CHEBI:42111 - (R)-lactic acid

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ChEBI Name (R)-lactic acid
ChEBI ID CHEBI:42111
ChEBI ASCII Name (R)-lactic acid
Definition An optically active form of lactic acid having (R)-configuration.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:42105, CHEBI:43701, CHEBI:341
Supplier Information ChemicalBook:CB4306618, eMolecules:517910, ZINC000004658562
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Lactic acid is an organic acid. It has the molecular formula C3H6O3. It is white in the solid state and it is miscible with water. When in the dissolved state, it forms a colorless solution. Production includes both artificial synthesis as well as natural sources. Lactic acid is an alpha-hydroxy acid (AHA) due to the presence of a hydroxyl group adjacent to the carboxyl group. It is used as a synthetic intermediate in many organic synthesis industries and in various biochemical industries. The conjugate base of lactic acid is called lactate (or the lactate anion). The name of the derived acyl group is lactoyl. In solution, it 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 lactic 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. Lactic acid is chiral, consisting of two enantiomers. One is known as L-lactic acid, (S)-lactic acid, or (+)-lactic acid, and the other, its mirror image, is D-lactic acid, (R)-lactic acid, or (−)-lactic acid. A mixture of the two in equal amounts is called DL-lactic acid, or racemic lactic acid. Lactic acid is hygroscopic. DL-Lactic acid is miscible with water and with ethanol above its melting point, which is about 16 to 18 °C (61 to 64 °F). D-Lactic acid and L-lactic acid have a higher melting point. Lactic acid produced by fermentation of milk is often racemic, although certain species of bacteria produce solely D-lactic acid. On the other hand, lactic 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, L-lactate is constantly produced from pyruvate via the enzyme lactate dehydrogenase (LDH) in a process of fermentation during normal metabolism and exercise. It does not increase in concentration until the rate of lactate production exceeds the rate of lactate removal, which is governed by a number of factors, including monocarboxylate transporters, concentration and isoform of LDH, and oxidative capacity of tissues. The concentration of blood lactate is usually 1–2 mMTooltip millimolar at rest, but can rise to over 20 mM during intense exertion and as high as 25 mM afterward. In addition to other biological roles, L-lactic acid is the primary endogenous agonist of hydroxycarboxylic acid receptor 1 (HCA1), which is a Gi/o-coupled G protein-coupled receptor (GPCR). In industry, lactic acid fermentation is performed by lactic acid bacteria, which convert simple carbohydrates such as glucose, sucrose, or galactose to lactic acid. These bacteria can also grow in the mouth; the acid they produce is responsible for the tooth decay known as cavities. In medicine, lactate is one of the main components of lactated Ringer's solution and Hartmann's solution. These intravenous fluids consist of sodium and potassium cations along with lactate and chloride anions in solution with distilled water, generally in concentrations isotonic with human blood. It is most commonly used for fluid resuscitation after blood loss due to trauma, surgery, or burns. Lactic 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. It may also occur when demand for oxygen is high such as with intense exercise. The process of lactic acidosis produces lactic acid which results in an oxygen debt which can be resolved or repaid when tissue oxygenation improves.
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Formula C3H6O3
Net Charge 0
Average Mass 90.07794
Monoisotopic Mass 90.03169
InChI InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m1/s1
InChIKey JVTAAEKCZFNVCJ-UWTATZPHSA-N
SMILES C[C@@H](O)C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
algal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
(via 2-hydroxypropanoic acid )
Daphnia magna metabolite
A Daphnia metabolite produced by the species Daphnia magna.
(via 2-hydroxypropanoic acid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (R)-lactic acid (CHEBI:42111) has role Escherichia coli metabolite (CHEBI:76971)
(R)-lactic acid (CHEBI:42111) has role human metabolite (CHEBI:77746)
(R)-lactic acid (CHEBI:42111) is a 2-hydroxypropanoic acid (CHEBI:78320)
(R)-lactic acid (CHEBI:42111) is conjugate acid of (R)-lactate (CHEBI:16004)
(R)-lactic acid (CHEBI:42111) is enantiomer of (S)-lactic acid (CHEBI:422)
Incoming (R)-S-lactoylglutathione (CHEBI:15694) has functional parent (R)-lactic acid (CHEBI:42111)
(R)-lactoyl-CoA (CHEBI:71164) has functional parent (R)-lactic acid (CHEBI:42111)
D-alanyl-(R)-lactic acid (CHEBI:61163) has functional parent (R)-lactic acid (CHEBI:42111)
D-prephenyl lactate (CHEBI:27441) has functional parent (R)-lactic acid (CHEBI:42111)
ethyl (2R)-lactate (CHEBI:78323) has functional parent (R)-lactic acid (CHEBI:42111)
methyl (R)-lactate (CHEBI:74611) has functional parent (R)-lactic acid (CHEBI:42111)
rac-lactic acid (CHEBI:28358) has part (R)-lactic acid (CHEBI:42111)
(R)-lactate (CHEBI:16004) is conjugate base of (R)-lactic acid (CHEBI:42111)
(S)-lactic acid (CHEBI:422) is enantiomer of (R)-lactic acid (CHEBI:42111)
(R)-lactoyl group (CHEBI:149487) is substituent group from (R)-lactic acid (CHEBI:42111)
IUPAC Name
(2R)-2-hydroxypropanoic acid
Synonyms Sources
(−)-lactic acid ChemIDplus
(R)-(−)-lactic acid ChemIDplus
D-2-Hydroxypropanoic acid KEGG COMPOUND
D-2-Hydroxypropionic acid KEGG COMPOUND
D-lactic acid ChemIDplus
D-Lactic acid KEGG COMPOUND
D-Milchsäure ChEBI
LACTIC ACID PDBeChem
Manual Xrefs Databases
C00019549 KNApSAcK
C00256 KEGG COMPOUND
DB03066 DrugBank
DB04398 DrugBank
HMDB0001311 HMDB
LAC PDBeChem
Lactic_acid Wikipedia
View more database links
Registry Numbers Types Sources
10326-41-7 CAS Registry Number KEGG COMPOUND
10326-41-7 CAS Registry Number ChemIDplus
1720252 Beilstein Registry Number Beilstein
1720252 Reaxys Registry Number Reaxys
362718 Gmelin Registry Number Gmelin
Citations
Zheng Z, Sheng B, Ma C, Zhang H, Gao C, Su F, Xu P (2012)
Relative catalytic efficiency of ldhL- and ldhD-encoded products is crucial for optical purity of lactic acid produced by lactobacillus strains.
Applied and environmental microbiology 78, 3480-3483 [PubMed:22344644]
[show Abstract]
Posada JA, Cardona CA, Gonzalez R (2012)
Analysis of the production process of optically pure D-lactic acid from raw glycerol using engineered Escherichia coli strains.
Applied biochemistry and biotechnology 166, 680-699 [PubMed:22127808]
[show Abstract]
Henry H, Marmy Conus N, Steenhout P, Béguin A, Boulat O (2012)
Sensitive determination of D-lactic acid and L-lactic acid in urine by high-performance liquid chromatography-tandem mass spectrometry.
Biomedical chromatography : BMC 26, 425-428 [PubMed:21842515]
[show Abstract]
Mimitsuka T, Na K, Morita K, Sawai H, Minegishi S, Henmi M, Yamada K, Shimizu S, Yonehara T (2012)
A membrane-integrated fermentation reactor system: its effects in reducing the amount of sub-raw materials for D-lactic acid continuous fermentation by Sporolactobacillus laevolacticus.
Bioscience, biotechnology, and biochemistry 76, 67-72 [PubMed:22277286]
[show Abstract]
Last Modified
23 October 2015