| Record Information |
|---|
| Version | 1.0 |
|---|
| Creation Date | 2016-09-30 22:26:29 UTC |
|---|
| Update Date | 2020-06-04 22:45:02 UTC |
|---|
| BMDB ID | BMDB0000190 |
|---|
| Secondary Accession Numbers | |
|---|
| Metabolite Identification |
|---|
| Common Name | L-Lactic acid |
|---|
| Description | L-Lactic acid, also known as D-lactate or D-milchsaeure, 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. L-Lactic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. L-Lactic acid exists in all living species, ranging from bacteria to humans. L-Lactic acid participates in a number of enzymatic reactions, within cattle. In particular, L-Lactic acid can be converted into pyruvic acid; which is catalyzed by the enzyme L-lactate dehydrogenase. In addition, L-Lactic acid can be converted into L-lactic acid through the action of the enzyme monocarboxylate transporter. In cattle, L-lactic acid is involved in the metabolic pathway called cancer (via the Warburg effect). L-Lactic acid is a potentially toxic compound. |
|---|
| Structure | |
|---|
| Synonyms | | Value | Source |
|---|
| (+)-Lactic acid | ChEBI | | (S)-(+)-Lactic acid | ChEBI | | (S)-2-Hydroxypropanoic acid | ChEBI | | (S)-2-Hydroxypropionic acid | ChEBI | | L-(+)-alpha-Hydroxypropionic acid | ChEBI | | L-(+)-Lactic acid | ChEBI | | L-Milchsaeure | ChEBI | | L-Lactate | Kegg | | (+)-Lactate | Generator | | (S)-(+)-Lactate | Generator | | (S)-2-Hydroxypropanoate | Generator | | (S)-2-Hydroxypropionate | Generator | | L-(+)-a-Hydroxypropionate | Generator | | L-(+)-a-Hydroxypropionic acid | Generator | | L-(+)-alpha-Hydroxypropionate | Generator | | L-(+)-Α-hydroxypropionate | Generator | | L-(+)-Α-hydroxypropionic acid | Generator | | L-(+)-Lactate | Generator | | (alpha)-Lactate | HMDB | | (alpha)-Lactic acid | HMDB | | (S)-(+)-2-Hydroxypropanoate | HMDB | | (S)-(+)-2-Hydroxypropanoic acid | HMDB | | (S)-2-Hydroxy-propanoate | HMDB | | (S)-2-Hydroxy-propanoic acid | HMDB | | (S)-Lactate | HMDB | | (S)-Lactic acid | HMDB | | 1-Hydroxyethane 1-carboxylate | HMDB | | 1-Hydroxyethane 1-carboxylic acid | HMDB | | 1-Hydroxyethanecarboxylate | HMDB | | 1-Hydroxyethanecarboxylic acid | HMDB | | 2-Hydroxypropanoate | HMDB | | 2-Hydroxypropanoic acid | HMDB | | 2-Hydroxypropionate | HMDB | | a-Hydroxypropanoate | HMDB | | a-Hydroxypropanoic acid | HMDB | | a-Hydroxypropionate | HMDB | | a-Hydroxypropionic acid | HMDB | | alpha-Hydroxypropanoate | HMDB | | alpha-Hydroxypropanoic acid | HMDB | | alpha-Hydroxypropionate | HMDB | | alpha-Hydroxypropionic acid | HMDB | | L-(+)- Lactic acid | HMDB | | L-2-Hydroxypropanoate | HMDB | | L-2-Hydroxypropanoic acid | HMDB | | Lactate | HMDB | | Lactic acid | HMDB | | Milk acid | HMDB | | Sarcolactic acid | HMDB | | 2-Hydroxypropionic acid | HMDB | | D-Lactic acid | HMDB | | D Lactic acid | HMDB | | Lactate, ammonium | HMDB | | 2 Hydroxypropanoic acid | HMDB | | 2 Hydroxypropionic acid | HMDB | | Ammonium lactate | HMDB | | L Lactic acid | HMDB | | D-Lactate | HMDB | | L-Lactic acid | ChEBI |
|
|---|
| Chemical Formula | C3H6O3 |
|---|
| Average Molecular Weight | 90.0779 |
|---|
| Monoisotopic Molecular Weight | 90.031694058 |
|---|
| IUPAC Name | (2S)-2-hydroxypropanoic acid |
|---|
| Traditional Name | (α)-lactate |
|---|
| CAS Registry Number | 79-33-4 |
|---|
| SMILES | C[C@H](O)C(O)=O |
|---|
| InChI Identifier | InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m0/s1 |
|---|
| InChI Key | JVTAAEKCZFNVCJ-REOHCLBHSA-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. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Organic acids and derivatives |
|---|
| Class | Hydroxy acids and derivatives |
|---|
| Sub Class | Alpha hydroxy acids and derivatives |
|---|
| Direct Parent | Alpha 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 Framework | Aliphatic acyclic compounds |
|---|
| External Descriptors | |
|---|
| Ontology |
|---|
| Status | Detected and Quantified |
|---|
| Origin | |
|---|
| Biofunction | Not Available |
|---|
| Application | Not Available |
|---|
| Cellular locations | |
|---|
| Physical Properties |
|---|
| State | Liquid |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Melting Point | 16.8 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
|
|---|
| Predicted Properties | |
|---|
| Spectra |
|---|
| Spectra | |
|---|
| Biological Properties |
|---|
| Cellular Locations | |
|---|
| Biospecimen Locations | - All Tissues
- Blood
- Colostrum
- Liver
- Longissimus Thoracis Muscle
- Mammary Gland
- Milk
- Muscle
- Placenta
- Ruminal Fluid
- Semen
- Semimembranosus Muscle
- Testis
|
|---|
| Pathways | |
|---|
| Normal Concentrations |
|---|
| |
| All Tissues | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 500 +/- 90 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 658-1600 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 320-550 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 4850 +/- 2017 uM | Not Specified | Not Specified | Normal | | details | | Colostrum | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected and Quantified | 12311 +/- 1719 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Longissimus Thoracis Muscle | Detected and Quantified | 31131 +/- 8268 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 73.34 +/- 93.23 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 138 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2 - 3538 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 32 - 136 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 45 - 95 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 75 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 97 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 102 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 47.31 +/- 26.19 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 61.4 +/- 0.3 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 57 +/- 3 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 55 +/- 1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 59 +/- 4 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 33.43 +/- 9.04 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 37175-131553 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 14817.25 +/- 555.7 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 16764.97 +/- 482.13 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 17300.81 +/- 1145.11 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 21406.66 +/- 443.4 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 14262-21850 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 7100 +/- 1140 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 392240 +/- 63980 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 367580 +/- 50520 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 383140 +/- 51350 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 53000 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 2230-3170 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 173.5 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 282 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 180.4 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 156.9 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 360 +/- 130 uM | Not Specified | Both | Normal | | details | | Ruminal Fluid | Detected and Quantified | 224-1560 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 159 +/- 22 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 252 +/- 61 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 180 +/- 118 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 134 +/- 17 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 134 +/- 17 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 10-73 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 700-1830 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 122 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 228 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 133 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 124 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 156.94 +/- 13.25 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 2029 +/- 1165 uM | Not Specified | Not Specified | Normal | | details | | Semen | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Semen | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Semimembranosus Muscle | Detected and Quantified | 37879 +/- 10580 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Testis | Detected and Quantified | 7702 +/- 1649 nmol/g of tissue | Not Specified | Not Specified | Normal | | details |
|
|---|
| Abnormal Concentrations |
|---|
| |
| Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Treated with growth-promoting hormones | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | All Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | High dose Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Low dose Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Sub/clinical ketosis | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Heat stress | | details | | Blood | Detected and Quantified | 2420 +/- 370 uM | Not Specified | Not Specified | Left displaced abomasum (LDA) | | details | | Blood | Detected and Quantified | 4510 +/- 1340 uM | Not Specified | Not Specified | Right displaced abomasum (RDA) | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Fatal bovine respiratory disease | | details | | Ruminal Fluid | Detected and Quantified | 180.41 +/- 114.22 uM | Not Specified | Not Specified | Rumen acidosis | | details |
|
|---|
| External Links |
|---|
| HMDB ID | HMDB0000190 |
|---|
| DrugBank ID | Not Available |
|---|
| Phenol Explorer Compound ID | Not Available |
|---|
| FooDB ID | FDB003294 |
|---|
| KNApSAcK ID | C00001191 |
|---|
| Chemspider ID | 96860 |
|---|
| KEGG Compound ID | C00186 |
|---|
| BioCyc ID | L-LACTATE |
|---|
| BiGG ID | 34179 |
|---|
| Wikipedia Link | Lactic_Acid |
|---|
| METLIN ID | 5205 |
|---|
| PubChem Compound | 107689 |
|---|
| PDB ID | Not Available |
|---|
| ChEBI ID | 422 |
|---|
| References |
|---|
| Synthesis Reference | Lao, Hanzhang; Sun, Jianrong; Wang, Jian; Qian, Zhiliang. Process for preparation of high-purity L-lactic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 9pp. |
|---|
| Material Safety Data Sheet (MSDS) | Not Available |
|---|
| General References | - 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. [PubMed:2760296 ]
- 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. [PubMed:11132867 ]
- 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. [PubMed:20338431 ]
- 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. [PubMed:22098372 ]
- 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. [PubMed:23438684 ]
- 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. [PubMed:23182357 ]
- 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. [PubMed:25087032 ]
- 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. [PubMed:23497994 ]
- 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. [PubMed:25108860 ]
- 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. [PubMed:29642378 ]
- A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
|
|---|
