Sodium (S)-lactate Chemical Properties

Melting point:

163-165 °C (lit.)

Boiling point:

115℃[at 101 325 Pa]

Density 

1.33

refractive index 

1,422-1,425

storage temp. 

2-8°C

solubility 

Aqueous Base (Sparingly), Water (Sparingly)

form 

Powder

color 

White to yellow

Odor

Odorless

biological source

synthetic (chemical)

optical activity

[α]20/D 12.5±0.5°, c = 1% in H2O

Water Solubility 

soluble

Sensitive 

Hygroscopic

BRN 

4567087

Stability:

Hygroscopic

LogP

-1.52 at 20℃

CAS DataBase Reference

867-56-1(CAS DataBase Reference)

EPA Substance Registry System

Propanoic acid, 2-hydroxy-, monosodium salt, (2S)- (867-56-1)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-36-26

WGK Germany 

1

F 

3-10

TSCA 

Yes

HS Code 

29181100

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Sodium (S)-lactate Usage And Synthesis

Chemical Properties

clear viscous liquid

Uses

Sodium L-lactate is used as a food additive, preservative, acidity regulator and bulking agent. It finds application in shampoo and liquid soaps and other related products. It acts as an effective humectant and moisturizer. It is used in the treatment of arrhythmias.

General Description

Sodium L-lactate is an alkalinizing compound, currently being researched for its efficacy in the treatment of acidosis.

Flammability and Explosibility

Non flammable

Biochem/physiol Actions

L-lactate is produced from pyruvate by the enzyme lactate dehydrogenase. Lactate production occurs during anaerobic glycolysis or in proliferatively active cells.

Synthesis

The general procedure for the synthesis of L-menthol, sodium L-lactate and (S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-hydroxypropionate from compound (CAS:923031-01-0) and compound (CAS:923031-02-1) is as follows: 1. Preparation of L-lactic acid L-menthyl ester (ML) by esterification reaction: - In a three-necked flask equipped with a Barrett trap, reflux condenser, thermocouple, heating jacket and magnetic stirrer, L-menthol (1440 g), L-(+)-lactic acid (2880 g, an aqueous solution of 88% lactic acid from Purac, HS-88 grade) and heptane (720 g) were added. - The mixture was stirred and refluxed and the resulting water was periodically drained from the trap. - After 32 hours, the reaction was stopped when 854 mL of the aqueous phase was collected and the temperature of the mixture rose to 128 °C. The reaction was stopped by a gas chromatograph. - After cooling to room temperature, the reaction mixture was analyzed by gas-liquid chromatography (GC), which showed the presence of 5.4% unreacted menthol, 67.7% ML, 0.6% propanedioate, 24.6% L-lactoyl-L-lactide (MLL), and 4-butyl L-lactoyl-L-lactoyl-L-lactic acid (MLLL). 2. Controlled hydrolysis: - Dilute the esterified product with water (4230 g) and heptane (960 g). - A 50% aqueous sodium hydroxide solution (809 g) was added dropwise over 30 minutes while stirring and cooling (cold water bath), keeping the temperature not exceeding 30 °C and pH not exceeding 12.9. - After the dropwise addition, stirring was continued for 20 min. the GC analysis showed almost complete conversion of MLL to ML. - The organic layer was separated and washed with 1.5% aqueous lactic acid (1000 g) and azeotroped to remove water. - The solvent (heptane) was evaporated and the residue was fractionated under vacuum to give three fractions: fraction 1 (100 g, 94.5% menthol and 2.0% ML), fraction 2 (111 g, 46.8% menthol and 51.8% ML), and fraction 3 (1860 g, 99.5% pure ML). - The overall yield of ML was 91% based on the initial menthol, and the yield of purified ML was 98% based on the reacted menthol. 3. Sulfuric acid-catalyzed esterification and controlled hydrolysis: - The esterification reaction was carried out using L-menthol (1000 g), L-(+)-lactic acid (1000 g), heptane (500 g) and concentrated sulfuric acid (6 g). - After 2 hours, 300mL of the aqueous phase was collected and the temperature of the mixture was raised to 119°C. - After cooling GC analysis showed the presence of 6.4% unreacted menthol, 57.6% ML, 0.4% propylenol, 32.2% MLL and 1.9% MLLL. - The controlled hydrolysis step was performed with water (800 g) and heptane (500 mL) to dilute the esterification product, and 50% aqueous sodium hydroxide (204 g) was added dropwise over 70 min, keeping the temperature to no more than 30 °C and the pH to no more than 13.1. - The organic layer was separated and further diluted with water (1350 g) and 50% aqueous sodium hydroxide solution (150 g) was added dropwise over 1 hour. - After stirring for 1 h, GC analysis showed almost complete conversion of MLL to ML. - The organic layers were separated, washed and combined, the solvents were evaporated, and vacuum fractionation yielded three fractions: fraction 1 (203 g, 87.1% menthol, 3.5% ML, and 6.2% menthol), fraction 2 (96.8 g, 57.2% menthol and 41.6% ML), and fraction 3 (2356 g, 99.4% pure ML). - The overall yield of ML was 81% based on the initial menthol, and the yield of purified ML was 91% based on the reacted menthol. 4. Controlled hydrolysis (normal addition mode): - In a 500-mL flask, crude ML (88.7 g) was mixed with water (89 g) and heptane (20 g) at a constant temperature to the test temperature. - Under stirring, 50% aqueous sodium hydroxide (35.5 g) was added gradually over 0.6-3.6 h. The pH was recorded periodically. - After the addition was completed, stirring was done until the GC peak of the MLL dropped below 1%. 5. Reverse addition: - A 50% aqueous sodium hydroxide solution (35.5 g) was added to a 500-mL flask and thermostated to the test temperature. - The esterification mixture was gradually added to the aqueous alkali solution with stirring and the pH change was recorded. - This method is not effective at pH 14 or above.

References

[1] Patent: US7173146, 2007, B1. Location in patent: Page/Page column 5-8

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