4358-87-6

Basic information

• Product Name: Methyl DL-mandelate
• Synonyms: Methyl 2-hydroxy-2-phenylacetate;rac-(2R*)-2-Hydroxy-2-phenylacetic acid methyl ester;rac-(R*)-Hydroxyphenylacetic acid methyl ester;rac-(R*)-Phenylhydroxyacetic acid methyl ester;rac-(αR*)-α-Hydroxybenzeneacetic acid methyl ester;DL-Methyl mandelate,97%;Methyl DL-mandelate ,99%;Methyl DL-Mandelate, 97%, 97%
• CAS NO: 4358-87-6
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• EINECS: 224-434-7
• Product Categories: C8 to C9;Carbonyl Compounds;Esters;FINE Chemical & INTERMEDIATES
• Mol File: 4358-87-6.mol

Chemical Properties

• Melting Point: 54-56 °C(lit.)
• Boiling Point: 135 °C12 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: white to slightly yellow crystals, crystalline
• Density: 1.1756
• Vapor Pressure: 0.00715mmHg at 25°C
• Refractive Index: 1.5351 (estimate)
• Storage Temp.: -20°C
• Solubility: methanol: 0.1 g/mL, clear
• PKA: 12.19±0.20(Predicted)
• BRN: 2047558
• CAS DataBase Reference: Methyl DL-mandelate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl DL-mandelate(4358-87-6)
• EPA Substance Registry System: Methyl DL-mandelate(4358-87-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 4358-87-6(Hazardous Substances Data)

Usage

Uses

Used in Enzyme Research:
Methyl DL-mandelate is used as a substrate for lipase B from Candida antarctica, an enzyme that plays a crucial role in various industrial applications, including the production of biofuels and the synthesis of pharmaceuticals. Its use as a substrate helps researchers study the enzyme's activity and optimize its performance in different applications.
Used in Pharmaceutical Industry:
Methyl DL-mandelate is used as an intermediate in the synthesis of various pharmaceutical compounds due to its unique chemical structure. This application is essential for the development of new drugs and the improvement of existing ones.
Used in Biofuel Production:
Methyl DL-mandelate is used as a substrate in the production of biofuels, particularly when employing lipase B from Candida antarctica. Its role in this process contributes to the development of sustainable and environmentally friendly energy sources.
Used in Flavor and Fragrance Industry:
Methyl DL-mandelate is used as a building block for the synthesis of various compounds used in the flavor and fragrance industry. Its unique chemical properties make it a valuable component in creating diverse and complex scents.
Used in Chemical Synthesis:
Methyl DL-mandelate is used as a versatile building block in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and specialty chemicals. Its ability to be easily modified and incorporated into different molecular structures makes it a valuable asset in the chemical industry.

InChI:InChI=1/C9H10O3/c1-12-9(11)8(10)7-5-3-2-4-6-7/h2-6,8,10H,1H3

Upstream product

• 67-56-1 methanol 
• 611-71-2 MANDELIC ACID 
• 1074-12-0 phenylglyoxal hydrate 
• 100-38-9 2-(diethylamine)ethanethiol 
• 104-53-0 3-phenyl-propionaldehyde 
• 103-82-2 phenylacetic acid 
• 532-28-5 (RS)-mandelonitrile 
• 62173-99-3 benzyl 2-hydroxy-2-phenylacetate 
• 14758-41-9 2-Hydroxy-2-phenyl-1,1,1-tris-(phenylmercapto)-aethan 
• 82722-12-1 2,2,2-Tris-ethylsulfanyl-1-phenyl-ethanol 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 930-68-7 cyclohexenone 
• 5878-19-3 Methoxyacetone 
• 109-49-9 5-Hexen-2-one 

Downstream Products

• 20907-13-5 2-methyl-1-phenylpropane-1,2-diol 
• 6296-95-3 1,1,2-triphenyl-1,2-ethanediol 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 7476-66-6 methyl 2-chloro-2-phenylethanoate 
• 4410-31-5 (RS)-mandelamide 
• 124786-85-2 (RS)-2-(3-Phenyl-2-propenoyl)-oxy-2-phenylessigsaeuremethylester 
• 855660-91-2 N-(2-hydroxy-ethyl)-mandelamide 
• 5465-47-4 1,2-bis-(4-methoxy-phenyl)-1-phenyl-ethane-1,2-diol 
• 122135-80-2 2-phenyl-1,1-di-p-tolyl-ethane-1,2-diol 
• 65645-88-7 N-methyl-2-hydroxy-2-phenylethanamide 
• 4410-32-6 N-benzyl-2-hydroxy-2-phenylacetamide 
• 85805-96-5 phenyl-(3-phenyl-propionyloxy)-acetic acid methyl ester 
• 62640-69-1 (+/-)-1.3-diphenyl-2-benzyl-propanediol-(1.2) 
• 62281-60-1 Carbmethoxybenzyloxytriethylsilan 

Relevant articles and documents

Efficient Synthesis of α-Hydroxy-β-ketoesters from Methyl Phenylglyoxalate and Acid Chlorides mediated by Titanium Trichloride

Methyl phenylglyoxalate and acid chlorides undergo rapid condensation reactions on treatment with a TiCl3-THF/CH2Cl2 solution, in the presence of pyridine, at room temperature.

Solvent Effect in the Reduction of α-Keto Esters by Aqueous Titanium Trichloride

In the reduction of 1 by Ti(III) ion the dimeric 3 or monomeric 4 reduction products could be made to predominate by the choice of the solvent.It is found that (a) dimerization, via coupling of two radicals 2, increases with increasing simultaneously the dielectric constant and the hydrogen ion concentration of the reaction medium and (b) alcohol formation, which occurs via electron transfer between radical species having different redox potentials, increases with decreasing the hydrogen ion concentration of the medium.Under appropriate reaction conditions, the dimerization process is partially stereoselective.Reaction mechanisms are proposed which account for the ratio of both dimer / alcohol and meso / dl under different experimental conditions.

A phosphetane catalyzes deoxygenative condensation of α-keto esters and carboxylic acids via PIII/PV=O redox cycling

A small-ring phosphacycle is found to catalyze the deoxygenative condensation of α-keto esters and carboxylic acids. The reaction provides a chemoselective catalytic synthesis of α-acyloxy ester products with good functional group compatibility. Based on both stoichiometric and catalytic mechanistic experiments, the reaction is proposed to proceed via catalytic PIII/PV=O cycling. The importance of ring strain in the phosphacyclic catalyst is substantiated by an observed temperature-dependent product selectivity effect. The results point to an inherent distinction in design criteria for organophosphorus-based catalysts operating via PIII/PV=O redox cycling as opposed to Lewis base (nucleophilic) catalysis.

Efficient synthesis of α-aryl serine derivatives via three-component reactions of aryldiazoacetates, anilines and formaldehyde

A three-component reaction based on trapping of ammonium ylides with formaldehyde was first reported. This reaction offers a new strategy for the synthesis of α-aryl serine derivatives and can be extended to the preparation of α-aryl threonine derivatives. Synthetic application of the three component reaction for the preparation of hydroquinoxaline derivative was also demonstrated.

Mechanistic rationale for the NaBH4 reduction of α-keto esters

An intramolecular hydride delivery process largely contributes during the double reduction of α-keto esters into diols by NaBH4. In the case of enolic α-keto esters, the first step of the process, the reduction of the keto group, occurred exclusively through an 1,2-hydride addition despite the predominance of the tautomeric enolic form. The clear-cut difference of reaction rate between enolic and non enolic substrate 4 for reaction carried out in methanol is interpreted in terms of competitive hydride consumption due to the extremely favorable reaction between this solvent and NaBH4.

Silyl Cyanopalladate-Catalyzed Friedel-Crafts-Type Cyclization Affording 3-Aryloxindole Derivatives

3-Aryloxindole derivatives were synthesized through a Friedel-Crafts-type cyclization. The reaction was catalyzed by a trimethylsilyl tricyanopalladate complex generated in situ from trimethylsilyl cyanide and Pd(OAc) 2. Wide varieties of diethyl phosphates derived from N -arylmandelamides were converted almost quantitatively into oxindoles. When N, N -dibenzylamide was used instead of an anilide substrate, a benzo-fused δ-lactam was obtained. An oxindole product was subjected to substitution reactions to afford 3,3-diaryloxindoles with two different aryl groups.

Visible Light-Promoted Sulfoxonium Ylides Synthesis from Aryl Diazoacetates and Sulfoxides

A visible light-promoted reaction of donor/acceptor diazoalkanes with sulfoxides towards the synthesis of synthetically useful sulfoxonium ylides was reported. The reaction occurred under sole visible light irradiation without the need of any transition-metals or additives, affording the corresponding sulfoxonium ylides in moderate to good yields. The success of late-stage modification of natural isolates or drug candidates, scale-up reaction and transformation of sulfoxonium ylides to other useful molecules further rendered the approach valuable.

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.

KB3H8: An environment-friendly reagent for the selective reduction of aldehydes and ketones to alcohols

Selective reduction of aldehydes and ketones to their corresponding alcohols with KB3H8, an air- and moisture-stable, nontoxic, and easy-to-handle reagent, in water and THF has been explored under an air atmosphere for the first time. Control experiments illustrated the good selectivity of KB3H8 over NaBH4 for the reduction of 4-acetylbenzaldehyde and aromatic keto esters. This journal is

Design, synthesis and antifungal evaluation of novel mandelic acid derivatives containing a 1,3,4-oxadiazothioether moiety

A series of novel mandelic acid derivatives containing a 1,3,4-oxadiazothioether moiety were designed and synthesized. Bioassay results showed that some target compounds exhibited certain antifungal activity against six kinds of pathogenic fungi in vitro. Among the compounds, the EC50 values of T41 against Gibberella saubinetii, Verticillium dahlia and Sclerotinia sclerotiorum were 31.0, 27.0 and 32.1?μg/ml, respectively, and the EC50 value of T14 against S. sclerotiorum was 14.7?μg/ml. The antifungal activity against the resistant fungus S. sclerotiorum indicated that this series of target compounds may have the similar action modes or sites as the commercialized succinate dehydrogenase inhibitor carboxin. A morphological study with fluorescence microscope demonstrated that T41 can significantly destroy the membrane integrity of G. saubinetii.