Ethyl (R)-3-hydroxybutyrate

Base Information

• Chemical Name: Ethyl (R)-3-hydroxybutyrate
• CAS No.: 24915-95-5
• Molecular Formula: C6H12O3
• Molecular Weight: 132.159
• Hs Code.: 29181990
• Mol file: 24915-95-5.mol

Synonyms:Butanoicacid, 3-hydroxy-, ethyl ester, (R)-;Butyric acid, 3-hydroxy-, ethyl ester,(-)- (8CI);(-)-Ethyl 3-hydroxybutyrate;(3R)-3-Hydroxybutanoic acid ethylester;(R)-(-)-Ethyl 3-hydroxybutyrate;(R)-3-Hydroxybutanoic acid ethyl ester;(R)-3-Hydroxybutyric acid ethyl ester;(R)-Ethyl 3-hydroxybutanoate;(R)-Ethyl3-hydroxybutyrate;(R)-Ethyl b-hydroxybutyrate;D-3-Hydroxybutyric acid ethyl ester;Ethyl (-)-b-hydroxybutyrate;

Chemical Property of Ethyl (R)-3-hydroxybutyrate

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: 0.362mmHg at 25°C
• Refractive Index: 1.4185 - 1.4215
• Boiling Point: 174.999 °C at 760 mmHg
• PKA: 14.45±0.20(Predicted)
• Flash Point: 64.444 °C
• PSA: 46.53000
• Density: 1.025 g/cm³
• LogP: 0.32040
• Storage Temp.: 2-8°C
• Water Solubility.: soluble

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Statements: 36/37/38-52
• Safety Statements: 24/25

MSDS Files:

Useful:

• Description: Ethyl (R)-(-)-3-Hydroxybutyrate is a chiral starting material for the production of numerous biologically active compounds.
• Uses: Ethyl (R)-(-)-3-hydroxybutyrate is a chiral building block for the preparation of bioactive compounds used in the pharmaceutical industry. It is formed during the hydrolysis of poly-3-hydroxybutyrate.

Technology Process of Ethyl (R)-3-hydroxybutyrate

There total 54 articles about Ethyl (R)-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: 100.0%

ethyl acetoacetate (141-97-9) → Ethyl (R)-3-hydroxybutanoate (24915-95-5)

Guidance literature:

With (S)-4,12-bis(diphenylphosphino)-<2.2>paracyclophane-Ru(II)bis(trifluoroacetate); hydrogen; tetra-(n-butyl)ammonium iodide; In methanol; water; at -5 ℃; for 18h; under 2585.7 Torr;

DOI:10.1016/S0040-4039(98)00842-9

Reference yield: 99.0%

ethyl 3-hydroxybutyrate (5405-41-4) → Ethyl (R)-3-hydroxybutanoate (24915-95-5)

Guidance literature:

With alcohol dehydrogenase from Thermoanaerobium brockii; NADH-specific (R)-selective-ADH; YcnD-oxidoreductase; at 30 ℃; for 24h; pH=7.5; optical yield given as %ee; enantiospecific reaction; aq. buffer; Resolution of racemate; Enzymatic reaction;

DOI:10.1021/ja804816a

Reference yield: 94.0%

(R)-ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanoate (1006696-12-3) → Ethyl (R)-3-hydroxybutanoate (24915-95-5)

Guidance literature:

With sodium perborate; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1002/anie.200703699

upstream raw materials:

ethanol

(R)-3-hydroxybutyric acid

ethyl 3-hydroxybutyrate

ethyl acetoacetate

Downstream raw materials:

(R)-3-(4-Methoxy-benzyloxy)-butyric acid ethyl ester

(R)-butane-1,3-diol

(R)-3-hydroxybutyric acid

D-allo-threonine

Refernces

• 1、 Chernysheva, V. V.,Klabunovskii, E. I.. "ENANTIOSELECTIVE HYDRGENATION OF ETHYL ACETOACETATE ON COPPER-NICKEL CATALYSTS: INFLUENCE OF pH ON MODIFICATION AND THE NATURE OF THE MODIFIER". . p. 1826 - 1828. Retrieved 1983.
• 2、 Griesbeck, Axel,Seebach, Dieter. "Einfache Umwandlung von (-)-(R)-3-Hydroxybuttersaeure in das (+)-(S)-Enantiomere und dessen Lacton (-)-(S)-4-Methyloxethan-2-on". . p. 1320 - 1325. Retrieved 1987.
• 3、 Schrader, Imke,Neumann, Sarah,Himstedt, Rieke,Zana, Alessandro,Warneke, Jonas,Kunz, Sebastian. "The effect of particle size and ligand configuration on the asymmetric catalytic properties of proline-functionalized Pt-nanoparticles". . p. 16221 - 16224. Retrieved 2015.
• 4、 O'Neill,Lindell,Simpson,Willis. "A simple enantioselective synthesis of γ-valerolactone". . p. 117 - 118. Retrieved 1994.
• 5、 Ramos, Aline de Souza,Ribeiro, Joyce Benzaquem,Vazquez, Leonardo,Fiaux, Sorele Batista,Leite, Selma Gomes Ferreira,Cruz, Renata de Andrade,Ramos, Maria da Conceicao Klaus V.,Neto, Francisco Radler de Aquino,Antunes, Octavio A.C.. "On the microbial reduction of ethyl α-methylacetoacetate". . p. 559 - 561. Retrieved 2009.
• 6、 Maugeri, Zaira,Dominguez De Maria, Pablo. "Whole-cell biocatalysis in deep-eutectic-solvents/aqueous mixtures". . p. 1535 - 1537. Retrieved 2014.
• 7、 Ehrler, Juerg von,Seebach, Dieter. "Note on Biotransformations with Halobacterium halobium: Reduction of Ethyl 3-Oxobutanoate and Hydrolysis of Ethyl 3-Hydroxybutanoate. Cooperative Effects of Reductase and Hydrolase". . p. 793 - 799. Retrieved 1989.
• 8、 Klabunovskii, E. I.,Pavlov, V. A.,Fridman, Ya. D.. "CHIRODIASTALTIC REACTIONS IN METAL-AMINO ACID-DIKETONE AND METAL-AMINO ACID-KETOESTER HETEROLIGAND COMPLEXES". . p. 924 - 928. Retrieved 1984.
• 9、 Klabunovskii, E. I.,Neupokoev, V. I.,Petrov, Yu. I.,Fasman, A. B.,Areshidze, G. Kh.. "ENANTIOSELECTIVE HYDROGENATION OF THE C=O BOND AT RANEY COBALT CATALYST MODIFIED WITH OPTICALLY ACTIVE ACIDS". . p. 106 - 109. Retrieved 1980.
• 10、 Xiao, Li,Mereiter, Kurt,Spindler, Felix,Weissensteiner, Walter. "A straightforward and modular synthesis of enantiopure C2- and C1-symmetrical 2,2″-phosphino-1,1″-biferrocenes". . p. 1105 - 1108. Retrieved 2001.