Lactic Acid

Base Information

• Chemical Name: Lactic Acid
• CAS No.: 50-21-5
• Deprecated CAS: 152-36-3,598-82-3,1334714-39-4,1334714-39-4,598-82-3,849585-22-4
• Molecular Formula: C3H6O3
• Molecular Weight: 90.0788
• Hs Code.: 29181100
• European Community (EC) Number: 200-018-0,295-890-2,209-954-4,825-250-5
• ICSC Number: 0501
• NSC Number: 367919
• UN Number: 3265
• UNII: 3B8D35Y7S4
• DSSTox Substance ID: DTXSID7023192
• Nikkaji Number: J1.358G
• Wikipedia: Lactic acid
• Wikidata: Q161249
• NCI Thesaurus Code: C80130,C71947,C76926
• RXCUI: 1314409,28393
• Metabolomics Workbench ID: 122706
• ChEMBL ID: CHEMBL1200559
• Mol file: 50-21-5.mol

Synonyms:2 Hydroxypropanoic Acid;2 Hydroxypropionic Acid;2-Hydroxypropanoic Acid;2-Hydroxypropionic Acid;Ammonium Lactate;D Lactic Acid;D-Lactic Acid;L Lactic Acid;L-Lactic Acid;Lactate;Lactate, Ammonium;Lactic Acid;Propanoic Acid, 2-Hydroxy-, (2R)-;Propanoic Acid, 2-Hydroxy-, (2S)-;Sarcolactic Acid

Chemical Property of Lactic Acid

Chemical Property:

• Appearance/Colour: colourless to yellow liquid
• Vapor Pressure: 0.015mmHg at 25°C
• Melting Point: 18 °C
• Refractive Index: n20/D 1.4262
• Boiling Point: 227.561 °C at 760 mmHg
• PKA: 3.08(at 100℃)
• Flash Point: 109.936 °C
• PSA: 57.53000
• Density: 1.277 g/cm³
• LogP: -0.54820
• Storage Temp.: 2-8°C
• Solubility.: Miscible with water and with ethanol (96 per cent).
• Water Solubility.: SOLUBLE
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 90.031694049
• Heavy Atom Count: 6
• Complexity: 59.1
• Transport DOT Label: Corrosive

Purity/Quality:

80%Min. ^*data from raw suppliers

DL-LacticAcid(90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, C
• Hazard Codes: Xi,C
• Statements: 38-41-34-37/38
• Safety Statements: 26-39-45-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: CC(C(=O)O)O
• Recent ClinicalTrials: Exploring the Effect of Lactate Administration After Ischemic Stroke on Brain Metabolism
• Recent EU Clinical Trials: Assessment of the effects on barrier impairment, clinical features and bacterial colonization of topical formulations in patients with atopic eczema; a phase IIa, single-center, randomized, observer-blind study
• Recent NIPH Clinical Trials: SYNbiotics Effect Research after sleeve Gastrectomy In Severely obese patients on intestinal flora: a double blind, randoMized controlled trial
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is corrosive to the eyes. The substance is irritating to the skin and respiratory tract. Corrosive on ingestion.
• Chirality and Physiological Implications: Lactic acid exists in two enantiomeric forms: D-lactic acid and L-lactic acid. L-Lactic acid is the natural enantiomer in humans and other higher forms of life. Elevated levels of L-lactate in blood, known as hyperlactatemia, can indicate pathological conditions, while low levels, termed hypolactatemia, are rare. Lactic acidosis occurs when L-lactate concentration exceeds 4 mmol/l in plasma.
• Production Methods: Lactic acid is primarily produced by fermentation, with almost all commercially available lactic acid derived from this process. Crystallization and distillation are common methods employed for lactide purification, a dehydrated cyclic dimer of lactic acid.
• Industrial Significance: Lactic acid is a key industrial product obtained from LAB fermentations, with its production expected to increase due to growing demand for polylactic acid (PLA), a biodegradable polymer. Most industrial production targets the L-(+) enantiomer due to its wider applicability, especially in the food industry.
• Production Techniques: Lactic acid can be produced via chemical synthesis or microbial fermentation, with biotechnological routes being predominant. Some LAB species produce only one enantiomer, allowing for specialized applications. Batch processes are traditionally used for production, but fed-batch and continuous fermentation methods offer advantages such as increased productivity and reduced substrate inhibition.

Technology Process of Lactic Acid

There total 7 articles about Lactic Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2-Hydroxy-3-(2-hydroxy-ethylsulfanyl)-propionic acid (81388-05-8) → L-(+)-lactic acid (50-21-5,106989-11-1,26811-96-1,31587-11-8,26100-51-6) + D-lactic acid (50-21-5,79-33-4,598-82-3,10326-41-7,106989-11-1,26811-96-1,31587-11-8,26100-51-6)

Guidance literature:

With nickel; In water; at 80 - 85 ℃; for 16h; Yield given. Yields of byproduct given;

DOI:10.1021/ja00373a062

Reference yield:

2-Hydroxy-3-(2-hydroxy-ethylsulfanyl)-propionic acid (81388-05-8) → L-(+)-lactic acid (50-21-5,106989-11-1,26811-96-1,31587-11-8,26100-51-6) + D-lactic acid (50-21-5,79-33-4,598-82-3,10326-41-7,106989-11-1,26811-96-1,31587-11-8,26100-51-6)

Guidance literature:

With nickel; In water; at 80 - 85 ℃; for 16h; Yield given. Yields of byproduct given;

DOI:10.1021/ja00373a062

Reference yield:

(S)-2-Amino-4-[(R)-1-(carboxymethyl-carbamoyl)-2-(2-ethylsulfanylcarbonyl-2-hydroxy-ethylsulfanyl)-ethylcarbamoyl]-butyric acid (81388-02-5) → L-(+)-lactic acid (50-21-5,106989-11-1,26811-96-1,31587-11-8,26100-51-6) + D-lactic acid (50-21-5,79-33-4,598-82-3,10326-41-7,106989-11-1,26811-96-1,31587-11-8,26100-51-6)

Guidance literature:

With alkaline solution; nickel; Yield given. Multistep reaction. Yields of byproduct given; 1.) H₂O, 2.) H₂O, 80-85 deg C, 16 h;

DOI:10.1021/ja00373a062

upstream raw materials:

sodium pyruvate

2-Hydroxy-3-(2-hydroxy-ethylsulfanyl)-propionic acid

(S)-2-Amino-4-[(R)-1-(carboxymethyl-carbamoyl)-2-(2-ethylsulfanylcarbonyl-2-hydroxy-ethylsulfanyl)-ethylcarbamoyl]-butyric acid

(S)-D-lactoylglutathione

Downstream raw materials:

2-Hydroxy-propionic acid methyl ester

ethyl L-lactate

(R)-2-chloropropionic acid

Refernces

• 1、 Mandler, Daniel,Willner, Itamar. "Photosensitized NAD(P)H Regeneration Systems; Application in the Reduction of Butan-2-one, Pyruvic, and Acetoacetic Acids and in the Reductive Amination of Pyruvic and Oxoglutaric Acid to Amino Acid". . p. 805 - 812. Retrieved 2007/10/02.