Methyl laurate
Ester
From Wikipedia, the free encyclopedia
Methyl laurate is an organic compound with the chemical formula CH3(CH2)10COOCH3. It is a colorless liquid. It has a fatty flavor. It is the methyl ester of lauric acid (dodecanoic acid). Methyl laurate belongs to the family of fatty acid esters. These are carboxylic esters of a fatty acid.[1]
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| Names | |
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| IUPAC name
Methyl dodecanoate | |
| Other names | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.003.556 |
| EC Number |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C13H26O2 | |
| Molar mass | 214.349 g·mol−1 |
| Appearance | Colorless liquid[3] |
| Odor | Fatty, floral, winey[1] |
| Density | 0.87 g/mL[3] |
| Melting point | 5.2 °C (41.4 °F; 278.3 K)[1] |
| Boiling point | 267 °C (513 °F; 540 K)[1] |
| Insoluble[1] | |
| Solubility | Miscible with ethanol, diethyl ether, acetone, soluble in most organic solvents[1] and dipropylene glycol[4] |
| Vapor pressure | 0.0055 hPa[3] |
Refractive index (nD) |
1.432[4] |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards |
Very toxic to the aquatic life with long-lasting effects |
| GHS labelling: | |
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| Warning | |
| H400, H411 | |
| P273, P391, P501 | |
| Flash point | 139 °C (282 °F)[3] |
| Related compounds | |
Related compounds |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis
Methyl laurate is synthesized by reaction between lauric acid and methanol by an esterification reaction, using Brønsted acid ionic liquids as catalysts (e.g., sulfuric acid).[5]
- CH3(CH2)10COOH + CH3OH → CH3(CH2)10COOCH3 + H2O
Lauric acid, as a component of triglycerides, comprises about a half of the fatty acid content in laurel oil, coconut oil, and palm kernel oil.[6][7][8]
Occurrence
Methyl laurate is found in species such as iyokan[9][1], mustard[10] and Mandragora autumnalis[1]. It is also found in alcoholic beverages, concord grape (Vitis labrusca), melon, pineapple, heated blackberry, red chilli (Capsicum frutescens) and other fruits. It is also present in cheese, hops oil, white wine, liquors and other foodstuffs.[1]
Uses
In food industry, methyl laurate is used as a flavoring agent. It is used as an intermediate for detergents, emulsifiers, wetting agents, stabilizers, lubricants, plasticizers, textiles, alkanolamides, fatty alcohols, and fatty acids.[1] It is also used as an emollient and skin conditioning agent in losions, skin creams, shampoos and hair oils. Methyl laurate is biodegradable. It is also used as a lubricant for machines and in metallurgy.[11] Methyl laurate is used as a component of biodiesel, because it takes high attention due to its favorable combustion properties, including its high cetane number and low viscosity.[12]