18604-51-8

Upstream product

• 97-53-0 4-allylguaiacol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 32601-56-2 4-allyl-2-methoxy-phenol; zinc bis-(4-allyl-2-methoxy-phenolate) 
• 83-87-4 D-glucose pentaacetate 
• 2280-44-6 D-Glucose 
• 604-69-3 β-D-glucose pentaacetate 

Downstream Products

• 18604-50-7 citrusin C 
• 18604-53-0 (4-allyl-2-methoxy-phenyl)-(O²,O³,O⁴-triacetyl-O⁶-trityl-β-D-glucopyranoside) 
• 17609-06-2 4-(3-hydroxypropyl)-2-methoxyphenyl-O-β-D-glucopyranoside 
• 97-53-0 4-allylguaiacol 

Relevant academic research and scientific papers

Synthesis and in vitro evaluation of antifungal and cytotoxic activities of eugenol glycosides

Six eugenol glycosides were prepared in order to assess their antifungal activity against Candida species. They were synthesized by glycosylation of eugenol with the appropriate glycosyl bromides followed by deacetylation with sodium methoxide in methanol and were evaluated in vitro for their antifungal activity through a Mueller-Hinton broth microdilution method. The peracetyl glycoside (derivative 4) was the most promising one since it was able to inhibit growth of C. albicans, C. tropicalis and C. glabrata with IC50 values much lower than that of the prototype eugenol. Derivative 4 showed to be 160.0 and 3.4 times more potent than eugenol and fluconazole, respectively, against C. glabrata with low cytotoxity (selectivity index of 45). Moreover, it was possible to verify the positive effect of gluco configuration and lipophilicity on antifungal activity, since glucose peracetyl derivatives were more active than the free sugars of galacto configuration.

Synthesis and structural characterization of new benzylidene glycosides, cytotoxicity against cancer cell lines and molecular modeling studies

This work describes the synthesis, structural characterization (by combined Fourier Transform Infrared - FTIR, 1H and 13C Nuclear Magnetic Resonance - NMR spectroscopy and High Resolution Mass Spectrometry - HRMS) and biological evaluation of a new series of glycosides designed from a benzylidene glucoside derived from eugenol (23) active against Candida glabrata. The mass accuracy between the calculated and found values observed in HRMS analyses were lower than 5 ppm, which are acceptable for proposing a molecular formula using this technique. We decided to keep the benzylidene group of 23, while changing either the saccharide unit (glucose or galactose) or the natural aglycone (eugenol, isoeugenol, dihydroeugenol or guaiacol) to check their influence in antifungal activity. Since the chemical modifications performed did not contribute to enhance the antifungal activity, the synthesized compounds (23–30) were further screened against four cancer cell lines (HeLa: cervix carcinoma; MDA-MB-231: breast carcinoma; T-24: urinary bladder carcinoma; and TOV-21G: ovarian carcinoma). The glucoside 27 showed promising activities (IC50 10.08–59.91 μM) against all the assayed cancer cell lines and higher values of selectivity index than doxorubicin, the control drug. The galactoside 28 demonstrated interesting results against HeLa, MDA-MB-231 and T-24 cells. This compound was active at 17.41 μM with a selectivity index greater than 13.7 against the HeLa cells, while doxorubicin was active at 10.01 μM with a selectivity index close to 1.5 considering this cell line. Further, we performed docking studies of these compounds with type II topoisomerase-DNA complex (TOP2) in order to try to explain their mechanism of action.

3'-KETOGLYCOSIDE COMPOUND FOR THE SLOW RELEASE OF A VOLATILE ALCOHOL

The present invention relates to a 3'-ketoglycoside compound defined by formula (I) and its use for controlled release of alcohols, in particular alcohols showing an insect repellent effect. It relates also to a process for preparing the 3'-ketoglycoside compound of formula (I). It further relates to a composition comprising a 3'- ketoglycoside compound of formula (I). It relates also to the use of a 3'-ketoglycoside compound of formula (I) for the controlled release of alcohols. It related also to a method of use of such composition.

Ice recrystallization inhibitor

【Challenge】Provide a small molecule ice recrystallization inhibitor with high IRI activity even in small quantities.Solution: The ice recrystallization inhibitor according to one aspect of the present invention includes a compound represented by the following chemical formula (1) as an active ingredient.【Chemical 1】 In the chemical formula (1), R1 is an alkyl group or hydrogen, R2 is an unsaturated hydrocarbon group or acyl group, and R3 is a monosaccharide or polysaccharide.【Selection Figure】Figure 2

Synthesis of eugenol-derived glucosides and evaluation of their ability in inhibiting the angiotensin converting enzyme

We report here a series of glucosides which are active as inhibitors of the angiotensin converting enzyme (ACE). They are structurally related to the natural compound eugenol and exhibited significant inhibition values. Their syntheses were expeditious and we could obtain informative docking plots of them complexed to this enzyme. A glucoside derived from eugenol, carrying a carboxylic group in the aglycone, was the most active of them (with an IC50 of 0.4 mM) and showed good binding energies in docking studies with ACE. Moreover, computational prediction of toxicity risks, physicochemical properties and drug score show that the glucoside derivative of eugenol is a suitable compound for optimisation studies aimed at finding new drug candidates.

Synthesis and antimicrobial activity of 6-triazolo-6-deoxy eugenol glucosides

A new series of 1,2,3-triazole eugenol glucosides were synthesized. The new compound structures were confirmed by MS, 1H NMR and 13C NMR. All of the synthesized compounds were screened for antimicrobial and cytotoxic activity. Five c

FeCl3-promoted and ultrasound-assisted synthesis of resveratrol O-derived glycoside analogs

Phenol derived O-glycosides were synthesized using a direct and convenient O-glycosidation, starting from acetylated sugars in the presence of FeCl 3, an inexpensive, mild and benign Lewis acid catalyst. The reactions were carried out under bot

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.

Glycosidically Bound Eugenol and Methyl Salicylate in the Fruit of Edible Passiflora Species

The β-D-glucopyranoside and 6-O-α-L-rhamnopyranosyl-β-D-glucopyranoside of methyl salicylate and the β-D-glucopyranoside of eugenol have been characterized in purple passion fruit (Passiflora edulis SIMS) by GC and GC/MS of their trifluoroacetylated deriv