(S)-Ethyl 2-hydroxy-4-phenylbutanoate

Base Information

• Chemical Name: (S)-Ethyl 2-hydroxy-4-phenylbutanoate
• CAS No.: 125639-64-7
• Molecular Formula: C12H16O3
• Molecular Weight: 208.257
• Hs Code.: 2918199090
• European Community (EC) Number: 690-881-3
• UNII: 2828BZ7CJW
• DSSTox Substance ID: DTXSID90450893
• Nikkaji Number: J275.579C
• Wikidata: Q72475323
• Mol file: 125639-64-7.mol

Synonyms:125639-64-7;(S)-Ethyl 2-hydroxy-4-phenylbutanoate;(S)-2-Hydroxy-4-phenylbutyric Acid Ethyl Ester;Ethyl (S)-2-hydroxy-4-phenylbutyrate;ETHYL (2S)-2-HYDROXY-4-PHENYLBUTANOATE;2828BZ7CJW;Ethyl (S)-2-hydroxy-4-phenybutyrate;ethyl (S)-2-hydroxy-4-phenylbutanoate;Ethyl 2-hydroxy-4-phenylbutyrate, (+)-;Ethyl 2-hydroxy-4-phenylbutyrate, (2S)-;Benzenebutanoic acid, alpha-hydroxy-, ethyl ester, (alphaS)-;UNII-2828BZ7CJW;SCHEMBL991355;DTXSID90450893;ZJYKSSGYDPNKQS-NSHDSACASA-N;MFCD03095465;AKOS016842495;BS-49165;ethyl (2S)-2-oxidanyl-4-phenyl-butanoate;CS-0227146;(S)-alpha-Hydroxybenzenebutyric acid ethyl ester;(2S)-2-hydroxy-4-phenylbutanoic acid ethyl ester;(S)-2-Hydroxy-4-phenylbutyric Acid, ethyl ester;2-(S)-Hydroxy-4-phenyl-butyric acid ethyl ester;A805405;(alphaS)-alpha-Hydroxybenzenebutanoic Acid Ethyl Ester;BENZENEBUTANOIC ACID, .ALPHA.-HYDROXY-, ETHYL ESTER, (.ALPHA.S)-

Chemical Property of (S)-Ethyl 2-hydroxy-4-phenylbutanoate

Chemical Property:

• Appearance/Colour: slightly yellowish oil
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.505
• Boiling Point: 330.936 °C at 760 mmHg
• PKA: 13.00±0.20(Predicted)
• Flash Point: 137.587 °C
• PSA: 46.53000
• Density: 1.098 g/cm³
• LogP: 1.54320
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 208.109944368
• Heavy Atom Count: 15
• Complexity: 185

Purity/Quality:

99% ^*data from raw suppliers

(S)-2-Hydroxy-4-phenylbutyricAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CCC1=CC=CC=C1)O
• Isomeric SMILES: CCOC(=O)[C@H](CCC1=CC=CC=C1)O
• Uses: ETHYL(S)-2-HYDROXY-4-PHENYLBUTYRATE is Used in the preparation of benzothiophenes, benzofurans, and indoles useful in the treatment of insulin resistance and hyperglycemia.

Technology Process of (S)-Ethyl 2-hydroxy-4-phenylbutanoate

There total 43 articles about (S)-Ethyl 2-hydroxy-4-phenylbutanoate 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: 98.0%

ethanol (64-17-5) + (2S)-2-hydroxy-4-oxo-4-phenyl-butyric acid ethyl ester (243658-52-8) → (S)-ethyl 2-hydroxy-4-phenylbutyrate (125639-64-7)

Guidance literature:

(2S)-2-hydroxy-4-oxo-4-phenyl-butyric acid ethyl ester; With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethanol; at 25 ℃; for 11.5h; under 825.066 Torr;

ethanol; With hydrogenchloride; at 20 ℃; for 24h;

DOI:10.1055/s-2003-40885

Reference yield: 97.7%

2-oxo-4-phenylbutanoic acid ethyl ester (64920-29-2) → (S)-ethyl 2-hydroxy-4-phenylbutyrate (125639-64-7)

Guidance literature:

With Acetobacter sp. CCTCC M₂₀₉₀₆₁ anti-Prelog carbonyl reductase mut-G₁₅₂L/Y₁₈₉N mutant; isopropyl alcohol; NADH; In aq. phosphate buffer; at 35 ℃; for 4h; pH=6.5; Reagent/catalyst; enantioselective reaction; Enzymatic reaction;

DOI:10.1016/j.mcat.2019.110613

Reference yield: 95.0%

ethanol (64-17-5) + (S)-2-hydroxy-4-phenylbutanoic acid (115016-95-0,111611-91-7) → (S)-ethyl 2-hydroxy-4-phenylbutyrate (125639-64-7)

Guidance literature:

With sulfuric acid; for 2h; Heating;

DOI:10.1016/S0957-4166(01)00285-3

upstream raw materials:

ethanol

(S)-2-hydroxy-4-phenylbutanoic acid

(Z)-(S)-4-Chloro-1-phenyl-hept-4-en-3-ol

2-oxo-4-phenylbutanoic acid ethyl ester

Downstream raw materials:

(S)-4-phenyl-1,2-butanediol

7,8-dihydrokawain

(4S)-4-(2-phenylethyl)-1,3,2-dioxathiolane 2-oxide

(αR)-α-amino-benzenebutanoic acid ethyl ester hydrochloride

Refernces

• 1、 Li, Bo,Li, Xiaohong,Ding, Yue,Wu, Peng. "Ordered mesoporous carbons with Ia3d symmetry supported Pt catalyst for efficient asymmetric hydrogenation". . p. 1033 - 1039. Retrieved 2012.
• 2、 Chadha, Anju,Baskar, Baburaj. "Biocatalytic deracemisation of α-hydroxy esters: High yield preparation of (S)-ethyl 2-hydroxy-4-phenylbutanoate from the racemate". . p. 1461 - 1464. Retrieved 2002.
• 3、 Chen, Zhijian,Guan, Zaihong,Li, Mingrun,Yang, Qihua,Li, Can. "Enhancement of the performance of a platinum nanocatalyst confined within carbon nanotubes for asymmetric hydrogenation". . p. 4913 - 4917. Retrieved 2011.
• 4、 Boaz, Neil W.,Mackenzie, Elaine B.,Debenham, Sheryl D.,Large, Shannon E.,Ponasik Jr., James A.. "Synthesis and application of phosphinoferrocenylaminophosphine ligands for asymmetric catalysis". . p. 1872 - 1880. Retrieved 2005.
• 5、 LeBlond,Wang,Liu,Andrews,Sun. "Highly enantioselective heterogeneously catalyzed hydrogenation of α- ketoesters under mild conditions [15]". . p. 4920 - 4921. Retrieved 1999.
• 6、 Oda,Inada,Kobayashi,Ohta. "Production of ethyl (R)-2-hydroxy-4-phenylbutanoate via reduction of ethyl 2-oxo-4-phenylbutanoate in an interface bioreactor.". . p. 1762 - 1767. Retrieved 1998.
• 7、 Li, Bo,Li, Xiaohong,Wang, Hongna,Wu, Peng. "Pt nanoparticles entrapped in ordered mesoporous carbon for enantioselective hydrogenation". . p. 81 - 89. Retrieved 2011.
• 8、 de Gonzalo, Gonzalo. "Biocatalysed reductions of α-ketoesters employing CyreneTM as cosolvent". . . Retrieved 2021/02/26.
• 9、 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.