40738-26-9

Basic information

• Product Name: MONOLAURIN
• Synonyms: LAURIC ACID MONOGLYCERIDE;1-LAUROYL-RAC-GLYCEROL;1-MONODODECANOYL-RAC-GLYCEROL;1-MONOLAURIN;1-MONOLAUROYL-RAC-GLYCEROL;RAC-GLYCEROL 1-LAURATE;RAC-1-LAUROYLGLYCEROL;MONOLAURIN
• CAS NO: 40738-26-9
• Molecular Formula: C₁₅H₃₀O₄
• Molecular Weight: 274.4
• EINECS: 205-526-6
• Mol File: 40738-26-9.mol
• Article Data: 38

Chemical Properties

• Melting Point: 63°C
• Boiling Point: 337.38°C (rough estimate)
• Appearance: /
• Density: 0.9248
• Refractive Index: 1.4350 (estimate)
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: MONOLAURIN(CAS DataBase Reference)
• NIST Chemistry Reference: MONOLAURIN(40738-26-9)
• EPA Substance Registry System: MONOLAURIN(40738-26-9)

Safety Data

• WGK Germany: 1
• Hazardous Substances Data: 40738-26-9(Hazardous Substances Data)

Usage

Description

MONOLAURIN, also known as Glycerol Monolaurate, is a nonionic surfactant derived from glycerol and lauric acid. It is characterized by its self-emulsifying properties and medium hydrophilic-lipophilic balance (HLB). MONOLAURIN is commonly used in various industries due to its unique chemical properties, which include forming beads.

Uses

Used in Food Industry:
MONOLAURIN is used as an additive for enhancing the stability and texture of vegetable oils, flavors, and spice oils. Its self-emulsifying properties help in improving the overall quality and consistency of these products.
Used in Food Processing Systems:
In the food processing industry, MONOLAURIN is utilized as a defoamer to reduce the formation of foam during the processing of various food products. This helps in maintaining the efficiency of the production process and ensuring the desired quality of the final product.
Used in Cosmetics and Personal Care Industry:
Although not explicitly mentioned in the provided materials, MONOLAURIN is also known for its applications in the cosmetics and personal care industry. It is used as an emulsifier, helping to blend oil and water-based ingredients in cosmetic formulations, such as creams, lotions, and shampoos. Its mild and non-irritating nature makes it suitable for use in personal care products.
Used in Pharmaceutical Industry:
Similarly, MONOLAURIN finds applications in the pharmaceutical industry as an excipient in the formulation of drugs. Its emulsifying properties aid in the creation of stable drug formulations, improving their bioavailability and overall effectiveness.

Synthetic route

(2,2-dimethyl-1,3-dioxolan-4-yl)methyl dodecanoate (40630-75-9) → rac-1-monolauroylglycerol (40738-26-9)

Conditions	Yield
With ion-exchange resin C-244 In methanol; dichloromethane at 20℃; for 4h;	93%
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;

lauric acid (143-07-7) + 4-hydroxymethyl-1,3-dioxolan-2-one (931-40-8) → rac-1-monolauroylglycerol (40738-26-9)

Conditions	Yield
With triethylamine at 143 - 145℃; for 8h;	91%

lauric acid (143-07-7) + oxiranyl-methanol (556-52-5) → rac-1-monolauroylglycerol (40738-26-9)

Conditions	Yield
With (4-aminobutyl)silyl-MCM-41 type silica In toluene at 119.9℃; for 24h;	90%
With tributyl-amine at 85℃; for 5h;	61%
With (3-aminopropyl)silyl-micelle-templated silica In toluene at 119.9℃; for 6h; Product distribution; other acids, silicas, reaction conditions;	15%

allyl dodecanoate (7003-75-0) → rac-1-monolauroylglycerol (40738-26-9)

Conditions	Yield
With cethyltrimethylammonium permanganate In dichloromethane for 5h; Ambient temperature;	80%

vinyl laurate (2146-71-6) + glycerol (56-81-5) → rac-1-monolauroylglycerol (40738-26-9) + 1,3-dilauroylglycerol (539-93-5)

Conditions	Yield
lipase from Candida Antarctica type B, immobilized at 0℃; for 24h; Product distribution / selectivity; Enzymatic reaction;	A n/a B 78%
With silica gel; Lipozyme RM IM In tert-butyl methyl ether at 25℃; for 24h; Product distribution / selectivity; Schneider's method; Enzymatic reaction;

methyl n-dodecanoate (111-82-0) + glycerol (56-81-5) → rac-1-monolauroylglycerol (40738-26-9) + 1,3-dilauroylglycerol (539-93-5) + glyceryl dilaurate (17598-94-6)

Conditions	Yield
at 180℃; for 16h; Inert atmosphere; regioselective reaction;	A 71% B n/a C n/a

lauric acid (143-07-7) + glycerol (56-81-5) → rac-1-monolauroylglycerol (40738-26-9) + 1,3-dilauroylglycerol (539-93-5)

Conditions	Yield
lipase from Candida Antarctica type B, immobilized In hexane at 0 - 25℃; Product distribution / selectivity; Enzymatic reaction;	A n/a B 65%
With toluene-4-sulfonic acid In water at 120℃; under 450 Torr; for 4.5h;

lauric acid (143-07-7) + glycerol (56-81-5) → rac-1-monolauroylglycerol (40738-26-9)

Conditions	Yield
With toluene-4-sulfonic acid at 130℃; for 6h;	60.34%
With layered double hydroxide, Mg-Al-CO3 In neat (no solvent) at 100℃; for 2h; Temperature;
With calcium hydroxide at 230℃; under 637.564 Torr; for 2.5h; Temperature; Pressure; Autoclave; Large scale;

Sodium laurate (629-25-4) + 3-monochloro-1,2-propanediol (96-24-2) → rac-1-monolauroylglycerol (40738-26-9)

Conditions	Yield
at 130℃;

potassium laurate (10124-65-9) + 3-monochloro-1,2-propanediol (96-24-2) → rac-1-monolauroylglycerol (40738-26-9)

Conditions	Yield
at 180℃;

glycerol laurate (1678-45-1) → rac-1-monolauroylglycerol (40738-26-9)

Conditions	Yield
In hexane at 30℃; for 168h; Rate constant; Equilibrium constant;

lauric acid (143-07-7) + glycerol (56-81-5) → rac-1-monolauroylglycerol (40738-26-9) + 1,3-dilauroylglycerol (539-93-5) + tridodecanoylglycerol (538-24-9) + glycerol laurate (1678-45-1) + glyceryl dilaurate (17598-94-6)

Conditions	Yield
With silylated MCM-41-SO3H at 111.85℃; for 24h; Product distribution; other homogeneous and heterogeneous catalysts; also reactions with propanediols and meso-erythritol;	A 53 % Chromat. B n/a C n/a D n/a E n/a
Stage #1: lauric acid; glycerol at 120℃; under 450 Torr; for 2.5h; Stage #2: In hexane for 0.166667h; Product distribution / selectivity; Separation stage;

lauric acid (143-07-7) + glycerol (56-81-5) → rac-1-monolauroylglycerol (40738-26-9) + 1,3-dilauroylglycerol (539-93-5) + tridodecanoylglycerol (538-24-9) + glyceryl dilaurate (17598-94-6)

Conditions	Yield
With lipozyme at 45℃; under 3 Torr; for 3h; Esterification;	A 14.07 % Chromat. B 67.35 % Chromat. C 6.68 % Chromat. D 1.75 % Chromat.

β-oxy-γ-lauroyloxy-propylamine hydrochloride → rac-1-monolauroylglycerol (40738-26-9)

Conditions	Yield
With acetic acid; sodium nitrite at 0℃;

γ-chloro-propylene-α laurate → rac-1-monolauroylglycerol (40738-26-9)

Conditions	Yield
With silver(I) nitrite at 120℃;

<β.γ-dibromo-propyl>-laurate → rac-1-monolauroylglycerol (40738-26-9)

Conditions	Yield
With silver(I) nitrite at 110℃; und Verseifung des erhaltenen Nitrits;

lauric acid-(2,3-dibromo-propyl ester) (860764-99-4) + AgNO2 → rac-1-monolauroylglycerol (40738-26-9)

glycerol-α,β-isopropylidene ether-laurate → rac-1-monolauroylglycerol (40738-26-9)

Conditions	Yield
With sulfuric acid at 40℃;
With hydrogenchloride; diethyl ether
With hydrogenchloride; chloroform

tridodecanoylglycerol (538-24-9) + glycerol (56-81-5) + Na3PO4 → rac-1-monolauroylglycerol (40738-26-9)

O1,O2-isopropylidene-O3-lauroyl-glycerol → rac-1-monolauroylglycerol (40738-26-9)

Conditions	Yield
With 2-methoxy-ethanol; boric acid und Behandeln der Reaktionsloesung in Aether mit Wasser;

lauric acid (143-07-7) + glycerol (56-81-5) → rac-1-monolauroylglycerol (40738-26-9) + dilaurin and trilaurin

Conditions	Yield
With (1S)-10-camphorsulfonic acid; phenol at 180℃;

acetic acid (64-19-7) + (+/-)-lauric acid-(3-amino-2-hydroxy-propyl ester); hydrochloride + sodium nitrite → rac-1-monolauroylglycerol (40738-26-9)

Conditions	Yield
at 0℃;

methanol (67-56-1) + tridodecanoylglycerol (538-24-9) → rac-1-monolauroylglycerol (40738-26-9) + methyl n-dodecanoate (111-82-0) + glyceryl dilaurate (17598-94-6) + glycerol (56-81-5)

Conditions	Yield
With potassium hydroxide at 60℃; for 0.25h; Kinetics; Product distribution;

tridodecanoylglycerol (538-24-9) → rac-1-monolauroylglycerol (40738-26-9) + glyceryl dilaurate (17598-94-6) + glycerol (56-81-5)

Conditions	Yield
With pseudomonas fluorescens lipase; ethanol In hexane at 28℃; for 0.5h; Product distribution; Further Variations:; Solvents; Reagents;

lauric anhydride (645-66-9) + glycerol (56-81-5) → rac-1-monolauroylglycerol (40738-26-9)

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

methyl n-dodecanoate (111-82-0) + glycerol (56-81-5) → rac-1-monolauroylglycerol (40738-26-9) + 1,3-dilauroylglycerol (539-93-5) + glycerol laurate (1678-45-1) + glyceryl dilaurate (17598-94-6)

Conditions	Yield
HMS-TBD In dimethyl sulfoxide at 110℃; for 20h; Product distribution; Further Variations:; Catalysts; Pressures;

glyceryl dilaurate (17598-94-6) → rac-1-monolauroylglycerol (40738-26-9) + 1,3-dilauroylglycerol (539-93-5) + glycerol laurate (1678-45-1) + glycerol (56-81-5)

Conditions	Yield
With toluene-4-sulfonic acid In Petroleum ether for 1h; Equilibrium constant; Heating;

1,3-dilauroylglycerol (539-93-5) → rac-1-monolauroylglycerol (40738-26-9) + glycerol laurate (1678-45-1) + glyceryl dilaurate (17598-94-6) + glycerol (56-81-5)

Conditions	Yield
With toluene-4-sulfonic acid In Petroleum ether for 1h; Equilibrium constant; Heating;

lauric acid (143-07-7) + neutral potassium laurate → rac-1-monolauroylglycerol (40738-26-9)

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

Upstream product

• 143-07-7 lauric acid 
• 556-52-5 oxiranyl-methanol 
• 56-81-5 glycerol 
• 538-24-9 tridodecanoylglycerol 
• 17598-94-6 glyceryl dilaurate 
• 539-93-5 1,3-dilauroylglycerol 
• 7732-18-5 water 
• 111-82-0 methyl n-dodecanoate 
• 2146-71-6 vinyl laurate 
• 931-40-8 4-hydroxymethyl-1,3-dioxolan-2-one 
• 112-16-3 n-dodecanoyl chloride 
• 645-66-9 lauric anhydride 
• 67-56-1 methanol 
• 64-19-7 acetic acid 

Downstream Products

• 539-93-5 1,3-dilauroylglycerol 
• 60138-10-5 1,2-bis-decanoyloxy-3-lauroyloxy-propane 
• 35405-55-1 1-Lauryl-2,3-distearin 
• 1678-45-1 glycerol laurate 
• 538-24-9 tridodecanoylglycerol 
• 84015-55-4 1-lauroyl-rac-glycerophosphate 
• 17598-94-6 glyceryl dilaurate 
• 56-81-5 glycerol 
• 100165-14-8 3-dodecyloxypropane-1,2-diol 
• 17174-67-3 2-dodecyloxy-propane-1,3-diol 
• 143-07-7 lauric acid 
• 61824-39-3 glycerol-1-laurate-2,3-dilinolate 
• 60138-12-7 1-lauroyloxy-2,3-bis-myristoyloxy-propane 

Relevant articles and documents

Lipase-catalyzed two-step esterification for solvent-free production of mixed lauric acid esters with antibacterial and antioxidative activities

Mixed lauric acid esters (MLE) with antibacterial and antioxidative activities were produced through lipase-catalyzed two-step esterification in solvent-free system without purification. In the first reaction, erythorbyl laurate was synthesized for 72 h. Successive reaction for 6 h at molar ratio of 1.0 (lauric acid to glycerol) produced MLE containing erythorbyl laurate and glyceryl laurate with small amounts of residual substrates, by converting 99.52% of lauric acid. MLE addition (0.5–2.0%, w/w) to Tween 20-stabilized emulsions decreased droplet size, polydispersity index, and zeta-potential, possibly enhancing the emulsion stability. In the emulsions, MLE at 0.5 and 2.0% (w/w) caused 4.4–4.6 and 5.9–6.1 log reductions of Gram-positive (Staphylococcus aureus, Listeria monocytogenes) and Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa), respectively, within 12 h. Lipid hydroperoxide concentrations decreased to 50.8–98.3% in the presence of 0.5–2.0% (w/w) MLE. These findings support a novel approach without needing purification to produce multi-functional food additives for emulsion foods.

Enzymatic esterification of lauric acid to give monolaurin in a microreactor

Monolaurin is a naturally occurring compound widely utilized in food and cosmetics. In this paper, we present a new method for the synthesis of monolaurin by esterification between lauric acid and glycerol catalyzed by Novozym 435 using a microreactor. The conversion of lauric acid is 87.04% in 20 min, compared with 70.54% via the batch approach in 5 h. Using an optimized solvent system consisting of t-BuOH/tert-amyl alcohol (1:1, v/v), the selectivity using the microreactor method is enhanced to 90.63% and the space–time yield of the process is 380.91 g/h/L. This newly devised method has the potential for application to other multiphase and enzymatic reactions.

High-selectivity synthesis method of long-chain fatty acid monoglyceride

The invention belongs to the field of fatty acid and synthetic fatty acid glycerides and relates to a high-selectivity synthesis method of long-chain fatty acid monoglyceride, in particular to a high-selectivity synthesis method of long-chain fatty acid and synthetic fatty acid glycerides. The method comprises the steps that tetraethyl silicate and glycerin are subjected to alcoholysis reaction, and part of glycerin is esterified to generate glyceryl silicate; then the glyceryl silicate is subjected to esterification reaction with fatty acid to generate fatty acid glyceride; finally the high activity (instability) of silicate ester is utilized to achieve hydrolysis under mild conditions to synthesize the synthetic fatty acid glyceride at high selectivity. A by-product is safe and harmlessSiO2. Accordingly, the product with high monoglyceride content is obtained by using a simple process under mild conditions.