17392-83-5

Basic information

• Product Name: Methyl (R)-(+)-lactate
• Synonyms: METHYL (R)-(+)-LACTATE;METHYL-(R)-LACTATE;METHYL D-(+)-LACTATE;METHYL D-LACTATE;DLAM;D-(+)-LACTIC ACID METHYL ESTER;D-LACTIC ACID METHYL ESTER;(R)-(+)-METHYL LACTATE
• CAS NO: 17392-83-5
• Molecular Formula: C₄H₈O₃
• Molecular Weight: 104.1
• EINECS: 241-420-6
• Product Categories: chiral;Building Blocks for Liquid Crystals;Chiral Compounds (Building Blocks for Liquid Crystals);Functional Materials
• Mol File: 17392-83-5.mol

Chemical Properties

• Boiling Point: 144-145 °C(lit.)
• Flash Point: 121 °F
• Appearance: Clear colorless/Liquid
• Density: 1.09 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.93mmHg at 25°C
• Refractive Index: n20/D 1.413(lit.)
• Storage Temp.: 2-8°C
• PKA: 13.07±0.20(Predicted)
• Water Solubility: miscible, hydrolyses
• Merck: 14,6094
• CAS DataBase Reference: Methyl (R)-(+)-lactate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl (R)-(+)-lactate(17392-83-5)
• EPA Substance Registry System: Methyl (R)-(+)-lactate(17392-83-5)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37
• Safety Statements: 16-24-24/25
• RIDADR: UN 3272 3/PG 3
• WGK Germany: 1
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 17392-83-5(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
Methyl (R)-(+)-lactate is used as a starting material for the asymmetric preparation of various biological agents, such as:
a. Neomethymycin, a macrolide containing a 12-membered macrolactone, which serves as a potent biological agent.
b. PM-toxin A, another biological agent derived from the asymmetric preparation using Methyl (R)-(+)-lactate.
2. Used in Chemical Synthesis:
Methyl (R)-(+)-lactate is used as a chiral pool, alongside D-(-)-tartaric acid, in the stereoselective total synthesis of separacenes A and B. This synthesis involves various reaction techniques, such as:
a. Trost-Rychnovsky alkyne rearrangement.
b. Horner-Wadsworth-Emmons olefination.
c. Corey-Bakshi-Shibata reaction.
3. Used in Solvent Applications:
Methyl (R)-(+)-lactate is used as a versatile solvent for CA membrane preparation due to its biodegradable, water miscible, and benign properties. This makes it a preferred choice for safer solvents and auxiliaries in various industries.
4. Used in Chemical and Polymer Production:
As an intermediate, Methyl (R)-(+)-lactate plays a crucial role in the production of other chemicals, polymers, and derivatives, contributing to the development of innovative and safer products in the chemical industry.

InChI:InChI=1/C4H8O3/c1-3(5)4(6)7-2/h3,5H,1-2H3/t3-/m1/s1

Upstream product

• 67-56-1 methanol 
• 10326-41-7 D-Lactic acid 
• 186581-53-3 diazomethane 
• 18668-00-3 (R)-(+)-2-acetoxypropionic acid 
• 600-22-6 pyruvic acid methyl ester 
• 170945-08-1 (S)-2-hydroxymethyl-N-((R)-2-hydroxy)-propanoyl pyrrolidine 
• 547-64-8 methyl lactate 
• 160289-70-3 (R)-(1-naphthyl)-glycyl-(R)-phenylglycine 
• 74-88-4 methyl iodide 
• 26680-10-4 3,6-dimethyl-1,4-dioxane-2,5-dione 
• 117-34-0 2,2-diphenylacetic acid 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 616-09-1 n-propyl lactate 

Downstream Products

• 598-81-2 (R)-lactamide 
• 20047-41-0 methyl (2S)-2-bromopropanoate 
• 58653-96-6 2-benzoyloxy-propionic acid methyl ester 
• 109579-04-6 methyl (2R)-2-{[(4-methylphenyl)sulfonyl]oxy}propanoate 
• 54656-63-2 methyl (2R)-2-methoxypropanoate 
• 135206-87-0 (2R)-1-morpholin-4-yl-1-oxopropane-2-ol 
• 144091-06-5 (S)-2-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxymethoxy)-propionic acid methyl ester 
• 113892-48-1 (2R)-2-phenylselenopropanoic acid, methyl ester 
• 115458-99-6 methyl (2R)-2-(benzyloxy)propanoate 
• 171230-81-2 (R)-2-(tert-butyl-dimethyl-silanyloxy)-propionic acid methyl ester 
• 4254-14-2 (2R)-propane-1,2-diol 
• 7699-00-5 (R)-Ethyl lactate 
• 3946-09-6 (R)-lactaldehyde 
• 255824-15-8 Methyl (α'R/S,2R)-2-(5'-benzyloxy-2'-methoxy-α'-methylbenzyloxy)propanoate 

Relevant articles and documents

A model for the enatioselective hydrogenation of pyruvate catalysed by alkaloid-modified platinum

A LEED and XPS study of the adsorption of naphthalene, quinoline, and 10,11-dihydrocinchonidine on Pt(111) at 300K has shown that only naphthalene forms an ordered ad-layer, and that quinoline and the alkaloid adsorb in a disordered state and without decomposition.These experiments do not support the hypothesis of ordered adsorption of alkaloid that forms the basis of the template model for the interpretation of enantioselectivity in Pt-catalysed pyruvate hydrogenation.The model is accordingly reviewed.Molecular modelling studies show that a highly specific 1:1 interaction between cinchonidine (or cinchonine) and pyruvate interprets the observed sense of the enantioselectivity, provided relative energy relationships derived for purely intermolecular interactions are valid for the same molecules in the absorbed state.Moreover, the 'product' of this 1:1 interaction is a satisfactory precursor to the H-bonded state considered responsible for the greatly enhanced rate that always accompanies enantioselective reaction over cinchona-modified Pt.The previously published dependencies of optical yield on (a) surface concentration of adsorbed cinchonidine modifier, and (b) modifier composition for mixtures of quinine and quinidine, are shown to be in quantitative agreement with the proposed 1:1 interaction model and at variance with the ordered adsorption model.Catalysts modified and used under strictly anaerobic conditions show negligible activity and enantioselectivity demonstrating that oxygen plays a crucial role in successful catalyst preparation.XPS experiments confirm that adsorption of cinchonidine from air-saturated ethanolic solution on Pt(111) provides an adlayer containing both alkaloid and adsorbed oxygen. (S)-(-)-1-benzyl-pyrrolidine-2-methanol, various configurations of ephedrine, D- and L-histidine and the methyl esters of D- and L-tryptophan have been examined as modifiers for supported Pt.Although there is evidence that these compounds can provide chiral direction to pyruvate hydrogenation, rate enhancement is slight and enantioselectivity is correspondingly low.

Chirally modified platinum nanoparticles stabilized by dendritic core-multishell architectures for the asymmetric hydrogenation of ethyl pyruvate

In this paper we present the asymmetric hydrogenation of α-keto esters with platinum nanoparticles homogeneously stabilized in dendritic coremultishell architectures. The main focus lies on recycling and metal leaching, because little is reported so far a

High enantioselectivity in the asymmetric hydrogenation of ketones by a supported Pt nanocatalyst on a mesoporous modified MCM-41 support

Catalysts containing metal nanotubes were prepared by the adsorption of platinum metal nanotubes onto functionalized and modified silica surfaces (MCM-41 and fumed silica). (3-Chloropropyl)trimethoxysilane and cinchonidine were used for functionalization and modification, respectively. Potassium chloroplatinate was used as the metal precursor to impregnate platinum metal nanotubes on the pretreated functionalized and modified silica surfaces. The solid catalysts were characterized by ESEM, TEM, EDAX, and XPS. The MCM-41 supported platinum nanotube catalyst showed >98% to ～100% enantioselectivity towards the hydrogenation of a range of pharmaceutically important chemicals such as methyl pyruvate, ethyl pyruvate, and acetophenone with nearly full conversion.

Platinum functionalized multiwall carbon nanotube composites as recyclable catalyst for highly efficient asymmetric hydrogenation of methyl pyruvate

Platinum functionalized carbon materials such as carbon fibres, graphene, MWNTs (multiwalled carbon nanotubes) and activated carbon were used as heterogeneous catalytic systems for asymmetric hydrogenation of α-ketoester i.e. methyl pyruvate using cinchonidine (CD) as a chiral modifier. Interestingly, the MWNTs exhibited excellent enantioselectivity (>99% ee) and conversion (99%) in comparison to other Pt/C systems due to their high surface area. Furthermore, in the case of Pt/MWNTs, Pt nanoparticles are found to be uniformly dispersed and bound to the MWNTs acting like a single atom catalyst. Time-dependent nuclear magnetic resonance (NMR) studies, cyclic voltammetry (CV) and diffuse reflectance spectroscopy (DRS) have been carried out to study substrate-modifier-catalyst interactions. Recyclability of the catalyst was also tested up to ten cycles without losing any significant catalytic activity.

Asymmetric hydrogenation of α-ketoesters over finely dispersed polymer-stabilized platinum clusters

Finely dispersed polyvinylpyrrolidone-stabilized platinum clusters (PVP-Pt) modified with cinchonidine catalyze the asymmetric hydrogenation of α-ketoesters, giving enantiomeric excesses in favour of R-(+)-methyl lactate up to 97.6%. The reaction is demonstrated to be structure insensitive and runs best over a tiny cluster with a mean size of 1.4 nm, which is quite different from conventional supported catalysts.

Enantioselective Hydrogenation. III. Methyl Pyruvate Hydrogenation Catalyzed by Alkaloid-Modified Iridium

Enantioselective hydrogenation of methyl pyruvate, MeCOCOOMe to methyl lactate, MeCH(OH)COOMe, is catalyzed in solution at room temperature by supported iridium catalysts modified with cinchona alkaloids.Modification with cinchonidine or quinine yields R-lactate in excess, whereas modification with cinchonine or quinidine favors S-lactate formation.Ir/SiO2 catalysts (20percent) calcined at 393 to 573 K and reduced at 523 to 593 K were highly active for racemic hydrogenation in the absence of a modifier (rates typically 1.8 mol h-1 gcat-1) and were comparably active when modified with cinchonidine but gave an enantiomeric excess of about 30percent.Use of higher calcination or reduction temperatures led to substantially inferior activity and selectivity.The high rates recorded for both racemic and enantioselective reactions are dependent on the catalysts being activated before use by a procedure involving exposure of the catalyst to air after the initial reduction.Use of a Cl-free precursor gave an Ir/SiO2 catalyst (20percent) of superior activity but inferior enantioselectivity.Ir/CaCO3 (5percent) was more active for racemic hydrogenation than for enantioselective hydrogenation, but provided the highest value of the enantiomeric excess 39percent.Kinetics of reaction are reported.Exchange of H for D in 10,11-dihydrocinchonidine at room temperature over Ir/CaCO3 occurred in the quinoline moiety byt not in the quinuclidine ring system, indicating that the alkaloid was adsorbed to the Ir surface via the interaction of its ?-electron system.For both silica-supported and calcium carbonate-supported Ir, the presence of chloride ion in the catalyst was advantageous for the achievement of enantioselectivity.

Synthesis of alkyl (R)-lactates and alkyl (S,S)-O-lactyllactates by alcoholysis of rac-lactide using Novozym 435

Enzymatic alcoholysis of rac-lactide for kinetic resolution was carried out in organic solvents. Effects of organic solvent, reaction temperature, and alcohol as a nucleophile were also investigated in Novozym 435-catalyzed alcoholysis of rac-lactide. Both alkyl (R)-lactate and alkyl (S,S)-O-lactyllactate were simultaneously obtained in high yields (>45%) and high enantiopurities (>97% ee) through Novozym 435-catalyzed ring-opening of rac-lactide and subsequent enantioselective alcoholysis of the resultant alkyl O-lactyllactate.

Carbonyl Cluster Derived Polystyrene Supported Platinum for Asymmetric Hydrogenation of α-Ketoesters

Ion-pairing of anionic carbonyl clusters with cinchona alkaloid groups on cross-linked polystyrene is a viable method for the synthesis of asymmetric catalysts for the hydrogenation of methyl pyruvate.

New insights into the relationship between conversion and enantioselectivity for the asymmetric hydrogenation of alkyl pyruvate

The initial transient period in the enantioselective hydrogenation of alkyl pyruvate esters is probed using the sequential reactions of ethyl and methyl pyruvate. The reaction of methyl pyruvate, subsequent to the hydrogenation of ethyl pyruvate, led to a higher e.e. when compared to the coreaction of these reactants, or prehydrogenation with methyl pyruvate followed by reaction of ethyl pyruvate. The initial transient effect, in which e.e. increases with conversion, is observed in both periods of the sequential reaction and the origin of this effect is discussed.

Solvent and substituent effects on the sense of the enantioselective hydrogenation of pyruvate esters catalysed by Pd and Pt in colloidal and supported forms

The outcome of the enantioselective hydrogenation of pyruvate esters using cinchona alkaloid-modified palladium catalysts is dependent on the choice of solvent/substituent; the sense of the enantioselectivity can be switched from S to R whilst maintaining the magnitude of the enantiomeric excess.