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2-Hydroxypropanoic acid is a naturally occurring organic acid with the chemical formula C₃H₆O₃, widely used in food, cosmetics, pharmaceuticals, and industrial applications due to its multifunctional properties such as pH regulation, exfoliation, and biodegradability.
Produced through fermentation of carbohydrates or synthetic processes, 2-Hydroxypropanoic acid serves as a key ingredient in biodegradable plastics like poly2-Hydroxypropanoic acid (PLA) and as an acidulant, preservative, and flavor enhancer in food products.
In medicine, 2-Hydroxypropanoic acid is a component of lactated Ringer's solution, used for fluid resuscitation after trauma or surgery, and is a metabolic intermediate produced in muscles during anaerobic glycolysis.
CAS Number: 50-21-5
EC Number: 200-018-0
Molecular Formula: C3H6O3
Molecular Weight: 90.08 g/mol
Synonyms: Lactic acid, 2-hydroxypropanoic acid, DL-Lactic acid, 50-21-5, 2-hydroxypropionic acid, Milk acid, lactate, Tonsillosan, Racemic Lactic acid, Ordinary Lactic acid, PolyLactic acid, EthylideneLactic acid, Lactovagan, Acidum lacticum, 26100-51-6, Lactic acid, dl-, Propanoic acid, 2-hydroxy-, Kyselina mlecna, Lacticum acidum, DL-Milchsaeure, (+/-)-Lactic acid, 598-82-3, 1-Hydroxyethanecarboxylic acid, Aethylidenmilchsaeure, alpha-Hydroxypropionic acid, (RS)-2-Hydroxypropionsaeure, FEMA No. 2611, Kyselina 2-hydroxypropanova, Propionic acid, 2-hydroxy-, Purac FCC 80, Purac FCC 88, CCRIS 2951, HSDB 800, (+-)-2-Hydroxypropanoic acid, Lurex, Lactic acid, tech grade, Propanoic acid, hydroxy-, SY-83, DL- Lactic acid, NSC 367919, 2-Hydroxypropionicacid, AI3-03130, MFCD00004520, HIPURE 88, NSC-367919, .alpha.-Hydroxypropanoic acid, .alpha.-Hydroxypropionic acid, (R)-2-Hydroxy-propionic acid;H-D-Lac-OH, INS NO.270, E 270, (+/-)-2-hydroxypropanoic acid, CHEBI:78320, INS-270, Poly(L-lactide), 3B8D35Y7S4, Lactic acid USP, NCGC00090972-01, Lactic acid, 1.0N Standardized Solution, 2-hydroxy-propionic acid, Lactic acid (natural), E-270, DSSTox_CID_3192, alpha-Hydroxypropanoic acid, C01432, DSSTox_RID_76915, DSSTox_GSID_23192, Milchsaure [German], Lactic acid [JAN], Milchsaure, FEMA Number 2611, Kyselina mlecna [Czech], 163894-00-6, Cheongin samrakhan, CAS-50-21-5, Cheongin Haewoohwan, Cheongin Haejanghwan, Kyselina 2-hydroxypropanova [Czech], EINECS 200-018-0, EINECS 209-954-4, Lactic acid [USP:JAN], EPA Pesticide Chemical Code 128929, BRN 5238667, lactasol, 1-Hydroxyethane 1-carboxylic acid, Biolac, UNII-3B8D35Y7S4, 2-Hydroxy-2-methylacetic acid, Lactide Polymer, Chem-Cast, L- Lactic acid, DL-PolyLactic acid, Lactate (TN), Lactic acid,buffered, 4b5w, Propanoic acid, (+-), DL-Lactic acid, Racemic, (.+/-.)-Lactic acid, EC 200-018-0, Lactic acid (7CI,8CI), Lactic acid (JP17/USP), Lactic acid, 85%, FCC, Lactic acid, Racemic, USP, NCIOpen2_000884, Lactic acid (+-), DL-Lactic acid [MI], Lactic acid, unspecified form, Lactic acid [WHO-IP], (RS)-2-hydroxypropanoic acid, Lactic acid (Fragrance Grade), LACTICUM ACIDUM [HPUS], DL-Lactic acid (90per cent), CHEMBL1200559, DTXSID7023192, Lactic acid, natural, >=85%, BDBM23233, L-Lactic acid or dl-Lactic acid, Lactic acid, 85 Percent, FCC, Lactic acid, DL- [II], DL-Lactic acid, ~90% (T), DL-Lactic acid, AR, >=88%, DL-Lactic acid, LR, >=88%, DL- Lactic acid [WHO-DD], Lactic acid, 10 Percent Solution, HY-B2227, Propanoic acid, 2-hydroxy- (9CI), Tox21_111049, Tox21_202455, Tox21_303616, BBL027466, NSC367919, STL282744, AKOS000118855, AKOS017278364, Tox21_111049_1, ACIDUM LACTICUM [WHO-IP LATIN], AM87208, DB04398, SB44647, SB44652, DL-Lactic acid, 85 % (w/w), syrup, Propanoic acid,2-hydroxy-,(.+/-.)-, 2-Hydroxypropionic acid, DL-Lactic acid, NCGC00090972-02, NCGC00090972-03, NCGC00257515-01, NCGC00260004-01, 26811-96-1, Lactic acid, 85 Percent, Reagent, ACS, DB-071134, CS-0021601, FT-0624390, FT-0625477, FT-0627927, FT-0696525, FT-0774042, L0226, Lactic acid solution, ACS reagent, >=85%, Lactic acid solution, USP, 88.0-92.0%, Lactic acid solution, p.a., 84.5-85.5%, Lactic acid, meets USP testing specifications, D00111, F71201, A877374, DL-Lactic acid, SAJ first grade, 85.0-92.0%, Q161249, DL-Lactic acid, JIS special grade, 85.0-92.0%, Lactic acid solution, Vetec(TM) reagent grade, 85%, F2191-0200, BC10F553-5D5D-4388-BB74-378ED4E24908, Lactic acid, United States Pharmacopeia (USP) Reference Standard, Lactic acid, Pharmaceutical Secondary Standard; Certified Reference Material, DL-Lactic acid 90%, synthetic, meets the analytical specifications of Ph. Eur., 152-36-3
2-Hydroxypropanoic acid is an organic acid with the chemical formula C₃H₆O₃, widely used in various industrial, pharmaceutical, and food applications.
2-Hydroxypropanoic acid is a naturally occurring compound found in many living organisms, produced during the fermentation of sugars by certain bacteria, and is a key component in processes such as muscle metabolism in humans and animals.
2-Hydroxypropanoic acid is a colorless or slightly yellowish liquid with a mildly acidic odor and a slightly viscous texture.
2-Hydroxypropanoic acid is soluble in water and alcohol and is commonly found in both its L- and D-enantiomeric forms, with L-2-Hydroxypropanoic acid being the form most commonly encountered in nature and used in commercial products.
2-Hydroxypropanoic acid is produced through the fermentation of carbohydrates, often derived from plant-based sources like corn or sugar beets, or through synthetic chemical processes.
In the food industry, 2-Hydroxypropanoic acid serves as an acidulant, preservative, and flavoring agent, commonly used in products such as dairy items, pickles, and beverages to enhance flavor and extend shelf life.
2-Hydroxypropanoic acid is also a key ingredient in the production of 2-Hydroxypropanoic acid-based polymers like poly2-Hydroxypropanoic acid (PLA), a biodegradable plastic that has gained attention for its environmentally friendly properties.
In cosmetics and personal care products, 2-Hydroxypropanoic acid is employed for its exfoliating and moisturizing properties, helping to improve skin texture and reduce the appearance of fine lines and wrinkles.
2-Hydroxypropanoic acid is also used in the pharmaceutical industry for the manufacture of various medications, particularly as a pH regulator in topical creams and ointments.
2-Hydroxypropanoic acid is considered a safe and effective compound for use in a wide range of applications, though high concentrations can cause skin irritation or sensitivity.
2-Hydroxypropanoic acid's versatility and biodegradability make it a valuable component in the production of sustainable materials and products.
Moreover, the growing interest in bio-based chemicals has driven 2-Hydroxypropanoic acid production from renewable resources, aligning with the global trend toward green chemistry and reducing reliance on petroleum-based products.
2-Hydroxypropanoic acid is a naturally occurring alpha-hydroxy acid (AHA) widely used in food, cosmetics, pharmaceuticals, and industrial applications.
2-Hydroxypropanoic acid is valued for its multifunctional properties, including its ability to act as a pH regulator, humectant, and exfoliant in various formulations.
With its natural origin and biodegradability, 2-Hydroxypropanoic acid is a preferred ingredient for sustainable and eco-friendly products.
2-Hydroxypropanoic acid is a naturally derived alpha-hydroxy acid, produced through the fermentation of carbohydrates or other natural sources.
2-Hydroxypropanoic acid is widely recognized for its gentle exfoliating, moisturizing, and pH-regulating properties, making it suitable for personal care, pharmaceutical, and industrial applications.
2-Hydroxypropanoic acid is biodegradable and eco-friendly, contributing to its use in sustainable products for various industries.
2-Hydroxypropanoic acid is highly versatile and can be used across a wide pH range, ensuring its compatibility with numerous formulations.
Known for its non-irritating nature, 2-Hydroxypropanoic acid is suitable for sensitive skin applications, offering gentle yet effective results.
The combination of natural origin and efficacy has made 2-Hydroxypropanoic acid a staple ingredient in the food, cosmetics, and pharmaceutical industries.
2-Hydroxypropanoic acid is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 100 to < 1 000 tonnes per annum.
2-Hydroxypropanoic acid is used by consumers, in articles, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.
2-Hydroxypropanoic acid is a versatile ingredient that is used in the food industry as well as in cosmetics and medicine.
2-Hydroxypropanoic acid's preservative, moisturizing and antibacterial properties make it indispensable in manufacturing.
2-Hydroxypropanoic acid is an organic acid.
2-Hydroxypropanoic acid has the molecular formula C3H6O3.
2-Hydroxypropanoic acid is white in the solid state and it is miscible with water.
When in the dissolved state, 2-Hydroxypropanoic acid forms a colorless solution.
Production includes both artificial synthesis as well as natural sources.
2-Hydroxypropanoic acid is an alpha-hydroxy acid (AHA) due to the presence of a hydroxyl group adjacent to the carboxyl group.
2-Hydroxypropanoic acid is used as a synthetic intermediate in many organic synthesis industries and in various biochemical industries.
The conjugate base of 2-Hydroxypropanoic acid is called lactate (or the lactate anion).
The name of the derived acyl group is lactoyl.
In solution, 2-Hydroxypropanoic acid can ionize by a loss of a proton to produce the lactate ion CH3CH(OH)CO−2.
Compared to acetic acid, its pKa is 1 unit less, meaning 2-Hydroxypropanoic 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.
2-Hydroxypropanoic acid is chiral, consisting of two enantiomers.
One is known as L-2-Hydroxypropanoic acid, (S)-2-Hydroxypropanoic acid, or (+)-2-Hydroxypropanoic acid, and the other, its mirror image, is D-2-Hydroxypropanoic acid, (R)-2-Hydroxypropanoic acid, or (−)-2-Hydroxypropanoic acid.
A mixture of the two in equal amounts is called DL-2-Hydroxypropanoic acid, or racemic 2-Hydroxypropanoic acid. 2-Hydroxypropanoic acid is hygroscopic.
2-Hydroxypropanoic acid is miscible with water and with ethanol above its melting point, which is about 16 to 18 °C (61 to 64 °F).
D-2-Hydroxypropanoic acid and L-2-Hydroxypropanoic acid have a higher melting point.
2-Hydroxypropanoic acid produced by fermentation of milk is often racemic, although certain species of bacteria produce solely D-2-Hydroxypropanoic acid.
On the other hand, 2-Hydroxypropanoic 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, 2-Hydroxypropanoic acid is constantly produced from pyruvate via the enzyme lactate dehydrogenase (LDH) in a process of fermentation during normal metabolism and exercise.
2-Hydroxypropanoic acid 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.
In addition to other biological roles, 2-Hydroxypropanoic acid is the primary endogenous agonist of hydroxycarboxylic acid receptor 1 (HCA1), which is a Gi/o-coupled G protein-coupled receptor (GPCR).
In industry, 2-Hydroxypropanoic acid fermentation is performed by 2-Hydroxypropanoic acid bacteria, which convert simple carbohydrates such as glucose, sucrose, or galactose to 2-Hydroxypropanoic acid.
These bacteria can also grow in the mouth; the acid they produce is responsible for the tooth decay known as cavities.
In medicine, 2-Hydroxypropanoic acid 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.
2-Hydroxypropanoic acid is most commonly used for fluid resuscitation after blood loss due to trauma, surgery, or burns.
2-Hydroxypropanoic 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.
2-Hydroxypropanoic acid may also occur when demand for oxygen is high such as with intense exercise.
The process of 2-Hydroxypropanoic acidosis produces 2-Hydroxypropanoic acid which results in an oxygen debt which can be resolved or repaid when tissue oxygenation improves.
A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.
2-Hydroxypropanoic acid is a metabolic intermediate that is produced in the muscle cells during anaerobic glycolysis.
2-Hydroxypropanoic acid is used to treat cancer and has been shown to be effective against squamous cell carcinoma.
2-Hydroxypropanoic acid also inhibits mitochondrial membrane potential, which may be one of the mechanisms by which it causes cell death.
2-Hydroxypropanoic acid has been found to have antibacterial efficacy against a number of bacteria, including Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, Proteus mirabilis, Pseudomonas aeruginosa, and Streptococcus pyogenes.
2-Hydroxypropanoic acid also inhibits enzyme activities that are necessary for bacterial growth such as phosphotransferase enzymes and urease.
2-Hydroxypropanoic acid is a metabolic intermediate that can be used to inhibit tumor growth and metastasis.
2-Hydroxypropanoic acid also inhibits transcriptional regulation in human serum.
2-Hydroxypropanoic acid is odorless.
2-Hydroxypropanoic acid consists of a mixture of 2-Hydroxypropanoic acid (C3H6O3) and 2-Hydroxypropanoic acid lactate (C6H10O5).
2-Hydroxypropanoic acid is usually available in solutions containing 50 to 90% 2-Hydroxypropanoic acid.
2-Hydroxypropanoic acid is a hygroscopic liquid that exists in three isometric forms.
2-Hydroxypropanoic acid is found in blood and animal tissue as a product of glucose and glycogen metabolism.
2-Hydroxypropanoic acid is obtained by fermentation of sucrose (corn refining), The racemic mixture is present in foods prepared by bacterial fermentation or prepared synthetically.
2-Hydroxypropanoic acid is soluble in water,alcohol,and ether.
2-Hydroxypropanoic acid is used as a solvent, in manufacturing confectionery, and in medicine.
2-Hydroxypropanoic acid consists of a mixture of 2-hydroxypropionic acid, its condensation products, such as lactoyl2-Hydroxypropanoic acid and other poly2-Hydroxypropanoic acids, and water.
2-Hydroxypropanoic acid is usually in the form of the racemate, (RS)-2-Hydroxypropanoic acid, but in some cases the (S)-(+)-isomer is predominant.
2-Hydroxypropanoic acid is a practically odorless, colorless or slightly yellowcolored, viscous, hygroscopic, nonvolatile liquid.
2-Hydroxypropanoic acid is obtained by the lactic fermentation of sugars or is prepared synthetically.
The commercial product is the racemic form.
2-Hydroxypropanoic acid is usually available in solutions containing the equivalent of from 50% to 90% 2-Hydroxypropanoic acid.
2-Hydroxypropanoic acid is hygroscopic, and when concentrated by boiling, the acid condenses to form 2-Hydroxypropanoic acid lactate, 2-(lactoyloxy)propanoic acid, which on dilution and heat ing hydrolyzes to 2-Hydroxypropanoic acid.
2-Hydroxypropanoic acid is miscible with water and with alcohol.
2-Hydroxypropanoic acid is used in various fields, including drug delivery systems, medical devices, fibers, and packaging materials.
2-Hydroxypropanoic 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 2-Hydroxypropanoic 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 2-Hydroxypropanoic acid.
Uses of 2-Hydroxypropanoic Acid:
2-Hydroxypropanoic acid has a wide range of uses across several industries due to its versatility and beneficial properties.
Below are some of the key applications:
Food and Beverage Industry:
2-Hydroxypropanoic acid is commonly used as an acidulant, preservative, and flavoring agent in various food products.
2-Hydroxypropanoic acid is found in dairy products like yogurt, cheese, and sour cream, as well as in pickled vegetables and beverages.
2-Hydroxypropanoic acid helps enhance the tartness of foods and extends shelf life by preventing the growth of harmful bacteria.
Cosmetics and Personal Care:
In cosmetics, 2-Hydroxypropanoic acid is used as an exfoliant and moisturizer.
2-Hydroxypropanoic acid is a key ingredient in products like face creams, cleansers, and chemical peels, where it helps to remove dead skin cells, promote cell turnover, and improve skin texture.
2-Hydroxypropanoic acid also helps hydrate the skin by attracting water molecules, making it a valuable ingredient in anti-aging formulations.
Pharmaceuticals:
2-Hydroxypropanoic acid plays a role in the pharmaceutical industry as a pH regulator in topical creams and ointments.
2-Hydroxypropanoic acid is also used in the formulation of medications, such as intravenous solutions for rehydration, as it helps maintain the proper acid-base balance in the body.
2-Hydroxypropanoic acid is also involved in the production of certain drugs and has applications in the synthesis of biodegradable polymers.
Biodegradable Plastics:
2-Hydroxypropanoic acid is a key building block for the production of poly2-Hydroxypropanoic acid (PLA), a biodegradable plastic derived from renewable resources like corn or sugarcane.
PLA is used in a variety of applications, including packaging, medical devices, and textiles.
2-Hydroxypropanoic acid's environmental benefits, such as being compostable and reducing dependence on petroleum-based plastics, have made PLA increasingly popular in sustainability efforts.
Chemical Industry:
2-Hydroxypropanoic acid is used in the manufacture of various chemicals, including biodegradable solvents, coatings, and adhesives.
2-Hydroxypropanoic acid is also involved in the synthesis of chemicals used in the textile and leather industries, where it helps to adjust pH levels and improve the texture of fabrics and hides.
Agriculture:
In agriculture, 2-Hydroxypropanoic acid is used as a preservative in silage, helping to improve the fermentation process and maintain the quality of animal feed.
2-Hydroxypropanoic acid also finds application in the production of organic fertilizers.
Cleaning and Industrial Applications:
2-Hydroxypropanoic acid is used as a cleaning agent in various industrial settings due to its ability to remove scale, mineral deposits, and rust.
2-Hydroxypropanoic acid can also be found in household cleaning products, where it helps to break down grime and stains.
2-Hydroxypropanoic acid's broad applicability and the growing trend towards sustainable and bio-based products have significantly increased its demand in various sectors.
Biocidal Uses:
2-Hydroxypropanoic acid is approved in the EEA and/or Switzerland for use in biocidal products more favourable for the environment, human or animal health.
2-Hydroxypropanoic acid is an authorised food additive.
Consumer Uses:
2-Hydroxypropanoic acid is used in the following products: adhesives and sealants, anti-freeze products, biocides (e.g. disinfectants, pest control products), fillers, putties, plasters, modelling clay, finger paints, non-metal-surface treatment products, pH regulators and water treatment products, lubricants and greases, polishes and waxes and washing & cleaning products.
Other release to the environment of 2-Hydroxypropanoic acid is likely to occur from: outdoor use and indoor use as processing aid.
Widespread uses by professional workers:
2-Hydroxypropanoic acid is used in the following products: pH regulators and water treatment products, adhesives and sealants, anti-freeze products, biocides (e.g. disinfectants, pest control products), fillers, putties, plasters, modelling clay, finger paints, non-metal-surface treatment products, lubricants and greases, polishes and waxes and laboratory chemicals.
2-Hydroxypropanoic acid is used in the following areas: agriculture, forestry and fishing, health services and printing and recorded media reproduction.
2-Hydroxypropanoic acid is used for the manufacture of: chemicals, food products, textile, leather or fur, wood and wood products, pulp, paper and paper products, rubber products, plastic products, mineral products (e.g. plasters, cement) and furniture.
Other release to the environment of 2-Hydroxypropanoic acid is likely to occur from: outdoor use, indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners), indoor use in close systems with minimal release (e.g. cooling liquids in refrigerators, oil-based electric heaters) and outdoor use in close systems with minimal release (e.g. hydraulic liquids in automotive suspension, lubricants in motor oil and break fluids).
Uses at industrial sites:
2-Hydroxypropanoic acid is used in the following products: pH regulators and water treatment products, laboratory chemicals, coating products, non-metal-surface treatment products, washing & cleaning products, water treatment chemicals, adhesives and sealants and lubricants and greases.
2-Hydroxypropanoic acid is used in the following areas: mining and building & construction work.
2-Hydroxypropanoic acid is used for the manufacture of: chemicals, food products and plastic products.
Release to the environment of 2-Hydroxypropanoic acid can occur from industrial use: in the production of articles, in processing aids at industrial sites, as an intermediate step in further manufacturing of another substance (use of intermediates), as processing aid, for thermoplastic manufacture, as processing aid and of substances in closed systems with minimal release.
Applications of 2-Hydroxypropanoic Acid:
2-Hydroxypropanoic acid is extensively used as a food acidulant, providing a tart flavor and pH regulation in beverages, baked goods, and dairy products.
2-Hydroxypropanoic acid is included in pickling solutions and fermented foods, where it enhances flavor, extends shelf life, and stabilizes formulations.
2-Hydroxypropanoic acid is applied in meat preservation, where it prevents spoilage and reduces microbial growth, ensuring food safety.
2-Hydroxypropanoic acid is a key ingredient in skincare formulations, such as creams and serums, where it acts as an exfoliant, improving skin texture and tone.
2-Hydroxypropanoic acid is found in moisturizing lotions and body creams, where it hydrates the skin and enhances its softness.
2-Hydroxypropanoic acid is used in anti-aging products, promoting cell renewal and reducing the appearance of fine lines and wrinkles.
2-Hydroxypropanoic acid is included in chemical peels for its ability to exfoliate gently and improve skin radiance.
2-Hydroxypropanoic acid is found in acne treatments, where it helps unclog pores, reduce breakouts, and promote clearer skin.
2-Hydroxypropanoic acid is used in hair care products, such as shampoos and conditioners, where it maintains scalp pH and enhances shine.
2-Hydroxypropanoic acid is employed in pharmaceutical formulations as an excipient and pH regulator for topical and oral medications.
2-Hydroxypropanoic acid is applied in wound care products, where it maintains an optimal pH environment to support healing and reduce infection risks.
2-Hydroxypropanoic acid is used in dental products, such as toothpaste and mouthwash, to enhance oral hygiene and reduce microbial growth.
2-Hydroxypropanoic acid is incorporated into industrial cleaners, where it acts as a biodegradable acid for removing scale and rust from surfaces.
2-Hydroxypropanoic acid is utilized in agricultural products to improve soil health and aid in nutrient delivery for crops.
2-Hydroxypropanoic acid is used in eco-friendly formulations for industrial descaling and cleaning applications, reducing environmental impact.
2-Hydroxypropanoic acid is found in animal feed, where it enhances feed palatability and improves livestock gut health.
2-Hydroxypropanoic acid is used in bioplastic production as a precursor for poly2-Hydroxypropanoic acid (PLA), a sustainable material for packaging and disposable products.
2-Hydroxypropanoic acid is a component of adhesives and coatings, where it provides pH regulation and enhances stability.
2-Hydroxypropanoic acid is applied in pharmaceutical-grade inhalation therapies for pH adjustment and stabilization of active ingredients.
2-Hydroxypropanoic acid is utilized in fermented beverages and dairy products as a flavor enhancer and preservative.
2-Hydroxypropanoic acid is included in specialty cleaning products for healthcare facilities, where it provides effective cleaning and disinfection.
2-Hydroxypropanoic acid is a multi-purpose ingredient used as a preservative, exfoliant, moisturizer, and to provide acidity to a formulation.
In the body, 2-Hydroxypropanoic acid is found in the blood and muscle tissue as a product of the metabolism of glucose and glycogen.
2-Hydroxypropanoic acid is also a component of the skin’s natural moisturizing factor.
2-Hydroxypropanoic 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 2-Hydroxypropanoic acid; that is, the greater the amount of absorbed 2-Hydroxypropanoic acid, the more pliable the stratum corneum layer.
Researchers report that continuous use of preparations formulated with 2-Hydroxypropanoic acid in concentrations ranging between 5 and 12 percent provided a mild to moderate improvement in fine wrinkling and promote softer, smoother skin.
2-Hydroxypropanoic acid's 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.
2-Hydroxypropanoic 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.
2-Hydroxypropanoic acid is caustic when applied to the skin in highly concentrated solutions.
2-Hydroxypropanoic acid is an acidulant that is a natural organic acid present in milk, meat, and beer, but is normally associated with milk.
2-Hydroxypropanoic acid is a syrupy liquid available as 50 and 88% aqueous solutions, and is mis- cible in water and alcohol.
2-Hydroxypropanoic acid is heat stable, nonvolatile, and has a smooth taste.
2-Hydroxypropanoic acid functions as a flavor agent, preservative, and acidity adjuster in foods.
2-Hydroxypropanoic acid 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.
2-Hydroxypropanoic acid showed good depressing effect on hornblende, pyroxene and biotite during flotation of hematite and ilmenite minerals.
Pharmaceutical Applications:
2-Hydroxypropanoic acid is used in beverages, foods, cosmetics, and pharmaceuticals as an acidifying agent and acidulant.
In topical formulations, particularly cosmetics, 2-Hydroxypropanoic acid is used for its softening and conditioning effect on the skin.
2-Hydroxypropanoic acid may also be used in the production of biodegradable polymers and microspheres, such as poly(D-2-Hydroxypropanoic acid), used in drug delivery systems.
2-Hydroxypropanoic acid is also used as a food preservative.
Therapeutically, 2-Hydroxypropanoic 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.
Fermented food:
2-Hydroxypropanoic 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 2-Hydroxypropanoic acid.
2-Hydroxypropanoic acid is also responsible for the sour flavor of sourdough bread.
In lists of nutritional information 2-Hydroxypropanoic 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.
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 2-Hydroxypropanoic acid is ignored in the calculation.
The energy density of 2-Hydroxypropanoic acid is 362 kilocalories (1,510 kJ) per 100 g.
Some beers (sour beer) purposely contain 2-Hydroxypropanoic acid, one such type being Belgian lambics.
Most commonly, 2-Hydroxypropanoic acid 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.
In winemaking, a bacterial process, natural or controlled, is often used to convert the naturally present malic acid to 2-Hydroxypropanoic acid, to reduce the sharpness and for other flavor-related reasons.
This malolactic fermentation is undertaken by 2-Hydroxypropanoic acid bacteria.
While not normally found in significant quantities in fruit, 2-Hydroxypropanoic acid is the primary organic acid in akebia fruit, making up 2.12% of the juice.
Benefits of 2-Hydroxypropanoic Acid:
2-Hydroxypropanoic acid offers numerous benefits across various industries, making it a highly versatile and valuable compound.
Some of the key benefits include:
Skin Health:
In the cosmetics and skincare industry, 2-Hydroxypropanoic acid is widely used for its exfoliating and moisturizing properties.
2-Hydroxypropanoic acid helps remove dead skin cells, unclog pores, and promote skin regeneration, leading to smoother, more radiant skin.
2-Hydroxypropanoic acid also helps improve skin hydration by attracting moisture, making it beneficial for dry and dehydrated skin.
pH Regulation:
2-Hydroxypropanoic acid plays an important role as a pH regulator in many formulations.
In food and beverages, 2-Hydroxypropanoic acid helps maintain the ideal acidity, improving flavor, preservation, and texture.
In pharmaceuticals and cosmetics, 2-Hydroxypropanoic acid helps stabilize products and ensure they are effective and safe for use.
Preservative and Antimicrobial Properties:
2-Hydroxypropanoic acid acts as a natural preservative, inhibiting the growth of harmful bacteria and fungi.
In the food industry, 2-Hydroxypropanoic acid helps extend shelf life and maintain the safety of products, while in cosmetics, it can help prevent microbial contamination in formulations.
Biodegradable Plastic Production:
2-Hydroxypropanoic acid is a key ingredient in the production of poly2-Hydroxypropanoic acid (PLA), a biodegradable plastic.
PLA is an eco-friendly alternative to traditional petroleum-based plastics and is used in a variety of applications, including packaging, medical devices, and textiles.
The production of PLA from renewable resources like corn or sugarcane helps reduce reliance on fossil fuels and lowers environmental impact.
Sustainable and Renewable:
2-Hydroxypropanoic acid is produced through fermentation processes using renewable resources such as corn, sugarcane, or other plant-based materials.
This makes 2-Hydroxypropanoic acid a more sustainable option compared to synthetic chemicals derived from petroleum, aligning with the growing demand for bio-based and green chemicals.
Improved Digestion:
In the food industry, 2-Hydroxypropanoic acid is a natural byproduct of fermentation, commonly found in fermented foods like yogurt and sauerkraut.
2-Hydroxypropanoic acid supports gut health by promoting the growth of beneficial bacteria (probiotics), which aid in digestion and help maintain a balanced gut microbiome.
Industrial and Cleaning Applications:
2-Hydroxypropanoic acid is used in industrial cleaning products due to its ability to remove mineral deposits, rust, and stains.
2-Hydroxypropanoic acid is effective at breaking down grime without being as harsh or toxic as some other chemicals.
In agriculture, 2-Hydroxypropanoic acid helps preserve silage and maintain the quality of animal feed.
Sustainable Agriculture:
2-Hydroxypropanoic acid can be used in agricultural applications, such as organic fertilizers and feed preservation, contributing to more sustainable farming practices by improving feed quality and promoting healthier crops.
Drug Delivery:
In the pharmaceutical industry, 2-Hydroxypropanoic acid is utilized in drug delivery systems, especially in biodegradable polymers like PLA.
These polymers can be used for controlled and sustained release of medications, ensuring more effective treatment with fewer side effects.
Overall, 2-Hydroxypropanoic acid's benefits stem from its natural origin, multifunctionality, and versatility, making it an essential compound in a wide range of applications, from personal care products to industrial uses and sustainable practices.
Occurrence of 2-Hydroxypropanoic Acid:
2-Hydroxypropanoic acid 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 2-Hydroxypropanoic 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.
Biochem/physiol Actions of 2-Hydroxypropanoic Acid:
In animals, 2-Hydroxypropanoic acid is a metabolic compound produced by proliferating cells and during anaerobic conditions such as strenuous exercise.
2-Hydroxypropanoic acid can be oxidized back to pyruvate or converted to glucose via gluconeogenesis.
2-Hydroxypropanoic acid is preferentially metabolized by neurons in several mammal species and during early brain development.
Production Methods of 2-Hydroxypropanoic Acid:
2-Hydroxypropanoic 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.
2-Hydroxypropanoic 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.
2-Hydroxypropanoic acid prepared by the fermentation of sugars is levorotatory; 2-Hydroxypropanoic acid prepared synthetically is racemic.
However, 2-Hydroxypropanoic acid prepared by fermentation becomes dextrorotatory on dilution with water owing to the hydrolysis of (R)-2-Hydroxypropanoic acid lactate to (S)- 2-Hydroxypropanoic acid.
1. Starch raw materials, molasses, starch sugar as raw materials, after saccharification with the appropriate acid 2-Hydroxypropanoic acid bacteria or Bacillus in the appropriate conditions of fermentation, the calcium carbonate and precipitation, and then dilute sulfuric acid to 2-Hydroxypropanoic acid , And then refined after 2-Hydroxypropanoic acid products can be obtained.
Starch saccharification ↓ saccharification enzyme ↓ 2-Hydroxypropanoic acid bacteria and pressure filtration concentrated cooling acidification bleaching ↓ activated carbon ↓ sulfuric acid pumping vacuum concentration cation exchange anion exchange vacuum concentration decolorization filter finished product purification method:
2-Hydroxypropanoic acid has a strong hygroscopicity, concentrated partial 2-Hydroxypropanoic acid anhydride, heating itself prone to esterification reaction.
Therefore, even if distilled under reduced pressure, 2-Hydroxypropanoic acid is difficult to obtain pure product.
The fraction was fractionated at 13.3 Pa, and the distillate was dissolved with a mixture of equal amounts of ether and isopropyl ether to cool the crystals at an ice salt temperature.
Filtered and then repeated twice.
2-Hydroxypropanoic acid can also be crystallized at the dry ice temperature.
The solvent may also be used in a mixed solvent of equal amounts of benzene and diethyl ether containing 5% petroleum ether (b.p. 60 to 80C).
2. There are three methods of producing 2-Hydroxypropanoic acid in industry, fermentation, acetaldehyde and acrylonitrile.
The most widely used is the fermentation method, is the raw material containing starch sucrose, beet sugar, molasses or grain starch as raw material, saccharification access 2-Hydroxypropanoic acid bacteria, ph = 5, 49 ℃ fermentation 3 to 4 days, with calcium carbonate And, while hot filter, refined with calcium lactate.
And then acidified with sulfuric acid, filtered, the filtrate concentrated, decolorization, impurity that product.
3 synthesis of chemical synthesis of acetaldehyde and acrylonitrile method, the resulting 2-Hydroxypropanoic acid DL.
(1) acetaldehyde method to acetaldehyde and hydrocyanic acid as raw materials to produce milk, the hydrolysis of crude 2-Hydroxypropanoic acid, crude 2-Hydroxypropanoic acid by ethanol esterification and then hydrolysis of 2-Hydroxypropanoic Acid: acetaldehyde and cold hydrocyanic acid into the reaction And then add the water and sulfuric acid catalyzed hydrolysis of 2-Hydroxypropanoic acid; ethanol after esterification distillation of ethyl lactate; finally sent to the concentration of concentrated decomposition of refined milk 2-Hydroxypropanoic acid.
(2) Acrylonitrile acrylonitrile hydrolysis of crude 2-Hydroxypropanoic acid, and then esterified by methanol after hydrolysis of 2-Hydroxypropanoic Acid: acrylonitrile sent to the reactor, in the catalytic hydrolysis of sulfuric acid to produce a mixture of 2-Hydroxypropanoic acid and ammonium sulfate.
The mixture into the esterification reactor and methanol esterification, separation of ammonium sulfate, the crude ester to send distillation tower, the bottom of the fine ester.
Refined ester distillation tower, heating decomposition, was dilute 2-Hydroxypropanoic acid.
Finally, 2-Hydroxypropanoic acid is concentrated by vacuum.
3. Tobacco:
In the food industry by the glucose, starch, milk fermentation preparation; acetaldehyde and hydrocyanic acid reaction to produce cyanoethanol, and then hydrolyzed to produce crude 2-Hydroxypropanoic acid, vinegar 2-Hydroxypropanoic acid into ethyl lactate, and then hydrolyzed to pure 2-Hydroxypropanoic acid.
Production
2-Hydroxypropanoic acid is produced industrially by bacterial fermentation of carbohydrates, or by chemical synthesis from acetaldehyde.
As of 2009, 2-Hydroxypropanoic acid was produced predominantly (70–90%) by fermentation.
Production of racemic 2-Hydroxypropanoic acid consisting of a 1:1 mixture of D and L stereoisomers, or of mixtures with up to 99.9% L-2-Hydroxypropanoic acid, is possible by microbial fermentation.
Industrial scale production of 2-Hydroxypropanoic acid by fermentation is possible, but much more challenging.
Chemical production:
Racemic 2-Hydroxypropanoic 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 2-Hydroxypropanoic acid by this route.
Synthesis of both racemic and enantiopure 2-Hydroxypropanoic acid's is also possible from other starting materials (vinyl acetate, glycerol, etc.) by application of catalytic procedures.
Handling and Storage of 2-Hydroxypropanoic Acid:
Handling:
Use appropriate safety equipment such as gloves and goggles.
Ensure adequate ventilation in work areas to prevent inhalation of fumes or vapors.
Avoid contact with eyes, skin, and clothing.
Avoid inhalation of vapors or mist.
Wash hands thoroughly after handling.
Storage:
Store in a cool, dry, well-ventilated area away from incompatible materials (e.g., strong bases, oxidizing agents).
Keep containers tightly closed to prevent moisture absorption and contamination.
Store in corrosion-resistant containers (preferably plastic or glass).
Avoid exposure to high temperatures, direct sunlight, or sources of heat.
Reactivity and Stability of 2-Hydroxypropanoic Acid:
Stability:
2-Hydroxypropanoic acid is stable under normal conditions of use and storage.
Conditions to Avoid:
Avoid high temperatures and direct sunlight.
Keep away from open flames and heat sources.
Avoid contamination with incompatible materials.
Incompatible Materials:
Strong bases, strong oxidizing agents, and alkali metals.
Hazardous Decomposition Products:
When heated to decomposition, 2-Hydroxypropanoic acid may release carbon monoxide and carbon dioxide.
First Aid Measures of 2-Hydroxypropanoic Acid:
Inhalation:
Remove the person from exposure to fresh air immediately.
If symptoms persist, seek medical attention.
Skin Contact:
Immediately wash the affected area with plenty of water and soap.
Remove contaminated clothing and wash before reuse.
If irritation persists, seek medical attention.
Eye Contact:
Rinse immediately with plenty of water for at least 15 minutes, holding the eyelids open.
Seek immediate medical attention if irritation persists or vision changes occur.
Ingestion:
Rinse mouth with water immediately.
Do not induce vomiting unless directed by a medical professional.
Seek medical attention if symptoms persist or ingestion is significant.
Firefighting Measures of 2-Hydroxypropanoic Acid:
Fire Hazard:
2-Hydroxypropanoic acid is a flammable liquid.
2-Hydroxypropanoic acid can catch fire when exposed to high temperatures or flame.
Extinguishing Media:
Use dry chemical, carbon dioxide (CO₂), foam, or water spray.
Water may be used to cool containers to prevent rupture or explosion.
Firefighting Instructions:
Firefighters should wear self-contained breathing apparatus (SCBA) and full protective gear.
Evacuate area and move containers away from the fire if 2-Hydroxypropanoic acid is safe to do so.
Accidental Release Measures of 2-Hydroxypropanoic Acid:
Personal Precautions:
Wear appropriate personal protective equipment (PPE) like gloves, goggles, and protective clothing.
Ensure adequate ventilation in the affected area.
Environmental Precautions:
Prevent large spills from entering water sources, drains, or the environment.
Contain the spill with an appropriate barrier or absorbent material.
Methods for Cleaning Up:
Absorb spills with inert material like sand or earth and place in a suitable waste disposal container.
Wash the area with water, and ensure that all residues are removed.
Exposure Controls / Personal Protective Equipment of 2-Hydroxypropanoic Acid:
Exposure Limits:
No specific OSHA or ACGIH exposure limits for 2-Hydroxypropanoic acid; however, general safety measures for chemical handling apply.
Engineering Controls:
Use adequate ventilation to maintain airborne concentrations below recommended exposure limits.
If necessary, use local exhaust ventilation to avoid inhalation exposure.
Personal Protective Equipment (PPE):
Eye Protection:
Wear safety glasses or goggles with side shields.
Use face shields if necessary.
Skin Protection:
Wear appropriate gloves (rubber, nitrile, or neoprene) and protective clothing to prevent skin contact.
Respiratory Protection:
Use an NIOSH-approved respirator if ventilation is inadequate or if exposure exceeds acceptable limits.
Work Practices:
Wash hands thoroughly after handling 2-Hydroxypropanoic acid, especially before eating or drinking.
Identifiers of 2-Hydroxypropanoic Acid:
CAS Number: 50-21-5
EC Number: 200-018-0
Molecular Formula: C₃H₆O₃
SMILES Notation: C(C(C(=O)O)O)C
InChI: InChI=1S/C3H6O3/c1-3(4)2-5/h3,5H,2H2,1H3,(H,4,5)
UN Number: 3265 (for 2-Hydroxypropanoic acid solutions)
PubChem CID: 7947
ChemSpider ID: 7662
RTECS Number: DG7000000
Beilstein Number: 1737995
Melting Point: 17.5°C (for the L-isomer)
Boiling Point: 122°C at 12 mmHg
Density: 1.209 g/cm³ (for L-2-Hydroxypropanoic acid)
Solubility: Very soluble in water, ethanol, and methanol
Flash Point: 98°C (closed cup)
Harmonized System Code (HS Code): 2918.99.85 (for 2-Hydroxypropanoic acid)
Properties of 2-Hydroxypropanoic Acid:
Chemical Formula: C3H6O3
Molecular Weight: 90.08 g/mol
Common Name: 2-Hydroxypropanoic acid
Appearance: Clear, colorless to pale yellow liquid
Density: Approx. 1.21 g/cm³
Boiling Point: 122°C (decomposes at higher temperatures)
Melting Point: Approx. 17°C
Solubility: Fully soluble in water and alcohol
Flash Point: Non-flammable
Reactivity: Stable under normal conditions; avoid strong oxidizing agents
Chemical Stability: Stable in recommended storage conditions
Storage Temperature: Store in a cool, dry place away from direct sunlight
Vapor Pressure: Low
Melting point: 18°C
Boiling point: 122 °C/15 mmHg (lit.)
Alpha: -0.05 º (c= neat 25 ºC)
Density: 1.209 g/mL at 25 °C (lit.)
Vapor density: 0.62 (vs air)
Vapor pressure: 19 mm of Hg (@ 20°C)
FEMA: 2611 | 2-Hydroxypropanoic acid
Refractive index: n20/D 1.4262
Fp: >230 °F
Storage temp.: 2-8°C
Solubility: Miscible with water and with ethanol (96 per cent).
Form: syrup
pka: 3.08(at 100℃)
Color: Colorless to yellow
Specific Gravity: 1.209
PH: 3.51(1 mM solution);2.96(10 mM solution);2.44(100 mM solution);
Odor: at 100.00 %. odorless
Odor Type: odorless
Water Solubility: SOLUBLE
Merck: 14,5336
JECFA Number: 930
BRN: 1209341
Dielectric constant: 22.0（16℃）
Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
InChIKey: JVTAAEKCZFNVCJ-UHFFFAOYSA-N
LogP: -0.72
CAS DataBase Reference: 50-21-5(CAS DataBase Reference)
NIST Chemistry Reference: 2-Hydroxypropanoic acid (50-21-5)
EPA Substance Registry System: 2-Hydroxypropanoic acid (50-21-5)
Specifications of 2-Hydroxypropanoic Acid:
2-Hydroxypropanoic acid: ≥ 88% (typical specification for food and pharmaceutical grade)
DL-2-Hydroxypropanoic acid: ≥ 85% (depending on the grade)
Density: 1.209 g/cm³ (for L-2-Hydroxypropanoic acid)
Boiling Point: 122°C at 12 mmHg
Melting Point: 17.5°C for L-2-Hydroxypropanoic acid
pH: 2.3 - 2.7 (1M aqueous solution)
Water Content: ≤ 5% (for food and pharmaceutical grades)
Color: Clear or slightly yellow (when in liquid form)
Refractive Index: 1.421
Flash Point: 98°C (closed cup)
Heavy Metals: ≤ 10 ppm (for food and pharmaceutical grade)
Iron (Fe): ≤ 2 ppm
Chlorides: ≤ 0.01%
Specific Rotation: (α) = -3.2° (for L-2-Hydroxypropanoic acid)
Residue on Ignition: ≤ 0.1%
Free Acid: ≤ 1.0%
Names of 2-Hydroxypropanoic Acid:
Regulatory process names:
Lactic acid
Lactic acid
Lactic acid
Lactic acid
Translated names:
Acid lactic (ro)
Acide lactique (fr)
Acido lattico (it)
Aċidu lattiku (mt)
Kwas mlekowy (pl)
Kyselina mliečna (sk)
Kyselina mléčná (cs)
Lactic acid (no)
Maitohappo (fi)
Melkzuur (nl)
Milchsäure (de)
Mjölksyra (sv)
Mlečna kislina (sl)
Mliječna kiselina (hr)
Mælkesyre (da)
Pieno rūgštis (lt)
Pienskābe (lv)
Piimhape (et)
Tejsav (hu)
Ácido láctico (es)
Ácido láctico (pt)
Γαλακτικό οξύ (el)
Млечна киселина (bg)
IUPAC names:
2- Hydroxy propanoic acid
2-HYDROXY-PROPANOIC ACID
2-hydroxy-propanoic acid
2-Hydroxypropanoic Acid
2-Hydroxypropanoic acid
2-hydroxypropanoic acid
2-Hydroxypropionic acid
2-hydroxypropionic acid
D-Lactic acid
DL-Lactic acid
dl-Lactic acid
Lactic acid
Lactic acid
Lactic acid
Lactic acid
Lactic acid
Milchsäure
Propanoic acid, 2-hydroxy-
Propanoic acid,2-hydroxy-
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