IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 (1987),p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 36 (1985),p. 75.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NTP Carcinogenesis Studies (feed); Equivocal Evidence: mouse NTPTR*    National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No. NTP-TR-223 ,1983. ; No Evidence: rat NTPTR*    National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No. NTP-TR-223 ,1983. . Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

The Eugenol is an organic compound with the formula C₁₀H₁₂O₂. The IUPAC name of this chemical is 2-methoxy-4-prop-2-enylphenol. With the CAS registry number 97-53-0, it is also named as phenol, 2-methoxy-4-(2-propen-1-yl)-. The product's categories are Antioxidant; Biochemistry. Besides, it is a clear colorless pale yellow or amber-colored liquid, which should be stored in a dark and cool place.It will be darkens and thickens on exposure to air. Also darkens with age. Eugenol may decompose on exposure to light. Insoluble in water.It reacts with strong alkalis. Eugenol is incompatible with strong oxidizers. This includes ferric chloride and potassium permanganate.

The Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anesthetic. It is also a key ingredient in Indonesian kretek (clove) cigarettes. It was used in the production of isoeugenol for the manufacture of vanillin, though most vanillin is now produced from phenol or from lignin. Eugenol is attractive to males of various species of orchid bees, so it is commonly used as bait to attract and collect these bees for study. Eugenol derivatives or methoxyphenol are used in formulating insect attractants and UV absorbers, biocides, analgesics, and antiseptics. They are also used in manufacturing stabilizers and antioxidants for plastics and rubbers.

Physical properties about Eugenol are:
(1)ACD/LogP: 2.20; (2)ACD/LogD (pH 5.5): 2.2; (3)ACD/LogD (pH 7.4): 2.2; (4)ACD/BCF (pH 5.5): 27.88; (5)ACD/BCF (pH 7.4): 27.85; (6)ACD/KOC (pH 5.5): 376.88; (7)ACD/KOC (pH 7.4): 376.41; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 4; (11)Polar Surface Area: 29.46 Å²; (12)Index of Refraction: 1.535; (13)Molar Refractivity: 48.72 cm³; (14)Molar Volume: 156.2 cm³; (15)Polarizability: 19.31×10^-24cm³; (16)Surface Tension: 36.5 dyne/cm; (17)Density: 1.05 g/cm³; (18)Flash Point: 119.8 °C; (19)Enthalpy of Vaporization: 51.24 kJ/mol; (20)Boiling Point: 255 °C at 760 mmHg; (21)Vapour Pressure: 0.0104 mmHg at 25°C.

Preparation of Eugenol:
The Eugenol can be prepared by 1-allyloxy-2-methoxy-benzene. This reaction will need reagent BF₃+2 CH₃COOH. The reaction temperature is 68 °C.


Uses of Eugenol: 
It can be used to produce 2-Methoxy-4-propyl-phenol at temperature of 20 °C. It will need reagent H₂, catalyst 10 percent Pd/C and solvent ethanol with reaction time of 5 hours. The yield is about 98%.


When you are using Eugenol, please be cautious about it as the following:
It is harmful if swallowed and may cause sensitisation by inhalation and skin contact. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, Eugenol is irritating to eyes, respiratory system and skin and limited evidence of a carcinogenic effect. When you are using it, wear suitable protective clothing, do not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer) and avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES:Oc1ccc(cc1OC)CC=C;
(2)Std. InChI:InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3;
(3)Std. InChIKey:RRAFCDWBNXTKKO-UHFFFAOYSA-N.

The toxicity data of Eugenol is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LDLo	oral	500mg/kg (500mg/kg)	BEHAVIORAL: ATAXIA GASTROINTESTINAL: NAUSEA OR VOMITING	Gastroenterology. Vol. 15, Pg. 481, 1950.
guinea pig	LD50	oral	2130mg/kg (2130mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.
hamster	LD50	intratracheal	17mg/kg (17mg/kg)	LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA	Archives of Toxicology. Vol. 59, Pg. 78, 1986.
mouse	LD50	intraperitoneal	500mg/kg (500mg/kg)		Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 250, Pg. 1148, 1960.
mouse	LD50	intravenous	72mg/kg (72mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION	Archives Internationales de Pharmacodynamie et de Therapie. Vol. 164, Pg. 30, 1966.
mouse	LD50	oral	3gm/kg (3000mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.
rat	LC	inhalation	> 2580mg/m3/4H (2580mg/m3)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Archives of Toxicology. Vol. 62, Pg. 381, 1988.
rat	LD50	intratracheal	11mg/kg (11mg/kg)	LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA	Archives of Toxicology. Vol. 59, Pg. 78, 1986.
rat	LD50	oral	1930mg/kg (1930mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: COMA LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Proceedings of the Society for Experimental Biology and Medicine. Vol. 73, Pg. 148, 1950.
rat	LDLo	intraperitoneal	800mg/kg (800mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: MUSCLE WEAKNESS KIDNEY, URETER, AND BLADDER: OTHER CHANGES	Revue Medicale de la Suisse Romande. Vol. 16, Pg. 449, 1896.
rat	LDLo	subcutaneous	5gm/kg (5000mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: MUSCLE WEAKNESS KIDNEY, URETER, AND BLADDER: OTHER CHANGES	Revue Medicale de la Suisse Romande. Vol. 16, Pg. 449, 1896.