Methyl (R)-(+)-lactate Chemical Properties

Boiling point:

144-145 °C(lit.)

alpha 

8.5 º (c=neat)

Density 

1.09 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.413(lit.)

Flash point:

121 °F

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform, Ethyl Acetate (Slightly), Methanol (Slightly)

form 

Liquid

pka

13.07±0.20(Predicted)

color 

Clear colorless

optical activity

[α]21/D +8.4°, neat

Water Solubility 

miscible, hydrolyses

Merck 

14,6094

InChIKey

LPEKGGXMPWTOCB-GSVOUGTGSA-N

LogP

-0.719 (est)

CAS DataBase Reference

17392-83-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

10-36/37

Safety Statements 

16-24-24/25

RIDADR 

UN 3272 3/PG 3

WGK Germany 

1

HazardClass 

3

PackingGroup 

III

HS Code 

29181100

MSDS

• Language:English Provider:Methyl (R)-(+)-lactate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Methyl (R)-(+)-lactate Usage And Synthesis

Chemical Properties

Colorless to light yellow liqui

Uses

(+)-Methyl D-lactate can be used as a starting material in the asymmetric preparation of:

• Neomethymycin, a macrolide which contains 12-membered macrolactone that is used as a potent biological agent.
• PM-toxin A.

It can also be used as a chiral pool along with D-(-)-tartaric acid in the stereoselective total synthesis of separacenes A and B via Trost-Rychnovsky alkyne rearrangement, Horner-Wadsworth-Emmons olefination as well as Corey-Bakshi-Shibata reaction.

Definition

ChEBI: A methyl lactate that has R configuration.

General Description

This compound has benign qualities and is biodegradable, water miscible, and functions as a versatile solvent for CA membrane preparation. This is also used as an intermediate for the production of other chemicals, polymers, and derivatives. Thus this product has been enhanced for Safer solvents and auxiliaries.

Synthesis

The general procedure for the synthesis of L-lactic acid and D-lactic acid methyl ester from methyl lactate was as follows: in a standard 500-μL hydrolysis reaction system, 140 μg of purified esterase PHE14, 50 mmol/L of racemic methyl lactate as substrate, and 50 mmol/L of phosphate buffer (pH 7.5) were added. The reaction system was incubated at 37°C for 1 hour. Upon completion of the reaction, the reaction samples were extracted using an equal volume of ethyl acetate, and the organic phase was subsequently analyzed to assess the enzymatic disassembly of (±)-lactic acid methyl ester.

References

[1] Chinese Journal of Catalysis, 2016, vol. 37, # 8, p. 1396 - 1402
[2] Green Chemistry, 2013, vol. 15, # 10, p. 2817 - 2824

Methyl (R)-(+)-lactate(17392-83-5)Related Product Information

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• 4-Methoxyphenol
• Methyl salicylate
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• Methylparaben
• Benyl propionic methyl ester
• Methyl 2-bromopropionate
• Hydroxyapatite
• Hydroxy silicone oil
• Bensulfuron methyl
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• Methyl formate
• Methyl levulinate
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• Methyl 2-chloropropionate
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• Thiophanate-methyl
• Potassium lactate