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1-Monomyristin Sale

(Synonyms: 1-肉豆蔻酸单甘油酯) 目录号 : GC35068

A monoacylglycerol

1-Monomyristin Chemical Structure

Cas No.:589-68-4

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产品描述

1-Myristoyl-rac-glycerol is a monoacylglycerol that contains myristic acid at the sn-1 position. It is active against H. pylori with a 50% bactericidal concentration (BC50) value of 0.3 mM.1 1-Myristoyl-rac-glycerol is cytotoxic to A498, PaCa-2, and PC3 cancer cells (EC50s = 3.58, 1.87, and 8.84 ?g/ml, respectively).2 It has been found in saw palmetto berries.

1.Sun, Q.C., O'Conner, C.J., and Roberton, A.M.Antibacterial actions of fatty acids and monoglycerides against Helicobacter pyloriFEMS Immunol. Med. Microbiol.36(1-2)9-17(2003) 2.Shimada, H., Tyler, V.E., and McLaughlin, J.L.Biologically active acylglycerides from the berries of saw-palmetto (Serenoa repens)J. Nat. Prod.60(4)417-418(1997)

Chemical Properties

Cas No. 589-68-4 SDF
别名 1-肉豆蔻酸单甘油酯
Canonical SMILES CCCCCCCCCCCCCC(OCC(O)CO)=O
分子式 C17H34O4 分子量 302.45
溶解度 DMSO: 250 mg/mL (826.58 mM) 储存条件 Store at -20°C
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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
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Research Update

Monomyristin and Monopalmitin Derivatives: Synthesis and Evaluation as Potential Antibacterial and Antifungal Agents

Molecules 2018 Nov 29;23(12):3141.PMID:30501124DOI:10.3390/molecules23123141.

In the present work, monoacylglycerol derivatives, i.e., 1-Monomyristin, 2-monomyristin, and 2-monopalmitin were successfully prepared from commercially available myristic acid and palmitic acid. The 1-Monomyristin compound was prepared through a transesterification reaction between ethyl myristate and 1,2-O-isopropylidene glycerol, which was obtained from the protection of glycerol with acetone, then followed by deprotection using Amberlyst-15. On the other hand, 2-monoacylglycerol derivatives were prepared through enzymatic hydrolysis of triglycerides in the presence of Thermomyces lanuginosa lipase enzymes. The synthesized products were analyzed using fourier transform infrared (FTIR) spectrophotometer, gas or liquid chromatography-mass spectrometer (GC-MS or LC-MS), and proton and carbon nuclear magnetic resonance (¹H- and 13C-NMR) spectrometers. It was found that monomyristin showed high antibacterial and antifungal activities, while 2-monopalmitin did not show any activity at all. The 1-Monomyristin compound showed higher antibacterial activity against Staphylococcus aureus and Aggregatibacter actinomycetemcomitans and also higher antifungal activity against Candida albicans compared to the positive control. Meanwhile, 2-monomyristin showed high antibacterial activity against Escherichia coli. The effect of the acyl position and carbon chains towards antibacterial and antifungal activities was discussed.

Adsorption of 1-Monoglycerides at the Hexane/Water Interface

J Colloid Interface Sci 1999 Jan 1;209(1):173-178.PMID:9878150DOI:10.1006/jcis.1998.5863.

The interfacial tension of a hexane solution of 1-Monomyristin against water was measured as a function of temperature and concentration under atmospheric pressure. The interfacial tension decreases after adding an extremely small amount of 1-Monomyristin. The thermodynamic quantity changes associated with the adsorption were evaluated by applying the thermodynamic relations. The adsorbed film of 1-Monomyristin exhibits the expanded state on its interfacial pressure vs area curve under this experimental condition. The large negative value of the entropy change at high concentration is related to the restricted orientation of the polar head group of 1-Monomyristin at the hexane/water interface. We conclude that the entropy change for the system of 1-Monomyristin is smaller than that of tetradecanol because of a greater interaction between the large hydrophilic group of 1-Monomyristin and water molecules. An explanation is also given about the difference in energy change for both the systems: the adsorbed film of 1-Monomyristin is more stabilized energetically than that of tetradecanol by the greater interaction with water molecules. Copyright 1999 Academic Press.

Adsorption of 1-Monoglycerides at the Hexane/Water Interface

J Colloid Interface Sci 1999 Dec 15;220(2):374-379.PMID:10607455DOI:10.1006/jcis.1999.6536.

The interfacial tension of a hexane solution of 1-monolaurin against water was measured as a function of temperature and concentration under atmospheric pressure. The thermodynamic quantity changes associated with the adsorption of 1-monolaurin were evaluated and compared with those of the previously reported 1-Monomyristin. The decrease of two carbon atoms in the hydrocarbon chain results in a slight expansion of the 1-monolaurin adsorbed film and in a slight decrease in entropy and energy changes compared with those of the 1-Monomyristin system. The large negative value of the entropy change at a high concentration is related to the restricted orientation of the polar head group of 1-monolaurin at the hexane/water interface due to the strong interaction between the large hydrophilic group of 1-monolaurin and the water molecules, as in the 1-Monomyristin system. The origin of the distinction in the entropy change behavior between the adsorption from the hexane phase and water phase was discussed. The usefulness of an easier calculation process for the partial molar entropy change is verified by comparison with the usual reliable value and with the entropy of adsorption. Copyright 1999 Academic Press.

The antileishmanial activity of the antarctic brown alga Ascoseira mirabilis Skottsberg

Nat Prod Res 2021 Dec;35(23):5470-5474.PMID:32567355DOI:10.1080/14786419.2020.1782403.

Leishmaniasis is a group of diseases that have limited and high toxic therapeutic options. Herein, we evaluated the antileishmanial potential and cytotoxicity of hexanic extract obtained from the Antarctic brown alga Ascoseira mirabilis using bioguided fractionation against Leishmania amazonensis and murine macrophages, which was fractionated by SPE, yielding seven fractions (F1-F7). The fraction F6 showed good anti-amastigote activity (IC50 = 73.4 ± 0.4 μg mL-1) and low cytotoxicity (CC50 > 100 μg mL-1). Thus, in order to identify the bioactive constituent(s) of F6, the fraction was separated in a semipreparative HPLC, yielding four fractions (F6.1-F6.4). F6.2 was the most bioactive fraction (IC50 = 66.5 ± 4.5 μg mL-1) and GC-MS analyses revealed that the compounds octadecane, propanoic acid, 1-Monomyristin and azelaic acid correspond to 61% of its composition. These data show for the first time the antileishmanial potential of the Antarctic alga A. mirabilis.

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.PMID:16181610DOI:10.1016/j.bbrc.2005.09.015.

Little is known as to the structural requirements of the acyl side chain for interaction of acylglycerols with monoacylglycerol lipase (MAGL), the enzyme chiefly responsible for the metabolism of the endocannabinoid 2-arachidonoylglycerol (2-AG) in the brain. In the present study, a series of twelve analogues of 1-AG (the more stable regioisomer of 2-AG) were investigated with respect to their ability to inhibit the metabolism of 2-oleoylglycerol by cytosolic and membrane-bound MAGL. In addition, the ability of the compounds to inhibit the hydrolysis of anandamide by fatty acid amide hydrolase (FAAH) was investigated. For cytosolic MAGL, compounds with 20 carbon atoms in the acyl chain and 2-5 unsaturated bonds inhibited the hydrolysis of 2-oleoylglycerol with similar potencies (IC50 values in the range 5.1-8.2 microM), whereas the two compounds with a single unsaturated bond were less potent (IC50 values 19 and 21 microM). The fully saturated analogue 1-monoarachidin did not inhibit the enzyme, whereas the lower side chain analogues 1-monopalmitin and 1-Monomyristin inhibited the enzyme with IC50 values of 12 and 32 microM, respectively. The 22-carbon chain analogue of 1-AG was also potent (IC50 value 4.5 microM). Introduction of an alpha-methyl group for the C20:4, C20:3, and C22:4 compounds did not affect potency in a consistent manner. For the FAAH and the membrane-bound MAGL, there was no obvious relationship between the degree of unsaturation of the acyl side chain and the ability to inhibit the enzymes. It is concluded that increasing the number of unsaturated bonds on the acyl side chain of 1-AG from 1 to 5 has little effect on the affinity of acylglycerols for cytosolic MAGL.