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Lactic acid

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Lactic acid
Skeletal formula of L-lactic acid
Skeletal formula of L-lactic acid
Names
Preferred IUPAC name
2-Hydroxypropanoic acid
Other names
Milk acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.017 Edit this at Wikidata
E number E270 (preservatives)
UNII
  • 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 53°C
Boiling point 122 °C (252 °F; 395 K) @ 15 mmHg
Acidity (pKa) 3.86,[1] 15.1[2]
Thermochemistry
1361.9 kJ/mol, 325.5 kcal/mol, 15.1 kJ/g, 3.61 kcal/g
Pharmacology
G01AD01 (WHO) QP53AG02 (WHO)
Hazards
GHS labelling:
class="wikitable collapsible" style="min-width: 50em;"
GHS hazard pictograms[3]
Pictogram Code Symbol description Image link
GHS01: Explosive GHS01 {{GHS exploding bomb}} Image:GHS-pictogram-explos.svg Explosive
GHS02: Flammable GHS02 {{GHS flame}} Image:GHS-pictogram-flamme.svg
GHS03: Oxidizing GHS03 {{GHS flame over circle}} Image:GHS-pictogram-rondflam.svg
GHS04: Compressed Gas GHS04 {{GHS gas cylinder}} Image:GHS-pictogram-bottle.svg
GHS05: Corrosive GHS05 {{GHS corrosion}} Image:GHS-pictogram-acid.svg Corrosive
GHS06: Toxic GHS06 {{GHS skull and crossbones}} Image:GHS-pictogram-skull.svg Accute Toxic
GHS07: Exclamation mark GHS07 {{GHS exclamation mark}} Image:GHS-pictogram-exclam.svg Irritant
GHS08: Health hazard GHS08 {{GHS health hazard}} Image:GHS-pictogram-silhouette.svg Health Hazard
GHS09: Environmental hazard GHS09 {{GHS environment}} Image:GHS-pictogram-pollu.svg Environment

See also

|-


|-

| style="padding-left:1em;" |

| H315, H318[4]

|-

|-

| style="padding-left:1em;" |

| P280, P305+P351+P338[4]

|- ! colspan=2 style="background: #f8eaba; text-align: center;" |Related compounds

|-

|

Other anions

| lactate |-

|

| 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 |-


| colspan=2 style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;" |

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

|-

|}

Lactic acid is an organic compound with the formula CH3CH(OH)CO2H. In its solid state, it is white and water-soluble. In its liquid state, it is colorless. It is produced both naturally and synthetically. With a hydroxyl group adjacent to the carboxyl group, lactic acid is classified as an alpha-hydroxy acid (AHA). In the form of its conjugate base called lactate, it plays a role in several biochemical processes.

In solution, it can ionize a proton from the carboxyl group, producing the lactate ion CH
3CH(OH)CO−
2. 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 bonding between the α-hydroxyl and the carboxylate group. Lactic acid is chiral, consisting of 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. 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 around 17 or 18 °C. D-lactic acid and L-lactic acid have a higher melting point.

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 mMTooltip millimolar at rest, but can rise to over 20 mM during intense exertion and as high as 25 mM afterward.[5][6] 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).[7][8]

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 caries.[9][10][11][12] 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.

History

Lactic acid was isolated for the first time by the Swedish chemist Carl Wilhelm Scheele in 1780 from sour milk. The name reflects the lact- combining form derived from the Latin word for milk. In 1808, Jöns Jacob Berzelius discovered that lactic acid (actually L-lactate) also is produced in muscles during exertion.[13] 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 metric tons with an average annual growth of 10%.[14]

Production

Lactic acid is produced industrially by bacterial fermentation of carbohydrates (sugar, starch) or by chemical synthesis from acetaldehyde, that is available from coal or crude oil.[15] In 2009 lactic acid was produced predominantly (70–90%)[16] 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.

Fermentative production

Fermented milk products are obtained industrially by fermentation of milk or whey by Lactobacillius species: Lactobacillus acidophilus, Lactobacillus casei, Lactobacillus delbrueckii subsp. bulgaricus (Lactobacillus bulgaricus) and Lactobacillus helveticus, and furthermore Streptococcus salivarius subsp. thermophilus (Streptococcus thermophilus) and Lactococcus lactis.

As a starting material for industrial production of lactic chemistry, that is applied for chemical synthesis, almost any carbohydrate source containing C5/C6 sugars could be used. Pure sucrose, glucose from starch, raw sugar beet juice are frequently applied.[17] Lactic acid producing bacteria could be divided in two classes: homofermentative bacteria like Lactobacillus casei and Lactococcus lactis, producing two moles of lactate from one mole of glucose, heterofermentative species producing one mole of lactate from one mole of glucose as well as carbon dioxide and acetic acid/ethanol.[18]

Chemical production

Racemic lactic acid is produced in industry by addition of hydrogen cyanide to acetaldehyde and subsequent hydrolysis of forming lactonitrile. Hydrolysis performed by hydrochloric acid and ammonium chloride forms as a by-product. Japanese concern Musashino is one of the last big manufactures of lactic acid by this route.[19] Synthesis of both racemic and enantiopure lactic acids is also possible from other starting materials (vinyl acetate, glycerol, etc.) by application of catalytic procedures.[20]

Biology

Molecular biology

L-lactic acid is the primary endogenous agonist of hydroxycarboxylic acid receptor 1 (HCA1), a Gi/o-coupled G protein-coupled receptor (GPCR).[7][8]

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 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 atoms that join to form NADH, and cannot regenerate NAD+ quickly enough.)

The resulting lactate can be used in two ways:

However, lactate is continually formed even at rest and during moderate exercise. Some causes of this are 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.[21]

In 2004 Robergs et al. maintained that lactic acidosis during exercise is a "construct" or myth, pointing out that part of the H+ comes from ATP hydrolysis (ATP4− + H2O → ADP3− + HPO2−
4 + H+), and that reducing pyruvate to lactate (pyruvate− + NADH + H+ → lactate− + NAD+) actually consumes H+.[22] Lindinger et al.[23] countered that they had ignored the causative factors of the increase in [H+]. After all, the production of lactate− from a neutral molecule must increase [H+] to maintain electroneutrality. The point of Robergs's paper, however, was that lactate− is produced from pyruvate−, which has the same charge. It is pyruvate− production from neutral glucose that generates H+:

    C6H12O6 + 2 NAD+ + 2 ADP3− + 2 HPO2−
4 		→ 2 CH
3COCO−
2 + 2 H+ + 2 NADH + 2 ATP4− + 2 H2O
Subsequent lactate− production absorbs these protons:
2 CH
3COCO−
2 + 2 H+ + 2 NADH 		→ 2 CH
3CH(OH)CO−
2 + 2 NAD+
Overall:
C6H12O6 + 2 NAD+ + 2 ADP3− + 2 HPO2−
4 		→ 2 CH
3COCO−
2 + 2 H+ + 2 NADH + 2 ATP4− + 2 H2O
→ 2 CH
3CH(OH)CO−
2 + 2 NAD+ + 2 ATP4− + 2 H2O

Although the reaction glucose → 2 lactate− + 2 H+ releases two H+ when viewed on its own, the H+ are absorbed in the production of ATP. On the other hand, the absorbed acidity is released during subsequent hydrolysis of ATP: ATP4− + H2O → ADP3− + HPO2−
4 + H+. So once the use of the ATP is included, the overall reaction is

C6H12O6 → 2 CH
3COCO−
2 + 2 H+

The generation of CO2 during respiration also causes an increase in [H+].

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 mammalian species (the notable ones being mice, rats, and humans).[24][25] According to the lactate-shuttle hypothesis, glial cells are responsible for transforming glucose into lactate, and for providing lactate to the neurons.[26][27] 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.[24]

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.[24] 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,[28] acting either through better support of metabolites,[24] or alterations in base intracellular pH levels,[29][30] or both.[31]

Studies of brain slices of mice show that beta-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.[32] 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 predominately from activity-induced concentration changes to the cellular NADH pools."[33]

Blood testing

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 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.

Reference ranges
Lower limit Upper limit Unit
Venous 4.5[34] 19.8[34] mg/dL
0.5[35] 2.2[35] mmol/L
Arterial 4.5[34] 14.4[34] mg/dL
0.5[35] 1.6[35] mmol/L

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

Polymer precursor

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

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.

Foods

Lactic acid is found primarily in sour milk products, such as koumiss, 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.[36] If this is the case then the calculated food energy may use the standard 4 calories per gram that is often used for all carbohydrates. But in some cases lactic acid is ignored in the calculation.[37] The energy density of lactic acid is 362 kilocalories (1,510 kJ) per 100 g.[38]

In beer brewing some styles of beer (sour beer) purposely contain lactic acid. Most commonly this is produced naturally by various strains of bacteria. These bacteria ferment sugars into acids, unlike yeast, who ferment sugar into ethanol. One such style are Belgian Lambics. After cooling the wort, yeast and bacteria are allowed to “fall” into the open fermenters. Most brewers of more common beer styles would ensure no such bacteria are allowed to enter the fermenter. Other sour styles of beer include Berliner weisse, Flanders red and American wild ale.[39][40]

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.

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.[41]

As a food additive it is approved for use in the EU,[42] USA[43] and Australia and New Zealand;[44] 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.[45] It is an ingredient in processed foods and is used as a decontaminant during meat processing.[46] Lactic acid is produced commercially by fermentation of carbohydrates such as glucose, sucrose, or lactose, or by chemical synthesis.[45] Carbohydrate sources include corn, beets, and cane sugar.[47]

Mosquito lure

Lactic acid, along with ammonium bicarbonate, is used in the Lurex brand mosquito attractant.[48]

Forgery

Lactic acid has historically been used to assist with the erasure of inks from official papers to be modified during forgery.[49]

See also

References

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  40. ^ Lambic (Classic Beer Style) – Jean Guinard
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  48. ^ "Lurex3 MSDS" (PDF). Mosquito Magnet.
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