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

Chemical Properties

White Solid

Uses

(S)-2-Hydroxy-4-phenylbutyric acid is used in the preparation of benzothiophenes, benzofurans, and indoles useful in the treatment of insulin resistance and hyperglycemia.

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

• 710-11-2 2-oxo-4-phenylbutyric acid 
• 93921-85-8 ethyl 2-hydroxy-4-phenylbutanoate 
• 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 
• 4263-93-8 2-hydroxy-4-phenylbutanoic acid 
• 85290-51-3 (S)-1-nitro-4-phenyl-2-butanol 
• 90239-50-2 C₁₄H₁₇NO₂ 
• 121054-03-3 2-hydroxy-4-phenylbutanenitrile 
• 103-63-9 1-phenyl-2-bromoethane 
• 64920-29-2 2-oxo-4-phenylbutanoic acid ethyl ester 
• 1327337-63-2 lithium 2-oxo-4-phenylbutanoate 
• 129029-61-4 2-hydroxy-4-phenylbut-3-enoic acid 
• 1914-59-6 (E)-2-oxo-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

Asymmetric hydrogenation method of alpha-ketone amide compound

The invention belongs to the field of asymmetric catalysis, and discloses an asymmetric hydrogenation method of an alpha-ketone amide compound. The asymmetric hydrogenation method comprises the following steps that under the existence of a catalyst, alkali and a solvent, an alpha-ketone-beta-alkene amide compound is subjected to reduction in the hydrogen atmosphere, and an alpha-hydroxyl-beta alkene amide compound is obtained; and the catalyst is obtained through complexing of metal iridium salt and a chiral ligand, and the chiral ligand is selected from the following compounds: (the formulasare shown in the description). The asymmetric hydrogenation method is easy to operate, high in conversion rate and selectivity and low in cost, has the advantages of being high in atom economy and environmentally friendly, and has a very good industrialized application prospect.

Improving enantioselectivity of lipase from Candida rugosa by carrier-bound and carrier-free immobilization

The enantioselectivity of carrier-bound and carrier-free immobilized lipase from Candida rugosa (CRL) was studied. CRL was immobilized in six agarose-based carriers functionalized with different reactive groups and in two different CRL cross-linked aggregates. Both, activity and enantioselectivity of all the immobilized lipase preparations were evaluated with different racemic esters under different reaction conditions (temperature, pH and solvent polarity). A strong effect of reaction media and immobilization protocol on enzyme activity and selectivity was found. Enzyme immobilization and reaction engineering allowed us obtaining the best immobilization protocol and reaction conditions to achieve high activity and enantioselectivty of CRL as heterogeneous catalyst. CRL immobilized on an agarose-based carrier activated with primary amino groups preferentially hydrolyzed (S)-phenylethyl acetate with E > 200 under pH 7, 4 °C and 30% of acetonitrile. On the other hand, CRL aggregated and cross-linked through their carboxylic groups preferentially hydrolyzed the (S)-isomer of ethyl 2-hydroxy-4-phenylbutyrate with an E = 39 under pH 5, 4 °C and 30% of acetonitrile. This work demonstrates the success of the combinatorial enzyme engineering for the production of highly enantioselective heterogeneous biocatalysts by screening different immobilization protocols and reaction media conditions.