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Ethyl lactate

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Ethyl (-)-L-lactate
Ethyl L-lactate
Ethyl L-lactate
Names
IUPAC name Ethyl (R)-2-hydroxypropanoate
Other names Ethyl lactate; Lactic acid ethyl ester; 2-Hydroxypropanoic acid ethyl ester; Actylol; Acytol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.363 Edit this at Wikidata
PubChem CID
RTECS number
  • OD5075000
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H10O3/c1-3-8-5(7)4(2)6/h4,6H,3H2,1-2H3Key: LZCLXQDLBQLTDK-UHFFFAOYSA-N
  • InChI=1/C5H10O3/c1-3-8-5(7)4(2)6/h4,6H,3H2,1-2H3Key: LZCLXQDLBQLTDK-UHFFFAOYAV
SMILES
  • CCOC(=O)C(C)O
Properties
Chemical formula C5H10O3
Molar mass 118.132 g·mol
Appearance Clear to slightly yellow liquid
Density 1.03 g/cm
Melting point −26 °C (−15 °F; 247 K)
Solubility in water Miscible
Solubility in ethanol
and most alcohols 		Miscible
Chiral rotation (D) −11.3°
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Irritant (Xi)
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1 1 0
Flash point 46 °C
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Ethyl lactate, also known as lactic acid ethyl ester, is a monobasic ester formed from lactic acid and ethanol, commonly used as a solvent. This compound is considered biodegradable and can be used as a water-rinsible degreaser. Ethyl lactate is found naturally in small quantities in a wide variety of foods including wine, chicken, and various fruits. The odor of ethyl lactate when dilute is mild, buttery, creamy, with hints of fruit and coconut.

Ethyl lactate is produced from biological sources, and can be either the levo (S) form or dextro (R) form, depending on the organism that is the source of the lactic acid. Most biologically sourced ethyl lactate is ethyl (-)-L-lactate. Ethyl lactate is also produced industrially from petrochemical stocks, and this ethyl lactate consists of the racemic mixture of levo and dextro forms. In some jurisdictions, the natural product is exempt from many restrictions placed upon use and disposal of solvents. Because both enantiomers are found in nature, and because ethyl lactate is easily biodegradable, it is considered to be a green solvent.

Due to its relatively low toxicity, ethyl lactate is used commonly in pharmaceutical preparations, food additives, and fragrances. Ethyl lactate is also used as solvent for nitrocellulose, cellulose acetate, and cellulose ethers.

Ethyl lactate hydrolyzes in the presence of water and acids or bases into lactic acid and ethanol.

Ethyl lactate can be used as a cosolvent to produce suitable conditions for the formation of aryl aldimines.

References

  1. U.S. Food and Drug Administration, Center for Food Safety and Applied Nutrition
  2. "Industrial Solvents Handbook" by Ernest W. Flick. 5th Edition. William Andrew Inc., 1998. ISBN 0815514131, 9780815514138
  3. Jacqueline S. Bennett, Kaitlyn L. Charles, Matthew R. Miner, Caitlin F. Heuberger, Elijah J. Spina, Michael F. Bartels and Taylor Foreman (2009). "Ethyl lactate as a tunable solvent for the synthesis of aryl aldimines". Green Chem. 11 (2): 166–168. doi:10.1039/b817379f.{{cite journal}}: CS1 maint: multiple names: authors list (link)

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