2-(S)-Hydroxy-4-oxo-4-phenylbutyric Acid

Base Information

• Chemical Name: 2-(S)-Hydroxy-4-oxo-4-phenylbutyric Acid
• CAS No.: 146912-63-2
• Molecular Formula: C10H10O4
• Molecular Weight: 194.187
• DSSTox Substance ID: DTXSID40433116
• Wikidata: Q82247241
• Mol file: 146912-63-2.mol

Synonyms:2-(S)-Hydroxy-4-oxo-4-phenylbutyric Acid;146912-63-2;(2S)-2-HYDROXY-4-OXO-4-PHENYLBUTANOIC ACID;(S)-2-Hydroxy-4-oxo-4-phenylbutanoic acid;starbld0009251;SCHEMBL6276435;DTXSID40433116;AKOS006286533

Chemical Property of 2-(S)-Hydroxy-4-oxo-4-phenylbutyric Acid

Chemical Property:

• Melting Point: 136-139°C
• PSA: 74.60000
• LogP: 0.70490
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Acetone (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 194.05790880
• Heavy Atom Count: 14
• Complexity: 218

Purity/Quality:

98%Min ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)CC(C(=O)O)O
• Isomeric SMILES: C1=CC=C(C=C1)C(=O)C[C@@H](C(=O)O)O
• Uses: 2-(S)-Hydroxy-4-oxo-4-phenylbutyric Acid can be used in the preparation of benzothiophenes, benzofurans, and indoles useful in the treatment of insulin resistance and hyperglycemia.

Technology Process of 2-(S)-Hydroxy-4-oxo-4-phenylbutyric Acid

There total 5 articles about 2-(S)-Hydroxy-4-oxo-4-phenylbutyric Acid 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: 73.0%

(S)-acetoxysuccinic anhydride (59025-03-5) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → (S)-2-hydroxy-4-oxo-4-phenylbutanoic acid (146912-63-2)

Guidance literature:

With aluminum (III) chloride;

DOI:10.1080/00397911.2018.1489057

Reference yield: 69.0%

C10H6O4(2-)*2Na(1+) → (S)-2-hydroxy-4-oxo-4-phenylbutanoic acid (146912-63-2)

Guidance literature:

With 1,4-dihydronicotinamide adenine dinucleotide; NAD; sodium formate; 2-amino-2-hydroxymethyl-1,3-propanediol; diothiothreitol; for 55h; S-lactate dehydrogenase (S-LDH) (Bacillus stearothermophilus); pH 6.0;

DOI:10.1016/S0040-4039(00)74747-2

Reference yield:

(2S)-2-hydroxy-4-oxo-4-phenyl-butyric acid ethyl ester (243658-52-8) → (S)-2-hydroxy-4-oxo-4-phenylbutanoic acid (146912-63-2)

Guidance literature:

With hydrogenchloride; In acetonitrile; at 20 ℃;

DOI:10.1016/j.tetasy.2004.09.007

upstream raw materials:

(S)-acetoxysuccinic anhydride

benzene

(2S)-2-hydroxy-4-oxo-4-phenyl-butyric acid ethyl ester

4-phenyl-2-hydroxy-4-oxobutyric acid ethyl ester

Downstream raw materials:

(3S,5R)-dihydro-3-hydroxy-5-phenylfuran-2(3H)-one

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

(S)-ethyl 2-hydroxy-4-phenylbutyrate

ethyl (R)-2-hydroxy-4-phenylbutyrate