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Eugenol

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Name

Eugenol

EINECS 202-589-1
CAS No. 97-53-0 Density 1.05 g/cm3
Solubility slightly soluble in water Melting Point -5 - -20 °C(lit.)
Formula C10H12O2 Boiling Point 255 °C at 760 mmHg
Molecular Weight 164.22 Flash Point 119.8 °C
Transport Information Appearance Clear colorless pale yellow or amber-colored liquid
Safety 26-36-24/25-23 Risk Codes 22-36/37/38-42/43-38-40
Molecular Structure Molecular Structure of 97-53-0 (Eugenol) Hazard Symbols HarmfulXn
Synonyms

Synthetic eugenol;Phenol, 2-methoxy-4- (2-propenyl)-;EPA Pesticide Chemical Code 102701;Allylguaiacol;p-Allylguaiacol;2-Metoksy-4-allilofenol [Polish];Caryophyllic acid;2-Methoxy-4-(3-propenyl)phenol;Eugenic acid;1-Hydroxy-2-methoxy-4-allylbenzene;1-Hydroxy-2-methoxy-4-propenylbenzene;Engenol;2-Methoxy-4-(2-propenyl)phenol;FEMA No. 2467;2-Methoxy-4-prop-2-enylphenol;Phenol,2-methoxy-4-(2-propenyl)-;FEMA Number 2467;4-Allylcatechol 2-methyl ether;Eugenol (natural);4-06-00-06337 (Beilstein Handbook Reference);4-allyl-2-methoxyphenol;2-Hydroxy-5-allylanisole;Phenol, 2-methoxy-4-(2-propenyl)-;2-Methoxy-4-(2-propen-1-yl)phenol;

 

Eugenol Consensus Reports

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.

Eugenol Specification

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.
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%.
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.

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