111505-52-3

Basic information

• Product Name: tert-Butyl (R)-2-hydroxy-3-phenylpropionate
• Synonyms: tert-Butyl (R)-2-hydroxy-3-phenylpropionate
• CAS NO: 111505-52-3
• Molecular Formula: C₁₃H₁₈O₃
• Molecular Weight: 222.28
• Product Categories: API intermediates
• Mol File: 111505-52-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 320.3°C at 760 mmHg
• Flash Point: 128.2°C
• Appearance: /
• Density: 1.077g/cm³
• Vapor Pressure: 0.000133mmHg at 25°C
• Refractive Index: 1.515
• PKA: 13.00±0.20(Predicted)
• CAS DataBase Reference: tert-Butyl (R)-2-hydroxy-3-phenylpropionate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl (R)-2-hydroxy-3-phenylpropionate(111505-52-3)
• EPA Substance Registry System: tert-Butyl (R)-2-hydroxy-3-phenylpropionate(111505-52-3)

Safety Data

• Hazardous Substances Data: 111505-52-3(Hazardous Substances Data)

Usage

General Description

Tert-Butyl (R)-2-hydroxy-3-phenylpropionate is a chemical compound commonly used as an antioxidant and stabilizer in various industrial products such as plastics, adhesives, and lubricants. It is a chiral molecule with the (R) configuration, meaning that it has a specific spatial arrangement of its atoms. This particular compound is a derivative of 2-hydroxy-3-phenylpropionic acid, which is a known and widely used antioxidant in the industry. Tert-butyl (R)-2-hydroxy-3-phenylpropionate is valued for its ability to prevent the degradation of organic materials and protect against the harmful effects of oxidation, making it a valuable additive for extending the shelf life and performance of various products.

InChI:InChI=1/C13H18O3/c1-13(2,3)16-12(15)11(14)9-10-7-5-4-6-8-10/h4-8,11,14H,9H2,1-3H3/t11-/m1/s1

Upstream product

• 75-65-0 tert-butyl alcohol 
• 1257267-02-9 (R)-N-(benzyloxycarbonyl)-O-(2-hydroxy-3-phenylpropanoyl)hydroxylamine 
• 1257267-20-1 C₂₃H₃₁NO₅Si 
• 380886-37-3 D-tert-butyl 2-phthalimid-N-oxy-3-phenylpropanoate 
• 146235-25-8 (2R)-2-acetoxy-3-phenylpropanoic acid 
• 673-06-3 D-(R)-phenylalanine 
• 159990-95-1 3-phenyl-2(R)-acetoxypropionic acid t-butyl ester 
• 828-01-3 D-phenyllactic acid 
• 101617-24-7 (S)-tert-butyl 2-chloropropanoate 
• 111505-49-8 4-Nitro-benzoic acid (R)-1-tert-butoxycarbonyl-2-phenyl-ethyl ester 

Downstream Products

• 1257267-18-7 1-(R)-(tert-butoxycarbonyl)-2-phenylethyl chloroformate 
• 1316671-14-3 C₃₄H₃₇NO₆ 
• 1316671-16-5 (R)-N-(9-fluorenylmethoxycarbonyl)-(S)-pipecolinylphenyllactic acid 
• 1581723-72-9 (R)-clavatustide B 
• 1602982-13-7 (R)-clavatustide A 
• 1445866-76-1 C₁₄H₁₇F₃O₅S 
• 174538-96-6 benzyloxycarbonyl D-alanyl L-α-hydroxyhydrocinnamyl L-valyl D-α-hydroxyhydrocinnamyl D-alanyl L-α-hydroxyhydrocinnamyl L-valyl D-α-hydroxyhydrocinnamic acid t-butyl ester 
• 174538-94-4 benzyloxycarbonyl D-alanyl L-α-hydroxyhydrocinnamyl L-valyl D-α-hydroxy hydrocinnamic acid pentafluorophenyl ester 
• 174538-92-2 benzyloxycarbonyl D-alanyl L-α-hydroxyhydrocinnamyl L-valyl D-α-hydroxy hydrocinnamic acid t-butyl ester 

Relevant articles and documents

Hybrid Peptides Based on α-Aminoxy Acids as Antimicrobial and Anticancer Foldamers

α-Aminoxy peptides represent an interesting group of peptidomimetics with high proteolytic stability and the ability to fold into specific, predictable secondary structures. Here, we present a series of hybrid peptides consisting of α-aminoxy acids and α-amino acids with cationic and aromatic, hydrophobic side chains in an alternating manner synthesized using an efficient protocol that combines solution- and solid-phase synthesis. 2D ROESY experiments with a representative hexamer suggested the presence of a 7/8 helical conformation in solution. Biological evaluation revealed a significant impact of the peptide chain length and the N-terminal cap on the antimicrobial and anticancer properties of this series of hybrid peptides. The Fmoc-capped peptide 6e displayed the most potent antimicrobial activity against a panel of Gram-negative and Gram-positive bacterial strains (e. g. against E. Coli: MIC=8 mg/L; S. aureus: MIC=4 mg/L).

Serendipitous discovery of α-hydroxyalkyl esters as β-lactamase substrates

O-(1-Carboxy-1-alkyloxycarbonyl) hydroxamates were found to spontaneously decarboxylate in aqueous neutral buffer to form O-(2-hydroxyalkylcarbonyl) hydroxamates. While the former molecules do not react rapidly with serine β-lactamases, the latter are quite good substrates of representative class A and C, but not D, enzymes, and particularly of a class C enzyme. The enzymes catalyze hydrolysis of these compounds to a mixture of the α-hydroxy acid and hydroxamate. Analogous compounds containing aryloxy leaving groups rather that hydroxamates are also substrates. Structure-activity experiments showed that the α-hydroxyl group was required for any substantial substrate activity. Although both d- and l-α-hydroxy acid derivatives were substrates, the former were preferred. The response of the class C activity to pH and to alternative nucleophiles (methanol and d-phenylalanine) suggested that the same active site functional groups participated in catalysis as for classical substrates. Molecular modeling was employed to explore how the α-hydroxy group might interact with the class C β-lactamase active site. Incorporation of the α-hydroxyalkyl moiety into novel inhibitors will be of considerable interest.

STEREOCONTROLLED SYNTHESIS OF D-α-HYDROXY CARBOXYLIC ACIDS FROM L-AMINO ACIDS

Optically active D-α-hydroxy carboxylic acids are obtained from L-amino acids via L-α-halocarboxylic acids and their stereoselective reaction with cesium p-nitrobenzoate.