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Sigma-Aldrich

(−)-Methyl L-lactate

greener alternative

98%, optical purity ee: 97% (GLC)

Synonym(s):

Methyl (S)-(−)-lactate

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5 G
$37.50
100 G
$45.00

About This Item

Linear Formula:
CH3CH(OH)CO2CH3
CAS Number:
27871-49-4
Molecular Weight:
104.10
Beilstein/REAXYS Number:
1720587
EC Number:
248-704-9
MDL number:
MFCD00064265
UNSPSC Code:
12352108
PubChem Substance ID:
24853796
NACRES:
NA.22
form:
liquid
assay:
98%

$37.50

In StockDetails

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Quality Level

100

assay

98%

form

liquid

optical activity

[α]18/D −8.1°, neat

optical purity

ee: 97% (GLC)

greener alternative product characteristics

Safer Solvents and Auxiliaries
Learn more about the Principles of Green Chemistry.

sustainability

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refractive index

n20/D 1.413 (lit.)

bp

144-145 °C (lit.)

density

1.09 g/mL at 25 °C (lit.)

functional group

ester
hydroxyl

greener alternative category

Aligned,

SMILES string

COC(=O)[C@H](C)O

InChI

1S/C4H8O3/c1-3(5)4(6)7-2/h3,5H,1-2H3/t3-/m0/s1

InChI key

LPEKGGXMPWTOCB-VKHMYHEASA-N

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General description

(-)-Methyl L-lactate can be used as a chiral auxiliary during the synthesis of Bao Gong Teng A, an antiglaucoma compound.[1]
We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Green Chemistry.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. Click here for more information.

pictograms

FlameExclamation mark
GHS02,GHS07

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Warning

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 1

flash_point_f

120.2 °F - closed cup

flash_point_c

49 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
STBL2521
STBK8915
STBK2882
STBJ1541
STBH8221

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Methyl (S)-lactate as a chiral auxiliary in the asymmetric synthesis of Bao Gong Teng A.
Pham VC and Charlton JL.
The Journal of Organic Chemistry, 60(24), 8051-8055 (1995)
Nicole Borho et al.
Organic & biomolecular chemistry, 1(23), 4351-4358 (2003-12-20)
Chiral recognition and subsequent selective self-organisation into hydrogen-bonded n-mers is observed in supersonic methyl lactate expansions. The nu(OH) and nu(C=O)-vibrations are investigated by ragout-jet FTIR-spectroscopy and lead to the assignment of homo- and heterochiral clusters of at least three different
Huoming Li et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 16(38), 11530-11534 (2010-08-31)
RCM + AD = T2: In the presence of the C16-methylene group, regioselective ring-closing metathesis (RCM) formed the (12E)-endocyclic double bond, which underwent Os-catalyzed asymmetric dihydroxylation (AD) to give the desired 12,13-diol intermediate required for the total synthesis of amphidinolide
Emma L Whitelaw et al.
Chemical communications (Cambridge, England), 47(36), 10004-10006 (2011-08-13)
In this communication we report the preparation of highly active catalysts for the production of polylactide and the subsequent conversion of polylactide to methyl lactate. The use of these catalysts for potential recycling applications is discussed.
K Bodenhöfer et al.
Nature, 387(6633), 577-580 (1997-06-05)
Odour perception in humans can sometimes discriminate different enantiomers of a chiral compound, such as limonene. Chiral discrimination represents one of the greatest challenges in attempts to devise selective and sensitive gas sensors. The importance of such discrimination for pharmacology
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