molecular formula C3H6O3<br>C3H6O3<br>CH3CHOHCOOH B036391 Lactic acid CAS No. 26100-51-6

Lactic acid

Cat. No.: B036391
CAS No.: 26100-51-6
M. Wt: 90.08 g/mol
InChI Key: JVTAAEKCZFNVCJ-UHFFFAOYSA-N
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Description

Lactic acid, also known as 2-hydroxypropanoic acid, is an organic compound belonging to the family of carboxylic acids. It is commonly found in certain plant juices, the blood and muscles of animals, and the soil. This compound is the primary acidic constituent of fermented milk products such as sour milk, cheese, and buttermilk . It is an alpha-hydroxy acid due to the presence of a hydroxyl group adjacent to the carboxyl group . This compound is chiral, consisting of two enantiomers: L-lactic acid and D-lactic acid .

Scientific Research Applications

Lactic acid has a wide range of applications in various fields:

Mechanism of Action

Target of Action

Lactic acid, also known as lactate, is a key metabolic intermediate that plays a significant role in various biological processes . It primarily targets immune cells, including T helper (Th)17 cells, macrophages (M2), tumor-associated macrophages, and neutrophils . Lactate and its associated H+ ions can have immunosuppressive effects, but they can also augment the functions of these immune cells depending on the cell type, receptor, mediator, and microenvironment .

Mode of Action

Lactate ions are metabolized to carbon dioxide and water, a process that requires the consumption of hydrogen cations . This metabolic process is fully aerobic, meaning it occurs during normal respiration . Lactate can also be used in gluconeogenesis, a process that takes place in both the liver and kidneys, converting this compound to glucose by consuming oxygen and ATP .

Biochemical Pathways

This compound is a crucial component of the fermentation process, specifically anaerobic glycolysis . During this process, glucose is converted into this compound to produce energy for cells . This compound is also involved in the gluconeogenesis pathway, where it can be converted back into glucose . These pathways are integral to energy production and regulation within the body.

Pharmacokinetics

The pharmacokinetics of this compound involve its metabolism to carbon dioxide and water, which requires the consumption of hydrogen cations . This process is integral to the body’s energy production.

Result of Action

The production of this compound results in a metabolic alkalinizing effect . It plays an important role in cellular respiration, glucose production, regulation of inflammation, and molecular signaling . This compound is an important fuel source for muscles during exercise, including those in the heart . It also has anti-inflammatory effects and promotes immune tolerance .

Action Environment

The action of this compound can be influenced by various environmental factors. For instance, the presence of this compound bacteria (LAB) can impact the metabolism and pharmacokinetics of substances like ginsenosides . LAB can also play a role in the production of this compound from renewable feedstocks in industrial biotechnology . Moreover, the pH and temperature of the environment can affect the stability and efficacy of this compound .

Safety and Hazards

Lactic acid is corrosive to metals and tissue . It is recommended to wash hands after use, not to eat, drink, and smoke in work areas, and to remove contaminated clothing and protective equipment before entering eating areas .

Future Directions

The lactic acid market has steadily grown with the introduction of novel and environmentally friendly products . Therefore, developing novel technologies for this compound production, with improved yield and reduced production costs, has become a major research goal .

Biochemical Analysis

Biochemical Properties

Lactic acid plays a significant role in biochemical reactions. It is produced during glycolysis, a metabolic pathway that breaks down glucose to produce energy . This compound is an important molecule in cellular respiration, glucose production, regulation of inflammation, and molecular signaling . Under anaerobic conditions, glucose (and more specifically, pyruvate) is converted into this compound in order to produce energy for the cells .

Cellular Effects

This compound has profound effects on various types of cells and cellular processes. It influences cell function, including any impact on cell signaling pathways, gene expression, and cellular metabolism . This compound is an important molecule in cellular respiration, glucose production, regulation of inflammation, and molecular signaling . Under anaerobic conditions, glucose (and more specifically, pyruvate) is converted into this compound in order to produce energy for the cells .

Molecular Mechanism

The molecular mechanism of this compound involves its conversion from pyruvate during glycolysis. This process is facilitated by the enzyme lactate dehydrogenase . This compound can also induce a novel post-translational modification, named lysine lactylation (Kla), which has inspired a ‘gold rush’ of academic and commercial interest .

Temporal Effects in Laboratory Settings

The influence of stress on this compound bacteria (LAB) is the subject of numerous studies due to the wide practical application of LAB in food fermentation, industrial biotechnology for the production of valuable compounds, and their promising role in medicine as probiotics, immunomodulatory agents and drug-delivery systems .

Dosage Effects in Animal Models

Some studies have injected this compound into animal models, and H+ ions are likely produced alongside lactate in many animal models. The pH effects can be buffered by bicarbonate or other molecules, but this varies with the organ involved .

Transport and Distribution

This compound and the associated H+ ions are still introduced in many biochemistry and general biology textbooks and courses as a metabolic by-product within fast or oxygen-independent glycolysis . The role of lactate as a fuel source has been well-appreciated in the field of physiology, and the role of lactate as a metabolic feedback regulator and distinct signaling molecule is beginning to gain traction in the field of immunology .

Subcellular Localization

Protein lactylation is widespread in cells. In addition to histones, certain non-histone proteins in the nucleus can also be lactylated. Lactylation is also present on some membrane proteins, and in the cytoplasm, there are proteins involved in lactylation .

Preparation Methods

Synthetic Routes and Reaction Conditions: Lactic acid can be produced through chemical synthesis or microbial fermentation. Chemical synthesis involves the hydrolysis of lactonitrile, which is obtained from acetaldehyde and hydrogen cyanide. This process yields a racemic mixture of this compound .

Industrial Production Methods: The industrial production of this compound is predominantly carried out through microbial fermentation. Renewable and low-cost raw materials such as molasses, starch, or whey are used as substrates. The fermentation broth is then purified to obtain pure this compound. Common purification methods include precipitation, solvent extraction, and separation with membranes .

Chemical Reactions Analysis

Types of Reactions: Lactic acid undergoes various chemical reactions, including:

    Oxidation: this compound can be oxidized to pyruvic acid.

    Reduction: this compound can be reduced to propionic acid.

    Esterification: this compound reacts with alcohols to form esters.

    Polymerization: this compound can be polymerized to form polythis compound (PLA).

Common Reagents and Conditions:

    Oxidation: Common oxidizing agents include potassium permanganate and hydrogen peroxide.

    Reduction: Common reducing agents include lithium aluminum hydride and sodium borohydride.

    Esterification: Catalysts such as sulfuric acid or p-toluenesulfonic acid are used.

Major Products:

    Oxidation: Pyruvic acid.

    Reduction: Propionic acid.

    Esterification: this compound esters.

    Polymerization: Polythis compound (PLA)

Comparison with Similar Compounds

Lactic acid’s unique properties, such as its chirality and higher acidity, make it a valuable compound in various scientific and industrial applications.

Properties

IUPAC Name

2-hydroxypropanoic acid
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InChI

InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)
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InChI Key

JVTAAEKCZFNVCJ-UHFFFAOYSA-N
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Canonical SMILES

CC(C(=O)O)O
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Molecular Formula

C3H6O3, Array, HC3H5O3
Record name LACTIC ACID
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Related CAS

26100-51-6
Record name (±)-Poly(lactic acid)
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DSSTOX Substance ID

DTXSID7023192
Record name Lactic acid
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Molecular Weight

90.08 g/mol
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Physical Description

Lactic acid appears as 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., Liquid, Colourless or yellowish, nearly odourless, syrupy liquid to solid, Thick liquid or crystals, colorless to yellow; mp = 17 deg C; [ICSC], VISCOUS COLOURLESS-TO-YELLOW LIQUID OR COLOURLESS-TO-YELLOW CRYSTALS., colourless to yellow hygroscopic crystals becoming syrupy liquid; odourless
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Record name Propanoic acid, 2-hydroxy-
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Boiling Point

122 °C at 15 mm Hg
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Flash Point

113 °C (235 °F) - closed cup, 110 °C c.c.
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Solubility

Completely soluble in water, Miscible with water, Completely soluble in ethanol, diethyl ether, and other organic solvents which are miscible with water. It is virtually insoluble in benzene and chloroform., Miscible with glycerol, Soluble in alcohol and furfurol; slightly soluble in ether; insoluble in chloroform, petroleum ether, carbon disulfide. Miscible with alcohol-ether solution., Solubility in water: miscible, miscible with water, glycerol, glycols, oils, miscible at room temperature (in ethanol)
Record name Lactic acid
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Density

1.2 at 68 °F (USCG, 1999) - Denser than water; will sink, 1.2060 g/cu cm at 21 °C, Relative density (water = 1): 1.2, 1.200-1.209
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Vapor Pressure

0.08 [mmHg], 0.0813 mm Hg at 25 °C
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Mechanism of Action

Lactate ions are metabolized ultimately to carbon dioxide and water, which requires the consumption of hydrogen cations.
Record name Lactic acid
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Color/Form

Crystals (melt at 16.8 °C), Yellow to colorless crystals or syrupy 50% liquid, Viscous, colorless to yellow liquid or colorless to yellow crystals

CAS No.

50-21-5, 598-82-3, 26100-51-6
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Description The International Chemical Safety Cards (ICSCs) are data sheets intended to provide essential safety and health information on chemicals in a clear and concise way. The primary aim of the Cards is to promote the safe use of chemicals in the workplace.
Explanation Creative Commons CC BY 4.0

Melting Point

16.8 °C, Crystals from ether and isopropyl ether; melting point = 52.8 °C; pK = 3.83; soluble in water, alcohol, acetone, ether, glycerol; practically insoluble in chloroform. /D-lactic acid/, Crystals from acetic acid or chloroform; melting point = 53 °C; pK = 3.79 at 25 °C. /L-lactic acid/, 17 °C
Record name Lactic acid
Source DrugBank
URL https://www.drugbank.ca/drugs/DB04398
Description The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information.
Explanation Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
Record name Lactic acid
Source Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
URL https://haz-map.com/Agents/1416
Description Haz-Map® is an occupational health database designed for health and safety professionals and for consumers seeking information about the adverse effects of workplace exposures to chemical and biological agents.
Explanation Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
Record name LACTIC ACID
Source Hazardous Substances Data Bank (HSDB)
URL https://pubchem.ncbi.nlm.nih.gov/source/hsdb/800
Description The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel.
Record name LACTIC ACID
Source ILO-WHO International Chemical Safety Cards (ICSCs)
URL https://www.ilo.org/dyn/icsc/showcard.display?p_version=2&p_card_id=0501
Description The International Chemical Safety Cards (ICSCs) are data sheets intended to provide essential safety and health information on chemicals in a clear and concise way. The primary aim of the Cards is to promote the safe use of chemicals in the workplace.
Explanation Creative Commons CC BY 4.0

Retrosynthesis Analysis

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Feasible Synthetic Routes

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