589-68-4

Basic information

• Product Name: MONOMYRISTIN
• Synonyms: Tetradecanoic acid, 2,3-dihydroxypropyl ester;1-Monotetradecanoyl-rac-glycerol, rac-1-Myristoylglycerol, DL-α-Myristin, Monomyristin;Myristic acid 2,3-dihydroxypropyl ester;(+)-L-Glycerol 1-myristate;(+)-Myristic acid (S)-2,3-dihydroxypropyl ester;1-O-Myristoyl-L-glycerol;Myristic acid (2S)-2,3-dihydroxypropyl ester;2,3-dihydroxypropyl tetradecanoate
• CAS NO: 589-68-4
• Molecular Formula: C₁₇H₃₄O₄
• Molecular Weight: 302.45
• EINECS: 248-329-0
• Product Categories: Ester Type (Surfactants);Functional Materials;Nonionic Surfactants;Surfactants
• Mol File: 589-68-4.mol
• Article Data: 15

Chemical Properties

• Melting Point: 68-70 °C
• Boiling Point: 363.47°C (rough estimate)
• Flash Point: 141.3 °C
• Appearance: /
• Density: 0.9748 (rough estimate)
• Refractive Index: 1.4230 (estimate)
• Storage Temp.: −20°C
• Solubility: very faint turbidity in Methanol
• PKA: 13.16±0.20(Predicted)
• BRN: 1727502
• CAS DataBase Reference: MONOMYRISTIN(CAS DataBase Reference)
• NIST Chemistry Reference: MONOMYRISTIN(589-68-4)
• EPA Substance Registry System: MONOMYRISTIN(589-68-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 589-68-4(Hazardous Substances Data)

Usage

Description

1-Monomyristin is a 1-monoglyceride with tetradecanoyl (myristoyl) as the acyl group. 1-Monomyristin has a role as a Caenorhabditis elegans metabolite. 1-Monomyristin is a 1-monoglyceride and a tetradecanoate ester. 1-Monomyristin, extracted from Serenoa repens, inhibits the hydrolysis of 2-oleoylglycerol (IC50=32 μM) and fatty acid amide hydrolase (FAAH) activity (IC50=18 μM). 1-Monomyristin shows antibacterial activity against Staphylococcus aureus and Aggregatibacter actinomycetemcomitans and also antifungal activity against Candida albicans.

Uses

α-Monomyristin, is used for the preparation of nonionic surfactant micelles. It is also a 1-monoglyceride of myristic acid, has antibacterial activity against several Gram-positive bacterial strains.

Definition

ChEBI: A rac-1-monoacylglycerol that is composed of equal amounts of 1-myristoyl-sn-glycerol and 3-myristoyl-sn-glycerol.

InChI:InChI=1/C17H32O5/c1-2-3-4-5-6-7-8-9-10-11-12-13-16(20)22-17(21)15(19)14-18/h15,18-19H,2-14H2,1H3

Synthetic route

(2,2-dimethyl-1,3-dioxolane-4-yl)methyl myristate (56630-71-8) → 1-monoglyceride myristic acid (589-68-4)

Conditions	Yield
With Amberlyst-15 In ethanol at 20℃; for 30h;	100%
With hydrogenchloride In methanol for 0.166667h; Hydrolysis; Heating;
With AmberlystTM 15 In ethanol; water for 3h; Reflux;
With amberlyst-15 In methanol at 20℃; for 16h;

4-hydroxymethyl-1,3-dioxolan-2-one (931-40-8) + n-tetradecanoic acid (544-63-8) → 1-monoglyceride myristic acid (589-68-4)

Conditions	Yield
With triethylamine at 143 - 145℃; for 9h;	90%

allyl tetradecanoate (45236-96-2) → 1-monoglyceride myristic acid (589-68-4)

Conditions	Yield
With cethyltrimethylammonium permanganate In dichloromethane for 5h; Ambient temperature;	76%

oxiranyl-methanol (556-52-5) + n-tetradecanoic acid (544-63-8) → 1-monoglyceride myristic acid (589-68-4)

Conditions	Yield
With tributyl-amine at 85℃; for 5h;	62%
With tributyl-amine at 85℃; for 5h; Inert atmosphere;
With tributyl-amine
With tributyl-amine

potassium myristate (13429-27-1) → 1-monoglyceride myristic acid (589-68-4)

potassium myristate (13429-27-1) + 3-monochloro-1,2-propanediol (96-24-2) → 1-monoglyceride myristic acid (589-68-4)

Conditions	Yield
at 180℃;

γ-chloro-propylene glycol-α-myristate → 1-monoglyceride myristic acid (589-68-4)

Conditions	Yield
With silver(I) nitrite at 125 - 130℃;

tetradecanoyl chloride (112-64-1) + glycerol-α.β-isopropylidene ether → 1-monoglyceride myristic acid (589-68-4)

Conditions	Yield
With quinoline unter Eiskuehlung und Zersetzung des in Aether geloesten Glycerin-α.β-isopropylidenaether-myristats mit kalter konz.Salzsaeure oder mit 0.25 n-Schwefelsaeure bei 40grad;

n-tetradecanoic acid (544-63-8) + glycerol-1.2-isopropylidene ether → 1-monoglyceride myristic acid (589-68-4)

Conditions	Yield
With hydrogenchloride anschliessend Behandeln des Reaktionsprodukts mit konz.HCl bei 0grad; inactive form;

n-tetradecanoic acid (544-63-8) + glycerol (56-81-5) → 1-monoglyceride myristic acid (589-68-4) + dimyristin and trimyristin

Conditions	Yield
at 250℃;

glycerol (56-81-5) + myristic anhydride (626-29-9) → 1-monoglyceride myristic acid (589-68-4)

Conditions	Yield
With Candida antarctica In 1,4-dioxane at 15℃; for 4h;	13 % Chromat.

methyl myristoate (124-10-7) + glycerol (56-81-5) → 1-monoglyceride myristic acid (589-68-4) + 1,2-dimyristoyl-rac-glycerol (20255-94-1) + glycerin monomyristate (3443-83-2) + glycerol 1,3-dimyristate (7770-09-4)

Conditions	Yield
HMS-TBD In dimethyl sulfoxide at 110℃; for 3h;

n-tetradecanoic acid (544-63-8) + neutral potassium myristate → 1-monoglyceride myristic acid (589-68-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 4-(dimethylamino)pyridine; N,N'-dicyclohexylcarbodiimide / diethyl ether / 4.5 h / 20 - 25 °C 2: aq. HCl / methanol / 0.17 h / Heating View Scheme

n-tetradecanoic acid (544-63-8) → 1-monoglyceride myristic acid (589-68-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: thioyl chloride / 2 h / Heating 2: 4.7 g / pyridine / 0.17 h / Ambient temperature 3: 76 percent / cetyltrimethylammonium permanganate / CH2Cl2 / 5 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 2: quinoline / unter Eiskuehlung und Zersetzung des in Aether geloesten Glycerin-α.β-isopropylidenaether-myristats mit kalter konz.Salzsaeure oder mit 0.25 n-Schwefelsaeure bei 40grad View Scheme
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / toluene / Reflux 2: AmberlystTM 15 / ethanol; water / 3 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16 h / 0 - 20 °C 2: amberlyst-15 / methanol / 16 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid / 4.5 h / Sonication 2: potassium carbonate / 30 h / 139.84 °C 3: Amberlyst-15 / ethanol / 30 h / 20 °C View Scheme

tetradecanoyl chloride (112-64-1) → 1-monoglyceride myristic acid (589-68-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 4.7 g / pyridine / 0.17 h / Ambient temperature 2: 76 percent / cetyltrimethylammonium permanganate / CH2Cl2 / 5 h / Ambient temperature View Scheme

n-tetradecanoic acid (544-63-8) + glycerol (56-81-5) → 1-monoglyceride myristic acid (589-68-4) + glycerol 1,3-dimyristate (7770-09-4)

Conditions	Yield
With Penicillium camembertii lipase immobilized on epoxy SiO2-PVA at 45 - 65℃; Enzymatic reaction;

n-tetradecanoic acid (544-63-8) + glycerol (56-81-5) → 1-monoglyceride myristic acid (589-68-4)

Conditions	Yield
With immobilized Candida antarctica Lipase B; 3-dodecyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate In tert-butyl alcohol at 60℃; Molecular sieve; Green chemistry; Enzymatic reaction;

C34H64O8Si → 1-monoglyceride myristic acid (589-68-4)

Conditions	Yield
With water at 50℃; for 4h;

1-monoglyceride myristic acid (589-68-4) + butylboronic acid (4426-47-5) → 2-butyl-4-tetradecanoyloxymethyl-[1,3,2]dioxaborolane (18885-80-8)

Conditions	Yield
In acetone

1-monoglyceride myristic acid (589-68-4) + phenylboronic acid (98-80-6) → 2-phenyl-4-tetradecanoyloxymethyl-[1,3,2]dioxaborolane (18885-84-2)

Conditions	Yield
In acetone

1-monoglyceride myristic acid (589-68-4) + pyridine-3-carbonyl chloride hydrochloride (20260-53-1) → 2,3-dinicotinoyl-1-tetradecanoyl-rac-glycerol

Conditions	Yield
With pyridine Ambient temperature;

1-monoglyceride myristic acid (589-68-4) + O2,O3-diacetyl-tartaric acid anhydride (122376-19-6) → 2,3-diacetoxy-succinic acid mono-(2-hydroxy-3-tetradecanoyloxy-propyl) ester

Conditions	Yield
at 110 - 140℃; Acylation;

1-monoglyceride myristic acid (589-68-4) → C20H39O5PS

Conditions	Yield
Multi-step reaction with 4 steps 1: dmap; triethylamine / dichloromethane / 17 h / 20 °C 2: tetrafluoroboric acid / hexane; dichloromethane / 2.5 h / 0 - 20 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C 4: 5-(ethylsulfanyl)-2H-tetrazole / dichloromethane / 2 h / 20 °C View Scheme

1-monoglyceride myristic acid (589-68-4) → C20H39O4PS2

Conditions	Yield
Multi-step reaction with 4 steps 1: dmap; triethylamine / dichloromethane / 17 h / 20 °C 2: tetrafluoroboric acid / hexane; dichloromethane / 2.5 h / 0 - 20 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C 4: 5-(ethylsulfanyl)-2H-tetrazole / dichloromethane / 2 h / 20 °C View Scheme

1-monoglyceride myristic acid (589-68-4) → 1-myristoyl-2-methoxy-glycerol-3-(2-thio-1,3,2-oxathiaphospholane) (1232676-47-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: dmap; triethylamine / dichloromethane / 17 h / 20 °C 2: tetrafluoroboric acid / hexane; dichloromethane / 2.5 h / 0 - 20 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C 4: 5-(ethylsulfanyl)-2H-tetrazole / dichloromethane / 2 h / 20 °C 5: sulfur / dichloromethane / 20 °C View Scheme
Multi-step reaction with 4 steps 1: triethylamine; dmap 2: tetrafluoroboric acid / dichloromethane 3: tetrabutyl ammonium fluoride / tetrahydrofuran 4: 5-(ethylthio)-1H-tetrazole; sulfur / dichloromethane View Scheme

1-monoglyceride myristic acid (589-68-4) → C20H39O4PS3 (1232676-52-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: dmap; triethylamine / dichloromethane / 17 h / 20 °C 2: tetrafluoroboric acid / hexane; dichloromethane / 2.5 h / 0 - 20 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C 4: 5-(ethylsulfanyl)-2H-tetrazole / dichloromethane / 2 h / 20 °C 5: sulfur / dichloromethane / 20 °C View Scheme
Multi-step reaction with 4 steps 1: triethylamine; dmap 2: tetrafluoroboric acid / dichloromethane 3: tetrabutyl ammonium fluoride / tetrahydrofuran 4: sulfur / dichloromethane View Scheme

1-monoglyceride myristic acid (589-68-4) → C21H40NO6PS (1232676-57-1)

Conditions

Yield

Multi-step reaction with 6 steps 1: dmap; triethylamine / dichloromethane / 17 h / 20 °C 2: tetrafluoroboric acid / hexane; dichloromethane / 2.5 h / 0 - 20 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C 4: 5-(ethylsulfanyl)-2H-tetrazole / dichloromethane / 2 h / 20 °C 5: sulfur / dichloromethane / 20 °C 6: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 20 °C View Scheme

1-monoglyceride myristic acid (589-68-4) → C21H40NO5PS2 (1232676-62-8)

Conditions

Yield

Multi-step reaction with 6 steps 1: dmap; triethylamine / dichloromethane / 17 h / 20 °C 2: tetrafluoroboric acid / hexane; dichloromethane / 2.5 h / 0 - 20 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C 4: 5-(ethylsulfanyl)-2H-tetrazole / dichloromethane / 2 h / 20 °C 5: sulfur / dichloromethane / 20 °C 6: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 20 °C View Scheme

Upstream product

• 13429-27-1 potassium myristate 
• 96-24-2 3-monochloro-1,2-propanediol 
• 56630-71-8 (2,2-dimethyl-1,3-dioxolane-4-yl)methyl myristate 
• 544-63-8 n-tetradecanoic acid 
• 56-81-5 glycerol 
• 626-29-9 myristic anhydride 
• 124-10-7 methyl myristoate 
• 112-64-1 tetradecanoyl chloride 
• 45236-96-2 allyl tetradecanoate 
• 556-52-5 oxiranyl-methanol 
• 931-40-8 4-hydroxymethyl-1,3-dioxolan-2-one 

Downstream Products

• 17637-37-5 1-Palmitoyl-3-myristoyl-glycerin 
• 18885-84-2 2-phenyl-4-tetradecanoyloxymethyl-[1,3,2]dioxaborolane 

Relevant articles and documents

Monomyristin and monopalmitin derivatives: Synthesis and evaluation as potential antibacterial and antifungal agents

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- and13C-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.

Highly selective biocatalytic synthesis of monoacylglycerides in sponge-like ionic liquids

The biocatalytic synthesis of monoacylglycerides (MAGs) was carried out by the direct esterification of fatty acids (i.e. capric, lauric, myristic, palmitic and oleic acids, respectively) with glycerol in different ionic liquids (ILs) based on cations with long alkyl side-chains (e.g. 1-hexadecyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide [C16mim][NTf2], 1-dodecyl-3-methylimidazolium tetrafluoroborate [C12mim][BF4], etc.). Although all ILs have been shown as suitable reaction media for Novozym 435-catalyzed esterification of glycerol with free fatty acids, a high selectivity of MAGs was only observed in the [C12mim][BF4] case (e.g. up to 100% selectivity and 100% yield for monolaurin). Furthermore, as these ILs are temperature switchable ionic liquid/solid phases that behave as sponge-like systems, a straightforward protocol for IL-free MAG recovery, based on iterative centrifugations at controlled temperature, has been developed.