123802-80-2

Basic information

• Product Name: (R)-2-BENZYL-3-HYDROXYPROPANOIC ACID
• Synonyms: (R)-2-BENZYL-3-HYDROXYPROPANOIC ACID;(S)-2-(hydroxyMethyl)-3-phenylpropanoic acid;(alphaR)-alpha-(Hydroxymethyl)benzenepropanoic acid;(R)-2-Hydroxymethyl-3-phenylpropionic acid
• CAS NO: 123802-80-2
• Molecular Formula: C₁₀H₁₂O₃
• Molecular Weight: 180.2
• Mol File: 123802-80-2.mol

Chemical Properties

• Melting Point: 67.5-68.5℃ (ethyl ether hexane )
• Boiling Point: 352.5±30.0 °C(Predicted)
• Appearance: /
• Density: 1.219±0.06 g/cm3(Predicted)
• PKA: 4.22±0.10(Predicted)
• CAS DataBase Reference: (R)-2-BENZYL-3-HYDROXYPROPANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-BENZYL-3-HYDROXYPROPANOIC ACID(123802-80-2)
• EPA Substance Registry System: (R)-2-BENZYL-3-HYDROXYPROPANOIC ACID(123802-80-2)

Safety Data

• Hazardous Substances Data: 123802-80-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-2-Benzyl-3-hydroxypropanoic acid is used as a chiral building block for the synthesis of various pharmaceuticals and fine chemicals. Its unique properties make it a valuable component in the development of new drugs and therapeutic agents.
Used in Flavors and Fragrances Industry:
(R)-2-Benzyl-3-hydroxypropanoic acid is used as a flavoring agent and fragrance ingredient due to its pleasant aroma and taste, adding to the sensory experience of various products in this industry.
Used in Antimicrobial Applications:
(R)-2-Benzyl-3-hydroxypropanoic acid is employed for its antimicrobial properties, making it suitable for use in applications where the inhibition of microbial growth is required.
Used in Antioxidant and Anti-inflammatory Applications:
The antioxidant and anti-inflammatory properties of (R)-2-Benzyl-3-hydroxypropanoic acid make it a potential candidate for use in treatments and products that target oxidative stress and inflammation-related conditions.

Upstream product

• 129779-05-1 (S)-3-((R)-2-Benzyloxymethyl-3-phenyl-propionyl)-4-isopropyl-oxazolidin-2-one 
• 2601-10-7 2‐benzyl‐3‐hydroxypropanenitrile 
• 131202-40-9 (E)-2-(Hydroxymethyl)-3-phenyl-2-propenoic acid 
• 124957-42-2 Methyl (2E)-2-(acetoxymethyl)-3-phenylprop-2-enoate 
• 104-53-0 3-phenyl-propionaldehyde 
• 2612-30-8 2-benzyl-1,3-propanediol 
• 85677-12-9 2-benzyl-3-hydroxypropionic acid methyl ester 
• 123803-51-0 2R-benzyl-3-benzyloxypropanoic acid 
• 195056-66-7 (R)-2-(acetoxymethyl)-3-phenylpropanoic acid 
• 50-00-0 formaldehyd 
• 1012-05-1 D,L-homophenylalanine 
• 709673-94-9 (R)-2-benzyl-3-hydroxypropanoic acid methyl ester 
• 220805-30-1 (S)-4-Benzyl-3-((R)-2-benzyloxymethyl-3-phenyl-propionyl)-oxazolidin-2-one 
• 170846-09-0 (4S)-4-benzyl-3-[(2R)-2-benzyl-3-hydroxypropanoyl]-1,3-oxazolidin-2-one 

Downstream Products

• 124815-67-4 (S)-2-acetylthiomethyl-3-phenylpropanoic acid 
• 129831-73-8 L-N-[(2S)-2-benzyl-3-hydroxypropionyl]norleucine tert-butyl ester 
• 1354899-35-6 (S)-2-[(R)-2-benzyl-3-(formyl-hydroxy-amino)-propionylamino]-3,3,N-trimethyl-butyramide 
• 1354899-38-9 C₁₈H₂₇N₃O₄ 
• 1354899-39-0 (R)-2-benzyl-3-(formyl-hydroxy-amino)-N-[(S)-1-methylcarbamoyl-2-phenyl-ethyl]-propionamide 
• 129779-08-4 (4S,5S)-5-{(S)-2-[(S)-2-Benzyl-3-(pyrimidine-2-sulfonyl)-propionylamino]-hexanoylamino}-2-ethyl-4-hydroxy-7-methyl-octanoic acid isobutyl-amide 
• 129779-07-3 (4S,5S)-5-[(S)-2-((S)-2-Benzyl-3-cyclopentanesulfonyl-propionylamino)-hexanoylamino]-2-ethyl-4-hydroxy-7-methyl-octanoic acid isobutyl-amide 
• 123803-52-1 L-N-[(2R)-2-benzyl-3-(p-toluenesulfonyloxy)propionyl]norleucine tert-butyl ester 
• 123802-56-2 (S)-2-[(S)-2-Benzyl-3-(pyrimidine-2-sulfonyl)-propionylamino]-hexanoic acid tert-butyl ester 
• 129831-74-9 (S)-2-((S)-2-Benzyl-3-cyclopentanesulfonyl-propionylamino)-hexanoic acid tert-butyl ester 
• 123803-30-5 (S)-2-[(S)-3-Phenyl-2-(pyrimidin-2-ylsulfanylmethyl)-propionylamino]-hexanoic acid tert-butyl ester 
• 129779-06-2 (S)-2-((S)-2-Cyclopentylsulfanylmethyl-3-phenyl-propionylamino)-hexanoic acid tert-butyl ester 
• 183182-07-2 (R)-α-benzyl-β-aminopropanoic acid 
• 123878-44-4 L-N-<(2R)-2-benzyl-3-hydroxypropionyl>norleucine t-butyl ester 

Relevant articles and documents

Chemoenzymatic Production of Enantiocomplementary 2-Substituted 3-Hydroxycarboxylic Acids from l-α-Amino Acids

A two-enzyme cascade reaction plus in situ oxidative decarboxylation for the transformation of readily available canonical and non-canonical l-α-amino acids into 2-substituted 3-hydroxycarboxylic acid derivatives is described. The biocatalytic cascade consisted of an oxidative deamination of l-α-amino acids by an l-α-amino acid deaminase from Cosenzaea myxofaciens, rendering 2-oxoacid intermediates, with an ensuing aldol addition reaction to formaldehyde, catalyzed by metal-dependent (R)- or (S)-selective carboligases namely 2-oxo-3-deoxy-l-rhamnonate aldolase (YfaU) and ketopantoate hydroxymethyltransferase (KPHMT), respectively, furnishing 3-substituted 4-hydroxy-2-oxoacids. The overall substrate conversion was optimized by balancing biocatalyst loading and amino acid and formaldehyde concentrations, yielding 36–98% aldol adduct formation and 91–98% ee for each enantiomer. Subsequent in situ follow-up chemistry via hydrogen peroxide-driven oxidative decarboxylation afforded the corresponding 2-substituted 3-hydroxycarboxylic acid derivatives. (Figure presented.).

Preparation method and detection method for ecadotril

The invention provides a preparation method and detection method for ecadotril. 2-benzyl-3-hydroxypropionic acid is used as a raw material, and a four-step method is employed for preparing an intermediate and ecadotril, so more options are provided for acquisition of the bulk drug ecadotril. At the same time, based on the fact that (R)-phenylethylamine has slightly different abilities in elution of ecadotril and ecadotril enantiomers, a liquid-phase detection method for racecadotril in European Pharmacopoeia is employed for separation and detection in a liquid-phase system of an achiral column. The detection method is simple to operate and easy to implement.

Synthesis of Enantiomerically Enriched 2-Hydroxymethylalkanoic Acids by Oxidative Desymmetrisation of Achiral 1,3-Diols Mediated by Acetobacter aceti

The stereoselective desymmetrisation of achiral 2-alkyl-1,3-diols is performed by oxidation of one of the two enantiotopic primary alcohol moieties by means of Acetobacter aceti MIM 2000/28 to afford the corresponding chiral 2-hydroxymethyl alkanoic acids (up to 94 % ee). The procedure, carried out in aqueous medium under mild conditions of pH, temperature and pressure, contributes to enlarge the portfolio of enzymatic oxidations available to organic chemists for the development of sustainable manufacturing processes.

Organocatalytic enantioselective α-hydroxymethylation of aldehydes: Mechanistic aspects and optimization

Further studies of the direct enantioselective α-hydroxymethylation of aldehydes employing the α,α-diarylprolinol trimethylsilyl ether class of organocatalysts are described. This process has proven efficient for access to β-hydroxycarboxylic acids and δ-hydroxy-α,β-unsaturated esters from aldehydes in generally good yields, excellent enantioselectivity, and compatibility with a broad range of functional groups in the aldehyde. The goal of these studies was to identify the critical reaction variables that influence the yield and enantioselectivity of the α-hydroxymethylation process such as catalyst structure, pH of the medium, purity of the reactants and reagents particularly with respect to the presence of acidic impurities, and the nature of the buffer, along with the standard variables including solvent, time, temperature and mixing efficiency. The previously identified intermediate lactol has been further characterized and its reactivity examined. These studies have led to identification of the most critical variables translating directly into improved substrate scope, reproducibility, enantioselectivity, and yields.

Synthesis of chiral α-benzyl-β2-hydroxy carboxylic acids through iridium-catalyzed asymmetric hydrogenation of α- oxymethylcinnamic acids

An asymmetric hydrogenation of α-oxymethylcinnamic acids was developed by using chiral spiro phosphine-oxazoline/iridium complexes as catalysts to prepare β2-hydroxycarboxylic acids with high reactivity (TON up to 2000) and excellent enantioselectivity (up to 99.5% ee). By using this highly efficient asymmetric hydrogenation as a key step, a concise total synthesis of natural product homoisoflavone (S)-(+)-4 was accomplished. An asymmetric hydrogenation of α-oxymethylcinnamic acids was developed to prepare β2-hydroxycarboxylic acids with high reactivity (TON up to 2000) and excellent enantioselectivity (up to 99.5% ee), which was applied to a concise total synthesis of a natural product homoisoflavone. Copyright

Inhibition of invasion and capillary-like tube formation by retrohydroxamate-based MMP inhibitors

Matrix metalloproteinases (MMPs), a family of zinc-containing endopeptidases, participate in many normal processes such as embryonic development and wound repair, and in many pathological situations such as cancer, atherosclerosis, and arthritis. Peptidomimetic MMP inhibitors were designed and synthesized with Nformylhydroxylamine (retrohydroxamate) as a zinc-binding group and various side chains on the α, P1′, and P2′ positions. Using in vitro MMP assays with purified MMPs (MMP-1, MMP-2, MMP-3, MMP-9, and MMP-14) and fluorogenic peptide substrates, it was found that compounds 2d and 2g selectively inhibit gelatinases (MMP-2 and MMP-9) and interstitial collagenase (MMP-1). They also inhibited the chemo-invasion of fibrosarcoma HT-1080 cells and tube formation of human umbilical vascular endothelial cells in a dosedependent manner. Our results suggest that retrohydroxamate-based MMP inhibitors, especially compounds 2d and 2g, have the potential to be used as therapeutic drugs for cancer and other MMP-related diseases.

Direct enantioselective organocatalytic hydroxymethylation of aldehydes catalyzed by α,α-diphenylprolinol trimethylsilyl ether

The direct enantioselective hydroxymethylation of aldehydes utilizing α,α-diphenylprolinol trimethylsilyl ether as an organocatalyst is described. The intermediate α-substituted β-hydroxyaldehydes were not isolated but converted to the more readily isolab

Dual-acting antihypertensive agents

The invention is directed to compounds of formula I: wherein Ar, r, R3, X, and R5-7 are as defined in the specification, and pharmaceutically acceptable salts thereof. The compounds of formula I have AT1 receptor antagonist activity and neprilysin inhibition activity. The invention is also directed to pharmaceutical compositions comprising such compounds; methods of using such compounds; and a process and intermediates for preparing such compounds.

Nitrile biotransformations for the synthesis of enantiomerically enriched β2-, and β3-hydroxy and -alkoxy acids and amides, a dramatic O-substituent effect of the substrates on enantioselectivity

Rhodococcus erythropolis AJ270, a nitrile hydratase/amidase-containing microbial whole cell catalyst, is able to catalyze the hydrolysis of a number of β-hydroxy and β-alkoxy nitriles under very mild conditions. Both the efficiency and enantioselectivity of the biocatalysis, however, were strongly dependent upon the structures of both nitrile and amide substrates. When biotransformations of racemic 3-hydroxy-3-phenylpropionitrile and 2-hydroxymethyl-3-phenylpropionitrile gave low enantioselectivity, their O-methylated isomers underwent highly efficient and enantioselective biocatalytic reactions to afford highly enantioenriched β2- and β3-hydroxy amide and acid derivatives in excellent yield. The study has provided an example of simple and very convenient substrate engineering method to increase the enantioselectivity of the biocatalytic reaction.

Sulfonic acid ester derivatives, method for production thereof and use thereof

Novel and useful optical active 2-aralkyl-3-sulfonyloxy-1-propanol and 2-aralkyl-3-sulfonyloxypropionic acid are provided by using an optical active 2-aralkyl-3-acyloxy-1-propanol as a starting material. Furthermore, an optical active 2-aralkyl-3-thiopropionic acid, which is an important intermediate of enkephalinase inhibitor, is provided. According to the present invention, industrially useful optical active sulfonic acid ester derivatives can be provided.