Lactic Acid (CHEM003751)

Record Information
Version1.0
Creation Date2014-09-11 05:16:56 UTC
Update Date2026-05-14 18:08:01 UTC
Accession NumberCHEM003751
Identification
Common NameLactic Acid
ClassSmall Molecule
Description
A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation.
Contaminant Sources
  • Cosmetic Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Animal Toxin
  • Food Toxin
  • Household Toxin
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-Lactic acidChEBI
(R)-(-)-Lactic acidChEBI
D-2-Hydroxypropanoic acidChEBI
D-2-Hydroxypropionic acidChEBI
D-MilchsaeureChEBI
LACTIC ACIDChEBI
D-LactateKegg
(-)-LactateGenerator
(R)-(-)-LactateGenerator
D-2-HydroxypropanoateGenerator
D-2-HydroxypropionateGenerator
LACTateGenerator
L-LactateHMDB
(R)-2-HydroxypropanoateHMDB
(R)-2-Hydroxypropanoic acidHMDB
(R)-2-HydroxypropionateHMDB
(R)-2-Hydroxypropionic acidHMDB
(R)-a-HydroxypropionateHMDB
(R)-a-Hydroxypropionic acidHMDB
(R)-alpha-HydroxypropionateHMDB
(R)-alpha-Hydroxypropionic acidHMDB
(R)-LactateHMDB
(R)-Lactic acidHMDB
D-(-)-LactateHMDB
D-(-)-Lactic acidHMDB
delta-(-)-LactateHMDB
delta-(-)-Lactic acidHMDB
delta-2-HydroxypropanoateHMDB
delta-2-Hydroxypropanoic acidHMDB
delta-2-HydroxypropionateHMDB
delta-2-Hydroxypropionic acidHMDB
delta-LactateHMDB
delta-Lactic acidHMDB
DLAHMDB
L-(+)-LactateHMDB
PropelHMDB
TisulacHMDB
2 Hydroxypropanoic acidHMDB
2 Hydroxypropionic acidHMDB
2-Hydroxypropanoic acidHMDB
Ammonium lactateHMDB
L Lactic acidHMDB
2-Hydroxypropionic acidHMDB
Sarcolactic acidHMDB
D Lactic acidHMDB
Lactate, ammoniumHMDB
L-Lactic acidHMDB
D-Lactic acidChEBI
Chemical FormulaC3H6O3
Average Molecular Mass90.078 g/mol
Monoisotopic Mass90.032 g/mol
CAS Registry Number50-21-5
IUPAC Name(2R)-2-hydroxypropanoic acid
Traditional NameD-lactic acid
SMILESC[C@@H](O)C(O)=O
InChI IdentifierInChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m1/s1
InChI KeyJVTAAEKCZFNVCJ-UWTATZPHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassAlpha hydroxy acids and derivatives
Direct ParentAlpha hydroxy acids and derivatives
Alternative Parents
Substituents
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point16.8°C
Boiling Point122°C at 1.50E+01 mm Hg
Solubility1E+006 mg/L
Predicted Properties
PropertyValueSource
Water Solubility562 g/LALOGPS
logP-0.79ALOGPS
logP-0.47ChemAxon
logS0.79ALOGPS
pKa (Strongest Acidic)3.78ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity18.84 m³·mol⁻¹ChemAxon
Polarizability8.05 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB03066
HMDB IDHMDB0001311
FooDB IDFDB030146
Phenol Explorer IDNot Available
KNApSAcK IDC00019549
BiGG ID34414
BioCyc IDD-LACTATE
METLIN ID6150
PDB IDNot Available
Wikipedia LinkLactic_acid
Chemspider ID55423
ChEBI ID42111
PubChem Compound ID61503
Kegg Compound IDC00256
YMDB IDYMDB00247
ECMDB IDECMDB00190
References
Synthesis Reference

Yoshihide Hagiwara, Miyauchi Tetsuji, Yuki Morimasa, “Process for preparing food products containing a lactic acid bacteria-fermented product of a cereal germ.” U.S. Patent US4056637, issued February, 1933.

MSDSNot Available
General References
1. Lao, Hanzhang; Sun, Jianrong; Wang, Jian; Qian, Zhiliang. Process for preparation of high-purity L-lactic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 9pp.
2. Faulkner A, Pollock HT: Changes in the concentration of metabolites in milk from cows fed on diets supplemented with soyabean oil or fatty acids. J Dairy Res. 1989 May;56(2):179-83.
3. Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2.
4. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.
5. Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.
6. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.
7. Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.
8. Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.
9. Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.
10. Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.
11. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.
12. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)
13. Hsieh, Chun Lung; Houng, Jer Yiing. Preparation of D-lactic acid from D,L-lactic acid ester using wheat germ or pancreatic lipase. U.S. (1997), 5 pp.
14. Hasegawa H, Fukushima T, Lee JA, Tsukamoto K, Moriya K, Ono Y, Imai K: Determination of serum D-lactic and L-lactic acids in normal subjects and diabetic patients by column-switching HPLC with pre-column fluorescence derivatization. Anal Bioanal Chem. 2003 Nov;377(5):886-91. Epub 2003 Jul 19.
15. Smith SM, Eng RH, Buccini F: Use of D-lactic acid measurements in the diagnosis of bacterial infections. J Infect Dis. 1986 Oct;154(4):658-64.
16. Ellis LC, Groesbeck MD, Farr CH, Tesi RJ: Contractility of seminiferous tubules as related to sperm transport in the male. Arch Androl. 1981 Jun;6(4):283-94.
17. Pedersen M: Ciliary activity and pollution. Lung. 1990;168 Suppl:368-76.
18. McLellan AC, Phillips SA, Thornalley PJ: Fluorimetric assay of D-lactate. Anal Biochem. 1992 Oct;206(1):12-6.
19. Schmid-Schonbein GW: Microlymphatics and lymph flow. Physiol Rev. 1990 Oct;70(4):987-1028.
20. Solito R, Alessandrini C, Fruschelli M, Pucci AM, Gerli R: An immunological correlation between the anchoring filaments of initial lymph vessels and the neighboring elastic fibers: a unified morphofunctional concept. Lymphology. 1997 Dec;30(4):194-202.
21. Brandt RB, Siegel SA: Methylglyoxal production in human blood. Ciba Found Symp. 1978;(67):211-23.
22. Zhang YJ, O'Neal WK, Randell SH, Blackburn K, Moyer MB, Boucher RC, Ostrowski LE: Identification of dynein heavy chain 7 as an inner arm component of human cilia that is synthesized but not assembled in a case of primary ciliary dyskinesia. J Biol Chem. 2002 May 17;277(20):17906-15. Epub 2002 Mar 4.
23. Tanyel FC, Ulusu NN, Tezcan EF, Buyukpamukcu N: Total calcium content of sacs associated with inguinal hernia, hydrocele or undescended testis reflects differences dictated by programmed cell death. Urol Int. 2003;70(3):211-5.
24. Kaneko T, Bando Y, Kurihara H, Satomi K, Nonoyama K, Matsuura N: Fecal microflora in a patient with short-bowel syndrome and identification of dominant lactobacilli. J Clin Microbiol. 1997 Dec;35(12):3181-5.
25. Hoijer MA, Melief MJ, van Helden-Meeuwsen CG, Eulderink F, Hazenberg MP: Detection of muramic acid in a carbohydrate fraction of human spleen. Infect Immun. 1995 May;63(5):1652-7.
26. Juturu V, Wu JC: Microbial production of lactic acid: the latest development. Crit Rev Biotechnol. 2016 Dec;36(6):967-977. doi: 10.3109/07388551.2015.1066305. Epub 2015 Aug 11.
27. Becker J, Lange A, Fabarius J, Wittmann C: Top value platform chemicals: bio-based production of organic acids. Curr Opin Biotechnol. 2015 Dec;36:168-75. doi: 10.1016/j.copbio.2015.08.022. Epub 2015 Sep 8.
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=21842515
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=22127808
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=22277286
31. https://www.ncbi.nlm.nih.gov/pubmed/?term=22344644