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1-Monomyristin

Cat No.:V30018 Purity: ≥98%
1-Monomyristin is found in Serenoa repens and inhibits the hydrolysis of 2-oleoylglycerol (IC50=32 μM) and fatty acid amide hydrolase (FAAH) activity (IC50=18 μM).
1-Monomyristin
1-Monomyristin Chemical Structure CAS No.: 589-68-4
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
1-Monomyristin is found in Serenoa repens and inhibits the hydrolysis of 2-oleoylglycerol (IC50=32 μM) and fatty acid amide hydrolase (FAAH) activity (IC50=18 μM). 1-Monomyristin has anti-bacterial effect against Staphylococcus aureus and Actinomyces aggregates and antifungal activity against Candida albicans.
Biological Activity I Assay Protocols (From Reference)
Targets
- Bacterial cell membrane (target for antibacterial activity): Against Staphylococcus aureus, MIC = 128 μg/mL; against Escherichia coli, MIC = 256 μg/mL [3]
- Fungal cell membrane (target for antifungal activity): Against Candida albicans, MIC = 64 μg/mL [3]
ln Vitro
- Antibacterial activity: 1-Monomyristin exhibited inhibitory activity against Gram-positive bacterium Staphylococcus aureus in vitro, with a minimum inhibitory concentration (MIC) of 128 μg/mL. For Gram-negative bacterium Escherichia coli, its inhibitory activity was weaker, showing an MIC of 256 μg/mL [3]
- Antifungal activity: 1-Monomyristin displayed stronger antifungal activity against Candida albicans compared to its antibacterial activity. Its MIC against Candida albicans was 64 μg/mL. When the concentration of 1-Monomyristin exceeded the MIC, the number of Candida albicans colonies formed was significantly reduced, and the inhibitory effect increased with the elevation of drug concentration [3]
Cell Assay
- Antibacterial activity assay (broth dilution method): Staphylococcus aureus and Escherichia coli were separately inoculated into LB broth medium, cultured with shaking at 37°C until the logarithmic growth phase (OD600 = 0.5), and then the bacterial solution was diluted to 1×10^6 CFU/mL. In a 96-well plate, 1-Monomyristin was dissolved in DMSO, and drug solutions with different concentrations (16–512 μg/mL) were prepared by two-fold serial dilution. Each well was added with 100 μL of diluted bacterial solution and 100 μL of drug solution at different concentrations. Meanwhile, a blank control group (LB broth only), a solvent control group (LB broth + DMSO), and a positive control group (LB broth + standard antibacterial drug) were set up. After incubation at 37°C for 24 h, the OD600 value of each well was measured, and the lowest drug concentration without bacterial growth was defined as the MIC [3]
- Antifungal activity assay (agar dilution method): Candida albicans was inoculated onto Sabouraud dextrose agar medium, cultured at 28°C for 48 h. A single colony was picked and inoculated into Sabouraud dextrose broth, cultured with shaking at 28°C until the logarithmic growth phase (OD600 = 0.6), and the fungal solution was diluted to 1×10^5 CFU/mL. 1-Monomyristin was dissolved in DMSO and mixed with melted Sabouraud dextrose agar medium to prepare agar plates containing drug solutions of different concentrations (8–256 μg/mL). Each plate was inoculated with 10 μL of diluted fungal solution, cultured at 28°C for 48 h, and then the growth of colonies was observed. The lowest drug concentration without fungal growth was defined as the MIC [3]
References

[1]. Biologically active acylglycerides from the berries of saw-palmetto (Serenoa repens). J Nat Prod. 1997 Apr;60(4):417-8.

[2]. Influence of the degree of unsaturation of the acyl side chain upon the interaction of analogues of 1-arachidonoylglycerol with monoacylglycerol lipase and fatty acid amide hydrolase. Biochem Biophys Res Commun. 2005 Nov 11;337(1):104-9.

[3]. Monomyristin and Monopalmitin Derivatives: Synthesis and Evaluation as Potential Antibacterial and Antifungal Agents. Molecules. 2018 Nov 29;23(12). pii: E3141.

Additional Infomation
1-Monomyristoylglycerol is a 1-monoglyceride with a tetradecanoyl (myristoyl) acyl group. It plays a metabolic role in Caenorhabditis elegans. It is a 1-monoglyceride and also a tetradecanoate.
2,3-Dihydroxypropyltetradecanoate has been reported in Aeromonas veronii and Caenorhabditis elegans, and there are relevant data.
- Compound background: 1-monomyristic acid (monomyristic acid) is a naturally occurring monoacylglycerol compound. Its molecular structure consists of a glycerol molecule and a myristic acid (tetradecanoic acid) linked by an ester bond. In reference [3], this compound was used as the parent structure to synthesize a series of derivatives, and it itself has also been evaluated as a potential antibacterial and antifungal agent [3].
- Mechanism of Action Speculation: Based on the chemical structure of 1-monomomiretin and its antibacterial/antifungal activity results, reference [3] speculates that its mechanism of action may be related to the disruption of the integrity of bacterial or fungal cell membranes. It is speculated that the compound inserts into the lipid bilayer of the cell membrane, altering the membrane's fluidity and permeability, leading to leakage of cell contents and ultimately causing microbial death. However, this mechanism has not yet been verified by further experiments [3].
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C17H34O4
Molecular Weight
302.4495
Exact Mass
302.245
CAS #
589-68-4
PubChem CID
79050
Appearance
White to off-white solid powder
Density
1.0±0.1 g/cm3
Boiling Point
424.8±25.0 °C at 760 mmHg
Melting Point
68-70ºC
Flash Point
141.3±16.7 °C
Vapour Pressure
0.0±2.3 mmHg at 25°C
Index of Refraction
1.468
LogP
5.1
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
16
Heavy Atom Count
21
Complexity
231
Defined Atom Stereocenter Count
0
InChi Key
DCBSHORRWZKAKO-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H34O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(20)21-15-16(19)14-18/h16,18-19H,2-15H2,1H3
Chemical Name
2,3-dihydroxypropyl tetradecanoate
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 (~330.63 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.27 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 3.3063 mL 16.5317 mL 33.0633 mL
5 mM 0.6613 mL 3.3063 mL 6.6127 mL
10 mM 0.3306 mL 1.6532 mL 3.3063 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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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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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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