|This article needs additional citations for verification. (October 2012)|
|CAS number||, (L) , (D)|
|Jmol-3D images||Image 1|
|Molar mass||90.08 g mol−1|
L: 53 °C
122 °C @ 12 mmHg
|Std enthalpy of
|1361.9 kJ/mol, 325.5 kcal/mol, 15.1 kJ/g, 3.61 kcal/g|
|Related carboxylic acids||acetic acid
|GHS hazard statements||H315, H318|
|GHS precautionary statements||P280, P305+351+338|
| (what is: / ?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 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 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 strongly attracting its proton.
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 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 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.
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 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, glucose is broken down and oxidized to pyruvate, and lactate is produced from the pyruvate faster than the tissues can remove it, so lactate concentration begins to rise. The production of lactate is a beneficial process because it regenerates NAD+ which is used up in the creation of pyruvate from glucose, and this ensures that energy production is maintained and exercise can continue. The increased lactate produced can be removed in two ways:
- Oxidation back 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 circulation; see Cori cycle.
- If not released, the glucose can be used to build up the liver's glycogen stores if they are empty.
The effect of lactate production on acidosis has been the topic of many recent conferences in the field of exercise physiology. Robergs et al. have discussed the creation of H+ ions that occurs during glycolysis. and claim that the idea that acidosis is caused by the production of lactic acid is a "construct" or myth, pointing out that part of the lowering of pH is due to the reaction ATP−4+H2O=ADP−3+HPO4−2+H+, and that reducing pyruvate to lactate (pyruvate+NADH+H+=lactate+NAD+) actually consumes H+. However, a response by Lindinger et al. has been written claiming that Robergs et al. ignored the causative factors of the increase in concentration of hydrogen ions (denoted [H+]). Specifically, lactate is an anion, and its production from a neutral molecule would cause a reduction in the amount of cations such as Na+ minus anions, and thus causes an increase in [H+] to maintain electroneutrality. However, pyruvate has the same charge as lactate, so interconversion of pyruvate and lactate does not affect electroneutrality: "lactate− production is not associated with a stoichiometrically equivalent net production of protons (H+)". The production, in the first place, of pyruvate anion from the neutral glucose is what requires extra cations for electroneutrality. Increasing partial pressure of CO2, 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-phosphoglyceraldehyde in order to maintain the production of anaerobic energy during glycolysis. During anaerobic glycolysis, NAD+ is “freed up” when NADH combines with pyruvate to form lactate (as mentioned above). If this did not occur, glycolysis would come to a stop. However, lactate is continually formed even at rest and during moderate exercise. This occurs due to metabolism in red blood cells that lack mitochondria, and limitations resulting from the enzyme activity that occurs in muscle fibers having a high glycolytic capacity.
Contrary to common belief, lactate or lactic acid buildup is not responsible for the muscle soreness felt in the days following strenuous exercise. The production of lactate and other metabolites during extreme exertion results in a burning sensation felt in active muscles. This painful sensation encourages one to stop overworking the body, thus forcing a recovery period in which the body clears the lactate and other metabolites.
Researchers who have examined lactate levels immediately following exercise found little correlation with the level of muscle soreness felt a few days later. This delayed onset muscle soreness (DOMS) is characterized by sometimes severe muscle tenderness as well as loss of strength and range of motion, usually reaching a peak 24 to 72 hours after the extreme exercise event.
The precise cause of DOMS is still unknown, though most research points to actual muscle cell damage and an elevated release of various metabolites into the tissue surrounding the muscle cells. These responses to extreme exercise result in an inflammatory-repair response, leading to swelling and soreness peaking a day or two after the event and resolves a few days later, depending on the severity of the damage. The type of muscle contraction is a key factor in the development of DOMS. When a muscle lengthens against a load the muscle contraction is said to be eccentric. The muscle is actively contracting, attempting to shorten its length, while failing. These eccentric contractions have been shown to result in more muscle cell damage than is seen with typical concentric contractions, in which a muscle successfully shortens during contraction against a load. Exercises that involve many eccentric contractions result in the most severe DOMS, even without any noticeable burning sensations in the muscles during the event.
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.
A more recent paper by Zilberter's group looked directly at the energy metabolism features in brain slices of 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 lactate can be an efficient energy substrate capable of sustaining and enhancing brain aerobic energy metabolism in vitro. The paper was positively commented by Kasischke: "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."
Blood tests for lactate are performed to determine the status of the acid base homeostasis in the body. Blood sampling for this purpose is often by arterial blood sampling (even if it is more difficult than venipuncture), because lactate differs substantially between arterial and venous levels, and the arterial level is more representative for this purpose.
|Lower limit||Upper limit||Unit|
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.
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.
|This section requires expansion. (October 2012)|
Lactic acid is found primarily in sour milk products, such as koumiss, laban, yogurt, kefir, some cottage cheeses and kombucha. 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 wort pH in order to reduce some undesirable substances such as tannins without giving off-flavors such as citric acid and increase the body of the beer. Some brewers and breweries will use food grade lactic acid to lower the pH in finished beers.
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.
As a food additive it is approved for use in the EU, USA and Australia and New Zealand; it is listed by its INS number 270 or as E number E270. Lactic acid is used as a food preservative, curing agent, and flavoring agent. It is an ingredient in processed foods and is used as a decontaminant during meat processing. Lactic acid is produced commercially by fermentation of carbohydrates such as glucose, sucrose, or lactose, or by chemical synthesis. Carbohydrate sources include corn, beets, and cane sugar.
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.
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- Blood Test Results - Normal Ranges Bloodbook.Com
- Derived from mass values using molar mass of 90.08 g/mol
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