Ethyl (S)-3-hydroxybutyrate

Base Information

• Chemical Name: Ethyl (S)-3-hydroxybutyrate
• CAS No.: 56816-01-4
• Molecular Formula: C6H12O3
• Molecular Weight: 132.159
• Hs Code.: 29181990
• European Community (EC) Number: 260-393-1
• DSSTox Substance ID: DTXSID301031807
• Nikkaji Number: J57.246B
• Wikidata: Q105194490
• Mol file: 56816-01-4.mol

Synonyms:56816-01-4;Ethyl (S)-3-hydroxybutyrate;(S)-Ethyl 3-hydroxybutanoate;ethyl (3S)-3-hydroxybutanoate;Ethyl (S)-(+)-3-Hydroxybutyrate;Ethyl (S)-3-hydroxybutanoate;(S)-(+)-3-Hydroxybutyric Acid Ethyl Ester;(S)-(+)-3-HYDROXY-N-BUTYRIC ACID ETHYL ESTER;MFCD00066206;Butanoic acid, 3-hydroxy-, ethyl ester, (3S)-;ethyl(s)-3-hydroxybutyrate;EINECS 260-393-1;Ethyl (S)-(-)-3-hydroxybutyrate;(s)-ethyl-3-hydroxybutyrate;SCHEMBL54111;ethyl(3s)-3-hydroxybutanoate;ethyl (3S)-3-oxidanylbutanoate;(S)-3-Hydroxybutyric acid ethyl;OMSUIQOIVADKIM-YFKPBYRVSA-N;DTXSID301031807;Ethyl (S)-3-hydroxybutyrate, 99%;AKOS015843310;HY-W076441;(3S)-3-hydroxybutanoic acid ethyl ester;AS-19211;BP-10061;CS-0112519;H0975;(S)-(+)-3-hydroxy-butyric acid ethyl ester;EN300-318286;F16431;Butanoic acid, 3-hydroxy-, ethyl ester, (S)-;A831188

Chemical Property of Ethyl (S)-3-hydroxybutyrate

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Refractive Index: 1.4185 - 1.4215
• Boiling Point: 175 °C at 760 mmHg
• PKA: 14.45±0.20(Predicted)
• Flash Point: 64.4 °C
• PSA: 46.53000
• Density: 1.024 g/cm³
• LogP: 0.32040
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Soluble in chloroform
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 132.078644241
• Heavy Atom Count: 9
• Complexity: 90.3

Purity/Quality:

99% ^*data from raw suppliers

Ethyl (S)-3-hydroxybutyrate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)CC(C)O
• Isomeric SMILES: CCOC(=O)C[C@H](C)O
• Description: Ethyl (S)-3-hydroxybutyrate is a chiral building block for the preparation of bioactive compounds such as pheromones and carbapenem antibiotics.
• Uses: Ethyl (S)-(+)-3-hydroxybutyrate is used for synthesis of optically active products, used as medical and organic intermediates, an important amino protective agents, pharmaceuticals and synthetic organic makes intermediates, organic synthesis used to introduce t-Boc protect gene. Ethyl (S)-3-Hydroxybutyrate is a product of reductions of keto esters with Baker''s yeast in organic solvents. Ethyl (S)-3-hydroxybutyrate may be used in the preparation of 3-(1′-hydroxyethyl)-2-azetidinones.

Technology Process of Ethyl (S)-3-hydroxybutyrate

There total 55 articles about Ethyl (S)-3-hydroxybutyrate 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: 99.0%

ethyl 3-hydroxybutyrate (5405-41-4) → ethyl (S)-3-hydroxybutyrate (56816-01-4)

Guidance literature:

With alcohol dehydrogenase from Lactobacillus kefir; alcohol dehydrogenase from Rhodococcus ruber DSM 44541; YcnD-oxidoreductase; at 30 ℃; for 6h; pH=7.5; optical yield given as %ee; enantiospecific reaction; aq. buffer; Resolution of racemate; Enzymatic reaction;

DOI:10.1021/ja804816a

Reference yield: 92.0%

ethanol (64-17-5) + carbon monoxide (201230-82-2) + (S)-Propylene oxide (16088-62-3) → ethyl (S)-3-hydroxybutyrate (56816-01-4)

Guidance literature:

With hydrogen; 4-aminopyridine; dicobalt octacarbonyl; at 40 ℃; for 24h; under 7500.75 Torr;

Reference yield: 90.0%

(S)-3-(3',5'-Dinitrobenzoyloxy)-buttersaeureaethylester (79427-05-7) → ethyl (S)-3-hydroxybutyrate (56816-01-4)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; ethanol;

DOI:10.1016/S0040-4039(03)01716-7

upstream raw materials:

ethyl acetoacetate

ethyl 3-hydroxybutyrate

vinyl n-butyrate

ethanol

Downstream raw materials:

(3S,4S)-3-((S)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one

(1'S,3S)-3-(1'-hydroxyethyl)-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone

(3S,4R)-3-<(S)-1-hydroxyethyl>-1-p-methoxyphenyl-4-styrylazetidin-2-one

(3R,4S)-3-<(S)-1-hydroxyethyl>-1-p-methoxyphenyl-4-styrylazetidin-2-one

Refernces

• 1、 Denmark, Scott E.,Marlin, John E.. "Carbanion-Accelerated Claisen Rearrangements. 4. Asymmetric Induction via 1,3,2-Oxazaphosphorinanes". . p. 5742 - 5745. Retrieved 1987.
• 2、 Lamouille, Thierry,Saluzzo, Christine,Ter Halle, Rob,Le Guyader, Fredéric,Lemaire, Marc. "Hydrogenation of ethyl acetoacetate catalyzed by hydrosoluble BINAP derivatives". . p. 663 - 664. Retrieved 2001.
• 3、 Saluzzo, Christine,Lamouille, Thierry,Herault, Damien,Lemaire, Marc. "Polymer-supported catalysts: enantioselective hydrogenation and hydrogen transfer reduction.". . p. 1841 - 1844. Retrieved 2002.
• 4、 Li, Aipeng,Wang, Ting,Tian, Qing,Yang, Xiaohong,Yin, Dongming,Qin, Yong,Zhang, Lianbing. "Single-Point Mutant Inverts the Stereoselectivity of a Carbonyl Reductase toward β-Ketoesters with Enhanced Activity". . p. 6283 - 6294. Retrieved 2021/03/16.
• 5、 -. "SYNTHESIS OF 3-HYDROXYBUTYRYL 3-HYDROXYBUTYRATE AND RELATED COMPOUNDS". Paragraph 0308; 0331-0333. . Retrieved 2021/04/02.