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Sigma-Aldrich

(−)-Methyl L-lactate

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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:
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
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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.)

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

Signal Word

Warning

Hazard Statements

H226,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 1

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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)
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
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
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
Zeolite-catalyzed isomerization of triose sugars.
Esben Taarning et al.
ChemSusChem, 2(7), 625-627 (2009-06-30)
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