DL-Lactic acid (CAS: 50-21-5)
Colorless to light yellow liquid
122 °C15 mm Hg(lit.)
1.209 g/mL at 25 °C
Lactic acid is a chemical compound that plays a role in various biochemical processes and was first isolated in 1780 by the Swedish chemist Carl Wilhelm Scheele. Lactic acid is a carboxylic acid with the chemical formula C3H6O3. It has ahydroxyl group adjacent to the carboxyl group, making it an alpha hydroxy acid (AHA).
In solution, it can lose a proton from the carboxyl group, producing the lactate ion CH3CH(OH)COO−. Compared to acetic acid, its pKa is 1 unit less, meaning lactic acid deprotonates ten times more easily than acetic acid does. This higher acidity is the consequence of the intramolecular hydrogen bridge between the α-hydroxyl and the carboxylate group, making the latter less capable of strongly attracting its proton.
Lactic acid is miscible with water and with ethanol, and is hygroscopic.
Lactic acid is chiral and has two optical isomers. One is known as L-(+)-lactic acid or (S)-lactic acid and the other, its mirror image, is D-(−)-lactic acid or (R)-lactic acid.
In animals, L-lactate is constantly produced from pyruvate via the enzyme lactate dehydrogenase (LDH) in a process offermentation during normal metabolism and exercise. It does not increase in concentration until the rate of lactate production exceeds the rate of lactate removal, which is governed by a number of factors, including monocarboxylate transporters, concentration and isoform of LDH, and oxidative capacity of tissues. The concentration of blood lactate is usually 1–2 mmol/L at rest, but can rise to over 20 mmol/L during intense exertion.
In industry, lactic acid fermentation is performed by lactic acid bacteria, which convert glucose and sucrose to lactic acid. These bacteria can also grow in the mouth; the acid they produce is responsible for the tooth decay known ascaries.
In medicine, lactate is one of the main components of lactated Ringer's solution and Hartmann's solution. Theseintravenous fluids consist of sodium and potassium cations along with lactate and chloride anions in solution with distilled water, generally in concentrations isotonic with human blood. It is most commonly used for fluid resuscitationafter blood loss due to trauma, surgery, or burn injury.
Pharmaceutical and cosmetic applications
Lactic acid is also employed in pharmaceutical technology to produce water-soluble lactates from otherwise-insoluble active ingredients. It finds further use in topical preparations and cosmetics to adjust acidity and for its disinfectant and keratolytic properties.