its ability to activate or inhibit quorum sensing in bacterial reporter strains. Typical assays use biosensor strains such as Agrobacterium tumefaciens or Chromobacterium violaceum that produce a visible readout (e.g., pigment production) in response to AHLs. The compound's activity is measured by its ability to induce reporter gene expression at various concentrations. The compound is also used to study biofilm formation and bacterial virulence. No specific IC₅₀ or EC₅₀ values are available for this compound.
ln Vivo
In vivo activity of N-Dodecanoyl-DL-homoserine lactone has been studied in animal models of bacterial infection. The compound can modulate bacterial virulence in vivo by affecting quorum sensing-regulated gene expression. However, the compound is primarily used as a research tool rather than a therapeutic agent. The compound's role in vivo is to study the effects of quorum sensing on bacterial pathogenesis and host interactions.
Enzyme Assay
The in vitro enzyme/receptor binding (non-cellular) experimental workflow for N-Dodecanoyl-DL-homoserine lactone typically involves binding assays with LuxR-type receptors or reporter strain assays. A typical workflow: prepare the compound in appropriate solvent (e.g., DMSO), prepare serial dilutions, and add to bacterial reporter strains. Incubate for a defined period, and measure the readout (e.g., β-galactosidase activity, pigment production). Calculate EC₅₀ values for activation. Characterization includes HPLC purity analysis (≥98%) and mass spectrometry confirmation.
Cell Assay
In vitro cell-based experimental workflows for N-Dodecanoyl-DL-homoserine lactone involve bacterial cell-based assays. Bacteria are cultured in appropriate medium, treated with varying concentrations of the compound, and analyzed for quorum sensing-regulated phenotypes such as biofilm formation, pigment production, or virulence factor expression. The compound's effects on bacterial growth and viability may also be assessed.
Animal Protocol
In vivo animal experimental workflows for N-Dodecanoyl-DL-homoserine lactone may involve infection models in rodents. Animals are infected with pathogenic bacteria, treated with the compound, and monitored for disease progression, bacterial load, and survival. The compound's effects on bacterial virulence and host immune responses are assessed.
ADME/Pharmacokinetics
The pharmacokinetic properties of N-Dodecanoyl-DL-homoserine lactone have been partially characterized in the context of quorum sensing research. The compound is a small lipophilic molecule that can diffuse across bacterial membranes. Its half-life in biological systems is influenced by lactonase enzymes that degrade AHLs. The compound is metabolized by bacterial and host enzymes.
Toxicity/Toxicokinetics
The toxicological data for N-Dodecanoyl-DL-homoserine lactone are limited. The compound is generally considered to have low toxicity at concentrations used for quorum sensing studies. Standard laboratory safety practices should be followed. The compound is intended for research use only.
References
[1]. Luckose F, et al. Effects of amino acid derivatives on physical, mental, and physiological activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-1144.
Additional Infomation
N-Dodecanoyl-DL-homoserine lactone is an N-acyl amino acid.
N-Dodecanoyl-DL-homoserine lactone is a bacterial quorum sensing molecule belonging to the class of N-acyl homoserine lactones (AHLs). The compound is used in research to study bacterial communication and biofilm formation. Quorum sensing molecules are used by Gram-negative bacteria to regulate gene expression in response to cell density. The compound is not a drug and has no clinical trials or approvals. The compound is for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C16H29NO3
Molecular Weight
283.41
Exact Mass
283.215
CAS #
18627-38-8
PubChem CID
11565426
Appearance
Light yellow to yellow solid powder
Melting Point
114-117 ℃
LogP
3.729
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
11
Heavy Atom Count
20
Complexity
291
Defined Atom Stereocenter Count
0
SMILES
CCCCCCCCCCCC(=O)NC1CCOC1=O
InChi Key
WILLZMOKUUPJSL-UHFFFAOYSA-N
InChi Code
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)
Chemical Name
N-(2-oxooxolan-3-yl)dodecanamide
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: 50 mg/mL (176.42 mM)
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.5285 mL 17.6423 mL 35.2846 mL
5 mM 0.7057 mL 3.5285 mL 7.0569 mL
10 mM 0.3528 mL 1.7642 mL 3.5285 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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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

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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