Methyl (S)-(-)-lactate

Base Information

• Chemical Name: Methyl (S)-(-)-lactate
• CAS No.: 27871-49-4
• Deprecated CAS: 103315-49-7,103515-49-7,103515-49-7
• Molecular Formula: C4H8O3
• Molecular Weight: 104.106
• Hs Code.: 29181100
• European Community (EC) Number: 248-704-9
• UNII: 0379G9C44S
• DSSTox Substance ID: DTXSID9074359
• Nikkaji Number: J183.056B
• Wikidata: Q27156697
• RXCUI: 1431993
• Mol file: 27871-49-4.mol

Synonyms:methyl 2-hydroxypropionate;methyl lactate;methyl lactate, (+)-isomer;methyl lactate, (+-)-isomer;methyl lactate, (S)-isomer

Chemical Property of Methyl (S)-(-)-lactate

Chemical Property:

• Appearance/Colour: clear liquid
• Vapor Pressure: 1.93mmHg at 25°C
• Melting Point: - 66 °C
• Refractive Index: n20/D 1.414
• Boiling Point: 145.3 °C at 760 mmHg
• PKA: 13.07±0.20(Predicted)
• Flash Point: 47.1 °C
• PSA: 46.53000
• Density: 1.085 g/cm³
• LogP: -0.45980
• Storage Temp.: Flammables area
• Sensitive.: Moisture Sensitive
• Water Solubility.: miscible, hydrolyses
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 104.047344113
• Heavy Atom Count: 7
• Complexity: 69.3

Purity/Quality:

99% ^*data from raw suppliers

L-Methyl lactate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36/37
• Safety Statements: 24

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C(=O)OC)O
• Isomeric SMILES: C[C@@H](C(=O)OC)O
• Uses: Methyl (S)-(-)-lactate is a methyl ester of L-Lactic acid.Methyl (S)-(-)-lactate is used in the synthesis of retinyl L-lactate by lipase-catalyzed transesterification . It is used in pharmaceutical industry, agricultural fields and is also used as a solvent.

Technology Process of Methyl (S)-(-)-lactate

There total 36 articles about Methyl (S)-(-)-lactate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.8%

pyruvic acid methyl ester (600-22-6) → (S)-Methyl lactate (27871-49-4,2155-30-8)

Guidance literature:

With hydrogen; Cinchonin; In acetic acid; at 25 ℃; for 12h; under 7500.75 Torr; enantioselective reaction;

DOI:10.1039/c6nj02405j

Reference yield: 99.5%

methanol (67-56-1) + L,L-dilactide (4511-42-6,26680-10-4,26969-66-4,615-95-2) → (S)-Methyl lactate (27871-49-4,2155-30-8)

Guidance literature:

With [Mg(tbpca)2]; In dichloromethane; at 25 ℃; for 6h; chemoselective reaction; Inert atmosphere;

DOI:10.1039/c1dt10087d

Reference yield: 93.5%

methanol (67-56-1) + L,L-dilactide (4511-42-6,26680-10-4,26969-66-4,615-95-2) → (S)-Methyl lactate (27871-49-4,2155-30-8) + (1-methoxy-1-oxopropane-2-yl)-2-hydroxypropionate

Guidance literature:

With [Mg(tbpca)2]; In dichloromethane; at 25 ℃; for 0.08h; chemoselective reaction; Inert atmosphere;

DOI:10.1039/c1dt10087d

upstream raw materials:

methanol

L-Lactic acid

diazomethane

methyl (S)-2-(benzyloxy)propanoate

Downstream raw materials:

(S)-(-)-lactamide

(S)-O-Acetyllactic acid Methyl Ester

methyl (S)-2-(benzyloxy)propanoate

(S)-(-)-2-(4'-Nitrophenylsulfonyloxy)-propionsaeure-methylester

Refernces

• 1、 Chen, Rong,Liu, Qinghai,Wang, Hualei,Wei, Dongzhi,Xie, Youyu,Yang, Zeyu,Ye, Wenjie. "Efficient Asymmetric Synthesis of Ethyl (S)-4-Chloro-3-hydroxybutyrate Using Alcohol Dehydrogenase SmADH31 with High Tolerance of Substrate and Product in a Monophasic Aqueous System". . p. 1068 - 1076. Retrieved 2020/07/06.
• 2、 Nemes, Anikó,Csóka, Tamás,Béni, Szabolcs,Garádi, Zsófia,Szabó, Dénes,Rábai, József. "Chiral α-Amino Acid-Based NMR Solvating Agents". . . Retrieved 2020/07/30.