Methyl laurate

Methyl laurate
Names
IUPAC name
Methyl dodecanoate
Other names
  • Lauric acid methyl ester[1]
  • Methyl laurate[1]
  • Dodecanoic acid methyl ester[2]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.556
EC Number
  • 203-911-3
UNII
  • InChI=1S/C13H26O2/c1-3-4-5-6-7-8-9-10-11-12-13(14)15-2/h3-12H2,1-2H3
    Key: UQDUPQYQJKYHQI-UHFFFAOYSA-N
  • CCCCCCCCCCCC(=O)OC
Properties
CH3(CH2)10COOCH3
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]
1.432[4]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Very toxic to the aquatic life with long-lasting effects
GHS labelling:
Warning
H400, H411
P273, P391, P501
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 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]

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]

References

  1. ^ a b c d e f g h i j k l PubChem. "Methyl Laurate". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-03-14.
  2. ^ ChemSpider. "Methyl laurate". chemspider.com. Retrieved 2026-03-14.
  3. ^ a b c d Sigma-Aldrich. "Methyl laurate". www.sigmaaldrich.com. Retrieved 2026-03-14.
  4. ^ a b Chemical Book. "METHYL LAURATE". www.chemicalbook.com. Retrieved 2026-03-14.
  5. ^ 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. Retrieved 15 March 2026 – via www.degruyterbrill.com.
  6. ^ 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. Retrieved 15 March 2026 – via www.degruyterbrill.com.
  7. ^ 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. Retrieved 15 March 2026.
  8. ^ 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.
  9. ^ 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. Retrieved 15 March 2026 – via J-Stage.
  10. ^ 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. Retrieved 15 March 2026 – via J-Stage.
  11. ^ ChemicalBull. "Methyl Laurate". www.chemicalbull.com. Retrieved 2026-03-14.
  12. ^ 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.
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