Lactic acid

Lactic acid

GHS hazard pictograms

Skeletal formula of L-lactic acid L-Lactic acid Ball-and-stick model of L-lactic acid
Names
IUPAC name 2-Hydroxypropanoic acid
Other names Milk acid
Identifiers
CAS Number	50-21-5 79-33-4 (L) 10326-41-7 (D)
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL330546 Y
ChemSpider	96860
ECHA InfoCard	100.000.017
E number	E270 (preservatives)
CompTox Dashboard (EPA)	DTXSID7023192
SMILES CC(O)C(=O)O
Properties
Chemical formula	C3H6O3
Molar mass	90.07948
Melting point	L: 53 °C D: 53 °C D/L: 16.8 °C
Boiling point	122 °C @ 12 mmHg
Acidity (pKa)	3.86
Thermochemistry
Std enthalpy of combustion (ΔcH⦵298)	1361.9 kJ/mol, 325.5 kcal/mol, 15.1 kJ/g, 3.61 kcal/g
Related compounds
Other anions	lactate
Hazards
GHS labelling:
Pictograms	class="wikitable collapsible" style="min-width: 50em;"
Pictogram	Code	Symbol description	Image link
	GHS01	{{GHS exploding bomb}}	Image:GHS-pictogram-explos.svg	Explosive
	GHS02	{{GHS flame}}	Image:GHS-pictogram-flamme.svg
	GHS03	{{GHS flame over circle}}	Image:GHS-pictogram-rondflam.svg
	GHS04	{{GHS gas cylinder}}	Image:GHS-pictogram-bottle.svg
	GHS05	{{GHS corrosion}}	Image:GHS-pictogram-acid.svg	Corrosive
	GHS06	{{GHS skull and crossbones}}	Image:GHS-pictogram-skull.svg	Accute Toxic
	GHS07	{{GHS exclamation mark}}	Image:GHS-pictogram-exclam.svg	Irritant
	GHS08	{{GHS health hazard}}	Image:GHS-pictogram-silhouette.svg	Health Hazard
	GHS09	{{GHS environment}}	Image:GHS-pictogram-pollu.svg	Environment

See also

• {{H-phrases}}
• {{P-phrases}}
• Category:GHS templates

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Hazard statements

| H315, H318

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Precautionary statements

| P280, P305+P351+P338

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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

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Lactic acid, also known as milk 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 a hydroxyl group adjacent to the carboxyl group, making it an alpha hydroxy acid (AHA).

In solution, it can lose a proton from the acidic group, producing the lactate ion (to be specific, an anion due to being negatively charged with an extra electron) CH₃CH(OH)COO⁻. Compared to acetic acid, its pK_a is 1 unit smaller, meaning lactic acid loses its proton ten times as easily as 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 keeping its proton tight.

Lactic acid is miscible with water or 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. L-(+)-Lactic acid is the biologically important isomer.

In animals, L-lactate is constantly produced from pyruvate via the enzyme lactate dehydrogenase (LDH) in a process of fermentation 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. These bacteria can also grow in the mouth; the acid they produce is responsible for the tooth decay known as caries.

In medicine, lactate is one of the main components of lactated Ringer's solution and Hartmann's solution. These intravenous 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 resuscitation after blood loss due to trauma, surgery, or burn injury.

History

Lactic acid was refined for the first time by the Swedish chemist Carl Wilhelm Scheele in 1780 from sour milk. In 1808 Jöns Jacob Berzelius discovered that lactic acid (actually L-lactate) also is produced in muscles during exertion. Its structure was established by Johannes Wislicenus in 1873.

In 1856, Louis Pasteur discovered Lactobacillus and its role in the making of lactic acid. Lactic acid started to be produced commercially by the German pharmacy Boehringer Ingelheim in 1895.

In 2006, global production of lactic acid reached 275,000 tonnes with an average annual growth of 10%.

Exercise and lactate

During power exercises such as sprinting, when the rate of demand for energy is high, lactate is produced faster than the ability of the tissues to remove it, so lactate concentration begins to rise. This is a beneficial process, since the regeneration of NAD⁺ ensures that energy production is maintained and exercise can continue. The increased lactate produced can be removed in a number of ways, including:

• Oxidation to pyruvate by well-oxygenated muscle cells.
  • Pyruvate is then directly used to fuel the Krebs cycle.
• Conversion to glucose via gluconeogenesis in the liver and release back into the circulation; see the Cori cycle.
  • If not released, the glucose can be used to build up the liver's glycogen stores if they are empty.

Contrary to popular belief, this increased concentration of lactate does not directly cause acidosis, nor is it responsible for delayed onset muscle soreness. This is because lactate itself is not capable of releasing a proton, and, second, the acidic form of lactate, lactic acid, "is not produced in muscle". Analysis of the glycolytic pathway in humans indicates that there are not enough hydrogen ions present in the glycolytic intermediates to produce lactic or any other acid.

The effect of lactate on acidosis has been the topic of many recent conferences in the field of exercise physiology. Robergs et al. have accurately chased the proton movement that occurs during glycolysis. However, in doing so, they have suggested that [H⁺] is an independent variable that determines its own concentration. A recent review by Lindinger et al. has been written to rebut the stoichiometric approach used by Robergs et al. In using this stoichiometric process, Robergs et al. have ignored the causative factors (independent variables) of the concentration of hydrogen ions (denoted [H⁺]). These factors are strong ion difference [SID], PCO₂, and weak acid buffers. Lactate is a strong anion, and causes a reduction in [SID], which causes an increase in [H⁺] to maintain electroneutrality. PCO₂ also causes an increase in [H⁺]. During exercise, the intramuscular lactate concentration and PCO₂ increase, causing an increase in [H⁺], and, thus, a decrease in pH . (See Le Chatelier's principle)

During intense exercise, the respiratory chain cannot keep up with the amount of hydrogen atoms that join to form NADH. NAD+ is required to oxidize 3-phosphoglycoeraldehyde in order to maintain the production of anaerobic energy during glycolysis. During anaerobic glycolysis, NAD + “frees up” when extra nonoxidized hydrogens combine with a pyruvate molecule and then form lactate. If this does not occur, glycolysis comes to a stop. However, there is lactate being continually formed at rest and during moderate exercise. This occurs due to the metabolism of red blood cells that do not have mitochondria and limitations resulting from enzyme activity that occurs in muscle fibers that contain a high glycolytic capacity .

Reference ranges for blood tests, comparing blood content of lactate (shown in violet at center-right) with other constituents.

Brain metabolism

Although glucose is usually assumed to be the main energy source for living tissues, there are some indications that it is lactate, and not glucose, that is preferentially metabolized by neurons in the brain of several mammals species (the notable ones being mice, rats, and humans). According to the lactate-shuttling hypothesis, glial cells are responsible for transforming glucose into lactate, and for providing lactate to the neurons. Because of this local metabolic activity of glial cells, the extracellular fluid, immediately surrounding neurons, strongly differs in composition from the blood or cerebro-spinal fluid, being much richer with lactate, as it was found in microdialysis studies.

The role of lactate for brain metabolism seems to be even more important at early stages of development (prenatal and early postnatal), with lactate at these stages having higher concentrations in body liquids, and being utilized by the brain even more preferentially over glucose. It was also hypothesized that lactate may exert a strong action over GABAergic networks in the developing brain, making them more inhibitory than it was previously assumed, acting either through better support of metabolites, or alterations in base intracellular pH levels, or both.

More recent paper by Zilberter's group looked directly at the energy metabolism features in brain slices of immature mice and showed that beta-Hydroxybutyrate, lactate and pyruvate acted as oxidative energy substrates causing an increase in the NAD(P)H oxidation phase, that glucose was insufficient as an energy carrier during intense synaptic activity and finally, that actate can be an efficient energy substrate capable of sustaining and enhancing brain aerobic energy metabolism in vitro. The paper was positively commented by Kasischke (2011): "The study by Ivanov et al. (2011) also provides novel data on biphasic NAD(P)H fluorescence transients, an important physiological response to neural activation that has been reproduced in many studies and that is believed to originate predominately from activity-induced concentration changes to the cellular NADH pools."

Polymer precursor

Main article: polylactic acid

Two molecules of lactic acid can be dehydrated to lactide, a cyclic lactone. A variety of catalysts can polymerize lactide to either heterotactic or syndiotactic polylactide, which as biodegradable polyesters with valuable (inter alia) medical properties are currently attracting much attention.

Lactic acid is used also as a monomer for producing polylactic acid (PLA), which later has developed application as biodegradable plastic. This kind of plastic is a good option for substituting conventional plastic produced from petroleum oil because of low emission of carbon dioxide. The commonly used process in producing lactic acid is via fermentation, and, later, to obtain the polylactic acid, the polymerization process follows.

Foods

Lactic acid is found primarily in sour milk products, such as koumiss, laban, yoghurt, kefir, and some cottage cheeses. The casein in fermented milk is coagulated (curdled) by lactic acid. Lactic acid is also responsible for the sour flavor of sourdough breads. This acid is used in beer brewing to lower the pH and increase the body of the beer.

In winemaking, a bacterial process, natural or controlled, is often used to convert the naturally present malic acid to lactic acid, to reduce the sharpness and for other flavor-related reasons. This malolactic fermentation is undertaken by the family of lactic acid bacteria.

Detergents

Lactic acid has gained importance in the detergent industry the last decade. It is a good descaler, soap-scum remover, and a registered anti-bacterial agent. It is also economically beneficial as well as part of a trend toward environmentally safer and natural ingredients.

See also

• 2-Hydroxybutyric acid
• Acids in wine
• Alanine cycle
• Biodegradable plastic
• Cori cycle
• Dental caries

External links

• Corn Plastic to the Rescue
• Lactic acid: a safe and natural ingredient
• Lactic Acid: Information and Resources
• Lactic Acid Is Not Muscles' Foe, It's Fuel