Lactic acid: Wikis

  
  

Note: Many of our articles have direct quotes from sources you can cite, within the Wikipedia article! This article doesn't yet, but we're working on it! See more info or our list of citable articles.

Did you know ...


More interesting facts on Lactic acid

Include this on your site/blog:

Encyclopedia

From Wikipedia, the free encyclopedia

Lactic acid
Identifiers
CAS number 598-82-3
D/L: [50-21-5]
L: [79-33-4]
D: [10326-41-7]
ChemSpider 96860
ATC code G01AD01,QP53AG02
SMILES
Properties
Molecular formula C3H6O3
Molar mass 90.08 g/mol
Melting point

L: 53 °C
D: 53 °C
D/L: 16.8 °C

Boiling point

122 °C @ 12 mmHg

Acidity (pKa) 3.86 at 25 °C
Related compounds
Other anions lactate
Related carboxylic acids acetic acid
glycolic acid
propionic acid
3-hydroxypropanoic acid
malonic acid
butyric acid
hydroxybutyric acid
Related compounds 1-propanol
2-propanol
propionaldehyde
acrolein
sodium lactate
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Lactic acid (IUPAC systematic name: 2-hydroxypropanoic acid), also known as milk acid, is a chemical compound that plays a role in several biochemical processes. It was first isolated in 1780 by a Swedish chemist, Carl Wilhelm Scheele, and is a carboxylic acid with a chemical formula of 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 CH3CH(OH)COO. It 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.

Industrially, lactic acid fermentation is performed by Lactobacillus bacteria, among others. These bacteria can operate in the mouth; the acid they produce is responsible for the tooth decay known as caries[citation needed].

In medicine, lactate is one of the main components of Ringer's lactate or lactated Ringer's solution (Compound Sodium Lactate or Hartmann's Solution in the UK). This intravenous fluid consists of sodium and potassium cations, with lactate and chloride anions, in solution with distilled water in concentration so as to be isotonic compared to human blood. It is most commonly used for fluid resuscitation after blood loss due to trauma, surgery, or a burn injury.

Contents

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 and 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

Contrary to popular belief, this increased concentration of lactate does not directly cause acidosis, nor is it responsible for delayed onset muscle soreness.[1] This is because lactate itself is not capable of releasing a proton [1], and secondly, the acidic form of lactate, lactic acid, "is not produced in muscle" [2]. 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 acidosis that is associated with increases in lactate concentration during heavy exercise arises from a separate reaction. When ATP is hydrolysed, a hydrogen ion is released. ATP-derived hydrogen ions are primarily responsible for the decrease in pH. During intense exercise, aerobic metabolism cannot produce ATP quickly enough to supply the demands of the muscle. As a result, anaerobic metabolism becomes the dominant energy producing pathway as it can form ATP at high rates. Due to the large amounts of ATP being produced and hydrolysed in a short period of time, the buffering systems of the tissues are overcome, causing pH to fall and creating a state of acidosis, a natural process which facilitates the easier dissociation of Oxyhaemoglobin and allows easier transfer of oxygen from the blood[3]. This may be one factor, among many, that contributes to the acute muscular discomfort experienced shortly after intense exercise.[citation needed]

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.[2] has been written to rebut the stoichiometric approach used by Robergs et al. (2004).[1] 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)

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

Polymer precursor

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

Nowadays, lactic acid is used as a monomer for producing polylactic acid (PLA) which later has 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 primarily found in sour milk products, such as: koumiss, leban, yogurt, kefir, and some cottage cheeses. The casein in fermented milk is coagulated (curdled) by lactic acid.

Detergents

Lactic acid has gained importance in the detergents industry the last decade. Being a good descaler, soap-scum remover and being a registered anti-bacterial agent - an economically beneficial as well as environmentally beneficial trend toward safer and natural ingredients has also contributed.

See also

References

  1. ^ a b c R. Robergs, F. Ghiasvand, D. Parker (2004). "Biochemistry of exercise-induced metabolic acidosis". Am J Physiol Regul Integr Comp Physiol 287 (3): R502–16. doi:10.1152/ajpregu.00114.2004. PMID 15308499. 
  2. ^ a b Michael I. Lindinger, John M. Kowalchuk, and George J. F. Heigenhauser (2004). "Applying physicochemical principles to skeletal muscle acid-base status". Am J Physiol Regul Integr Comp Physiol 289: R890–94. doi:110.1152/ajpregu.00225.2005.. PMID 16105823. 
  3. ^ Siggaard-Andersen, O.; Gøthgen, I. H. (1995). "Oxygen and acid-base parameters of arterial and mixed venous blood, relevant versus redundant". Acta Anaesthesiologica Scandinavica 39: 21–44. doi:10.1111/j.1399-6576.1995.tb04325.x.  edit

External links


Lactic acid
Identifiers
CAS number 50-21-5
D/L: [50-21-5]
L: [79-33-4]
D: [10326-41-7]
ChemSpider 96860
ATC code G01AD01,QP53AG02
SMILES
Properties
Molecular formula C3H6O3
Molar mass 90.08 g/mol
Melting point

L: 53 °C
D: 53 °C
D/L: 16.8 °C

Boiling point

122 °C @ 12 mmHg

Acidity (pKa) 3.86 at 25 °C
Related compounds
Other anions lactate
Related carboxylic acids acetic acid
glycolic acid
propionic acid
3-hydroxypropanoic acid
malonic acid
butyric acid
hydroxybutyric acid
Related compounds 1-propanol
2-propanol
propionaldehyde
acrolein
sodium lactate
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Lactic acid (IUPAC systematic name: 2-hydroxypropanoic acid), also known as milk acid, is a chemical compound that plays a role in several biochemical processes.It is a ketonic carboxylic acid. It was first isolated in 1780 by the Swedish chemist Carl Wilhelm Scheele. It is a carboxylic acid, whose chemical formula C3H6O3 has its 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 CH3CH(OH)COO. It 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 Lactobacillus bacteria, among others. These bacteria can operate in the mouth; the acid they produce is responsible for the tooth decay known as caries.[1][2][3][4]

In medicine, lactate is one of the main components of Ringer's lactate or lactated Ringer's solution (Compound Sodium Lactate or Hartmann's Solution in the UK). This intravenous fluid consists of sodium and potassium cations, with lactate and chloride anions, in solution with distilled water in concentration so as to be isotonic compared to human blood. It is most commonly used for fluid resuscitation after blood loss due to trauma, surgery, or a burn injury.

Contents

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 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.

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:

Contrary to popular belief, this increased concentration of lactate does not directly cause acidosis, nor is it responsible for delayed onset muscle soreness.[5] This is because lactate itself is not capable of releasing a proton,[5] and, second, the acidic form of lactate, lactic acid, "is not produced in muscle".[6] Analysis of the glycolytic pathway in humans indicates that there is not enough hydrogen ions present in the glycolytic intermediates to produce lactic or any other acid.

The acidosis that is associated with increases in lactate concentration during heavy exercise arises from a separate reaction. When ATP is hydrolysed, a hydrogen ion is released. ATP-derived hydrogen ions are responsible primarily for the decrease in pH. During intense exercise, aerobic metabolism cannot produce ATP quickly enough to supply the demands of the muscle. As a result, anaerobic metabolism becomes the dominant energy-producing pathway, as it can form ATP at high rates. Due to the large amounts of ATP being produced and hydrolysed in a short period of time, the buffering systems of the tissues are overcome, causing pH to fall and creating a state of acidosis, a natural process that facilitates the easier dissociation of oxyhaemoglobin and allows easier transfer of oxygen from the blood.[7] This may be one factor, among many, that contributes to the acute muscular discomfort experienced shortly after intense exercise.[citation needed]

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.[6] has been written to rebut the stoichiometric approach used by Robergs et al. (2004).[5] 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)

File:Blood values sorted by mass and molar
Reference ranges for blood tests, comparing blood content of lactate (shown in violet at center-right) with other constituents.

Polymer precursor

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

Nowadays, lactic acid is used 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, leban, yogurt, 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.

Detergents

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

See also

References

  1. ^ Ecology of Lactobacilli in the Oral Cavity: A Review of Literature The Open Microbiology Journal, 2008, Vol. 2, pages 38-48.
  2. ^ Correlations of oral bacterial arginine and urea catabolism with caries experience Oral Microbiol. Immunol. 2009, Vol. 24(2), pages 89–95.
  3. ^ Bacteria of Dental Caries in Primary and Permanent Teeth in Children and Young Adults Journal of Clinical Microbiology, 2008, Vol. 46(4), pages 1407–1417
  4. ^ Diversity of Lactobacilli in the Oral Cavities of Young Women with Dental Caries Caries Res. 2007, Vol. 41(1), pages 2–8
  5. ^ a b c Biochemistry of exercise-induced metabolic acidosis Am J Physiol Regul Integr Comp Physiol, 2004, Vol. 287, pages R502–R516
  6. ^ a b Applying physicochemical principles to skeletal muscle acid-base status Am J Physiol Regul Integr Comp Physiol, 2004, Vol. 289(3), pages R890–94
  7. ^ Siggaard-Andersen, O.; Gøthgen, I. H. (1995). [Expression error: Unexpected < operator "Oxygen and acid-base parameters of arterial and mixed venous blood, relevant versus redundant"]. Acta Anaesthesiologica Scandinavica 39: 21–44. doi:10.1111/j.1399-6576.1995.tb04325.x.  edit

External links


Simple English

Lactic acid is an acid that is very common in nature. Lactic Acid is a carboxylic acid with a chemical formula of C3H6O3.Carl Wilhelm Scheele discovered it in milk that had gone sour, in 1780. Today it is used as an additive to food, to produce a sour taste. It is also made in muscles when a person exercises.

is a carboxylic acid with a chemical formula of C3H6O3.









Got something to say? Make a comment.
Your name
Your email address
Message