Chemistry:Methyl laurate
| |
| Names | |
|---|---|
| IUPAC name
Methyl dodecanoate
| |
| Other names | |
| Identifiers | |
3D model (JSmol)
|
|
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| EC Number |
|
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| 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 | |
| Main hazards | Very toxic to the aquatic life with long-lasting effects |
| GHS pictograms | 
|
| GHS Signal word | Warning |
| HH400Script error: No such module "Preview warning".Category:GHS errors, HH411Script error: No such module "Preview warning".Category:GHS errors | |
| PP273Script error: No such module "Preview warning".Category:GHS errors, PP391Script error: No such module "Preview warning".Category:GHS errors, PP501Script error: No such module "Preview warning".Category:GHS errors | |
| Flash point | 139 °C (282 °F)[3] |
| Related compounds | |
Related compounds
|
|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Methyl laurate is an organic compound with the chemical formula CH
3(CH
2)
10COOCH
3. 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]
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]
- CH
3(CH
2)
10COOH + CH
3OH → CH
3(CH
2)
10COOCH
3 + H
2O
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]
References
- ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 1.11 PubChem. "Methyl Laurate" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/Methyl-Laurate.
- ↑ ChemSpider. "Methyl laurate" (in en). https://www.chemspider.com/Chemical-Structure.7847.html.
- ↑ 3.0 3.1 3.2 3.3 Sigma-Aldrich. "Methyl laurate" (in en). https://www.sigmaaldrich.com/GB/en/sds/aldrich/234591.
- ↑ 4.0 4.1 Chemical Book. "METHYL LAURATE" (in en). https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6274029.htm.
- ↑ Han, Benyong; Yin, Fang; Liu, Shiqing; Zhao, Xingling; Liu, Jing; Wang, Changmei; Yang, Hong; Zhang, Wudi (1 March 2019). "Synthesis and Optimization of Methyl Laurate Using Sulfonated Pyrrolidonium Ionic Liquid as a Catalyst". International Journal of Chemical Reactor Engineering 17 (3). doi:10.1515/ijcre-2018-0144. https://www.degruyterbrill.com/document/doi/10.1515/ijcre-2018-0144/html. Retrieved 15 March 2026.
- ↑ Beare-Rogers, J. L.; Dieffenbacher, A.; Holm, J. V. (1 January 2001). "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry 73 (4): 685–744. doi:10.1351/pac200173040685. https://www.degruyterbrill.com/document/doi/10.1351/pac200173040685/html. Retrieved 15 March 2026.
- ↑ Anneken, David J.; Both, Sabine; Christoph, Ralf; Fieg, Georg; Steinberner, Udo; Westfechtel, Alfred (15 December 2006). "Fatty Acids". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a10_245.pub2. ISBN 978-3-527-30385-4. https://onlinelibrary.wiley.com/doi/10.1002/14356007.a10_245.pub2. Retrieved 15 March 2026.
- ↑ Eyres, Laurence; Eyres, Michael F.; Chisholm, Alexandra; Brown, Rachel C. (April 2016). "Coconut oil consumption and cardiovascular risk factors in humans". Nutrition Reviews 74 (4): 267–280. doi:10.1093/nutrit/nuw002.
- ↑ Uchida, Keiko; Matsumoto, Mitsuyo; Kobayashi, Akio; Yamanishi, Tei (15 March 1983). "Composition of Oxygenated Compoundsin Peel Oil from Citrus iyo and Its Variation during Storage". Agricultural and Biological Chemistry 47 (8): 1841–1845. doi:10.1271/bbb1961.47.1841. https://www.jstage.jst.go.jp/article/bbb1961/47/8/47_8_1841/_article. Retrieved 15 March 2026.
- ↑ Uda, Yasushi; Maeda, Yasuhiko (15 March 1986). "Volatile Constituents Occurring in Autolyzed Leaves of Three Cruciferous Vegetables". Agricultural and Biological Chemistry 50 (1): 205–208. doi:10.1271/bbb1961.50.205. https://www.jstage.jst.go.jp/article/bbb1961/50/1/50_1_205/_article. Retrieved 15 March 2026.
- ↑ ChemicalBull. "Methyl Laurate" (in en). https://www.chemicalbull.com/products/methyl-laurate.
- ↑ Alamsyah, Fikrul Akbar; Cheng, Chi-Cheng (2 March 2025). "Analysis of Flame Evolution Generated from Methyl Laurate Droplet Using Deep Learning". Applied Sciences 15 (5): 2678. doi:10.3390/app15052678.
 |  |
