115016-95-0

Basic information

• Product Name: (S)-2-Hydroxy-4-phenylbutyric acid
• Synonyms: 2-(S)-HYDROXY-4-PHENYL-BUTYRIC ACID;(S)-2-HYDROXY-4-PHENYLBUTYRIC ACID;(S)-2-Hydroxy-4-phenylbutanoic acid;(S)-4-Phenyl-2-hydroxybutyric acid;Benzenebutanoic acid, a-hydroxy-, (aS)-;(S)-2-Hydroxy-4-phenylbutyric Acid
• CAS NO: 115016-95-0
• Molecular Formula: C₁₀H₁₂O₃
• Molecular Weight: 180.2
• Product Categories: Heterocyclic Compounds;Aromatics Compounds;Aromatics;Chiral Reagents;Intermediates
• Mol File: 115016-95-0.mol
• Article Data: 28

Chemical Properties

• Melting Point: 110-112°C
• Boiling Point: 356.9 °C at 760 mmHg
• Flash Point: 183.9 °C
• Appearance: White solid
• Density: 1.219 g/cm³
• Vapor Pressure: 1.03E-05mmHg at 25°C
• Refractive Index: 1.564
• Storage Temp.: -20?C Freezer
• Solubility: Chloroform (Slightly), Ethanol (Slightly), Ethyl Acetate (Slightly), Methanol (S
• PKA: 3.79±0.10(Predicted)
• CAS DataBase Reference: (S)-2-Hydroxy-4-phenylbutyric acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-Hydroxy-4-phenylbutyric acid(115016-95-0)
• EPA Substance Registry System: (S)-2-Hydroxy-4-phenylbutyric acid(115016-95-0)

Safety Data

• Hazardous Substances Data: 115016-95-0(Hazardous Substances Data)

Usage

Description

(S)-2-Hydroxy-4-phenylbutyric acid is a chiral organic compound characterized by its white solid appearance. It is a specific stereoisomer of 2-hydroxy-4-phenylbutyric acid, with the hydroxyl group positioned on the second carbon and the phenyl group on the fourth carbon in the (S)-configuration. (S)-2-Hydroxy-4-phenylbutyric acid is known for its potential applications in the synthesis of various pharmaceutically relevant heterocycles.

Uses

Used in Pharmaceutical Industry:
(S)-2-Hydroxy-4-phenylbutyric acid is used as a key intermediate in the synthesis of benzothiophenes, benzofurans, and indoles. These heterocyclic compounds are valuable for the development of drugs targeting insulin resistance and hyperglycemia, which are critical factors in the management of diabetes and related metabolic disorders.
Used in Chemical Synthesis:
As a white solid, (S)-2-Hydroxy-4-phenylbutyric acid serves as a versatile building block in organic chemistry, enabling the preparation of a wide range of chemical entities with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science. Its unique structural features and chiral nature make it an attractive candidate for the development of enantioselective synthetic methods and the creation of novel molecular architectures.

InChI:InChI=1/C10H12O3/c11-9(10(12)13)7-6-8-4-2-1-3-5-8/h1-5,9,11H,6-7H2,(H,12,13)/t9-/m0/s1

Upstream product

• 140696-23-7 (S)-2-hydroxy-4-phenyl-3-butenoic acid 
• 710-11-2 2-oxo-4-phenylbutyric acid 
• 93921-85-8 ethyl 2-hydroxy-4-phenylbutanoate 
• 146912-63-2 (S)-2-hydroxy-4-oxo-4-phenylbutanoic acid 
• 85290-51-3 (S)-1-nitro-4-phenyl-2-butanol 
• 64-17-5 ethanol 
• 243658-52-8 (2S)-2-hydroxy-4-oxo-4-phenyl-butyric acid ethyl ester 
• 125639-64-7 (S)-ethyl 2-hydroxy-4-phenylbutyrate 
• 29678-81-7 (R)-2-hydroxy4-phenylbutanoic acid 
• 123736-87-8 (S)-2-acetoxy-4-phenylbutanoic acid 
• 883723-47-5 2-acetoxy-4-phenylbutanoic acid 
• 4263-93-8 2-hydroxy-4-phenylbutanoic acid 
• 866251-33-4 (+/-)-2-acetoxy-4-phenyl-3-butenoic acid 
• 866251-36-7 (S)-2-acetoxy-4-phenyl-3-butenoic acid 

Downstream Products

• 125639-64-7 (S)-ethyl 2-hydroxy-4-phenylbutyrate 
• 111496-30-1 1-<(S)-2-hydroxy-1-oxo-4-phenylbutyl>-L-proline phenylmethyl ester 
• 129990-77-8 (2S)-2-Hydroxy-4-phenylbutyric acid methyl ester 
• 68844-69-9 (2R)-2-Hydroxy-4-phenylbutyric acid methyl ester 
• 29678-81-7 (R)-2-hydroxy4-phenylbutanoic acid 
• 870290-51-0 (2S)-2-methoxymethoxy-4-phenylbutan-1-ol 
• 870290-48-5 methyl (2S)-2-methoxymethoxy-4-phenylbutanoate 
• 870290-57-6 (2E,4S)-4-methoxymethoxy-6-phenylhex-2-en-1-ol 
• 870290-54-3 ethyl (2E,4S)-4-methoxymethoxy-6-phenylhex-2-enoate 
• 870290-61-2 2,2,2-Trichloro-acetimidic acid (E)-(S)-4-methoxymethoxy-6-phenyl-hex-2-enyl ester 
• 870290-64-5 (3R,4S)-3-(trichloromethylcarbonylamino)-4-(methoxymethoxy)-6-phenylhexa-1-ene 
• 90315-82-5 ethyl (R)-2-hydroxy-4-phenylbutyrate 
• 371255-35-5 ethyl (R)-2-azido-4-phenylbutanoate 
• 129277-07-2 ethyl (S)-2-methanesulfonyloxy-4-phenylbutanoate 

Relevant articles and documents

Chirality switching in the enantioseparation of 2-hydroxy-4-phenylbutyric acid: Role of solvents in selective crystallization of the diastereomeric salt

Chirality switching was induced by solvents in the enantioseparation of 2-hydroxy-4-phenylbutyric acid (HPBA) via diastereomeric salt formation with an enantiopure aminoalcohol. The (S)-salt was crystallized from butanol solutions and the (R)-salt was obt

Iridium/f-Amphox-Catalyzed Asymmetric Hydrogenation of Styrylglyoxylamides

We report an iridium-catalyzed asymmetric hydrogenation reaction for the preparation of chiral homophenylalanine derivatives. Catalyzed by an iridium/f-amphox complex, the asymmetric hydrogenation of styrylglyoxylamides was conducted smoothly with turnover numbers of up to 10,000 and up to 98% ee. This method was successfully applied in a synthesis of a fragment of benazepril, a drug used for the treatment of high blood pressure.

Enzymatic Resolution by a d-Lactate Oxidase Catalyzed Reaction for (S)-2-Hydroxycarboxylic Acids

Oxidase-catalyzed kinetic resolution is important for the production of enantiopure 2-hydroxycarboxylic acids (2-HAs), which are versatile building blocks for the synthesis of many significant compounds. However, in contrast to that of (R)-2-HAs, the production of (S)-2-HA is challenging because of the lack of related oxidases. Herein, suitable enzymes were screened systematically through the analysis of numerous putative d-lactate oxidase sequences and identification of several required properties. Finally, a d-lactate oxidase from Gluconobacter oxydans 621H with advantageous characteristics, such as good solubility, broad substrate spectrum, and high stereoselectivity, was selected to resolve 2-HAs into (S)-2-HAs. A variety of (S)-2-HAs was produced successfully using this d-lactate oxidase with excellent enantiomeric excess values (>99 %). The presented screening criteria and approach for target biocatalysis suggested a guideline for the production of optically active chemicals such as (S)-2-HAs.