890-98-2

Basic information

• Product Name: BENZYL DL-MANDELATE
• Synonyms: DL-MANDELIC ACID BENZYL ESTER 98+%;Benzyl-DL-mandelat;mandelic acid benzyl ester;2-Hydroxy-2-phenylacetic acid benzyl ester;Hydroxyphenylacetic acid benzyl ester;Phenylhydroxyacetic acid benzyl ester;α-Hydroxybenzeneacetic acid benzyl ester;α-Hydroxybenzeneacetic acid phenylmethyl ester
• CAS NO: 890-98-2
• Molecular Formula: C₁₅H₁₄O₃
• Molecular Weight: 242.26986
• EINECS: 212-965-7
• Mol File: 890-98-2.mol
• Article Data: 18

Chemical Properties

• Melting Point: 93-95 °C
• Boiling Point: 386.8±27.0 °C(Predicted)
• Appearance: /
• Density: 1.204±0.06 g/cm3(Predicted)
• Solubility: soluble in Methanol
• PKA: 12.15±0.20(Predicted)
• CAS DataBase Reference: BENZYL DL-MANDELATE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL DL-MANDELATE(890-98-2)
• EPA Substance Registry System: BENZYL DL-MANDELATE(890-98-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 890-98-2(Hazardous Substances Data)

Usage

General Description

Benzyl DL-mandelate, also known as mandelic acid, benzyl ester or benzyl mandelate, is a chemical compound used primarily in cosmetic products. It is generally recognized as a skin-conditioning agent serving both as a humectant and anti-aging ingredient. BENZYL DL-MANDELATE is a benzyl ester of mandelic acid, which is known for its antibacterial properties. Benzyl DL-mandelate is a mixture of two stereoisomers, making it a racemic mixture. Despite its benefits, it should be used cautiously as it may provoke skin irritation in sensitive individuals.

InChI:InChI=1/C15H14O3/c16-14(13-9-5-2-6-10-13)15(17)18-11-12-7-3-1-4-8-12/h1-10,14,16H,11H2

Upstream product

• 908094-04-2 phenyldiazomethane 
• 611-71-2 MANDELIC ACID 
• 100-51-6 benzyl alcohol 
• 14758-41-9 2-Hydroxy-2-phenyl-1,1,1-tris-(phenylmercapto)-aethan 
• 100-44-7 benzyl chloride 
• 91-01-0 1,1-Diphenylmethanol 
• 144-55-8 sodium hydrogencarbonate 
• 100-39-0 benzyl bromide 
• 62977-82-6 benzyl oxo(phenyl)acetate 
• 611-73-4 Benzoylformic acid 
• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 25726-04-9 phenylglyoxylyl chloride 
• 218792-82-6 α-diazo-α-phenylacetic acid benzyl ester 
• 102-16-9 benzyl 2-phenylacetate 

Downstream Products

• 4358-87-6 (RS)-methyl mandelate 
• 774-40-3 hydroxy-phenyl-acetic acid ethyl ester 
• 14007-02-4 butyl mandelate 
• 62977-82-6 benzyl oxo(phenyl)acetate 
• 97415-09-3 (R)-benzyl 2-hydroxy-2-phenyl-acetate 
• 931119-44-7 (1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-phenyl-acetic acid benzyl ester 
• 165337-03-1 4-(benzyloxy)-5-phenylfuran-2(5H)-one 
• 102-16-9 benzyl 2-phenylacetate 
• 1041400-01-4 2-(benzyloxy)-2-oxo-1-phenylethyl pyrrolidine-1-carboxylate 
• 1186216-42-1 benzyl O-(tert-butyl)mandelate 
• 62173-99-3 (S)-benzyl 2-hydroxy-2-phenylacetate 
• 1007877-91-9 benzyl 2-(4-hydroxypiperidin-1-yl)-2-phenylacetate 
• 1007877-93-1 benzyl (S)-2-(4-hydroxypiperidin-1-yl)-2-phenylacetate 
• 1007877-95-3 benzyl (S)-2-(4-hydroxypiperidin-1-yl)-2-phenylacetate 

Relevant articles and documents

Direct Aerobic α-Hydroxylation of Arylacetates for the Synthesis of Mandelates

Aerobic α-hydroxylation of α-methylene esters has proven challenging due to overoxidation and hydrolysis of the materials. In this article, KOtBu-promoted TBAB-catalyzed α-hydroxylation of α-methylene aryl esters using O2as the oxyge

Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles

Trichloroacetimidates are useful reagents for the synthesis of esters under mild conditions that do not require an exogenous promoter. These conditions avoid the undesired decomposition of substrates with sensitive functional groups that are often observed with the use of strong Lewis or Br?nsted acids. With heating, these reactions have been extended to benzyl esters without electron-donating groups. These inexpensive and convenient methods should find application in the formation of esters in complex substrates.

Silica-supported HClO4 promotes catalytic solvent- and metal-free O-H insertion reactions with diazo compounds

Solvent-free O-H insertion reactions in the presence of diazo carbonyl compounds were carried-out in very mild conditions. Unlike the traditional metal-catalysed version, employing rhodium acetate dimer, this method uses eco-friendly silica-supported HClO4 as the catalyst. Only 0.3 mol% of this Br?nsted acid catalyst, that can also be recycled several times, is necessary to guarantee very good yields (up to 97%) in the O-H insertion reactions. Reaction set-up is simple and permitted the preparation of forty-three α-hydroxy and α-alkoxy esters/ketones in just 1 h and at room temperature.