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277762

Sigma-Aldrich

(+)-Methyl D-lactate

greener alternative

98%, optical purity ee: 96% (GLC)

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Synonym(s):
D-Lactic acid methyl ester, Methyl (R)-(+)-lactate
Linear Formula:
CH3CH(OH)CO2CH3
CAS Number:
17392-83-5
Molecular Weight:
104.10
EC Number:
241-420-6
MDL number:
MFCD00004517
UNSPSC Code:
12352108
PubChem Substance ID:
24856785
NACRES:
NA.22

Quality Level

100

Assay

98%

form

liquid

optical activity

[α]21/D +8.4°, neat

optical purity

ee: 96% (GLC)

greener alternative product characteristics

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

sustainability

Greener Alternative Product

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-/m1/s1

InChI key

LPEKGGXMPWTOCB-GSVOUGTGSA-N

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General description

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.

Application

(+)-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.

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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Asymmetric total synthesis of PM-toxin A, a corn host-specificpathotoxin
Hayakawa H, et al.
Chemical Communications (Cambridge, England), 66(13), 1219-1220 (1997)
Total synthesis of neomethymycin and novamethymycin
O Hong-Se and K Han-Young
Tetrahedron, 66(24), 4307-4317 (2010)
Total synthesis of marine natural products separacenes A and B
D Subhendu and G Rajib Kumar
Organic & Biomolecular Chemistry, 15(22), 4842-4850 (2017)
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
Zeolite-catalyzed isomerization of triose sugars.
Esben Taarning et al.
ChemSusChem, 2(7), 625-627 (2009-06-30)
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