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E51791 Aldrich

Eugenol

ReagentPlus®, 99%

Synonym: 2-Methoxy-4-(2-propenyl)phenol, 4-Allyl-2-methoxyphenol, 4-Allylguaiacol

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Description

Packaging

5, 100, 500 g in glass bottle

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Price and Availability


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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Hazard Codes (Europe) 
Xi
Risk Statements (Europe) 
Safety Statements (Europe) 
26-36/37
WGK Germany 
1
RTECS 
SJ4375000
Flash Point(F) 
233.6 °F
Flash Point(C) 
112 °C

Protocols & Articles

Peer-Reviewed Papers

References

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Calcium Current Diversity In Physiologically Different Local Interneuron Types Of The Antennal Lobe. Husch, A., et al. J. Neurosci. 29, 716-26, (2009)

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Expanding the ChemGPS chemical space with natural products. Josefin Larsson et al J. Nat. Prod. 68, 985-91, (2005)

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Methyl eugenol: its occurrence, distribution, and role in nature, especially in relation to insect behavior and pollination. Tan KH and Nishida R J. Insect Sci. 12, 56, (2012)

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Antioxidant and prooxidant action of eugenol-related compounds and their cytotoxicity. Fujisawa S, Atsumi T, Kadoma Y, et al. Toxicology 177(1), 39-54, (2002)

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[Pharmacological action of eugenol]. Oliveira Filho RM, Nahas MS, Valle LB, et al. Ars Curandi Odontol. 2(3), 3-13, (1975)

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Cement-associated signs of inflammation: retrospective analysis of the effect of excess cement on peri-implant tissue. Korsch M, Robra BP, and Walther W Int. J. Prosthodont. 28(1), 11-8, (2015)

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Retentiveness of various luting agents used with implant-supported prosthesis: an in vitro study. Garg P, Pujari M, Prithviraj DR, et al. J. Oral Implantol. 40(6), 649-54, (2014)

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Cinnamon bark oil and its components inhibit biofilm formation and toxin production. Kim YG, Lee JH, Kim SI, et al. Int. J. Food Microbiol. 195, 30-9, (2015)

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Action mechanism of small and large molecule surfactant-based clove oil nanoemulsions against food-borne pathogens and real-time detection of their subpopulations. Majeed H, Antoniou J, Shoemaker CF, et al. Arch. Microbiol. 197(1), 35-45, (2015)

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The effect of powder:liquid ratio and pre-mixing on sealing properties of Roth 801 sealer. Boda KK, Bowles WR, and McClanahan SB Northwest Dent. 92(3), 21-5, (2013)

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Sealing ability of various restorative materials as coronal barriers between endodontic appointments. Tapsir Z, Aly Ahmed HM, Luddin N, et al. J. Contemp. Dent. Pract. 14(1), 47-50, (2013)

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[Determination of 2-metoxy-4-allylhydroxybenzene during chemico-toxicological studies of the biological materials]. Astashkina AP, Shormanov VK, Kirichek AV, et al. Sud. Med. Ekspert. 55(6), 42-5, (2012)

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Therapeutic uses of Ocimum sanctum Linn (Tulsi) with a note on eugenol and its pharmacological actions: a short review. Prakash P and Gupta N Indian J. Physiol. Pharmacol. 49(2), 125-31, (2005)

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Biologic properties of eugenol and zinc oxide-eugenol. A clinically oriented review. Markowitz K, Moynihan M, Liu M, et al. Oral Surg. Oral Med. Oral Pathol. 73(6), 729-37, (1992)

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Nanodispersed eugenol has improved antimicrobial activity against Escherichia coli O157:H7 and Listeria monocytogenes in bovine milk. Shah B, Davidson PM, and Zhong Q Int. J. Food Microbiol. 161(1), 53-9, (2013)

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Safety assessment of allylalkoxybenzene derivatives used as flavouring substances - methyl eugenol and estragole. Smith RL, Adams TB, Doull J, et al. Food Chem. Toxicol. 40(7), 851-70, (2002)

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Elucidation of density profile of self-assembled sitosterol + oryzanol tubules with small-angle neutron scattering. Bot A, Gilbert EP, Bouwman WG, et al. Faraday Discuss. 158, 223-38; discussion 239-66, (2012)

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Sensitive high-performance liquid chromatographic assay for the determination of eugenol in body fluids. Fischer IU and Dengler HJ J. Chromatogr. A 525(2), 369-77, (1990)

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Formation of hepatic DNA adducts by methyleugenol in mouse models: drastic decrease by Sult1a1 knockout and strong increase by transgenic human SULT1A1/2. Herrmann K, Engst W, Meinl W, et al. Carcinogenesis 35(4), 935-41, (2014)

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Efficient management of fruit pests by pheromone nanogels. Bhagat D, Samanta SK, and Bhattacharya S Sci. Rep. 3, 1294, (2013)

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Use of biomonitoring data to evaluate methyl eugenol exposure. Robison SH and Barr DB Environ. Health Perspect. 114(11), 1797-801, (2006)

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Eugenol with antioxidant activity inhibits MMP-9 related to metastasis in human fibrosarcoma cells. Nam H and Kim MM Food Chem. Toxicol. 55, 106-12, (2013)

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Rapid inactivation of Salmonella Enteritidis on shell eggs by plant-derived antimicrobials. Upadhyaya I, Upadhyay A, Kollanoor-Johny A, et al. Poult. Sci. 92(12), 3228-35, (2013)

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A comparison of spacer on water-soluble cyclodextrin grafted chitosan inclusion complex as carrier of eugenol to mucosae. Sajomsang W, Nuchuchua O, Saesoo S, et al. Carbohydr. Polym. 92(1), 321-7, (2013)

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Piper betel leaf extract: anticancer benefits and bio-guided fractionation to identify active principles for prostate cancer management. Paranjpe R, Gundala SR, Lakshminarayana N, et al. Carcinogenesis 34(7), 1558-66, (2013)

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Effect of essential oils, such as raspberry ketone and its derivatives, on antiandrogenic activity based on in vitro reporter gene assay. Yoshihisa Ogawa et al Bioorg. Med. Chem. Lett. 20, 2111-4, (2010)

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A novel technique for the direct fabrication of fixed interim restorations. Konstantinidis I, Kotsakis G, Pallis K, et al. J. Prosthet. Dent. 109(3), 198-201, (2013)

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Design and synthesis of eugenol derivatives, as potent 15-lipoxygenase inhibitors. Hamid Sadeghian et al Bioorg. Med. Chem. 16, 890-901, (2008)

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Recent advances in methyl eugenol and cue-lure technologies for fruit fly detection, monitoring, and control in Hawaii. Vargas RI, Shelly TE, Leblanc L, et al. Vitam. Horm. 83, 575-95, (2010)

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Eugenol--from the remote Maluku Islands to the international market place: a review of a remarkable and versatile molecule. Kamatou GP, Vermaak I, and Viljoen AM Molecules 17(6), 6953-81, (2012)

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Downregulation of yidC in Escherichia coli by antisense RNA expression results in sensitization to antibacterial essential oils eugenol and carvacrol. Patil SD, Sharma R, Srivastava S, et al. PLoS ONE 8(3), e57370, (2013)

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CYP53A15 of Cochliobolus lunatus, a target for natural antifungal compounds. Barbara Podobnik et al J. Med. Chem. 51, 3480-6, (2008)

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Attractive toxic sugar baits mixed with pyriproxyfen sprayed on plants against adult and larval Aedes albopictus (Diptera: Culicidae). Fulcher A, Scott JM, Qualls WA, et al. J. Med. Entomol. 51(4), 896-9, (2014)

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Enhancement of production of eugenol and its glycosides in transgenic aspen plants via genetic engineering. Koeduka T, Suzuki S, Iijima Y, et al. Biochem. Biophys. Res. Commun. 436(1), 73-8, (2013)

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Effects of eugenol on T-type Ca2+ channel isoforms. Seo H, Li HY, Perez-Reyes E, et al. J. Pharmacol. Exp. Ther. 347(2), 310-7, (2013)

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Design and synthesis of 4-methoxyphenylacetic acid esters as 15-lipoxygenase inhibitors and SAR comparative studies of them. Hamid Sadeghian et al Bioorg. Med. Chem. 17, 2327-35, (2009)

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Phenolic glycosides from berries of Pimenta dioica. Hiroe Kikuzaki et al J. Nat. Prod. 71, 861-5, (2008)

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Eugenol inhibits quorum sensing at sub-inhibitory concentrations. Zhou L, Zheng H, Tang Y, et al. Biotechnol. Lett. 35(4), 631-7, (2013)

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Changes of metabolic profiles in an oral squamous cell carcinoma cell line induced by eugenol. Koh T, Murakami Y, Tanaka S, et al. In Vivo 27(2), 233-43, (2013)

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Structure-activity relationships of 1'S-1'-acetoxychavicol acetate for inhibitory effect on NO production in lipopolysaccharide-activated mouse peritoneal macrophages. Hisashi Matsuda et al Bioorg. Med. Chem. Lett. 15, 1949-53, (2005)

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Neural coding of binary mixtures in a structurally related odorant pair. Cruz G and Lowe G Sci. Rep. 3, 1220, (2013)

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Design, synthesis and SAR studies of 4-allyoxyaniline amides as potent 15-lipoxygensae inhibitors. Seyed Mohammad Seyedi et al Bioorg. Med. Chem. 17, 1614-22, (2009)

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Eugenol: a natural compound with versatile pharmacological actions. Pramod K, Ansari SH, and Ali J Nat. Prod. Commun. 5(12), 1999-2006, (2010)

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Methyleugenol hepatocellular cancer initiating effects in rat liver. Williams GM, Iatropoulos MJ, Jeffrey AM, et al. Food Chem. Toxicol. 53, 187-96, (2013)

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Influence of dentine on the pulpward release of eugenol or acids from restorative materials. Hume WR J. Oral Rehabil. 21(4), 469-73, (1994)

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Inhibition by capsaicin and its related vanilloids of compound action potentials in frog sciatic nerves. Tomohiro D, Mizuta K, Fujita T, et al. Life Sci. 92(6-7), 368-78, (2013)

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In chemico evaluation of skin metabolism: Investigation of eugenol and isoeugenol by electrochemistry coupled to liquid chromatography and mass spectrometry. Melles D, Vielhaber T, Baumann A, et al. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 913-914, 106-12, (2013)

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Antiproliferative and molecular mechanism of eugenol-induced apoptosis in cancer cells. Jaganathan SK and Supriyanto E Molecules 17(6), 6290-304, (2012)

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Biotechnological and molecular approaches for vanillin production: a review. Kaur B and Chakraborty D Appl. Biochem. Biotechnol. 169(4), 1353-72, (2013)

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Allyl/propenyl phenol synthases from the creosote bush and engineering production of specialty/commodity chemicals, eugenol/isoeugenol, in Escherichia coli. Kim SJ, Vassão DG, Moinuddin SG, et al. Arch. Biochem. Biophys. 541, 37-46, (2014)

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Anethole and eugenol reduce in vitro and in vivo leukocyte migration induced by fMLP, LTB4, and carrageenan. Estevão-Silva CF, Kummer R, Fachini-Queiroz FC, et al. J. Nat. Med. 68(3), 567-75, (2014)

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Evaluation of selected biomarkers for the detection of chemical sensitization in human skin: a comparative study applying THP-1, MUTZ-3 and primary dendritic cells in culture. Hitzler M, Bergert A, Luch A, et al. Toxicol. In Vitro 27(6), 1659-69, (2013)

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Apoptosis-like death in Leishmania donovani promastigotes induced by eugenol-rich oil of Syzygium aromaticum. Islamuddin M, Sahal D, and Afrin F J. Med. Microbiol. 63(Pt 1), 74-85, (2014)

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Anesthetizing solar-powered sea slugs for photobiological studies. Cruz S, Dionísio G, Rosa R, et al. Biol. Bull. 223(3), 328-36, (2012)

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Characterization of an isoeugenol monooxygenase (Iem) from Pseudomonas nitroreducens Jin1 that transforms isoeugenol to vanillin. Ryu JY, Seo J, Park S, et al. Biosci. Biotechnol. Biochem. 77(2), 289-94, (2013)

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Enhanced toxicity of binary mixtures of Bacillus thuringiensis subsp. israelensis and three essential oil major constituents to wild Anopheles sinensis (Diptera: Culicidae) and Aedes albopictus (Diptera: Culicidae). Chang KS, Shin EH, Yoo DH, et al. J. Med. Entomol. 51(4), 804-10, (2014)

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Cytotoxicity of dental compounds towards human oral squamous cell carcinoma and normal oral cells. Koh T, Machino M, Murakami Y, et al. In Vivo 27(1), 85-95, (2013)

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Effects of thymol and isoeugenol feed supplementation on quail adult performance, egg characteristics and hatching success. Luna A, Dambolena JS, Zygadlo JA, et al. Br. Poult. Sci. 53(5), 631-9, (2012)

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Hydroxychavicol, a betel leaf component, inhibits prostate cancer through ROS-driven DNA damage and apoptosis. Gundala SR, Yang C, Mukkavilli R, et al. Toxicol. Appl. Pharmacol. 280(1), 86-96, (2014)

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Production of natural value-added compounds: an insight into the eugenol biotransformation pathway. Mishra S, Sachan A, and Sachan SG J. Ind. Microbiol. Biotechnol. 40(6), 545-50, (2013)

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Retentiveness of various luting agents used with implant-supported prostheses: a preliminary in vitro study. Garg P, Gupta G, Prithviraj DR, et al. Int. J. Prosthodont. 26(1), 82-4, (2013)

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Performance of methyl eugenol + matrix + toxicant combinations under field conditions in Hawaii and California for trapping Bactrocera dorsalis (Diptera: Tephritidae). Jang EB, Ramsey A, and Carvalho LA J. Econ. Entomol. 106(2), 727-34, (2013)

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Study of anti-inflammatory activities of α-D-glucosylated eugenol. Zhang P, Zhang E, Xiao M, et al. Arch. Pharm. Res. 36(1), 109-15, (2013)

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Antidepressant-like effect of bis-eugenol in the mice forced swimming test: evidence for the involvement of the monoaminergic system. do Amaral JF, Silva MI, de Aquino Neto MR, et al. Fundam. Clin. Pharmacol. 27(5), 471-82, (2013)

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Eugenol reduces acute pain in mice by modulating the glutamatergic and tumor necrosis factor alpha (TNF-α) pathways. Dal Bó W, Luiz AP, Martins DF, et al. Fundam. Clin. Pharmacol. 27(5), 517-25, (2013)

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Re-evaluation of anti-inflammatory potential of eugenol in IL-1β-stimulated gingival fibroblast and pulp cells. Koh T, Murakami Y, Tanaka S, et al. In Vivo 27(2), 269-73, (2013)

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A new hydroxychavicol dimer from the roots of Piper betle. Lin CF, Hwang TL, Chien CC, et al. Molecules 18(3), 2563-70, (2013)

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Merck 14,3898

Beil. 6,IV,6337

Arctander, 1369 / Corp MSDS 1 (1), 1670:D / FT-IR 1 (1), 1091:A / FT-IR 2 (2), 1868:B / FT-NMR 1 (2), 278:A / Fenaroli / IR-Spectra (2), 585:E / IR-Spectra (3), 656:B / NMR-Reference 2 (1), 896:D / RegBook 1 (1), 1283:E / RegBook 69 (1), 1283:E / Sax 6, 1402 / Sigma FT-IR 1 (2), 559:D / Structure Index 1, 195:D:8 / Vapor Phase 3, 1028:A

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