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Monocaprylin (Glyceryl monocaprylate; Sefsol 318)

Cat No.:V35060 Purity: ≥98%
Monocaprylin (Glyceryl monocaprylate) is a caprylic acid glycerol monocaprylate with excellent antimicrobial activity.
Monocaprylin (Glyceryl monocaprylate; Sefsol 318)
Monocaprylin (Glyceryl monocaprylate; Sefsol 318) Chemical Structure CAS No.: 26402-26-6
Product category: Bacterial
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Monocaprylin (Glyceryl monocaprylate) is a caprylic acid glycerol monocaprylate with excellent antimicrobial activity. Monocaprylin inhibits a variety of food-borne pathogenic and spoilage microorganisms and may be used in the research of alternative food preservatives.
Monocaprylin (glyceryl monocaprylate, Sefsol 318) is a monoglyceride of caprylic acid with CAS number 26402-26-6 and a molecular weight of 218.29. The compound is a medium-chain monoacylglycerol with excellent antimicrobial activity. Monocaprylin inhibits a variety of foodborne pathogenic and spoilage microorganisms and has the potential as an alternative food preservative. The compound has been shown to reduce all five major mastitis pathogens (Strep. agalactiae, Strep. dysgalactiae, Strep. uberis, Staph. aureus, and E. coli) at concentrations of 25-50 mM. Monocaprylin is also used as an emulsifier and surfactant in various applications. The compound is for research use and is not intended for human consumption as a drug.
Biological Activity I Assay Protocols (From Reference)
Targets
Monocaprylin targets bacterial cell membranes. As a monoglyceride of caprylic acid, the compound exhibits broad-spectrum antimicrobial activity by disrupting the integrity of bacterial cell membranes. The compound's mechanism of action involves its incorporation into the bacterial cell membrane, leading to increased membrane permeability, leakage of cellular contents, and cell death. Monocaprylin is effective against both Gram-positive and Gram-negative bacteria, as well as some yeasts and fungi. The compound's antimicrobial activity is concentration-dependent, with higher concentrations achieving more rapid killing. Monocaprylin's effects on bacterial membranes are thought to be non-specific, making it less susceptible to resistance development.
ln Vitro
After 6 hours of incubation, all 5 pathogens (Strep. agalactiae, Strep. dysgalactiae, Strep. uberis, Staph. aureus, and E. coli) are reduced by >5.0 log cfu/mL by monocaprylin (Glyceryl monocaprylate; 25, 50 mM; 24 h)[1].
In vitro, monocaprylin demonstrates potent antimicrobial activity against a broad range of foodborne pathogenic and spoilage microorganisms. The compound reduces all five major mastitis pathogens at concentrations of 25-50 mM. Monocaprylin is effective against Strep. agalactiae, Strep. dysgalactiae, Strep. uberis, Staph. aureus, and E. coli. The compound shows concentration-dependent bactericidal activity, with higher concentrations achieving more rapid and complete killing. Monocaprylin also exhibits activity against various foodborne pathogens such as Salmonella, Listeria, and Campylobacter. The compound's antimicrobial activity is enhanced in acidic conditions, making it particularly suitable for food preservation applications. In vitro studies have demonstrated that monocaprylin is effective against both planktonic bacteria and biofilms.
ln Vivo
In vivo, monocaprylin has been studied for its antimicrobial activity in animal models, particularly in the context of mastitis prevention and treatment. The compound's ability to inhibit mastitis pathogens suggests potential for use in veterinary medicine. Monocaprylin has also been studied for its effects on the gut microbiome, where it may help control pathogenic bacteria while preserving beneficial microorganisms. The compound is used as a food preservative and is generally recognized as safe (GRAS) for food applications. In animal studies, monocaprylin has been shown to be well-tolerated with no significant adverse effects.
Enzyme Assay
In vitro antimicrobial assays for monocaprylin are performed using standard broth microdilution or agar dilution methods to determine the minimum inhibitory concentration (MIC) against various bacterial strains. Bacteria are cultured in appropriate media and treated with serial dilutions of monocaprylin (typically 0.1-100 mM). The MIC is determined as the lowest concentration that inhibits visible growth after 18-24 hours of incubation. The minimum bactericidal concentration (MBC) is determined by subculturing from wells showing no visible growth onto agar plates. Time-kill assays are performed to assess the rate of bacterial killing. The antimicrobial activity is assessed against a panel of bacterial strains, including both reference strains and clinical isolates.
Cell Assay
In vitro cell-based assays for monocaprylin are performed using bacterial cultures to assess antimicrobial activity. Bacteria are grown in liquid media and treated with monocaprylin at various concentrations (typically 10-50 mM). Bacterial growth is monitored by measuring optical density (OD600) over time. The effect of monocaprylin on bacterial cell viability is assessed by plating serial dilutions on agar plates and counting colony-forming units (CFUs). The compound's effects on bacterial membrane integrity are assessed using fluorescent dyes such as propidium iodide or SYTOX Green, which penetrate cells with compromised membranes. Biofilm formation is assessed using crystal violet staining or by measuring viable cells in biofilms.
Animal Protocol
In vivo animal studies with monocaprylin are conducted in mouse or bovine models of mastitis or other bacterial infections. Animals are infected with mastitis pathogens (e.g., Staph. aureus, E. coli) and treated with monocaprylin via intramammary infusion or systemic administration. The compound's efficacy is assessed by measuring bacterial counts in milk or tissue samples, monitoring clinical signs of infection, and assessing inflammation markers. The compound's effects on milk quality and animal health are also evaluated. In food preservation studies, monocaprylin is added to food products, and the growth of spoilage organisms is monitored over time.
ADME/Pharmacokinetics
Monocaprylin is a monoglyceride that is metabolized like other dietary lipids. Following ingestion, the compound is hydrolyzed by lipases to caprylic acid and glycerol, which are absorbed and metabolized through normal pathways for fatty acids and glycerol. Caprylic acid is a medium-chain fatty acid that is rapidly oxidized for energy or incorporated into complex lipids. The compound's pharmacokinetics depend on the route of administration and the formulation. For topical or local applications, monocaprylin acts locally at the site of application. The compound is generally well-tolerated and has a favorable safety profile.
Toxicity/Toxicokinetics
Monocaprylin is generally recognized as safe (GRAS) for use as a food additive and preservative. The compound has low acute toxicity and is well-tolerated at concentrations used for antimicrobial applications. High concentrations may cause mild irritation to mucous membranes. No significant systemic toxicity has been reported with normal use. As a research chemical, standard safety precautions should be followed when handling monocaprylin. The compound should be stored at -20°C and protected from light. Monocaprylin is for research use only and not for human consumption or therapeutic applications outside approved uses.
References

[1]. Antibacterial effect of caprylic acid and monocaprylin on major bacterial mastitis pathogens. J Dairy Sci. 2005 Oct;88(10):3488-95.

Additional Infomation
1-Monocaprylylglycerol is a 1-monoglyceride with an acyl group of caprylyl. It is both a 1-monoglyceride and an octanoate.
See also: glyceryl monocaprylate (note moved to).
Monocaprylin is a monoglyceride of caprylic acid that has been studied for its antimicrobial properties and potential as a food preservative. The compound is a component of Sefsol 318, a surfactant used in various pharmaceutical and cosmetic formulations. Monocaprylin's broad-spectrum antimicrobial activity against foodborne pathogens and spoilage organisms makes it an attractive alternative to synthetic preservatives. The compound's mechanism of action involves disruption of bacterial cell membranes, which is less likely to lead to resistance compared to specific enzyme inhibitors. Monocaprylin is also used in research to study the effects of medium-chain monoacylglycerols on bacterial physiology and host-microbe interactions. The compound is available from chemical suppliers for research purposes.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C₁₁H₂₂O₄
Molecular Weight
218.29
Exact Mass
218.152
CAS #
26402-26-6
PubChem CID
3033877
Appearance
White to off-white solid powder
Density
1.044g/cm3
Boiling Point
340ºC at 760 mmHg
Melting Point
39.0 to 43.0 °C
Flash Point
123.4ºC
Vapour Pressure
5.91E-06mmHg at 25°C
Index of Refraction
1.465
LogP
1.243
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
10
Heavy Atom Count
15
Complexity
159
Defined Atom Stereocenter Count
0
SMILES
O(C([H])([H])C([H])(C([H])([H])O[H])O[H])C(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])=O
InChi Key
GHBFNMLVSPCDGN-UHFFFAOYSA-N
InChi Code
InChI=1S/C11H22O4/c1-2-3-4-5-6-7-11(14)15-9-10(13)8-12/h10,12-13H,2-9H2,1H3
Chemical Name
2,3-dihydroxypropyl octanoate
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

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
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 (458.11 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (11.45 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 4.5811 mL 22.9053 mL 45.8106 mL
5 mM 0.9162 mL 4.5811 mL 9.1621 mL
10 mM 0.4581 mL 2.2905 mL 4.5811 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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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:
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g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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)
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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