1277161-39-3

Upstream product

• 108-05-4 vinyl acetate 
• 121-34-6 3-methoxy-4-hydroxybenzoic acid 

Downstream Products

• 934767-95-0 6'-O-vanilloyl-arbutin 
• 1456513-33-9 methyl 6-O-vanilloyl-α-D-glucopyranoside 
• 99499-12-4 4-hydroxy-N-isobutyl-3-methoxybenzamide 

Relevant academic research and scientific papers

Biocatalyzed Synthesis of Vanillamides and Evaluation of Their Antimicrobial Activity

A series of vanillamides were easily synthesized, exploiting an acyltransferase from Mycobacterium smegmatis (MsAcT). After their evaluation as antimicrobial agents against a panel of Gram-positive and Gram-negative bacteria, three compounds were demonstrated to be 9-fold more effective toward Pseudomonas aeruginosa than the vanillic acid precursor. Taking into consideration the scarce permeability of the Gram-negative bacteria cell envelope when compared to Gram-positive strains or yeasts, these molecules can be considered the basis for the generation of new nature-inspired antimicrobials. To increase the process productivity and avoid any problem related to the poor water solubility of the starting material, a tailored flow biocatalyzed strategy in pure toluene was set up. While a robust immobilization protocol exploiting glyoxyl-agarose was employed to increase the stability of MsAcT, in-line work-up procedures were added downstream the process to enhance the system automation and reduce the overall costs.

Chemo-enzymatic synthesis of vinyl and L-ascorbyl phenolates and their inhibitory effects on advanced glycation end products

This study successfully established the feasibility of a two-step chemo-enzymatic synthesis of L-ascorbyl phenolates. Intermediate vinyl phenolates were first chemically produced and then underwent trans-esterification with L-ascorbic acid in the presence of Novozyme 435 (Candida Antarctica lipase B) as a catalyst. Twenty vinyl phenolates and 11 ascorbyl phenolates were subjected to in vitro bioassays to investigate their inhibitory activity against advanced glycation end products (AGEs). Among them, vinyl 4-hydroxycinnamate (17VP), vinyl 4-hydroxy-3-methoxycinnamate (18VP), vinyl 4-hydroxy-3,5-dimethoxycinnamate (20VP), ascorbyl 4-hydroxy-3-methoxycinnamate (18AP) and ascorbyl 3,4-dimethoxycinnamate (19AP) showed 2–10 times stronger inhibitory activities than positive control (aminoguanidine and its precursors). These results indicated that chemo-enzymatically synthesized compounds have AGE inhibitory effect and thus are effective in either preventing or retarding glycation protein formation.

COMPOUNDS FOR INHIBITING LIPID OXIDATION AND A METHOD FOR PRODUCING THE SAME

The present invention relates to a compound for inhibiting lipid oxidation, and a producing method thereof. The compound for inhibiting lipid oxidation is synthesized by a transesterification reaction though a vinyl reaction and a lipase-catalyzed reaction. The produced compound for inhibiting lipid oxidation has an excellent effect of inhibiting oxidation according to a total oxidation value (TOTOX) which is a combination of a P-anisidine value (P-AnV) and a peroxide value (PV) and an analysis of a thiobarbituric acid reaction substance (TBARS).COPYRIGHT KIPO 2016

Donor specificity and regioselectivity in Lipolase mediated acylations of methyl α-d-glucopyranoside by vinyl esters of phenolic acids and their analogues

Methyl α-d-glucopyranoside as a model acceptor was acylated by several phenolic and non-phenolic vinyl esters using immobilised Lipolase. Donor specificity and regioselectivity of reaction were investigated. Conversion and rate of acylation by structurally varied donors indicates that the synthetic reactivity of Lipolase corresponds to the hydrolytic activity of feruloyl esterase type A. Lipolase exhibited remarkable regioselectivity for primary position of methyl α-d-glucopyranoside. The acylation occurred exclusively at 6-O primary position when vinyl esters of phenolic acids (hydroxybenzoates, hydroxyphenylalkanoates and hydroxycinnamates) served as acyl donors (5-77%). In addition to the major 6-O-acyl products (52-79%), 2,6-di-O-acylated derivatives were isolated from reaction mixtures (2-13%) when non-phenolic donors were used (vinyl esters of fully methoxylated derivatives of phenolic acids, along with vinyl benzoates, cinnamates or some heterocyclic analogues).