13704-09-1

Basic information

• Product Name: L-(+)-MANDELIC ACID ETHYL ESTER
• Synonyms: ETHYL L-(+)-MANDELATE;ETHYL (S)-(+)-MANDELATE;L-(+)-MANDELIC ACID ETHYL ESTER;(S)-(+)-MANDELIC ACID ETHYL ESTER;(S)-MANDELIC ACID ETHYL ESTER;(S)-(+)-Ethyl Mandelate;L-(+)-MANDELIC ACID ETHYL ESTER 98+%;Ethyl (S)-(+)-mandelate 99%, optical purity ee: 99% (GLC)
• CAS NO: 13704-09-1
• Molecular Formula: C₁₀H₁₂O₃
• Molecular Weight: 180.2
• Product Categories: Chiral Building Blocks;Esters (Chiral);Synthetic Organic Chemistry;Chiral Building Blocks;Esters;Organic Building Blocks
• Mol File: 13704-09-1.mol

Chemical Properties

• Melting Point: 32-34 °C(lit.)
• Boiling Point: 106-107 °C4 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.12
• Vapor Pressure: 0.00918mmHg at 25°C
• Refractive Index: 1.5392 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 12.33±0.20(Predicted)
• CAS DataBase Reference: L-(+)-MANDELIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: L-(+)-MANDELIC ACID ETHYL ESTER(13704-09-1)
• EPA Substance Registry System: L-(+)-MANDELIC ACID ETHYL ESTER(13704-09-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 13704-09-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
L-(+)-MANDELIC ACID ETHYL ESTER is used as a starting material for the preparation of N-benzyl 2-phenylacetamide derivatives. These derivatives are known as potent anticonvulsant agents, which are essential in the treatment of various seizure disorders and epilepsy. The compound's role in the synthesis of these anticonvulsant agents highlights its importance in the development of new and effective medications for neurological conditions.

InChI:InChI=1/C10H12O3/c1-2-13-10(12)9(11)8-6-4-3-5-7-8/h3-7,9,11H,2H2,1H3/t9-/m0/s1

Upstream product

• 75-03-6 ethyl iodide 
• 13049-42-8 C₁₂H₁₆O₂ 
• 123-20-6 vinyl n-butyrate 
• 774-40-3 hydroxy-phenyl-acetic acid ethyl ester 
• 64-17-5 ethanol 
• 1075-06-5 2,2-dihydroxy-1-phenyl-ethanone 
• 100-58-3 phenylmagnesium bromide 
• 611-71-2 MANDELIC ACID 
• 108-05-4 vinyl acetate 
• 17199-29-0 (S)-Mandelic acid 
• 924-44-7 glyoxylic acid ethyl ester 
• 98-80-6 phenylboronic acid 
• 2935-35-5 (S)-2-phenylglycine 
• 22065-57-2 ethyl 2-phenyldiazoacetate 

Downstream Products

• 130821-77-1 (S) 1-phenyl 2,2-pentamethylene 1,2-dihydroxyethane 
• 2882-19-1 ethyl 2-phenyl-2-bromoacetate 
• 297749-52-1 ethyl (S)-(+)-2-benzyloxy-2-phenylacetate 
• 21210-43-5 (S)-Methyl mandelate 
• 53439-96-6 (S)-α-hydroxyphenylacetic acid iso-propyl ester 
• 153293-97-1 ethyl (R)-2-(tert-butyldimethylsilyloxy)-2-phenylacetate 
• 1190370-08-1 C₁₂H₁₃ClO₄ 
• 1579992-43-0 ethyl (S)-4-iodomandelate 
• 1579992-53-2 (1S)-1-(4-((trimethylsilyl)ethynyl)phenyl)ethane-1,2-diol 
• 1579992-37-2 (1S)-1-(4-ethynylphenyl)ethane-1,2-diol 
• 1579992-45-2 (S)-2-(4,4'-dimethoxytrityloxy)-1-(4-ethynylphenyl)ethanol 
• 1579992-46-3 (S)-1-O-[(2-cyanoethyloxy)(N,N-diisopropylamino)phosphanyl]-2-(4,4'-dimethoxytrityloxy)-1-(4-ethynylphenyl)ethanol 
• 492435-13-9 (S)-N-allyl-2-hydroxy-2-phenylacetamide 

Relevant articles and documents

Biocatalytic aminolysis of ethyl (S)-mandelate by lipase from Candida antarctica

Enzymes play many roles in the advancement of biotechnology, discovery of new therapeutic agents and industrial processes. In this perspective, aminolysis reactions using lipase from Candida antarctica (CAL-B) were performed from ethyl (S)-mandelate and several aliphatic amines (45 °C, hexane, 3–6 h). By means of optimized conditions, amides with excellent isolated yields (60–97%) were synthetized. The biotechnological potential of CAL-B as a promising approach for the synthesis of organic compounds in a more sustainable, rapid, efficient and green chemistry perspective was verified on these results.

Preparation of γ-Al2O3/α-Al2O3 ceramic foams as catalyst carriers via the replica technique

This work describes an effective method for the preparation of open-cell ceramic foams for their further use as catalyst supports. The polyurethane sponge replica technique was applied using a ceramic suspension based on a mixture of α-alumina, magnesia a

Biocatalysed reductions of α-ketoesters employing CyreneTM as cosolvent

The search for novel reaction media with environmental friendly properties is an area of great interest in enzyme catalysis. Water is the medium of biocatalysed processes, but due to its properties, sometimes the presence of organic (co)solvents is required. CyreneTM represents one of the newest approaches to this medium engineering. This polar solvent has been employed for the first time in biocatalysed reductions employing purified alcohol dehydrogenases. A set of α-ketoesters has been reduced to the corresponding chiral α-hydroxyesters with high conversions and optical purities, being possible to obtain good results at Cyrene contents of 30% v/v and working at substrate concentrations of 1.0 M in presence of 2.5% v/v of this solvent. At this concentration, the presence of Cyrene has a beneficial effect in the bioreduction conversion.

Structural insights into the desymmetrization of bulky 1,2-dicarbonyls through enzymatic monoreduction

Benzil reductases are dehydrogenases preferentially active on aromatic 1,2-diketones, but the reasons for this peculiar substrate recognition have not yet been clarified. The benzil reductase (KRED1-Pglu) from the non-conventional yeast Pichia glucozyma showed excellent activity and stereoselectivity in the monoreduction of space-demanding aromatic 1,2-dicarbonyls, making this enzyme attractive as biocatalyst in organic chemistry. Structural insights into the stereoselective monoreduction of 1,2-diketones catalyzed by KRED1-Pglu were investigated starting from its 1.77 ? resolution crystal structure, followed by QM and classical calculations; this study allowed for the identification and characterization of the KRED1-Pglu reactive site. Once identified the recognition elements involved in the stereoselective desymmetrization of bulky 1,2-dicarbonyls mediated by KRED1-Pglu, a mechanism was proposed together with an in silico prediction of substrates reactivity.

Exploiting Cofactor Versatility to Convert a FAD-Dependent Baeyer–Villiger Monooxygenase into a Ketoreductase

Cyclohexanone monooxygenases (CHMOs) show very high catalytic specificity for natural Baeyer–Villiger (BV) reactions and promiscuous reduction reactions have not been reported to date. Wild-type CHMO from Acinetobacter sp. NCIMB 9871 was found to possess an innate, promiscuous ability to reduce an aromatic α-keto ester, but with poor yield and stereoselectivity. Structure-guided, site-directed mutagenesis drastically improved the catalytic carbonyl-reduction activity (yield up to 99 %) and stereoselectivity (ee up to 99 %), thereby converting this CHMO into a ketoreductase, which can reduce a range of differently substituted aromatic α-keto esters. The improved, promiscuous reduction activity of the mutant enzyme in comparison to the wild-type enzyme results from a decrease in the distance between the carbonyl moiety of the substrate and the hydrogen atom on N5 of the reduced flavin adenine dinucleotide (FAD) cofactor, as confirmed using docking and molecular dynamics simulations.

Chiral-at-Iron Catalyst: Expanding the Chemical Space for Asymmetric Earth-Abundant Metal Catalysis

A new class of chiral iron catalysts is introduced that contains exclusively achiral ligands with the overall chirality being the result of a stereogenic iron center. Specifically, iron(II) is cis-coordinated to two N-(2-pyridyl)-substituted N-heterocycli

Ferroceno quinoline compound with planar chirality and synthesis method thereof

The invention provides a ferroceno quinoline compound with planar chirality as shown in description, R1-R8 are H or C1-C10 alkyl, the C1-C10 alkyl comprises one or multiple substituents of the methoxyand halogen. The invention further provides a synthesis

Enantioselective hydrogenation of α-ketoesters catalyzed by cinchona alkaloid stabilized Rh nanoparticles in ionic liquid

The heterogeneous enantioselective hydrogenation of α-ketoesters catalyzed by rhodium nanoparticles (Rh NPs) in ionic liquid was studied with the stabilization and modification of cinchona alkaloids. TEM characterization showed that well-dispersed Rh NPs of about 1.96?nm were obtained in ionic liquid. The results showed that cinchona alkaloids not only had good enantiodifferentiating ability but also accelerated the catalytic reaction. Under the optimum reaction conditions, the enantiomeric excess in ethyl benzoylformate hydrogenation could reach as high as 60.9%.

Asymmetric Transfer Hydrogenation in Thermomorphic Microemulsions Based on Ionic Liquids

A thermomorphic ionic-liquid-based microemulsion system was successfully applied for the Ru-catalyzed asymmetric transfer hydrogenation of ketones. On the basis of the temperature-dependent multiphase behavior of the targeted microemulsion, simple product separation as well as catalyst recycling could be realized. The use of water-soluble ligands improved the immobilization of the catalyst in the microemulsion phase and significantly decreased the catalyst leaching into the organic layer upon extraction of the product. Eventually, the optimized microemulsion system could be applied to a wide range of aromatic ketones that were reduced with good isolated yields (up to 98%) and enantioselectivities (up to 97%), while aliphatic ketones were less successful.

Fine tuning the enantioselectivity and substrate specificity of alcohol dehydrogenase from Kluyveromyces polysporus by single residue at 237

Here, S237 was identified to be important in fine tuning the substrate specificity and enantioselectivity of alcohol dehydrogenase from Kluyveromyces polysporus (KpADH). In the reduction of a diaryl ketone, (4-chlorophenyl)-(pyridin-2-yl)-methanone (1a), the highest and lowest enantioselectivity of 96.1% and 27.0% e.e. (R) were obtained with S237A and S237C. Kinetic parameters analysis revealed that S237G, S237A, S237H and S237D displayed improved kcat/Km toward 1a. Various prochiral ketones, including acetophenone, 4-chloroacetophenone and ethyl 2-oxo-4-phenylbutyrate could be asymmetrically reduced by S237C, S237G and S237E with > 99% e.e. This study provides guidance for the application of KpADH in the preparation of chiral secondary alcohols.