Ácido láctico
Descripción general
Descripción
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. Lactic acid 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 . Lactic acid is chiral, consisting of two enantiomers: L-lactic acid and D-lactic acid .
Aplicaciones Científicas De Investigación
Lactic acid has a wide range of applications in various fields:
Chemistry: Used as a synthetic intermediate in organic synthesis.
Biology: Plays a role in metabolic processes such as glycolysis and fermentation.
Medicine: Used in the production of biodegradable polymers for medical implants and drug delivery systems.
Industry: Used in food preservation, leather tanning, textile dyeing, and as a raw material for biodegradable plastics .
Mecanismo De Acción
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 lactic acid to glucose by consuming oxygen and ATP .
Biochemical Pathways
Lactic acid is a crucial component of the fermentation process, specifically anaerobic glycolysis . During this process, glucose is converted into lactic acid to produce energy for cells . Lactic acid 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 lactic acid 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 lactic acid results in a metabolic alkalinizing effect . It plays an important role in cellular respiration, glucose production, regulation of inflammation, and molecular signaling . Lactic acid 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 lactic acid can be influenced by various environmental factors. For instance, the presence of lactic acid bacteria (LAB) can impact the metabolism and pharmacokinetics of substances like ginsenosides . LAB can also play a role in the production of lactic acid from renewable feedstocks in industrial biotechnology . Moreover, the pH and temperature of the environment can affect the stability and efficacy of lactic acid .
Análisis Bioquímico
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 . Lactic acid 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 lactic acid in order to produce energy for the cells .
Cellular Effects
Lactic acid 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 . Lactic acid 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 lactic acid in order to produce energy for the cells .
Molecular Mechanism
The molecular mechanism of lactic acid involves its conversion from pyruvate during glycolysis. This process is facilitated by the enzyme lactate dehydrogenase . Lactic acid 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 lactic acid 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 lactic acid 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
Lactic acid 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 .
Métodos De Preparación
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 lactic acid .
Industrial Production Methods: The industrial production of lactic acid 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 lactic acid. Common purification methods include precipitation, solvent extraction, and separation with membranes .
Análisis De Reacciones Químicas
Types of Reactions: Lactic acid undergoes various chemical reactions, including:
Oxidation: Lactic acid can be oxidized to pyruvic acid.
Reduction: Lactic acid can be reduced to propionic acid.
Esterification: Lactic acid reacts with alcohols to form esters.
Polymerization: Lactic acid can be polymerized to form polylactic acid (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: Lactic acid esters.
Polymerization: Polylactic acid (PLA)
Comparación Con Compuestos Similares
- Acetic acid
- Glycolic acid
- Propionic acid
- 3-Hydroxypropanoic acid
Lactic acid’s unique properties, such as its chirality and higher acidity, make it a valuable compound in various scientific and industrial applications.
Propiedades
IUPAC Name |
2-hydroxypropanoic acid | |
---|---|---|
Source | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6) | |
Source | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
InChI Key |
JVTAAEKCZFNVCJ-UHFFFAOYSA-N | |
Source | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CC(C(=O)O)O | |
Source | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C3H6O3, Array, HC3H5O3 | |
Record name | LACTIC ACID | |
Source | CAMEO Chemicals | |
URL | https://cameochemicals.noaa.gov/chemical/8774 | |
Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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Record name | LACTIC ACID | |
Source | EU Food Improvement Agents | |
URL | https://eur-lex.europa.eu/legal-content/EN/ALL/?uri=CELEX%3A32012R0231 | |
Description | Commission Regulation (EU) No 231/2012 of 9 March 2012 laying down specifications for food additives listed in Annexes II and III to Regulation (EC) No 1333/2008 of the European Parliament and of the Council Text with EEA relevance | |
Record name | LACTIC ACID | |
Source | ILO-WHO International Chemical Safety Cards (ICSCs) | |
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Explanation | Creative Commons CC BY 4.0 | |
Record name | lactic acid | |
Source | Wikipedia | |
URL | https://en.wikipedia.org/wiki/Lactic_acid | |
Description | Chemical information link to Wikipedia. | |
Source | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
Related CAS |
26100-51-6 | |
Record name | (±)-Poly(lactic acid) | |
Source | CAS Common Chemistry | |
URL | https://commonchemistry.cas.org/detail?cas_rn=26100-51-6 | |
Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
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DSSTOX Substance ID |
DTXSID7023192 | |
Record name | Lactic acid | |
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Molecular Weight |
90.08 g/mol | |
Source | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
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 | |
Record name | LACTIC ACID | |
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Record name | Propanoic acid, 2-hydroxy- | |
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Record name | LACTIC ACID | |
Source | EU Food Improvement Agents | |
URL | https://eur-lex.europa.eu/legal-content/EN/ALL/?uri=CELEX%3A32012R0231 | |
Description | Commission Regulation (EU) No 231/2012 of 9 March 2012 laying down specifications for food additives listed in Annexes II and III to Regulation (EC) No 1333/2008 of the European Parliament and of the Council Text with EEA relevance | |
Record name | Lactic acid | |
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Record name | LACTIC ACID | |
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Record name | Lactic acid | |
Source | Joint FAO/WHO Expert Committee on Food Additives (JECFA) | |
URL | https://www.fao.org/food/food-safety-quality/scientific-advice/jecfa/jecfa-flav/details/en/c/781/ | |
Description | The flavoring agent databse provides the most recent specifications for flavorings evaluated by JECFA. | |
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Boiling Point |
122 °C at 15 mm Hg | |
Record name | Lactic acid | |
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URL | https://www.drugbank.ca/drugs/DB04398 | |
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Record name | LACTIC ACID | |
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Flash Point |
113 °C (235 °F) - closed cup, 110 °C c.c. | |
Record name | LACTIC ACID | |
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URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/800 | |
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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 | |
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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 | |
Source | DrugBank | |
URL | https://www.drugbank.ca/drugs/DB04398 | |
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Record name | LACTIC ACID | |
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Record name | LACTIC ACID | |
Source | ILO-WHO International Chemical Safety Cards (ICSCs) | |
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Record name | Lactic acid | |
Source | Joint FAO/WHO Expert Committee on Food Additives (JECFA) | |
URL | https://www.fao.org/food/food-safety-quality/scientific-advice/jecfa/jecfa-flav/details/en/c/781/ | |
Description | The flavoring agent databse provides the most recent specifications for flavorings evaluated by JECFA. | |
Explanation | Permission from WHO is not required for the use of WHO materials issued under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Intergovernmental Organization (CC BY-NC-SA 3.0 IGO) licence. | |
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 | |
Record name | LACTIC ACID | |
Source | CAMEO Chemicals | |
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URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/800 | |
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Record name | LACTIC ACID | |
Source | ILO-WHO International Chemical Safety Cards (ICSCs) | |
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Record name | Lactic acid | |
Source | Joint FAO/WHO Expert Committee on Food Additives (JECFA) | |
URL | https://www.fao.org/food/food-safety-quality/scientific-advice/jecfa/jecfa-flav/details/en/c/781/ | |
Description | The flavoring agent databse provides the most recent specifications for flavorings evaluated by JECFA. | |
Explanation | Permission from WHO is not required for the use of WHO materials issued under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Intergovernmental Organization (CC BY-NC-SA 3.0 IGO) licence. | |
Vapor Pressure |
0.08 [mmHg], 0.0813 mm Hg at 25 °C | |
Record name | Lactic acid | |
Source | Haz-Map, Information on Hazardous Chemicals and Occupational Diseases | |
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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 | |
Source | DrugBank | |
URL | https://www.drugbank.ca/drugs/DB04398 | |
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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 | |
Record name | LACTIC ACID | |
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URL | https://cameochemicals.noaa.gov/chemical/8774 | |
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Record name | Lactic acid | |
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Record name | Lactic acid [USP:JAN] | |
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Record name | Lactic acid | |
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Record name | Propanoic acid, (+-) | |
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Record name | Propanoic acid, 2-hydroxy- | |
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Record name | Lactic acid | |
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Record name | Lactic acid | |
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Record name | Dl-lactic acid | |
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URL | https://echa.europa.eu/information-on-chemicals | |
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Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
Record name | LACTIC ACID, DL- | |
Source | FDA Global Substance Registration System (GSRS) | |
URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/3B8D35Y7S4 | |
Description | The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions. | |
Explanation | Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. | |
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 | |
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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