890-98-2

Usage

Uses

Used in Cosmetic Industry:
BENZYL DL-MANDELATE is used as a skin-conditioning agent for its humectant and anti-aging properties, helping to improve the skin's texture and appearance.
Used in Antimicrobial Applications:
BENZYL DL-MANDELATE is used as an antibacterial agent in cosmetic products, leveraging the antimicrobial properties of mandelic acid to maintain a clean and healthy skin environment.
Used in Skincare Products:
BENZYL DL-MANDELATE is used as a humectant in skincare products to help retain moisture, ensuring that the skin remains hydrated and supple.
Used in Anti-aging Formulations:
BENZYL DL-MANDELATE is used in anti-aging formulations to combat the signs of aging, such as wrinkles and fine lines, by promoting skin elasticity and firmness.
Used in Sensitive Skin Products:
While BENZYL DL-MANDELATE may cause irritation in some individuals, it is used in sensitive skin products with careful consideration to provide the benefits of mandelic acid without causing excessive skin irritation.

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 
• 91-01-0 1,1-Diphenylmethanol 
• 100-39-0 benzyl bromide 
• 62977-82-6 benzyl oxo(phenyl)acetate 
• 102-16-9 benzyl 2-phenylacetate 
• 100-51-6 benzyl alcohol 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 218792-82-6 α-diazo-α-phenylacetic acid benzyl ester 
• 25726-04-9 phenylglyoxylyl chloride 
• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 611-73-4 Benzoylformic acid 
• 144-55-8 sodium hydrogencarbonate 
• 100-44-7 benzyl chloride 

Downstream Products

• 14007-02-4 butyl mandelate 
• 1041400-01-4 2-(benzyloxy)-2-oxo-1-phenylethyl pyrrolidine-1-carboxylate 
• 1186216-42-1 benzyl O-(tert-butyl)mandelate 
• 62977-82-6 benzyl oxo(phenyl)acetate 
• 62173-99-3 (S)-benzyl 2-hydroxy-2-phenylacetate 
• 97415-09-3 (R)-benzyl 2-hydroxy-2-phenyl-acetate 
• 74004-88-9 2-bromo-2-phenylacetic acid benzyl ester 
• 774-40-3 hydroxy-phenyl-acetic acid ethyl ester 
• 4358-87-6 (RS)-methyl mandelate 
• 1007877-81-7 benzyl 2-phenyl-2-(tosyloxy)acetate 
• 1007877-99-7 (R)-2-(4-hydroxypiperidin-1-yl)-2-phenylacetic acid 
• 1007877-93-1 benzyl (S)-2-(4-hydroxypiperidin-1-yl)-2-phenylacetate 
• 1007877-95-3 benzyl (S)-2-(4-hydroxypiperidin-1-yl)-2-phenylacetate 
• 1007877-91-9 benzyl 2-(4-hydroxypiperidin-1-yl)-2-phenylacetate 

Relevant academic research and scientific papers

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

Cobalt-Catalyzed Transfer Hydrogenation of α-Ketoesters and N-Cyclicsulfonylimides Using H2O as Hydrogen Source

A Co-catalyzed effective transfer hydrogenation of various α-ketoesters and N-cyclicsulfonylimides by safe and environmentally benign H2O as hydrogen source is described. The reaction used easily available and easy to handle zinc metal as a reductant. Interestingly, the catalytic system does not require ligand for reduction of N-cyclicsulfonylimides. (Figure presented.).

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.

Boron-Catalyzed O-H Bond Insertion of α-Aryl α-Diazoesters in Water

A catalytic, metal-free O-H bond insertion of α-diazoesters in water in the presence of B(C6F5)3·nH2O (2 mol %) was developed, affording a series of α-hydroxyesters in good to excellent yields. The reaction features easy operation and wide substrate scope, and importantly, no metal is needed as compared with the conventional methods. Significantly, this approach further expands the applications of B(C6F5)3 under water-tolerant conditions.

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.

Zirconocene-catalyzed direct (trans)esterification of acyl acids (esters) and alcohols in a strict 1:1 ratio under solvent-free conditions

A highly efficient way for the direct (trans)esterification of acyl acids (esters) and alcohols in a strict 1:1 ratio using a zirconocene complex (1, 1 mol%), a strong Lewis acid of good water tolerance, as a catalyst under solvent-free conditions has been developed. A wide range of acid and alcohol (esters) substrates undergo (trans)esterification to produce carboxylic ester motifs in moderate to good or excellent yields with good functional tolerance, such as that towards C-Br as well as CC and CC bonds. And complex 1 can be recycled six times without showing a significant decline in catalytic efficiency. It was demonstrated that cyclandelate, which is used to treat high blood pressure as well as heart and blood-vessel diseases, can be directly synthesized on a gram scale with 81% yield (6.70 g) using complex 1.

Enantio- and chemoselective Br?nsted-acid/Mg(nBu) 2 catalysed reduction of α-keto esters with catecholborane

The first enantio- and chemoselective Br?nsted-acid catalysed reduction of α-keto esters with catecholborane has been developed. The α-hydroxy esters were obtained under mild reaction conditions in virtually quantitative yields and excellent enantioselectivities. With slight modifications both enantiomers can be obtained without any loss of selectivity. This journal is the Partner Organisations 2014.

Chemoselective esterification of α-hydroxyacids catalyzed by salicylaldehyde through induced intramolecularity

A new, direct and chemoselective esterification of α-hydroxyacids was developed using a reversible covalent-binding strategy. By taking advantage of acetal chemistry, simple aldehydes can be used to efficiently catalyze the esterification of α-hydroxy carboxylic acids in the presence of β-hydroxyacid moieties or other carboxylic acids in amounts equal to or in excess of the alcohols. A diverse array of α-aryl, α-alkyl, α-heteroaryl, and functionalized α-hydroxyacids were smoothly esterified with 1° and 2° alcohols catalyzed by 10 mol% inexpensive and commercially available salicylaldehyde, furnishing the resultant esterification products in 83-95% yields after a simple basic aqueous workup to remove the unreacted hydroxyacids. In addition, the salicylaldehyde can be recovered through vacuum distillation or silica gel purification, thereby meeting the standards of green chemistry. A mechanistic study proved that the formation of covalent adduct III during our proposed catalytic cycle (Scheme 1A) is responsible for the real catalysis.

Selective reduction of aldehydes and ketones to alcohols with ammonia borane in neat water

Chemoselective reduction of various carbonyl compounds to alcohols with ammonia borane (AB), a nontoxic, environmentally benign, and easily handled reagent, in neat water was achieved in quantitative conversions and high isolated yields. Interestingly, α- and β-keto esters were selectively reduced to corresponding hydroxyl esters by AB, while diols were obtained when sodium borohydride was used as a reducing agent. The procedure is also compatible with the presence of a variety of base-labile protecting groups, such as tosyl, acetyl, benzoyl, ester groups, and acid-labile protecting groups such as trityl and TBDMS groups, and others, such as the unsaturated double bond, nitro and cyano groups. Finally, a kilo scale reaction of methyl benzoylformate with AB was conducted in water and gave methyl mandelate in 94% yield.

Asymmetric aerobic oxidation of α-hydroxy acid derivatives catalyzed by reusable, polystyrene-supported chiral N-salicylidene oxidovanadium tert-leucinates

The direct immobilization of two different C-5-propargyl ether-modified, chiral N-salicylidene vanadyl(V) tert-leucinates onto 4-azidomethyl-substituted polystyrene by click chemistry was examined. Among the eight different solvents investigated, the resulting polystyrene-supported catalysts promote the asymmetric, aerobic oxidation of α-hydroxy (thio)esters and amides with enantioselectivities of up to 99% ee (selectivity factor up to 41) in chloroform. These polystyrene-supported catalysts can be readily recovered by filtration and reused for at least four consecutive runs without discernible loss of reactivity and enantioselectivity.