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Lactic acid

(Redirected from D-lactate)

Lactic acid is an organic acid. It has the molecular formula C3H6O3. It is white in the solid state and it is miscible with water.[2] When in the dissolved state, it forms a colorless solution. Production includes both artificial synthesis as well as natural sources. Lactic acid is an alpha-hydroxy acid (AHA) due to the presence of a hydroxyl group adjacent to the carboxyl group. It is used as a synthetic intermediate in many organic synthesis industries and in various biochemical industries. The conjugate base of lactic acid is called lactate (or the lactate anion). The name of the derived acyl group is lactoyl.

Lactic acid
Names
Preferred IUPAC name
2-Hydroxypropanoic acid[1]
Other names
  • Lactic acid[1]
  • Milk acid
Identifiers
3D model (JSmol)
3DMet
1720251
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.017 Edit this at Wikidata
EC Number
  • 200-018-0
E number E270 (preservatives)
362717
KEGG
RTECS number
  • OD2800000
UNII
UN number 3265
  • InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m0/s1 checkY
    Key: JVTAAEKCZFNVCJ-REOHCLBHSA-N checkY
  • CC(O)C(=O)O
Properties
C3H6O3
Molar mass 90.078 g·mol−1
Melting point 18 °C (64 °F; 291 K)
Boiling point 122 °C (252 °F; 395 K) at 15 mmHg
Miscible[2]
Acidity (pKa) 3.86,[3] 15.1[4]
Thermochemistry
1361.9 kJ/mol, 325.5 kcal/mol, 15.1 kJ/g, 3.61 kcal/g
Related compounds
Other anions
 Lactate
Related compounds
Pharmacology
G01AD01 (WHO) QP53AG02 (WHO)
Hazards
GHS labelling:
GHS05: Corrosive[5]
H315, H318[5]
P280, P305+P351+P338[5]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

In solution, it can ionize by a loss of a proton to produce the lactate ion CH
3CH(OH)CO−
2. Compared to acetic acid, its pKa is 1 unit less, meaning lactic acid is ten times more acidic than acetic acid. This higher acidity is the consequence of the intramolecular hydrogen bonding between the α-hydroxyl and the carboxylate group.

Lactic acid is chiral, consisting of two enantiomers. One is known as L-lactic acid, (S)-lactic acid, or (+)-lactic acid, and the other, its mirror image, is D-lactic acid, (R)-lactic acid, or (−)-lactic acid. A mixture of the two in equal amounts is called DL-lactic acid, or racemic lactic acid. Lactic acid is hygroscopic. DL-Lactic acid is miscible with water and with ethanol above its melting point, which is about 16 to 18 °C (61 to 64 °F). D-Lactic acid and L-lactic acid have a higher melting point. Lactic acid produced by fermentation of milk is often racemic, although certain species of bacteria produce solely D-lactic acid.[6] On the other hand, lactic acid produced by fermentation in animal muscles has the (L) enantiomer and is sometimes called "sarcolactic" acid, from the Greek sarx, meaning "flesh".

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.[7] 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.[7] The concentration of blood lactate is usually 1–2 mMTooltip millimolar at rest, but can rise to over 20 mM during intense exertion and as high as 25 mM afterward.[8][9] In addition to other biological roles, L-lactic acid is the primary endogenous agonist of hydroxycarboxylic acid receptor 1 (HCA1), which is a Gi/o-coupled G protein-coupled receptor (GPCR).[10][11]

In industry, lactic acid fermentation is performed by lactic acid bacteria, which convert simple carbohydrates such as glucose, sucrose, or galactose to lactic acid. These bacteria can also grow in the mouth; the acid they produce is responsible for the tooth decay known as cavities.[12][13][14][15] 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 burns.

Lactic acid is produced in human tissues when the demand for oxygen is limited by the supply. This occurs during tissue ischemia when the flow of blood is limited as in sepsis or hemorrhagic shock. It may also occur when demand for oxygen is high such as with intense exercise. The process of lactic acidosis produces lactic acid which results in an oxygen debt which can be resolved or repaid when tissue oxygenation improves.[16]

History

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Swedish chemist Carl Wilhelm Scheele was the first person to isolate lactic acid in 1780 from sour milk.[17] The name reflects the lact- combining form derived from the Latin word lac, meaning "milk". In 1808, Jöns Jacob Berzelius discovered that lactic acid (actually L-lactate) is also produced in muscles during exertion.[18] Its structure was established by Johannes Wislicenus in 1873.

In 1856, the role of Lactobacillus in the synthesis of lactic acid was discovered by Louis Pasteur. This pathway was used commercially by the German pharmacy Boehringer Ingelheim in 1895.[citation needed]

In 2006, global production of lactic acid reached 275,000 tonnes with an average annual growth of 10%.[19]

Production

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Lactic acid is produced industrially by bacterial fermentation of carbohydrates, or by chemical synthesis from acetaldehyde.[20] As of 2009, lactic acid was produced predominantly (70–90%)[21] by fermentation. Production of racemic lactic acid consisting of a 1:1 mixture of D and L stereoisomers, or of mixtures with up to 99.9% L-lactic acid, is possible by microbial fermentation. Industrial scale production of D-lactic acid by fermentation is possible, but much more challenging.[citation needed]

Fermentative production

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Fermented milk products are obtained industrially by fermentation of milk or whey by Lactobacillus bacteria: Lactobacillus acidophilus, Lacticaseibacillus casei (Lactobacillus casei), Lactobacillus delbrueckii subsp. bulgaricus (Lactobacillus bulgaricus), Lactobacillus helveticus, Lactococcus lactis , Bacillus amyloliquefaciens, and Streptococcus salivarius subsp. thermophilus (Streptococcus thermophilus).[citation needed]

As a starting material for industrial production of lactic acid, almost any carbohydrate source containing C
5 (Pentose sugar) and C
6 (Hexose sugar) can be used. Pure sucrose, glucose from starch, raw sugar, and beet juice are frequently used.[22] Lactic acid producing bacteria can be divided in two classes: homofermentative bacteria like Lactobacillus casei and Lactococcus lactis, producing two moles of lactate from one mole of glucose, and heterofermentative species producing one mole of lactate from one mole of glucose as well as carbon dioxide and acetic acid/ethanol.[23]

Chemical production

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Racemic lactic acid is synthesized industrially by reacting acetaldehyde with hydrogen cyanide and hydrolysing the resultant lactonitrile. When hydrolysis is performed by hydrochloric acid, ammonium chloride forms as a by-product; the Japanese company Musashino is one of the last big manufacturers of lactic acid by this route.[24] Synthesis of both racemic and enantiopure lactic acids is also possible from other starting materials (vinyl acetate, glycerol, etc.) by application of catalytic procedures.[25]

Biology

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Molecular biology

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L-Lactic acid is the primary endogenous agonist of hydroxycarboxylic acid receptor 1 (HCA1), a Gi/o-coupled G protein-coupled receptor (GPCR).[10][11]

Metabolism and exercise

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See also: N-Lactoylphenylalanine

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 then produced from the pyruvate faster than the body can process it, causing lactate concentrations to rise. The production of lactate is beneficial for NAD+ regeneration (pyruvate is reduced to lactate while NADH is oxidized to NAD+), which is used up in oxidation of glyceraldehyde 3-phosphate during production of pyruvate from glucose, and this ensures that energy production is maintained and exercise can continue. During intense exercise, the respiratory chain cannot keep up with the amount of hydrogen ions that join to form NADH, and cannot regenerate NAD+ quickly enough, so pyruvate is converted to lactate to allow energy production by glycolysis to continue.[26]

The resulting lactate can be used in two ways:

Lactate is continually formed at rest and during all exercise intensities. Lactate serves as a metabolic fuel being produced and oxidatively disposed in resting and exercising muscle and other tissues.[26] Some sources of excess lactate production are metabolism in red blood cells, which lack mitochondria that perform aerobic respiration, and limitations in the rates of enzyme activity in muscle fibers during intense exertion.[27] Lactic acidosis is a physiological condition characterized by accumulation of lactate (especially L-lactate), with formation of an excessively high proton concentration [H+] and correspondingly low pH in the tissues, a form of metabolic acidosis.[26]

The first stage in metabolizing glucose is glycolysis, the conversion of glucose to pyruvate− and H+:

C6H12O6 + 2 NAD+ + 2 ADP3− + 2 HPO2−4 → 2 CH3COCO−2 + 2 H+ + 2 NADH + 2 ATP4− + 2 H2O

When sufficient oxygen is present for aerobic respiration, the pyruvate is oxidized to CO2 and water by the Krebs cycle, in which oxidative phosphorylation generates ATP for use in powering the cell. When insufficient oxygen is present, or when there is insufficient capacity for pyruvate oxidation to keep up with rapid pyruvate production during intense exertion, the pyruvate is converted to lactate− by lactate dehydrogenase), a process that absorbs these protons:[28]

2 CH3COCO−2 + 2 H+ + 2 NADH → 2 CH3CH(OH)CO−2 + 2 NAD+

The combined effect is:

C6H12O6 + 2 ADP3− + 2HPO2−4 → 2 CH3CH(OH)CO−2 + 2 ATP4− + 2 H2O

The production of lactate from glucose (glucose → 2 lactate− + 2 H+), when viewed in isolation, releases two H+. The H+ are absorbed in the production of ATP, but H+ is subsequently released during hydrolysis of ATP:

ATP4− + H2O → ADP3− + HPO2−4 + H+

Once the production and use of ATP is included, the overall reaction is

C6H12O6 → 2 CH3CH(OH)CO−2 + 2 H+

The resulting increase in acidity persists until the excess lactate and protons are converted back to pyruvate, and then to glucose for later use, or to CO2 and water for the production of ATP.[26]

Neural tissue energy source

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Although glucose is usually assumed to be the main energy source for living tissues, there is evidence that lactate, in preference to glucose, is preferentially metabolized by neurons in the brains of several mammalian species that include mice, rats, and humans.[29][30][26] According to the lactate-shuttle hypothesis, glial cells are responsible for transforming glucose into lactate, and for providing lactate to the neurons.[31][32] Because of this local metabolic activity of glial cells, the extracellular fluid immediately surrounding neurons strongly differs in composition from the blood or cerebrospinal fluid, being much richer with lactate, as was found in microdialysis studies.[29]

Brain development metabolism

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Some evidence suggests that lactate is important at early stages of development for brain metabolism in prenatal and early postnatal subjects, with lactate at these stages having higher concentrations in body liquids, and being utilized by the brain preferentially over glucose.[29] 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,[33] acting either through better support of metabolites,[29] or alterations in base intracellular pH levels,[34][35] or both.[36]

Studies of brain slices of mice show that β-hydroxybutyrate, lactate, and pyruvate act 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.[37] The study "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 predominantly from activity-induced concentration changes to the cellular NADH pools."[38]

Lactate can also serve as an important source of energy for other organs, including the heart and liver. During physical activity, up to 60% of the heart muscle's energy turnover rate derives from lactate oxidation.[17]

Blood testing

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

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 arterial (even if it is more difficult than venipuncture), because lactate levels differ substantially between arterial and venous, and the arterial level is more representative for this purpose.

Reference ranges
Lower limit Upper limit Unit
Venous 4.5[39] 19.8[39] mg/dL
0.5[40] 2.2[40] mmol/L
Arterial 4.5[39] 14.4[39] mg/dL
0.5[40] 1.6[40] mmol/L

During childbirth, lactate levels in the fetus can be quantified by fetal scalp blood testing.

Uses

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Polymer precursor

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Main article: polylactic acid

Two molecules of lactic acid can be dehydrated to the lactone lactide. In the presence of catalysts lactide polymerize to either atactic or syndiotactic polylactide (PLA), which are biodegradable polyesters. PLA is an example of a plastic that is not derived from petrochemicals.

Pharmaceutical and cosmetic applications

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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.

Lactic acid containing bacteria have shown promise in reducing oxaluria with its descaling properties on calcium compounds.[41]

Foods

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Fermented food

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Lactic acid is found primarily in sour milk products, such as kumis, laban, 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 bread.

In lists of nutritional information lactic acid might be included under the term "carbohydrate" (or "carbohydrate by difference") because this often includes everything other than water, protein, fat, ash, and ethanol.[42] If this is the case then the calculated food energy may use the standard 4 kilocalories (17 kJ) per gram that is often used for all carbohydrates. But in some cases lactic acid is ignored in the calculation.[43] The energy density of lactic acid is 362 kilocalories (1,510 kJ) per 100 g.[44]

Some beers (sour beer) purposely contain lactic acid, one such type being Belgian lambics. Most commonly, this is produced naturally by various strains of bacteria. These bacteria ferment sugars into acids, unlike the yeast that ferment sugar into ethanol. After cooling the wort, yeast and bacteria are allowed to "fall" into the open fermenters. Brewers of more common beer styles would ensure that no such bacteria are allowed to enter the fermenter. Other sour styles of beer include Berliner weisse, Flanders red and American wild ale.[45][46]

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 lactic acid bacteria.

While not normally found in significant quantities in fruit, lactic acid is the primary organic acid in akebia fruit, making up 2.12% of the juice.[47]

Separately added

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As a food additive it is approved for use in the EU,[48] United States[49] and Australia and New Zealand;[50] 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.[51] It is an ingredient in processed foods and is used as a decontaminant during meat processing.[52] Lactic acid is produced commercially by fermentation of carbohydrates such as glucose, sucrose, or lactose, or by chemical synthesis.[51] Carbohydrate sources include corn, beets, and cane sugar.[53]

Forgery

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Lactic acid has historically been used to assist with the erasure of inks from official papers to be modified during forgery.[54]

Cleaning products

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Lactic acid is used in some liquid cleaners as a descaling agent for removing hard water deposits such as calcium carbonate.[55]

See also

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References

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  2. ^ a b Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
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  39. ^ a b c d Blood Test Results – Normal Ranges Archived 2 November 2012 at the Wayback Machine Bloodbook.Com
  40. ^ a b c d Derived from mass values using molar mass of 90.08 g/mol
  41. ^ Campieri, C.; Campieri, M.; Bertuzzi, V.; Swennen, E.; Matteuzzi, D.; Stefoni, S.; Pirovano, F.; Centi, C.; Ulisse, S.; Famularo, G.; De Simone, C. (September 2001). "Reduction of oxaluria after an oral course of lactic acid bacteria at high concentration". Kidney International. 60 (3): 1097–1105. doi:10.1046/j.1523-1755.2001.0600031097.x. ISSN 0085-2538. PMID 11532105.
  42. ^ "USDA National Nutrient Database for Standard Reference, Release 28 (2015) Documentation and User Guide" (PDF). 2015. p. 13.
  43. ^ For example, in this USDA database entry for yoghurt the food energy is calculated using given coefficients for carbohydrate, fat, and protein. (One must click on "Full report" to see the coefficients.) The calculated value is based on 4.66 grams of carbohydrate, which is exactly equal to the sugars.
  44. ^ Greenfield H, Southgate D (2003). Food Composition Data: Production, Management and Use. Rome: FAO. p. 146. ISBN 9789251049495.
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  46. ^ Lambic (Classic Beer Style) – Jean Guinard
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  54. ^ Druckerman P (2 October 2016). "If I Sleep for an Hour, 30 People Will Die". The New York Times.
  55. ^ Naushad, Mu.; Lichtfouse, Eric (2019). Sustainable Agriculture Reviews 34: Date Palm for Food Medicine and the Environment. Springer. p. 162. ISBN 978-3-030-11345-2.
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