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
• Article Data: 101

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

Description

L-(+)-MANDELIC ACID ETHYL ESTER, also known as Ethyl (S)-(+)-mandelate, is an organic compound derived from mandelic acid. It is characterized by its ester functional group, which is formed by the reaction of mandelic acid with ethanol. L-(+)-MANDELIC ACID ETHYL ESTER is known for its potential applications in the pharmaceutical and chemical industries due to its unique chemical properties.

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

• 64-17-5 ethanol 
• 17199-29-0 (S)-Mandelic acid 
• 74327-04-1 ethyl 2-acetoxy-2-phenylacetate 
• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 67-56-1 methanol 
• 774-40-3 hydroxy-phenyl-acetic acid ethyl ester 
• 2935-35-5 (S)-2-phenylglycine 
• 123-20-6 vinyl n-butyrate 
• 1075-06-5 2,2-dihydroxy-1-phenyl-ethanone 
• 31491-20-0 (1-ethoxy-2-phenylvinyloxy)trimethylsilane 
• 611-71-2 MANDELIC ACID 
• 108-05-4 vinyl acetate 
• 100-58-3 phenylmagnesium bromide 
• 924-44-7 glyoxylic acid ethyl ester 

Downstream Products

• 82270-62-0 (S)-N-benzylmandelamide 
• 133187-22-1 (2S)-2-(tert-butyldimethylsilyloxy)-2-phenylacetaldehyde 
• 135560-64-4 (3R,4S)-3-ethyl-4-<(S)-1-hydroxymethylphenyl>-2-azetidinone 
• 135560-68-8 (3R,4S)-3-isopropyl-4-<(S)-1-hydroxymethylphenyl>-2-azetidinone 
• 174513-18-9 (S)-2-<(tert-butyldimethylsilyl)oxy>-2-phenyl-N-(trimethylsilyl)ethanimine 
• 135560-63-3 (3R,4S)-3-ethyl-4-<(S)-1-<(tert-butyldimethylsilyl)oxy>-phenylmethyl>-2-azetidinone 
• 135560-66-6 (3R,4S)-3-isopropyl-4-<(S)-1-<(tert-butyldimethylsilyl)oxy>phenylmethyl>-2-azetidinone 
• 215311-47-0 4-methyl-2-oxo pentanoic 1-(S)-ethoxycarbonyl phenyl methyl ester acid 
• 85879-96-5 (S)-2-acetoxy-2-phenylacetic acid ethyl ester 
• 153293-97-1 ethyl (R)-2-(tert-butyldimethylsilyloxy)-2-phenylacetate 
• 108998-83-0 (S)-1,1,2-triphenyl-1,2-ethanediol 
• 1190370-08-1 C₁₂H₁₃ClO₄ 
• 1579992-43-0 ethyl (S)-4-iodomandelate 
• 1579992-53-2 (1S)-1-(4-((trimethylsilyl)ethynyl)phenyl)ethane-1,2-diol 

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.

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.

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