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Monocaprylin is a monoglyceride emulsifier, specifically the ester formed from glycerol and caprylic acid (a C8 fatty acid). Its chemical formula is C₁₁H₂₂O₄.
As an amphiphilic molecule, it has a hydrophilic head and a lipophilic tail, allowing it to mix oil and water. This property makes it a valuable food additive for stabilizing textures in products like ice cream and whipped toppings.
Furthermore, it possesses antimicrobial properties and is used in pharmaceuticals and nutraceuticals as an absorption enhancer and a source of medium-chain triglycerides (MCTs).
Monocaprylin is a monoglyceride, a type of glyceride ester where one fatty acid is bonded to a glycerol backbone. Specifically, it is the monoester of glycerol and caprylic acid (an 8-carbon saturated fatty acid).
Its systematic chemical name is 1(or 2)-Monooctanoylglycerol, reflecting the fact that the fatty acid can be attached to either the first or second carbon of glycerol.
Backbone: Glycerol (a 3-carbon molecule with three hydroxyl groups, -OH).
Fatty Acid: Caprylic acid (also called octanoic acid), a saturated fatty acid with the formula CH₃(CH₂)₆COOH.
Bond: An ester linkage is formed between the carboxylic acid group (-COOH) of caprylic acid and one of the hydroxyl groups (-OH) of glycerol. This is a condensation reaction, releasing a molecule of water.
The two remaining hydroxyl groups on the glycerol molecule are free, making monocaprylin a polar molecule.
Structural Formula:
A common representation shows the fatty acid on the first (sn-1) position:
O
‖
CH₃-(CH₂)₆-C-O-CH₂
|
HO-CH
|
CH₂-OH
*(It's important to note that in practice, it can exist as either the 1- or 2- isomer, and commercial products are often a mixture.)*
Chemical Formula: C₁₁H₂₂O₄
Molecular Weight: 218.29 g/mol
CAS Number: 26402-26-6
Appearance: Typically a white to off-white waxy solid or a colorless, viscous liquid above its melting point.
Amphiphilic Nature: This is its most important chemical property. The molecule has:
A lipophilic (hydrophobic) tail: the caprylic acid chain, which repels water but mixes well with fats and oils.
A hydrophilic (lipophobic) head: the free glycerol and hydroxyl groups, which are attracted to water.
This structure makes it a non-ionic surfactant (emulsifier).
Surfactant/Emulsifier: Due to its amphiphilic structure, it reduces the surface tension between oil and water, allowing them to mix and form stable emulsions. It can form micelles in solution.
Melting Point: It has a relatively low melting point due to the medium-chain length of its fatty acid, but the exact value can depend on the isomeric form (1- or 2-).
Solubility:
Soluble in organic solvents like ethanol, ethyl acetate, and chloroform.
Sparingly soluble in water, but its solubility increases significantly upon heating. It disperses readily in water to form hydrating liquid crystalline phases.
Hydrolysis: The ester bond can be broken (hydrolyzed) under acidic or basic conditions, or by enzymatic action (e.g., by lipases), reverting back to glycerol and caprylic acid.
Monocaprylin is rarely found in significant amounts in nature. It is produced synthetically through several methods:
Glycerolysis: The most common industrial method. It involves the reaction of glycerol with triglycerides (oils/fats) rich in caprylic acid, such as coconut or palm kernel oil, often in the presence of a basic catalyst (e.g., NaOH).
Triglyceride (from oil) + Glycerol → Mixture of Mono-, Di-, and Triglycerides
Direct Esterification: The reaction of glycerol with pure caprylic acid, typically using an acid catalyst and heat.
Glycerol + Caprylic Acid → Monocaprylin + Water
Enzymatic Synthesis: A more specific and "green" method using lipase enzymes as biocatalysts to esterify glycerol and caprylic acid. This method can offer better control over the isomeric purity.
The resulting product is usually a mixture of mono-, di-, and triglycerides, from which monocaprylin is purified.
| Application | Chemical Function |
|---|---|
| Food Industry (Emulsifier) | Allows mixing of oil and water in products like ice cream, margarine, and whipped toppings, improving texture and stability. |
| Pharmaceuticals / Nutraceuticals | Used as an absorption enhancer for drugs due to its surfactant properties. It is also a source of medium-chain triglycerides (MCTs). |
| Antimicrobial Agent | Caprylic acid and its monoglyceride form are known to have effective antimicrobial (antibacterial, antiviral, antifungal) properties, disrupting microbial cell membranes. |
| Cosmetics & Personal Care | Acts as an emulsifier, emollient, and solubilizer in creams, lotions, and other products. |
| Aspect | Description |
|---|---|
| Chemical Classification | Monoglyceride (Monoacylglycerol) |
| Backbone | Glycerol |
| Fatty Acid Component | Caprylic Acid (C8:0) |
| Key Functional Groups | Ester bond, Free hydroxyl groups |
| Most Important Property | Amphiphilic nature (Surfactant/Emulsifier) |
| Chemical Formula | C₁₁H₂₂O₄ |
In essence, monocaprylin is a surfactant molecule synthesized from glycerol and caprylic acid, whose chemical structure赋予 it the ability to bridge oil and water phases, leading to its widespread use as an emulsifier and functional ingredient.
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