20772-23-0

Usage

Uses

Used in Pharmaceutical Industry:
Thymol-β-D-glucopyranoside is used as an antimicrobial agent for its ability to inhibit the growth of various microorganisms, making it a promising candidate for the development of new antibiotics and antifungal medications.
Used in Cosmetic Industry:
In the cosmetic industry, Thymol-β-D-glucopyranoside is utilized as an antioxidant and antimicrobial preservative to extend the shelf life of products and protect them from microbial contamination.
Used in Traditional Medicine:
Thymol-β-D-glucopyranoside is employed in traditional medicine for its anti-inflammatory, antifungal, and antimicrobial properties, which contribute to the treatment of various ailments and conditions.
Used in Food Preservation:
Due to its antimicrobial properties, Thymol-β-D-glucopyranoside is used as a natural preservative in the food industry to prevent spoilage and extend the shelf life of perishable products.
Used in Agricultural Applications:
In agriculture, Thymol-β-D-glucopyranoside is applied as a biopesticide to control pests and diseases in crops, reducing the need for chemical pesticides and promoting sustainable farming practices.

InChI:InChI=1/C16H24O6/c1-8(2)10-5-4-9(3)6-11(10)21-16-15(20)14(19)13(18)12(7-17)22-16/h4-6,8,12-20H,7H2,1-3H3/t12-,13-,14+,15-,16-/m1/s1

Upstream product

• 117887-62-4 thymyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 133-89-1 UDP-glucose 
• 89-83-8 thymol 
• 2106-10-7 1-deoxy-1-fluoro-α-D-glucose 
• 604-69-3 β-D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 117887-62-4 thymyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

Two trifunctional leloir glycosyltransferases as biocatalysts for natural products glycodiversification

Two promiscuous Bacillus licheniformis glycosyltransferases, YdhE and YojK, exhibited prominent stereospecific but nonregiospecific glycosylation activity of 20 different classes of 59 structurally different natural and non-natural products. Both enzymes transferred various sugars at three nucleophilic groups (OH, NH2, SH) of diverse compounds to produce O-, N-, and S-glycosides. The enzymes also displayed a catalytic reversibility potential for a one-pot transglycosylation, thus bestowing a cost-effective application in biosynthesis of glycodiversified natural products in drug discovery.

Rapid phenolic O-glycosylation of small molecules and complex unprotected peptides in aqueous solvent

Glycosylated natural products and synthetic glycopeptides represent a significant and growing source of biochemical probes and therapeutic agents. However, methods that enable the aqueous glycosylation of endogenous amino acid functionality in peptides without the use of protecting groups are scarce. Here, we report a transformation that facilitates the efficient aqueous O-glycosylation of phenolic functionality in a wide range of small molecules, unprotected tyrosine, and tyrosine residues embedded within a range of complex, fully unprotected peptides. The transformation, which uses glycosyl fluoride donors and is promoted by Ca(OH)2, proceeds rapidly at room temperature in water, with good yields and selective formation of unique anomeric products depending on the stereochemistry of the glycosyl donor. High functional group tolerance is observed, and the phenol glycosylation occurs selectively in the presence of virtually all side chains of the proteinogenic amino acids with the singular exception of Cys. This method offers a highly selective, efficient, and operationally simple approach for the protecting-group-free synthesis of O-aryl glycosides and Tyr-O-glycosylated peptides in water.

An improved synthesis of the antimicrobial thymol- and Carvacrol-β-D-Glucopyranosides

Thymol (1) and Carvacrol (2) are monoterpenoid natural products that display in vitro antimicrobial activity against Campylobacter jejuni and coli, food-borne pathogens found in animal distal guts/avian crops that commonly contaminate meat and poultry dur

Synthesis of selected naturally occurring glucosides of volatile compounds. Their chromatographic and spectroscopic properties

Naturally occurring glucosides of benzyl alcohol, (±)-menthol, (+)-borneol, thymol, carvacrol and eugenol were synthesized by the Koenigs-Knorr-Zemplen method (yields 19.5-52.2 %). Their β-D-glucopyranosidic structures were determined by one- and two-dimensional homo-and heteronuclear 1H and 13C NMR spectroscopy. The β-configuration was additionally confirmed by the hydrolysis with β-glucosidase. Tetraacetyl-β-D-glucopyranosides, as intermediates, were GC-MS analyzed. Diastereomeric β-glucoside tetraacetates of (±)-menthol were well separated on the HP-101 column. The mass spectra of glucopyranoside tetraacetates were mutually compared, as well as with the spectra of their aglycones.

Preparation of New Terpenyl β-D-Glucopyranosides by a Modified Koenigs-Knorr Procedure.

Ten new hemi- and monoterpenyl β-D-glucopyranosides have been prepared by a modification of the Koenigs-Knorr procedure which utilises silver fluoroacetate as a soluble catalyst coupled with the introduction of a basic ion-exchange resin to effect the deacetylation step.Most of these compounds could not be obtained in acceptable yields using the classical procedure.