Eugenol

Details:

Chemical Properties of Eugenol

Cas No.	97-53-0
PubChem ID	3314	Appearance	Colorless-yellow liquid
Formula	C10H12O2	M.Wt	164.20
Type of Compound	Phenylpropanoids	Storage	Desiccate at -20°C
Synonyms	4-Allylguaiacol; 1-Allyl 4-hydroxy 3-methoxybenzene; 4-Allyl 2-methoxyphenol; Caryophyllic acid; Eugenic acid; 2-Hydroxy 5-allylanisole; 2-Methoxy 4-allylphenol
Solubility	DMSO : ≥ 100 mg/mL (609.01 mM) *"≥" means soluble, but saturation unknown.
Chemical Name	2-methoxy-4-prop-2-enylphenol
SMILES	COC1=C(C=CC(=C1)CC=C)O
Standard InChIKey	RRAFCDWBNXTKKO-UHFFFAOYSA-N
Standard InChI	InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3
General tips	For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging	1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment.
Shipping Condition	Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Eugenol

The flower of Syzygium aromaticum

Biological Activity of Eugenol

Description	Eugenol is an essential oil found in cloves with herbicide,sedative,analgesic,antibacterial,anthelmintic,anti-inflammatory, cancer chemopreventive and antioxidant activities. Eugenol is shown to inhibit lipid peroxidation, the mRNA expression of COX-2, but not COX-1 and inhibit the GABAA current in trigeminal ganglion neurons. It could be developed as therapeutic agent against diseases with excessive osteoclast activity.
Targets	GABA Receptor | ROS | MAPK | MMP(e.g.TIMP) | NF-kB | PGE | COX
In vitro	Eugenol inhibits the GABAA current in trigeminal ganglion neurons.[Pubmed: 25635877] PLoS One. 2015 Jan 30;10(1):e0117316. Eugenol has sedative, antioxidant, anti-inflammatory, and analgesic effects, but also serves as an irritant through the regulation of a different set of ion channels. Activation of gamma aminobutyric acid (GABA) receptors on sensory neurons leads to the stabilization of neuronal excitability but contributes to formalin-induced inflammatory pain. METHODS AND RESULTS: In this study, we examined the effect of Eugenol on the GABA-induced current in rat trigeminal ganglia (TG) neurons and in human embryonic kidney (HEK) 293 cells expressing the GABAA receptor α1β2γ2 subtype using the whole-cell patch clamp technique. RT-PCR and Western blot analysis were used to confirm the expression of GABAA receptor γ2 subunit mRNA and protein in the TG and hippocampus. Eugenol decreased the amplitude ratio of the GABA-induced current to 27.5 ± 3.2% (p < 0.05) in TG neurons, which recovered after a 3-min washout. In HEK 293 cells expressing the α1β2γ2 subtype, Eugenol inhibited GABA-induced currents in a dose-dependent manner. Application of Eugenol also decreased the GABA response in the presence of a G-protein blocker. Eugenol pretreatment with different concentrations of GABA resulted in similar inhibition of the GABA-induced current in a non-competitive manner. In conclusion, Eugenol inhibits the GABA-induced current in TG neurons and HEK 293 cells expressing the GABAA receptor in a reversible, dose-dependent, and non-competitive manner, but not via the G-protein pathway. CONCLUSIONS: We suggest that the GABAA receptor could be a molecular target for Eugenol in the modulation of nociceptive information. Eugenol-inhibited root growth in Avena fatua involves ROS-mediated oxidative damage.[Pubmed: 25752432] Pestic Biochem Physiol. 2015 Feb;118:64-70. Plant essential oils and their constituent monoterpenes are widely known plant growth retardants but their mechanism of action is not well understood. We explored the mechanism of phytotoxicity of Eugenol, a monoterpenoid alcohol, proposed as a natural herbicide. METHODS AND RESULTS: Eugenol (100-1000 μM) retarded the germination of Avena fatua and strongly inhibited its root growth compared to the coleoptile growth. We further investigated the underlying physiological and biochemical alterations leading to the root growth inhibition. Eugenol induced the generation of reactive oxygen species (ROS) leading to oxidative stress and membrane damage in the root tissue. ROS generation measured in terms of hydrogen peroxide, superoxide anion and hydroxyl radical content increased significantly in the range of 24 to 144, 21 to 91, 46 to 173% over the control at 100 to 1000 μM Eugenol, respectively. The disruption in membrane integrity was indicated by 25 to 125% increase in malondialdehyde (lipid peroxidation byproduct), and decreased conjugated diene content (~10 to 41%). The electrolyte leakage suggesting membrane damage increased both under light as well as dark conditions measured over a period from 0 to 30 h. In defense to the oxidative damage due to Eugenol, a significant upregulation in the ROS-scavenging antioxidant enzyme machinery was observed. The activities of superoxide dismutases, catalases, ascorbate peroxidases, guaiacol peroxidases and glutathione reductases were elevated by ~1.5 to 2.8, 2 to 4.3, 1.9 to 5.0, 1.4 to 3.9, 2.5 to 5.5 times, respectively, in response to 100 to 1000 μM Eugenol. CONCLUSIONS: The study concludes that Eugenol inhibits early root growth through ROS-mediated oxidative damage, despite an activation of the antioxidant enzyme machinery. Eugenol suppresses cyclooxygenase-2 expression in lipopolysaccharide-stimulated mouse macrophage RAW264.7 cells.[Pubmed: 12757841] Life Sci. 2003 Jun 6;73(3):337-48. Inducible cyclooxygenase (COX-2) has been implicated in the processes of inflammation and carcinogenesis. Thus, the potential COX-2 inhibitors have been considered as anti-inflammatory or cancer chemopreventive agents. METHODS AND RESULTS: In this study, the methanolic extract of the cortex of Eugenia caryophyllata Thunberg (Myrtaceae) was found to potently inhibit the prostaglandin E(2) production in lipopolysaccharide (LPS)-activated mouse macrophage RAW264.7 cells (98.3% inhibition at the test concentration of 10 microg/ml). Further, hexane-soluble layer was the most active partition compared to ethyl acetate, n-butanol, and water-soluble parts. By bioassay-guided fractionation of hexane-soluble partition, Eugenol was isolated and exhibited a significant inhibition of PGE(2) production (IC(50) = 0.37 microM). In addition, Eugenol suppressed the cyclooxygenase-2 (COX-2) gene expression in LPS-stimulated mouse macrophage cells. On the line of COX-2 playing an important role in colon carcinogenesis further study was designed to investigate the effect of Eugenol on the growth and COX-2 expression in HT-29 human colon cancer cells. Eugenol inhibited the proliferation of HT-29 cells and the mRNA expression of COX-2, but not COX-1. CONCLUSIONS: This result suggests that Eugenol might be a plausible lead candidate for further developing the COX-2 inhibitor as an anti-inflammatory or cancer chemopreventive agent. Eugenol (an essential oil of clove) acts as an antibacterial agent against Salmonella typhi by disrupting the cellular membrane.[Pubmed: 20435121 ] J Ethnopharmacol. 2010 Jul 6;130(1):107-15. To evaluate the antibacterial activity of Eugenol and its mechanism of bactericidal action against Salmonella typhi. METHODS AND RESULTS: The antibacterial activity was checked by disc-diffusion method, MIC, MBC, time course assay and pH sensitivity assay. The chemo-attractant property of Eugenol was verified by chemotaxis assay. The mode of action of Eugenol was determined by crystal violet assay, measurement of release of 260 nm absorbing material, SDS-PAGE, FT-IR spectroscopy, AFM and SEM. Treatment with Eugenol at their MIC (0.0125%) and MBC (0.025%) reduced the viability and resulted in complete inhibition of the organism. Eugenol inactivated Salmonella typhi within 60 min exposure. The chemo-attractant property of Eugenol combined with the observed high antibacterial activity at alkaline pH favors the fact that the compound can work more efficiently when given in vivo. Eugenol increased the permeability of the membrane, as evidenced by crystal violet assay. The measurement of release of 260 nm absorbing intracellular materials, SDS-PAGE, SEM and AFM analysis confirmed the disruptive action of Eugenol on cytoplasmic membrane. The deformation of macromolecules in the membrane, upon treatment with Eugenol was verified by FT-IR spectroscopy. CONCLUSIONS: The results suggest that the antibacterial activity of Eugenol against Salmonella typhi is due to the interaction of Eugenol on bacterial cell membrane.

Protocol of Eugenol

Kinase Assay	Inhibitory effects of eugenol on RANKL-induced osteoclast formation via attenuation of NF-κB and MAPK pathways.[Pubmed: 25405641] Connect Tissue Res. 2014 Dec 11:1-9. Bone loss diseases are often associated with increased receptor activator of NF-κB ligand (RANKL)-induced osteoclast formation. Compounds that can attenuate RANKL-mediated osteoclast formation are of great biomedical interest. Eugenol, a phenolic constituent of clove oil possesses medicinal properties; however, its anti-osteoclastogenic potential is unexplored hitherto. METHODS AND RESULTS: Here, we found that Eugenol dose-dependently inhibited the RANKL-induced multinucleated osteoclast formation and TRAP activity in RAW264.7 macrophages. The underlying molecular mechanisms included the attenuation of RANKL-mediated degradation of IκBα and subsequent activation of NF-κB pathway. Furthermore, increase in phosphorylation and activation of RANKL-induced mitogen-activated protein kinase pathways (MAPK) was perturbed by Eugenol. RANKL-induced expression of osteoclast-specific marker genes such as TRAP, cathepsin K (CtsK) and matrix metalloproteinase-9 (MMP-9) was remarkably downregulated by Eugenol. CONCLUSIONS: These findings provide the first line of evidence that Eugenol mediated attenuation of RANKL-induced NF-κB and MAPK pathways could synergistically contribute to the inhibition of osteoclast formation. Eugenol could be developed as therapeutic agent against diseases with excessive osteoclast activity.
Cell Research	Eugenol triggers apoptosis in breast cancer cells through E2F1/survivin down-regulation.[Pubmed: 24330704] BMC Cancer. 2013 Dec 13;13:600. Cell lines:Breast cancer cells(MDA-MB-231, MCF7 and T47-D) and the non-tumorigenic MCF 10A cell line Concentrations: 1, 2, 4, 10 μM Incubation Time: 24 h Method: Cells are seeded into 96-well plates and incubated overnight. The medium is replaced with fresh one containing the desired concentrations of Eugenol. After 20 hrs, 10 μl of the WST-1 reagent is added to each well and the plates are incubated for 4 hrs at 37°C. The amount of formazan is quantified using ELISA reader at 450 nm of absorbance.
Animal Research	The protective effects of eugenol on carbon tetrachloride induced hepatotoxicity in rats.[Pubmed: 8574354] Free Radic Res. 1995 Dec;23(6):617-27. Animal Models: Wistar/NIN rats Formulation: 5% soluble starch Dosages:5 or 25 mg/kg body Administration: p.o.

Preparing Stock Solutions of Eugenol

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	6.0901 mL	30.4507 mL	60.9013 mL	121.8027 mL	152.2533 mL
5 mM	1.218 mL	6.0901 mL	12.1803 mL	24.3605 mL	30.4507 mL
10 mM	0.609 mL	3.0451 mL	6.0901 mL	12.1803 mL	15.2253 mL
50 mM	0.1218 mL	0.609 mL	1.218 mL	2.4361 mL	3.0451 mL
100 mM	0.0609 mL	0.3045 mL	0.609 mL	1.218 mL	1.5225 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

References on Eugenol

Eugenol suppresses cyclooxygenase-2 expression in lipopolysaccharide-stimulated mouse macrophage RAW264.7 cells.[Pubmed:12757841]

Life Sci. 2003 Jun 6;73(3):337-48.

Inducible cyclooxygenase (COX-2) has been implicated in the processes of inflammation and carcinogenesis. Thus, the potential COX-2 inhibitors have been considered as anti-inflammatory or cancer chemopreventive agents. In this study, the methanolic extract of the cortex of Eugenia caryophyllata Thunberg (Myrtaceae) was found to potently inhibit the prostaglandin E(2) production in lipopolysaccharide (LPS)-activated mouse macrophage RAW264.7 cells (98.3% inhibition at the test concentration of 10 microg/ml). Further, hexane-soluble layer was the most active partition compared to ethyl acetate, n-butanol, and water-soluble parts. By bioassay-guided fractionation of hexane-soluble partition, Eugenol was isolated and exhibited a significant inhibition of PGE(2) production (IC(50) = 0.37 microM). In addition, Eugenol suppressed the cyclooxygenase-2 (COX-2) gene expression in LPS-stimulated mouse macrophage cells. On the line of COX-2 playing an important role in colon carcinogenesis further study was designed to investigate the effect of Eugenol on the growth and COX-2 expression in HT-29 human colon cancer cells. Eugenol inhibited the proliferation of HT-29 cells and the mRNA expression of COX-2, but not COX-1. This result suggests that Eugenol might be a plausible lead candidate for further developing the COX-2 inhibitor as an anti-inflammatory or cancer chemopreventive agent.

Eugenol (an essential oil of clove) acts as an antibacterial agent against Salmonella typhi by disrupting the cellular membrane.[Pubmed:20435121]

J Ethnopharmacol. 2010 Jul 6;130(1):107-15.

AIM OF THE STUDY: To evaluate the antibacterial activity of Eugenol and its mechanism of bactericidal action against Salmonella typhi. MATERIALS AND METHODS: The antibacterial activity was checked by disc-diffusion method, MIC, MBC, time course assay and pH sensitivity assay. The chemo-attractant property of Eugenol was verified by chemotaxis assay. The mode of action of Eugenol was determined by crystal violet assay, measurement of release of 260 nm absorbing material, SDS-PAGE, FT-IR spectroscopy, AFM and SEM. RESULTS: Treatment with Eugenol at their MIC (0.0125%) and MBC (0.025%) reduced the viability and resulted in complete inhibition of the organism. Eugenol inactivated Salmonella typhi within 60 min exposure. The chemo-attractant property of Eugenol combined with the observed high antibacterial activity at alkaline pH favors the fact that the compound can work more efficiently when given in vivo. Eugenol increased the permeability of the membrane, as evidenced by crystal violet assay. The measurement of release of 260 nm absorbing intracellular materials, SDS-PAGE, SEM and AFM analysis confirmed the disruptive action of Eugenol on cytoplasmic membrane. The deformation of macromolecules in the membrane, upon treatment with Eugenol was verified by FT-IR spectroscopy. CONCLUSION: The results suggest that the antibacterial activity of Eugenol against Salmonella typhi is due to the interaction of Eugenol on bacterial cell membrane.

Inhibitory effects of eugenol on RANKL-induced osteoclast formation via attenuation of NF-kappaB and MAPK pathways.[Pubmed:25405641]

Connect Tissue Res. 2015 Jun;56(3):195-203.

Bone loss diseases are often associated with increased receptor activator of NF-kappaB ligand (RANKL)-induced osteoclast formation. Compounds that can attenuate RANKL-mediated osteoclast formation are of great biomedical interest. Eugenol, a phenolic constituent of clove oil possesses medicinal properties; however, its anti-osteoclastogenic potential is unexplored hitherto. Here, we found that Eugenol dose-dependently inhibited the RANKL-induced multinucleated osteoclast formation and TRAP activity in RAW264.7 macrophages. The underlying molecular mechanisms included the attenuation of RANKL-mediated degradation of IkappaBalpha and subsequent activation of NF-kappaB pathway. Furthermore, increase in phosphorylation and activation of RANKL-induced mitogen-activated protein kinase pathways (MAPK) was perturbed by Eugenol. RANKL-induced expression of osteoclast-specific marker genes such as TRAP, cathepsin K (CtsK) and matrix metalloproteinase-9 (MMP-9) was remarkably downregulated by Eugenol. These findings provide the first line of evidence that Eugenol mediated attenuation of RANKL-induced NF-kappaB and MAPK pathways could synergistically contribute to the inhibition of osteoclast formation. Eugenol could be developed as therapeutic agent against diseases with excessive osteoclast activity.

Eugenol-inhibited root growth in Avena fatua involves ROS-mediated oxidative damage.[Pubmed:25752432]

Pestic Biochem Physiol. 2015 Feb;118:64-70.

Plant essential oils and their constituent monoterpenes are widely known plant growth retardants but their mechanism of action is not well understood. We explored the mechanism of phytotoxicity of Eugenol, a monoterpenoid alcohol, proposed as a natural herbicide. Eugenol (100-1000 microM) retarded the germination of Avena fatua and strongly inhibited its root growth compared to the coleoptile growth. We further investigated the underlying physiological and biochemical alterations leading to the root growth inhibition. Eugenol induced the generation of reactive oxygen species (ROS) leading to oxidative stress and membrane damage in the root tissue. ROS generation measured in terms of hydrogen peroxide, superoxide anion and hydroxyl radical content increased significantly in the range of 24 to 144, 21 to 91, 46 to 173% over the control at 100 to 1000 microM Eugenol, respectively. The disruption in membrane integrity was indicated by 25 to 125% increase in malondialdehyde (lipid peroxidation byproduct), and decreased conjugated diene content (~10 to 41%). The electrolyte leakage suggesting membrane damage increased both under light as well as dark conditions measured over a period from 0 to 30 h. In defense to the oxidative damage due to Eugenol, a significant upregulation in the ROS-scavenging antioxidant enzyme machinery was observed. The activities of superoxide dismutases, catalases, ascorbate peroxidases, guaiacol peroxidases and glutathione reductases were elevated by ~1.5 to 2.8, 2 to 4.3, 1.9 to 5.0, 1.4 to 3.9, 2.5 to 5.5 times, respectively, in response to 100 to 1000 microM Eugenol. The study concludes that Eugenol inhibits early root growth through ROS-mediated oxidative damage, despite an activation of the antioxidant enzyme machinery.

Studies on the inhibitory effects of curcumin and eugenol on the formation of reactive oxygen species and the oxidation of ferrous iron.[Pubmed:7845373]

Mol Cell Biochem. 1994 Aug 17;137(1):1-8.

The spice principles curcumin (from turmeric) and Eugenol (from cloves) are good inhibitors of lipid peroxidation. Lipid peroxidation is known to be initiated by reactive oxygen species. The effect of curcumin and Eugenol on the generation of reactive oxygen species in model systems were investigated. Both curcumin and Eugenol inhibited superoxide anion generation in xanthine-xanthine oxidase system to an extent of 40% and 50% at concentrations of 75 microM and 250 microM respectively. Curcumin and Eugenol also inhibited the generation of hydroxyl radicals (.OH) to an extent of 76% and 70% as measured by deoxyribose degradation. The .OH-radical formation measured by the hydroxylation of salicylate to 2,3-dihydroxy benzoate was inhibited to an extent of 66% and 46%, respectively, by curcumin and Eugenol at 50 microM and 250 microM. These spice principles also prevented the oxidation of Fe2+ in Fentons reaction which generates .OH radicals.

Eugenol inhibits the GABAA current in trigeminal ganglion neurons.[Pubmed:25635877]

PLoS One. 2015 Jan 30;10(1):e0117316.

Eugenol has sedative, antioxidant, anti-inflammatory, and analgesic effects, but also serves as an irritant through the regulation of a different set of ion channels. Activation of gamma aminobutyric acid (GABA) receptors on sensory neurons leads to the stabilization of neuronal excitability but contributes to formalin-induced inflammatory pain. In this study, we examined the effect of Eugenol on the GABA-induced current in rat trigeminal ganglia (TG) neurons and in human embryonic kidney (HEK) 293 cells expressing the GABAA receptor alpha1beta2gamma2 subtype using the whole-cell patch clamp technique. RT-PCR and Western blot analysis were used to confirm the expression of GABAA receptor gamma2 subunit mRNA and protein in the TG and hippocampus. Eugenol decreased the amplitude ratio of the GABA-induced current to 27.5 +/- 3.2% (p < 0.05) in TG neurons, which recovered after a 3-min washout. In HEK 293 cells expressing the alpha1beta2gamma2 subtype, Eugenol inhibited GABA-induced currents in a dose-dependent manner. Application of Eugenol also decreased the GABA response in the presence of a G-protein blocker. Eugenol pretreatment with different concentrations of GABA resulted in similar inhibition of the GABA-induced current in a non-competitive manner. In conclusion, Eugenol inhibits the GABA-induced current in TG neurons and HEK 293 cells expressing the GABAA receptor in a reversible, dose-dependent, and non-competitive manner, but not via the G-protein pathway. We suggest that the GABAA receptor could be a molecular target for Eugenol in the modulation of nociceptive information.

Anthelmintic activity of essential oil of Ocimum gratissimum Linn. and eugenol against Haemonchus contortus.[Pubmed:12383625]

Vet Parasitol. 2002 Oct 16;109(1-2):59-63.

The ovicidal activity of the essential oil of Ocimum gratissimum Linn. (Labideae) and its main component Eugenol was evaluated against Haemonchus contortus, gastrointestinal parasite of small ruminants. The oil and Eugenol were diluted in Tween 20 (0.5%) at five different concentrations. In the egg hatch test, H. contortus eggs were obtained from feces of goats experimentally infected. At 0.50% concentration, the essential oil and Eugenol showed a maximum eclodibility inhibition. These results suggest a possible utilization of the essential oil of O. gratissimum as an aid to the control of gastrointestinal helmintosis of small ruminants.

Description

Eugenol is an essential oil found in cloves with antibacterial, anthelmintic and antioxidant activity. Eugenol is shown to inhibit lipid peroxidation.

Keywords:

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