10590-85-9

Usage

Molecular Structure

A chemical compound with a glucose molecule attached to a salicylic acid structure through an ester bond, and a benzyl group attached to the salicylic acid structure through an ester bond.

Pharmaceutical Applications

Has potential use as an active ingredient in drugs targeted for metabolic disorders due to the presence of the glucose moiety in its structure.

Cosmetic Applications

Commonly found in skincare products for its anti-inflammatory and antimicrobial properties, which are derived from the salicylic acid structure.

Food Industry Applications

Has potential as a flavoring agent due to its benzyl ester group.

Diverse Potential Applications

Can be used in the fields of medicine, cosmetics, and food science.

InChI:InChI=1/C20H22O9/c21-9-15-16(23)17(24)18(25)20(29-15)28-14-7-6-12(22)8-13(14)19(26)27-10-11-4-2-1-3-5-11/h1-8,15-18,20-25H,9-10H2/t15-,16-,17+,18-,20-/m1/s1

Upstream product

• 21782-87-6 2,5-dihydroxybenzoic acid benzyl ester 
• 490-79-9 2,5-dihydroxybenzoic acid. 
• 17019-77-1 benzyl 2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-acetoxybenzoate 

Downstream Products

• 490-79-9 2,5-dihydroxybenzoic acid. 
• 21782-87-6 2,5-dihydroxybenzoic acid benzyl ester 

Relevant academic research and scientific papers

Divergent Synthesis of Natural Benzyl Salicylate and Benzyl Gentisate Glucosides

Herein is reported the first total synthesis of benzyl salicylate and benzyl gentisate glucosides present in various plant species, in particular the Salix genus, such as Populus balsamifera and P. trichocarpa. The method permits the synthesis of several natural phenolic acid derivatives and their glucosides starting from salicylic or gentisic acid. The divergent approach afforded access to three different acetylated glucosides from a common synthetic intermediate. The key step in the total synthesis of naturally occurring glycosides - the selective deacetylation of the sugar moiety - was achieved in the presence of a labile benzyl ester group by employing mild deacetylation conditions. The protocol permitted synthesis of trichocarpine (4 steps, 40% overall yield), isotrichocarpine (3 steps, 51% overall yield), trichoside (6 steps, 40% overall yield), and deoxytrichocarpine (3 steps, 42% overall yield) for the first time (>95% purity). Also, the optimized mild deacetylation conditions allowed synthesis of 2-O-acetylated derivatives of all four glycosides (5-17% overall yield, 90-95% purity), which are rare plant metabolites.

External preparation for skin

An external preparation for the skin comprising at least one of the glycosides or hydroxysaliyclic acid and/or the glycosides of aliphatic esters of hydroxysalicylic acid represented by the following formula 1: STR1 wherein R1 represents one selected from the group consisting of saturated hydrocarbon group and an unsaturated hydrocarbon group which have 1 to 20 carbon atoms and which may be either a straight-chain or a branched chain, and one of R2 and R3 represents a sugar residue and the other hydrogen. The external preparation for the skin has an excellent whitening effect and/or an excellent skin care effect.