ChemicalBook Product Catalog Chemical Reagents Organic reagents Esters Methyl ester compound Methyl (R)-(+)-lactate

Methyl (R)-(+)-lactate

Product NameMethyl (R)-(+)-lactate
CAS17392-83-5
MFC4H8O3
MW104.1
EINECS241-420-6
MOL File17392-83-5.mol

Chemical Properties

alpha	8.5 º (c=neat)
Boiling point	144-145 °C(lit.)
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
InChI	1S/C4H8O3/c1-3(5)4(6)7-2/h3,5H,1-2H3/t3-/m1/s1
InChIKey	LPEKGGXMPWTOCB-GSVOUGTGSA-N
SMILES	COC(=O)[C@@H](C)O
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
Storage Class	3 - Flammable liquids
Hazard Classifications	Eye Irrit. 2 Flam. Liq. 3 STOT SE 3

MSDS

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

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

547-64-8

79-33-4

17392-83-5

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

Chemical Properties

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MSDS

Usage And Synthesis

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