Lactic acid

Description

Lactic acid (2-hydroxypropionic acid, CH3-CHOH-COOH) is the most widely occurring organic acid in nature. Due to its chiral a-carbon atom, lactic acid (LA) has two enantiomeric forms. Of these, L-(+)-lactic acid is more important in food and pharmaceutical industries because humans have only L-lactate dehydrogenase. The chemical behavior of lactic acid is mostly determined by the two functional groups. Besides the acidic character in aqueous medium, the bifunctionality (a terminal carboxylic acid and a hydroxyl group) allows lactic acid molecules to form ‘‘interesters’’ such as the cyclic dimers, the trimers, or longer lactic acid oligomers.
After its first isolation by the Swedish chemist Scheel in 1780 from sour milk, lactic acid has been produced commercially since the 1880s in the United States and later in Europe. Worldwide, lactic acid production was approximately 250,000 metric tons per year in 2012 and is expected to reach 330,000 metric tons by the year 2015, with an average price of 1.25 US$ per kilogram in 2013 (food grade, 80–85 % purity).
Approximately 85 % of the demand for LA is from the food industry. The primary use of lactic acid is as a pH-adjusting agent in the beverage sector and as a preservative in the food industry. It is included in the Generally Recognized as Safe (GRAS) by the U.S. Food and Drug Administration [158] as a food ingredient and was deemed safe by the European Food Safety Authority as well [159]. The acceptable daily intake for LA was defined by the Joint FAO/WHO Expert Committee on Food Additives as ‘‘not limited,’’ and it is also supported by the Scientific Committee of Food.
In recent decades, the consumption of lactic acid due to its novel applications has grown quite rapidly, by 19 % per year. Nonfood use of lactic acid for polymer production contributes to this growth. Biodegradable polylactic acid is considered to be an environmentally friendly alternative to other plastics from petroleum. It is used in various fields, including drug delivery systems, medical devices, fibers, and packaging materials.
Lactic acid can be produced via chemical synthesis or carbohydrate fermentation. The chemical route has various issues, including toxic raw materials, low conversion rates, and especially the inability to produce the optically pure isomer. Therefore, approximately 90 % of lactic acid worldwide is produced by biotechnological processes, namely fermentations using renewable resources, which is relatively fast, economical, and able to supply selectively one or two stereoisomers of lactic acid.

Chemical properties

Lactic acid, CH3CHOHCOOH, also known as 2-hydroxypropanoic acid, is a hygroscopic liquid that exists in three isometric forms. I-lactic acid is found in blood and animal tissue as a product of glucose and glycogen metabolism. d-Iactic acid is obtained by fermentation of sucrose (corn refining), The racemic mixture is present in foods prepared by bacterial fermentation or prepared synthetically. Lactic acid is soluble in water,alcohol,and ether. It is used as a solvent, in manufacturing confectionery, and in medicine.

Chemical properties

A colorless or yellowish, nearly odorless, syrupy liquid consisting of a mixture of lactic acid (C3H6O3) and lactic acid lactate (C6H10O5). It is obtained by the lactic fermentation of sugars or is prepared synthetically. The commercial product is the racemic form. It is usually available in solutions containing the equivalent of from 50% to 90% lactic acid. It is hygroscopic, and when concentrated by boiling, the acid condenses to form lactic acid lactate, 2-(lactoyloxy)propanoic acid, which on dilution and heat ing hydrolyzes to lactic acid. It is miscible with water and with alcohol.

Chemical properties

Lactic acid is odorless. It consists of a mixture of lactic acid (C3H6O3) and lactic acid lactate (C6H10O5). The commercial product is the racemic form. It is usually available in solutions containing 50 to 90% lactic acid.

Chemical properties

Lactic acid consists of a mixture of 2-hydroxypropionic acid, its condensation products, such as lactoyllactic acid and other polylactic acids, and water. It is usually in the form of the racemate, (RS)-lactic acid, but in some cases the (S)-(+)-isomer is predominant.
Lactic acid is a practically odorless, colorless or slightly yellowcolored, viscous, hygroscopic, nonvolatile liquid.

Occurrence

Reported found in Papaver somniferum L.; it is a constituent of wine and sour milk; the two optically active isomers are found in muscular tissues and are formed by the action of lactic acid–producing bacteria in several fermentation processes. Also reported found in guava, grapes, melon, wheat bread, cheeses, yogurt, milk, cream, buttermilk, egg, cooked beef, cognac, cider, sherry, grape wine, beer, grape brandy, whiskey, cocoa, coffee, tea, mango, sake, wort, dried, bonito, cassava, Bourbon vanilla, chicory root, Cape gooseberry and cherimoya.

The Uses of Lactic acid

lactic acid (sodium lactate) is a multi-purpose ingredient used as a preservative, exfoliant, moisturizer, and to provide acidity to a formulation. In the body, lactic acid is found in the blood and muscle tissue as a product of the metabolism of glucose and glycogen. It is also a component of the skin’s natural moisturizing factor. Lactic acid has better water intake than glycerin. Studies indicate an ability to increase the water-retention capacity of the stratum corneum. They also show that the pliability of the stratum corneum layer is closely related to the absorption of lactic acid; that is, the greater the amount of absorbed lactic acid, the more pliable the stratum corneum layer. Researchers report that continuous use of preparations formulated with lactic acid in concentrations ranging between 5 and 12 percent provided a mild to moderate improvement in fine wrinkling and promote softer, smoother skin. Its exfoliating properties can help in the process of removing excess pigment from the surface of the skin, as well as improving skin texture and feel. Lactic acid is an alpha hydroxy acid occurring in sour milk and other lesser-known sources, such as beer, pickles, and foods made through a process of bacterial fermentation. It is caustic when applied to the skin in highly concentrated solutions.

The Uses of Lactic acid

Prostaglandin E1 analogue

The Uses of Lactic acid

Lactic Acid is an acidulant that is a natural organic acid present in milk, meat, and beer, but is normally associated with milk. it is a syrupy liquid available as 50 and 88% aqueous solutions, and is mis- cible in water and alcohol. it is heat stable, nonvolatile, and has a smooth, milk acid taste. it functions as a flavor agent, preservative, and acidity adjuster in foods. it is used in spanish olives to prevent spoilage and provide flavor, in dry egg powder to improve disper- sion and whipping properties, in cheese spreads, and in salad dress- ing mixes.

Background

A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed) Sodium lactate is the sodium salt of lactic acid, and has a mild saline taste. It is produced by fermentation of a sugar source, such as corn or beets, and then, by neutralizing the resulting lactic acid to create a compound having the formula NaC3H5O3.
Lactic acid was one of active ingredients in Phexxi, a non-hormonal contraceptive agent that was approved by the FDA on May 2020.

Indications

For use as an alkalinizing agent.

What are the applications of Application

Lactic acid is an α hydroxy acid

Definition

ChEBI: A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.

Production Methods

Lactic acid is prepared by the fermentation of carbohydrates, such as glucose, sucrose, and lactose, with Bacillus acidi lacti or related microorganisms. On a commercial scale, whey, corn starch, potatoes, or molasses are used as a source of carbohydrate. Lactic acid may also be prepared synthetically by the reaction between acetaldehyde and carbon monoxide at 130–200°C under high pressure, or by the hydrolysis of hexoses with sodium hydroxide.
Lactic acid prepared by the fermentation of sugars is levorotatory; lactic acid prepared synthetically is racemic. However, lactic acid prepared by fermentation becomes dextrorotatory on dilution with water owing to the hydrolysis of (R)-lactic acid lactate to (S)- lactic acid.

Biotechnological Production

Lactic acid is produced biotechnologically in general by fermentation of lactic acid bacteria. More information about this process and new trends are described later in this chapter.

Taste threshold values

Taste characteristics at 20 ppm: acidic sour creamy, dairylike with a fruity mango nuance

General Description

A colorless to yellow odorless syrupy liquid. Corrosive to metals and tissue. Used to make cultured dairy products, as a food preservative, and to make chemicals.

Air & Water Reactions

Soluble in water.

Reactivity Profile

Lactic acid is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in Lactic acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions. Slowly corrodes most metals [USCG, 1999].

Health Hazard

Inhalation of mist causes coughing and irritation of mucous membranes. Ingestion, even of diluted preparations, has a corrosive effect on the esophagus and stomach. Contact with more concentrated solutions can cause severe burns of skin or eye.

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

Pharmaceutical Applications

Lactic acid is used in beverages, foods, cosmetics, and pharmaceuticals as an acidifying agent and acidulant.
In topical formulations, particularly cosmetics, it is used for its softening and conditioning effect on the skin. Lactic acid may also be used in the production of biodegradable polymers and microspheres, such as poly(D-lactic acid), used in drug delivery systems.
Lactic acid is also used as a food preservative. Therapeutically, lactic acid is used in injections, in the form of lactate, as a source of bicarbonate for the treatment of metabolic acidosis; as a spermicidal agent; in pessaries for the treatment of leukorrhea; in infant feeds; and in topical formulations for the treatment of warts.

Industrial uses

lactic acid showed good depressing effect on hornblende, pyroxene and biotite during flotation of hematite and ilmenite minerals.

Biochem/physiol Actions

In animals, lactic acid is a metabolic compound produced by proliferating cells and during anaerobic conditions such as strenuous exercise. Lactic acid can be oxidized back to pyruvate or converted to glucose via gluconeogenesis. Lactic acid is preferentially metabolized by neurons in several mammal species and during early brain development.

Pharmacokinetics

Lactic acid produces a metabolic alkalinizing effect.

Safety

Lactic acid occurs in appreciable quantities in the body as an end product of the anaerobic metabolism of carbohydrates and, while harmful in the concentrated form , can be considered nontoxic at the levels at which it is used as an excipient. A 1% v/v solution, for example, is harmless when applied to the skin.
There is evidence that neonates have difficulty in metabolizing (R)-lactic acid, and this isomer and the racemate should therefore not be used in foods intended for infants aged less than 3 months old.
There is no evidence that lactic acid is carcinogenic, teratogenic, or mutagenic.
LD50 (guinea pig, oral): 1.81 g/kg
LD50 (mouse, oral): 4.88 g/kg
LD50 (mouse, SC): 4.5 g/kg
LD50 (rat, oral): 3.73 g/kg

Metabolism

Not Available

storage

Lactic acid is hygroscopic and will form condensation products such as polylactic acids on contact with water. The equilibrium between the polylactic acids and lactic acid is dependent on concentration and temperature. At elevated temperatures lactic acid will form lactide, which is readily hydrolyzed back to lactic acid.
Lactic acid should be stored in a well-closed container in a cool, dry place.

Incompatibilities

Incompatible with oxidizing agents, iodides, and albumin. Reacts violently with hydrofluoric acid and nitric acid.

Regulatory Status

GRAS listed. Accepted for use as a food additive in Europe. Included in the FDA Inactive Ingredients Database (IM, IV, and SC injections; oral syrups and tablets; topical and vaginal preparations). Included in medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.