ethyl (2S)-2-hydroxypropanoate

Base Information

• Chemical Name: ethyl (2S)-2-hydroxypropanoate
• CAS No.: 687-47-8
• Deprecated CAS: 13171-69-2
• Molecular Formula: C5H10O3
• Molecular Weight: 118.133
• Hs Code.: 29181100
• European Community (EC) Number: 211-694-1
• UNII: GA1IKU79WZ
• DSSTox Substance ID: DTXSID9042336
• Nikkaji Number: J70.573J
• Wikidata: Q27147757
• Metabolomics Workbench ID: 132015
• ChEMBL ID: CHEMBL3560966
• Mol file: 687-47-8.mol

Synonyms:687-47-8;Ethyl L-lactate;ethyl (2S)-2-hydroxypropanoate;(S)-ethyl 2-hydroxypropanoate;(L)-ethyl lactate;(L)-(-)-ethyl lactate;ethyl (2S)-lactate;(-)-ETHYL L-LACTATE;Ethyl L-(-)-Lactate;Propanoic acid, 2-hydroxy-, ethyl ester, (2S)-;Ethyl (S)-2-hydroxypropionate;(S)-Ethyl lactate;(-)-ethyl lactate;Ethyl (S)-2-hydroxypropanoate;Ethyl L(-)-lactate;GA1IKU79WZ;Ethyl (S)-(-)-lactate;DTXSID9042336;L-Ethyl lactate;EINECS 211-694-1;MFCD00004518;EC 211-694-1;Propanoic acid, 2-hydroxy-, ethyl ester, (S)-;ethyl d-lactate;ethyl llactate;ethyl-l-lactate;ethyl (s)-lactate;Ethyl (L)-lactate;L-Lactic acid ethyl;(S)-(-)-2-Hydroxypropionic acid ethyl ester;ethyl L-(+)-lactate;2-hydroxy-(2S)-propanoic acid ethyl ester;UNII-GA1IKU79WZ;L-Lactic acid ethyl ester;(S)-(+)-ethyl lactate;(S)-(-)-ethyl lactate;ETHYL LACTATE, S-;ETHYL LACTATE NATURAL;(S)-Lactic acid-ethyl ester;SCHEMBL284806;ethyl-(S)-2 hydroxypropionate;(-)-Ethyl L-lactate, 98%;CHEMBL3560966;DTXCID7022336;L-(+)-lactic acid ethyl ester;Lactic acid, ethyl ester, (S);CHEBI:78322;L-(-)-Lactic Acid Ethyl Ester;(-)-Ethyl L-lactate, 98.5%;FEMA NO. 2440, L-;Tox21_303905;(-)-Ethyl (S)-2-hydroxypropionate;BBL009712;STL141077;AKOS005111060;ethyl (2S)-(-)-2-hydroxypropanoate;(-)-ETHYL 2-HYDROXYPROPIONATE;(S)-2-hydroxypropionic acid ethyl ester;NCGC00357157-01;(S)-2-hydroxy-propionic acid ethyl ester;CAS-687-47-8;LACTIC ACID, ETHYL ESTER, (-)-;(-)-Ethyl L-lactate, analytical standard;(2S)-2-hydroxy-propionic acid ethyl ester;Ethyl lactate;(Ethyl (s)-(-)-lactate);CS-0096322;L0162;EN300-67374;D75729;(-)-Ethyl L-lactate, photoresist grade, >=99.0%;Q-201086;Q27147757;(-)-Ethyl L-lactate, purum, >=98.0% (sum of enantiomers, GC)

Chemical Property of ethyl (2S)-2-hydroxypropanoate

Chemical Property:

• Appearance/Colour: clear liquid
• Vapor Pressure: 2 mm Hg ( 20 °C)
• Melting Point: -26 °C
• Refractive Index: n20/D 1.4130(lit.)
• Boiling Point: 154.5 °C at 760 mmHg
• PKA: 13.21±0.20(Predicted)
• Flash Point: 54.6 °C
• PSA: 46.53000
• Density: 1.05 g/cm³
• LogP: -0.06970
• Storage Temp.: 2-8°C
• Water Solubility.: SOLUBLE
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 118.062994177
• Heavy Atom Count: 8
• Complexity: 79.7

Purity/Quality:

98% ^*data from raw suppliers

(-)-EthylL-Lactate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,F
• Hazard Codes: Xi,F
• Statements: 10-37-41
• Safety Statements: 24-26-39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Solvents -> Esters (
• Canonical SMILES: CCOC(=O)C(C)O
• Isomeric SMILES: CCOC(=O)[C@H](C)O
• Uses: (-)-Ethyl L-Lactate is a naturally occuring chemical compound that is often used as an industrial solvent in chemical reactions. Ethyl L-lactate is used in the preparation of food additives, aryl aldimines, fragrances and in pharmaceutical preparations. It can be considered as a green solvent in chemical industries due to its biodegradable nature. As a solvent, it used in the production of nitrocellulose, cellulose acetate and cellulose ethers.

Technology Process of ethyl (2S)-2-hydroxypropanoate

There total 46 articles about ethyl (2S)-2-hydroxypropanoate 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: 99.9%

2-oxo-propionic acid ethyl ester (617-35-6) → (S)-Ethyl lactate (687-47-8)

Guidance literature:

With hydrogen; Cinchonin; In acetic acid; at 25 ℃; for 12h; under 7500.75 Torr; Pressure; Solvent; Time; Reagent/catalyst; enantioselective reaction; Catalytic behavior;

DOI:10.1039/c6nj02405j

Reference yield: 95.0%

ethyl (S)-2-tert-butoxypropanoate (174417-26-6) → (S)-Ethyl lactate (687-47-8)

Guidance literature:

With sodium iodide; cerium(III) chloride; In acetonitrile; at 70 ℃; for 14h;

DOI:10.1002/adsc.200505469

Reference yield: 92.0%

ethanol (64-17-5) + L,L-dilactide (4511-42-6,26680-10-4,26969-66-4,615-95-2) → (S)-Ethyl lactate (687-47-8)

Guidance literature:

With Ca[N(SiMe₃)2]2*2THF; In toluene; at 30 ℃; for 0.166667h;

DOI:10.1039/b800308d

upstream raw materials:

ethanol

L-Lactic acid

D-Lactic acid

2-oxo-propionic acid ethyl ester

Downstream raw materials:

S-butyl lactate

Ethyl (S)-(-)-2-tetrahydropyran-2-yloxypropionate

ethyl (2S)-2-(tetrahydropyran-2-yloxy)propionate

(2R,3R,6S)-6-((2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-2-(4-methoxy-benzyloxy)-heptane-1,3,6-triol

Refernces

• 1、 Nakamura, Kaoru,Kondo, Shin-ichi,Kawai, Yasushi,Ohno, Atsuyoshi. "Stereochemical Control in Microbial Reduction. XXI. Effect of Organic Solvents on Reduction of α-Keto Esters Mediated by Bakers' Yeast". . p. 2738 - 2743. Retrieved 1993.
• 2、 Xiong, Wei,Ma, Hongxia,Hong, Yanyi,Chen, Hua,Li, Xianjun. "Enantioselective hydrogenation of ethyl pyruvate catalyzed by alumina support rhodium modified with quinine". . p. 1449 - 1452. Retrieved 2005.
• 3、 Margitfalvi, Jozsef L.,Talas, Emilia,Hegedus, Mihaly. "Improvement of the enantioselectivity in the enantioselective hydrogenation of ethyl pyruvate by addition of achiral tertiary amines". . p. 645 - 646. Retrieved 1999.
• 4、 Bartok, Mihaly,Sutyinszki, Maria,Felfoeldi, Karoly. "Enantioselective hydrogenation of ethyl pyruvate catalyzed by α- and β-isocinchonine-modified Pt/Al2O3 in acetic acid". . p. 207 - 214. Retrieved 2003.
• 5、 Chung, Iljun,Kim, Jeongmyeong,Song, Byeongju,Yun, Yongju. "Mesoporous silica-supported Pt catalysts in enantioselective hydrogenation of ethyl pyruvate". . . Retrieved 2020.
• 6、 Solladie-Cavallo, Arlette,Marsol, Claire,Azyat, Khalid,Roje, Marin,Welch, Christopher,Chilenski, Jennifer,Taillasson, Philippe,D'Orchymont, Hugues. "Enantiopure (9-anthryl)(2-piperidyl)- and (9-anthryl)(2-pyridyl)methanols - Their use as chiral modifiers for heterogeneous hydrogenation of keto esters over Pt/Al2O3". . p. 826 - 830. Retrieved 2007.
• 7、 Nakamura, Kaoru,Kondo, Shin-Ichi,Nakajima, Nobuyoshi,Ohno, Atsuyoshi. "Mechanistic study for stereochemical control of microbial reduction of α-keto esters in an organic solvent". . p. 687 - 694. Retrieved 1995.
• 8、 Huck, Wolf-Rüdiger,Mallat, Tamas,Baiker, Alfons. "Non-Linear Effect of Modifier Composition on Enantioselectivity in Asymmetric Hydrogenation over Platinum Metals". . p. 255 - 260. Retrieved 2003.
• 9、 Von Arx, Matthias,Buergi, Thomas,Mallat, Tamas,Baiker, Alfons. "Enantioselective hydrogenation over cinchona-modified Pt: The special role of carboxylic acids". . p. 1430 - 1437. Retrieved 2002.
• 10、 Riatto, Valéria B.,Victor, Mauricio M.,Sousa, Jaqueline F.,Menegola, Carla. "Biotechnological properties of sponges from northeast Brazil: Cliona varians as a Biocatalyst for Enantioselective Reduction of Carbonyl Compounds". . p. 149 - 157. Retrieved 2018/12/13.