How can a compound like eugenol

It is a noncannabinoid phenol compound found in cannabis plants PMID: Eugenol is used in perfumeries, flavorings and essential oils.

Eugenol is hepatotoxic, meaning it may cause damage to the liver, if consumed in high doses. It has high antioxidant, anti-proliferative, and anti-inflammatory activities with potential roles in alleviating and preventing cancer and inflammatory reactions PMID: Synonym Source 1,3,4-Eugenol. Belongs to the class of organic compounds known as methoxyphenols.

Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Organic compounds. Phenoxy compounds Methoxybenzenes Anisoles Alkyl aryl ethers 1-hydroxyunsubstituted benzenoids Hydrocarbon derivatives. Methoxyphenol Phenoxy compound Methoxybenzene Phenol ether Anisole 1-hydroxyunsubstituted benzenoid Alkyl aryl ether Monocyclic benzene moiety Ether Organic oxygen compound Hydrocarbon derivative Organooxygen compound Aromatic homomonocyclic compound.

Property Value Reference Physical state Solid. Descriptor ID Definition Reference acaricide. A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy. An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.

A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E to E A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites. A drug that prevents or reduces fever by lowering the body temperature from a raised state.

An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. Photochemistry of Phenols. The chemical composition and biological activity of clove essential oil,Eugenia caryophyllata Syzigium aromaticum L. Myrtaceae : a short review. Phytotherapy Research , 21 6 , Journal of Agricultural and Food Chemistry , 54 23 , Eugenol isolated from the essential oil of Eugenia caryophyllata induces a reactive oxygen species-mediated apoptosis in HL human promyelocytic leukemia cells.

Cancer Letters , 1 , Goodner , Philip E. Journal of Agricultural and Food Chemistry , 50 6 , Moulin , A. Petit , J. Selective laser photolysis of organic molecules in complex matrices. Journal of Photochemistry and Photobiology A: Chemistry , 85 , Pair your accounts. Your Mendeley pairing has expired. Please reconnect. This website uses cookies to improve your user experience.

For example, Ciszewsky and Milczarek Ciszewsky, A. Bailly and co-workers Hagenaars, A. De la Mata and co-workers Arevalo, S. On the other hand, Masuda and co-workers Rahim, E. Eugenol can be engaged into oligomerization reactions. Acta , 86, These polyhydroxy aromatics play a versatile role in organic synthesis, especially for the preparation of calixarenes and macrocyclic crown ethers. On the other hand, Shibata and co-workers Shibata, M. However, BB resins and NB resins are the result of an ene reaction and subsequent thermal addition copolymerization.

Bifunctional monomers containing maleimide and allylphenyl groups were synthesized by the condensation of maleimidobenzoic acid chloride and eugenol.

The ene-addition reaction and Diels-Alder polymerization afforded new polyesters. Monomers Polym. Eugenol and rosin have been used as feedstocks for biobased epoxy resins. An epoxy component based on eugenol and an anhydride curing agent based on rosin were prepared and cured.

The properties of the resulting material were studied, and the results suggest that the eugenol epoxy has similar reactivity, dynamic mechanical properties and thermal stability than commercial materials. Eugenol derivatives of higher chlorocyclophosphazenes and related epoxy oligomers were prepared and characterized.

B , 55, Another important field of applied polymer science is the prevention of microbial contamination in the personal care and food industries for consumer protection. Taking into account that eugenol is known to possess antioxidant properties and antimicrobial activity against a range of bacteria, it was incorporated into poly lactic-co-glycolic acid PLGA nanoparticles.

Food Sci. Attempting to design a slower and more controllable release solution, Uhrich and co-workers Carbone-Howell, A. Other phenolics, such as carvacrol and thymol were also prepared and tested. Functional assays demonstrated that the polymer exhibited bioactivity similar to that of eugenol and that the hydrolytic degradation of the polymer was complete in 16 days, resulting in the release of eugenol and EDTA Anuradha and Sarojadevi Anuradha, G.

Finally, the cyanate esters were cyclotrimerized to by thermal curing. Harvey et al. This common intermediate was transformed into polycyanurate via the dicyanate , and into polycarbonate An blend of cyanate ester:polycarbonate was prepared and thermally cured, observing that the presence of the polycarbonate had no significant effect on the cure behavior of the cyanate ester. No phase separation was observed either during or after cure, suggesting that a homogenous network was generated.

Furthermore, the polycarbonate could be quantitatively separated from the thermoset matrix after cure by solvent extraction, proving the absence of chemical grafting under the curing conditions. These polymeric blends may have applications for fabrication of toughened composite structures.

Other dicyanate monomers containing methylene spacers have also been prepared. Polybenzoxazines are a class of phenolic resins that possess dimensional and thermal stability and can be used as matrices for high performance composites with superior physical and mechanical properties.

This is a relatively new family of phenolic resins which combine the thermal properties and flame retardance of phenolics, with the mechanical performance and design flexibility of epoxies.

Polymerization takes place by thermal treatment, through the ring opening of the heterocyclic precursor monomers, without the need of catalysts and without producing by-products or volatiles.

Benzoxazines are generated by the Mannich-like condensation of a phenol, formaldehyde and a suitable primary amine Scheme 28 ; Calo, E. Some eugenol-derived benzoxazines demonstrated to be lethal in the brine shrimp assay. Muthusami and co-workers Thirukumaran, P. Their higher surface area to volume ratio convey to them enormous advantages over traditional micro or macroparticles. Colloid Interface Sci. In addition, the LOI values suggested that these products can be used for flame retardancy applications.

Silicone polycarbonates containing polydimethyl siloxane and heptamethyl trisiloxane moieties in the interior chain and terminal positions were recently synthesized Scheme The polymeric chains were capped with eugenol moieties. A bifunctional eugenosiloxane was also used to include this motif within the polymer The polymers showed satisfactory thermo-oxidative stability and transparency.

Their flexibility and wettability increased with increasing of the silicone content. Siloxane copolyesters containing phenylindane bisphenol, diphenyl terephthalate, and eugenol end-capped siloxanes, were prepared and characterized. The copolyesters were soluble in organic solvents and had film forming properties. Polymer Sci. Poly phthalazinone ether nitrile PPEN block copolymers Scheme 30 with an hydrophobic surface were prepared by the nucleophilic aromatic substitution polycondensation of eugenol end-capped polydimethylsiloxane PDMS, oligomers with fluoro-terminated PPEN oligomers Polymers with eugenol moieties covalently bonded to the macromolecular chains were synthesized for potential application in orthopedic and dental cements Scheme Polymerization of each of the novel monomers, at low conversion, provided soluble polymers and , consisting of hydrocarbon macromolecules with pendant eugenol moieties.

At high conversions, cross-linked polymers were obtained due to participation of the allyl side chain in the polymerization reaction.

Co-polymers with ethyl methacrylate were also prepared. Analysis of the thermal properties, suggested that the eugenyl methacrylate derivatives are potentially good candidates for dental and orthopedic cements. On the other hand, amino acid based synthetic polymers are expected to show biocompatibility and biodegradability similar to those of polypeptides.

Reaction of the latter with alanine furnished the alanyl intermediate , which was amidated or esterified in good yields. The molecular weights of the polymers ranged from to A different behavior was observed between the poly N -propargylamide s and poly propargyl ester s. This was attributed to the presence and absence of hydrogen bonding between the side-chain amide groups, which seems to play an important role in the formation of helical conformations.

The TiO 2 -photocatalyzed production of vanillin from eugenol has been studied. However, biotechnological processes are usually less damaging to the environment than classical chemical processes and therefore considered as environmental friendly. Due to environmental concerns regarding the production processes for fine chemicals, recent research has shifted toward the exploitation of the metabolic and biocatalytic potential of microorganisms to transform readily available substrates into value-added products.

The flavor and fragrances sector is a pioneer in this field. Although eugenol is highly toxic for microorganisms even at low concentrations, Friedman, M. Food Prot. The subject has been reviewed; Mishra, S. Lambert and co-workers Lambert, F. The resulting strain produced up to Esters of eugenol have been traditionally produced by chemical esterification of eugenol with acid chlorides. Several compounds were chemically synthesized and evaluated as potential inhibitors of the enzyme lipoxygenase.

In addition, eugenyl esters of aspirin, ibuprofen, 4-biphenylacetic acid the active metabolite of fenbufen , mefenamic acid and indomethacin were synthesized, in attempts to reduce the side-effects of the parent drugs, Zhao, X. However, the enzymatic synthesis is an alternative to the chemical process. It offers some advantages including milder reaction conditions, low energy requirements, high product yields and purity, shorter reaction times, and biocatalyst reusability.

Reactions are usually carried out in water-containing media; however, the solventless enzymatic synthesis of eugenol esters has also been reported.

The enzymatic synthesis of eugenol benzoate by immobilized Staphylococcus aureus lipase was informed, as a strategy to modulate the antioxidant activity of the natural product. In the 1,1-diphenylpicrylhydrazyl radical scavenging test, the IC 50 values were found to be Analogous preparations of eugenol caprylate and acetate have been reported.

The former was synthesized using the commercial immobilized Thermomyces lanuginose lipase, Lipozyme TLIM, as the biocatalyst. The biotransformation was statistically optimized, providing a maximum conversion yield of On the other hand, eugenyl acetate was prepared employing Novozym , a commercial lipase from Candida antarctica immobilized on a macroporous anionic resin.

The results indicated that the esterification of eugenol improved its antimicrobial properties. Traditionally, glycosides have been synthesized by chemical means. For example, six eugenol glycosides, including Figure 4 , were prepared by glycosylation of eugenol with various glycosyl bromides, followed by deacetylation with sodium methoxide in methanol, and their antifungal activity was assessed against Candida species.

The peracetyl glycoside was able to inhibit growth of C. However, the paradigm is slowly changing toward the enzymatic synthesis of useful glycosides. Floral aroma is an important factor in determining the quality of various fruits, flowers and teas.

Therefore, Yamamoto and co-workers Yamamoto, S. De Winter et al. Process Res. Eugenol exhibited a rather moderate ability to undergo the transformation toward The various applications of eugenol, as feedstock for the chemo-enzymatic production of high valued low molecular weight compounds, as starting material for the synthesis of natural products and their analogs, and as building block for the elaboration of complexly functionalized bioactive compounds and co-drugs designed with improved physicochemical properties, macrocycles, heterocycles and polymers, fully justify considering eugenol as a highly versatile molecule.

Taking into account the growing pressure toward replacing fossil-derived resources with more sustainable alternatives with regard to the easy availability, structural characteristics and unique reactivity of eugenol, it can be foreseen that Chemists will be increasingly seduced to choose the natural product as part of future synthetic endeavors.

Therefore, it is expected that new, more complex and imaginative synthetic and biotechnologically-assisted solutions will be published in the near future, with eugenol or its simple derivatives at the center of the scene.

Abrir menu Brasil. Journal of the Brazilian Chemical Society. Abrir menu. Teodoro S. Introduction All the major groups of angiosperms biosynthesize phenylpropenes. Figure 1 Chemical structures of eugenol 1 , methyleugenol 2 and isoeugenol 3.

Scheme 1 Reagents and conditions: a 1. HF aq. Scheme 5 Reagents and conditions: a 1. Scheme 6 Reagents and conditions: a 1. Scheme 7 Reagents and conditions: a 1. NaH, THF; 2. Scheme 8 Reagents and conditions: a 1.

Scheme 10 Reagents and conditions: a 1. Grubbs II 0. TMP 2 Zn. MgCl 2. OsO 4 cat. LDA 2 equiv. OsO 4 , NMO; 2. Scheme 15 Reagents and conditions: a 1 3 equiv. Br 3 10 equiv. Scheme 17 Reagents and conditions: a 1. Figure 2 Selected synthetic bioactive compounds prepared from eugenol. Figure 3 Selected synthetic bioactive compounds prepared from eugenol. Scheme 23 Reagents and conditions: a 1. BEG: bis-eugenol. Scheme 26 Synthesis and degradation of the eugenol-ethylenediamine-tetraacetic acid EDTA poly anhydride-ester For : propargyl alcohol, EDCI.

Table 1 Production of small molecules of interest employing eugenol as substrate. Scheme 33 Biotransformation of eugenol into other valuable compounds. Figure 4 Selected relevant eugenyl glycosides. Sakamoto, C. Network Polym. Shibata, M. Tsuruhami, K. Yamamoto, S. Overhage, J. Rabenhorst, J. Patent , Furukawa, H.

Unno, T. Ashengroph, M. Priefert, H. Brandt, K. Lambert, F. References 1 Koeduka, T. Milind, P. Ayurveda Pharmacol. Chaieb, K. Miele, M. Tan, K. Insect Sci. Ouk, S. Kulkarni, M. Taylor, J. Fogliano, V. Tuck, K. Mateos, R. Baldioli, M. Deffieux, D. Taber, D. Blackwell, H. Bilel, H. Awang, D. Murad, N.

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