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L-Homoserine lactone hydrochloride

L-Homoserine lactone HCl is a biochemical compound that could be utilized as a biomaterial or organic/chemical reagent for biomedical research.
L-Homoserine lactone hydrochloride
L-Homoserine lactone hydrochloride Chemical Structure CAS No.: 2185-03-7
Product category: Biochemical Assay Reagents
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100g
Other Sizes
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Product Description
L-Homoserine lactone HCl is a biochemical compound that could be utilized as a biomaterial or organic/chemical reagent for biomedical research.
L-Homoserine lactone hydrochloride (CAS 2185-03-7) is a chiral lactone derivative with molecular formula C₄H₈ClNO₂ and molecular weight 137.57 g/mol. It is the hydrochloride salt of L-homoserine lactone, featuring a lactone ring (cyclic ester) and an amino group. The hydrochloride form enhances solubility in aqueous solutions, making it ideal for various in vitro experiments. L-Homoserine lactone hydrochloride is widely used as an intermediate in organic synthesis and is a key intermediate in the synthesis of the chiral herbicide L-glufosinate.
Biological Activity I Assay Protocols (From Reference)
Targets
L-Homoserine lactone hydrochloride does not have a defined pharmacological target of its own, as it is a synthetic intermediate. However, it is used in the synthesis of bacterial quorum-sensing signaling molecules, particularly N-(3-oxododecanoyl)-L-homoserine lactone, which act as immune modulators. The compound's lactone ring and amino group provide handles for derivatization in the synthesis of biologically active compounds.
ln Vitro
In vitro, L-Homoserine lactone hydrochloride is primarily used as a chemical reagent and synthetic intermediate. It is used in the synthesis of organoselenium chemistry intermediates and analogs of bacterial quorum-sensing signaling molecules. The compound's hydrochloride form enhances its solubility in aqueous solutions, making it ideal for various in vitro experiments. It is a key intermediate in the synthesis of the chiral herbicide L-glufosinate.
ln Vivo
In vivo activity data for L-Homoserine lactone hydrochloride itself are not available, as the compound is not intended for direct in vivo administration. Rather, it is a precursor used in the synthesis of quorum-sensing signaling molecules that are subsequently evaluated as immune modulators in vivo. The compound's in vivo relevance is indirect, through the biological activities of the final compounds derived from it.
Enzyme Assay
For in vitro enzyme/receptor binding studies, L-Homoserine lactone hydrochloride is not typically evaluated as a test compound itself. Instead, it serves as a reagent for the synthesis of test compounds. The compound's properties include a molecular weight of 137.57 g/mol and a molecular formula of C₄H₈ClNO₂. The lactone ring and amino group provide handles for further derivatization in medicinal chemistry and quorum sensing research.
Cell Assay
For in vitro cell-based experiments, L-Homoserine lactone hydrochloride is used as an intermediate in the synthesis of compounds that are tested in cell-based assays. The compound itself is not typically evaluated in cell-based assays. Standard cell culture protocols for test compounds synthesized from this intermediate involve dissolving the final product in DMSO or aqueous buffer and diluting to working concentrations in appropriate cell culture medium.
Animal Protocol
In vivo animal studies using L-Homoserine lactone hydrochloride are conducted on the final compounds synthesized from it, such as quorum-sensing signaling molecules evaluated as immune modulators. Standard in vivo protocols involve administration to rodents via appropriate routes with pharmacokinetic and immunomodulatory endpoints. Specific protocols for the intermediate compound are not documented.
ADME/Pharmacokinetics
Pharmacokinetic properties of L-Homoserine lactone hydrochloride as a standalone compound are not characterized in the literature. The compound has a molecular weight of 137.57 g/mol, which is within the favorable range for oral bioavailability. The hydrochloride salt form enhances aqueous solubility. The compound should be stored as powder at -20°C for up to 3 years or in solvent at -80°C for up to 1 year.
Toxicity/Toxicokinetics
L-Homoserine lactone hydrochloride is a research chemical and should be handled with appropriate laboratory safety precautions. As a lactone and amine salt, it may pose risks of skin and eye irritation. Specific LD₅₀ values, acute toxicity classifications, and chronic toxicity data are not available in the public literature. Standard safety practices include the use of personal protective equipment (gloves, safety goggles, lab coat) and working in a well-ventilated area.
References
[1]. Koch, T., and Buchardt, O.Synthesis of L-(+)-selenomethionineSynthesis1065-1067(1993)
[2]. Chhabra, SR, Harty, C., Hooi, DSW, et al.Synthetic analogues of the bacterial signal (quorum seeing) molecule N-(3-oxododecanoyl)-L-homoserine lactone as immune modulators J. Med. Chem. 46(1) 97-104(2003)
Additional Infomation
L-Homoserine lactone hydrochloride ((3S)-3-Aminodihydro-2(3H)-furanoine hydrochloride, CAS 2185-03-7) is primarily a research-grade chemical intermediate, not an FDA-approved pharmaceutical drug. Its primary applications are in organic synthesis as a key intermediate for the synthesis of the chiral herbicide L-glufosinate and in the synthesis of organoselenium chemistry intermediates and analogs of bacterial quorum-sensing signaling molecules. The compound's hydrochloride form enhances aqueous solubility for in vitro experiments. No clinical trials or approved indications exist for this compound.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C4H8CLNO2
Molecular Weight
137.56
Exact Mass
137.024
CAS #
2185-03-7
PubChem CID
2733667
Appearance
White to off-white solid powder
Boiling Point
257.1ºC at 760 mmHg
Melting Point
221-226ºC
Flash Point
120.1ºC
Vapour Pressure
0.000411mmHg at 25°C
Index of Refraction
-26 ° (C=0.2, H2O)
LogP
0.762
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
0
Heavy Atom Count
8
Complexity
91.7
Defined Atom Stereocenter Count
1
SMILES
Cl[H].O1C([C@]([H])(C([H])([H])C1([H])[H])N([H])[H])=O
InChi Key
XBKCXPRYTLOQKS-DFWYDOINSA-N
InChi Code
InChI=1S/C4H7NO2.ClH/c5-3-1-2-7-4(3)6;/h3H,1-2,5H2;1H/t3-;/m0./s1
Chemical Name
(3S)-3-aminooxolan-2-one;hydrochloride
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)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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 7.2696 mL 36.3478 mL 72.6956 mL
5 mM 1.4539 mL 7.2696 mL 14.5391 mL
10 mM 0.7270 mL 3.6348 mL 7.2696 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
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)
  • Click the “Calculate” button
  • 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:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
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.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • 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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