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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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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

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.

refractive index

n20/D 1.413 (lit.)

bp

144-145 °C (lit.)

density

1.09 g/mL at 25 °C (lit.)

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.
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

signalword

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Changhua Xu et al.
Langmuir : the ACS journal of surfaces and colloids, 24(16), 9118-9124 (2008-07-12)
This study reports the development of novel chiral sensors based on the self-assembly of perfunctionalized beta-cyclodextrins (beta-CD) on a quartz crystal microbalance transducer for real time chiral recognition. Ten chiral sensors immobilized with mercaptyl perfunctionalized beta-cyclodextrins were found to exhibit
Philipp Zielke et al.
Physical chemistry chemical physics : PCCP, 8(24), 2826-2830 (2006-06-16)
Raman active symmetric O-H stretching modes are detected and assigned for the first time in isolated methanol, ethanol and methyl lactate trimers, providing insights into cluster structure, vibrational assignments and hydrogen-bond mediated couplings.
Jun-Ho Choi et al.
The Journal of chemical physics, 132(7), 074506-074506 (2010-02-23)
Determining absolute configuration of chiral molecule can be achieved by using vibrational optical activity (VOA) measurement methods, such as vibrational circular dichroism and Raman optical activity (ROA). Recently, vibrationally resonant sum frequency generation and difference frequency generation utilizing circularly polarized
L A Nafie et al.
Enantiomer, 3(4-5), 283-297 (1998-12-23)
Vibrational circular dichroism (VCD) is the extension of circular dichroism (CD) from electronic to vibrational transitions in molecules. In this review, we present the basic concepts of VCD and focus on its growing strength for stereochemical applications. There are three
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