Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anaesthetic. Eugenol can be combined with zinc oxide to form a material – known as zinc oxide eugenol – which has restorative and prosthodontic applications in dentistry. For example, zinc oxide eugenol is used for root canal sealing It can be used to reduce the presence of Listeria monocytogenes and Lactobacillus sakei in food. They are also used in manufacturing stabilizers and antioxidants for plastics and rubbers. Attempts have been made to develop eugenol derivatives for intravenous injection, such as propanidid and G.29.505. The latter produced unacceptable side effects around the site of injection in many patients. It is one of many compounds that is attractive to males of various species of orchid bees, which apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study. It also attracts female cucumber beetle and different types of pollinators of Gymnadenia. Clove oil is growing in popularity as an anaesthetic for use on aquarium fish as well as on wild fish when sampled for research and management purposes. Where readily available, it presents a humane method to euthanise sick and diseased fish either by direct over-dose or to induce sleep before an overdose of ethanol. It is also used in some mousetraps and kills certain human colon cancer cell lines in vitro and in vivo.
Eugenol is hepatotoxic, meaning it may cause damage to the liver. Overdose is possible, causing a wide range of symptoms from blood in the patient's urine, to convulsions, diarrhoea, nausea, unconsciousness, dizziness, or rapid heartbeat. According to a published 1993 report, a 2-year old boy nearly died after taking between 5 and 10 ml. Eugenol is subject to restrictions on its use in perfumery as some people may become sensitised to it, however, the degree to which eugenol can cause an allergic reaction in humans is disputed.
^Jadhav BK, Khandelwal KR, Ketkar AR, Pisal SS.; Khandelwal; Ketkar; Pisal (February 2004). "Formulation and evaluation of mucoadhesive tablets containing eugenol for the treatment of periodontal diseases". Drug Dev Ind Pharm.30 (2): 195–203. doi:10.1081/DDC-120028715. PMID15089054.
^Jack L. Ferracane, Materials in Dentistry: Principles and Applications, 2001, 2d Edition, Lippincott Williams & Wilkins, ISBN 0-7817-2733-2
^Mechanisms of Bactericidal Action of Cinnamaldehyde against Listeria monocytogenes and of Eugenol against L. monocytogenes and Lactobacillus sakei. Alexander O. Gill and Richard A. Holley, Appl. Environ. Microbiol., October 2004, vol. 70, no. 10, pages 5750–5755, doi:10.1128/AEM.70.10.5750-5755.2004
^Pathak, SB; Niranjan, K; Padh, H; Rajani, M (2004). "TLC Densitometric Method for the Quantification of Eugenol and Gallic Acid in Clove". Chromatographia60 (3–4): 241–244. doi:10.1365/s10337-004-0373-y.
^ abBullerman, LB; Lieu, FY; Seier, SA (July 1977). "INHIBITION OF GROWTH AND AFLATOXIN PRODUCTION BY CINNAMON AND CLOVE OILS. CINNAMIC ALDEHYDE AND EUGENOL". Journal of Food Science42 (4): 1107–1109. doi:10.1111/j.1365-2621.1977.tb12677.x.
^Lee, Kwang-Geun; Takayuki Shibamoto (2001). "Antioxidant property of aroma extract isolated from clove buds [Syzygium aromaticum (L.) Merr. et Perry]". Food Chemistry74 (4): 443–448. doi:10.1016/S0308-8146(01)00161-3.
^Kreydiyyeh, SI; Usta, J; Copti, Rtitle = Effect of cinnamon, clove and some of their constituents on the Na+-K+-ATPase activity and alanine absorption in the rat jejunum (2000). "Effect of cinnamon, clove and some of their constituents on the Na(+)-K(+)-ATPase activity and alanine absorption in the rat jejunum". Food and Chemical Toxicology38 (9): 755–762. doi:10.1016/S0278-6915(00)00073-9. PMID10930696.
^Dighe, VV; Gursale, AA; Sane, RT; Menon, S; Patel, PH (2005). "Quantitative Determination of Eugenol from Cinnamomum tamala Nees and Eberm. Leaf Powder and Polyherbal Formulation Using Reverse Phase Liquid Chromatography". Chromatographia61 (9–10): 443–446. doi:10.1365/s10337-005-0527-6.
^Bennett, A; Stamford, IF; Tavares, IA; Jacobs, S; Capasso, F; Mascolo, N; Autore, G; Romano, V; Di Carlo, G (1988). "The biological activity of eugenol, a major constituent of nutmeg (Myristica fragrans): Studies on prostaglandins, the intestine and other tissues". Phytotherapy Research2 (3): 124–130. doi:10.1002/ptr.2650020305.
^Johnson, CB; Kirby, J; Naxakis, G; Pearson, S (1999). "Substantial UV-B-mediated induction of essential oils in sweet basil (Ocimum basilicum L.)". Phytochemistry51 (4): 507–510. doi:10.1016/S0031-9422(98)00767-5.
^Ize-Ludlow, D; Ragone, S; Bruck, IS; Bernstein, JN; Duchowny, M; Peña, BM (2004). "Neurotoxicities in Infants Seen With the Consumption of Star Anise Tea". Pediatrics114 (5): e653–e656. doi:10.1542/peds.2004-0058. PMID15492355.