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| CAS No.: | 97-53-0 |
|---|---|
| Name: | Eugenol |
| Molecular Structure: | |
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| Formula: | C10H12O2 |
| Molecular Weight: | 164.204 |
| 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; |
| EINECS: | 202-589-1 |
| Density: | 1.05 g/cm3 |
| Melting Point: | -5 - -20 °C(lit.) |
| Boiling Point: | 255 °C at 760 mmHg |
| Flash Point: | 119.8 °C |
| Solubility: | slightly soluble in water |
| Appearance: | Clear colorless pale yellow or amber-colored liquid |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 22-36/37/38-42/43-38-40 |
| Safety: | 26-36-24/25-23 |
| PSA: | 29.46000 |
| LogP: | 2.12930 |
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4-allyl-2-methoxy-1-(methoxymethoxy)benzene
- 97-53-0
4-allylguaiacol
| Conditions | Yield |
|---|---|
| With toluene-4-sulfonic acid In neat (no solvent, solid phase) at 20℃; for 0.583333h; Green chemistry; | 96% |
| With p-toluenesulfonic acid monohydrate In dichloromethane Solvent; | 95.5% |
| With toluene-4-sulfonic acid In dichloromethane Solvent; | 95.5% |
| With bismuth(III) chloride In water; acetonitrile at 50℃; for 1h; chemoselective reaction; | 89% |
- 144150-79-8
2-methoxy-4-(prop-2-en-1-yl)phenyl 4-methylbenzenesulfonate
- 97-53-0
4-allylguaiacol
| Conditions | Yield |
|---|---|
| With magnesium In methanol for 6h; Ambient temperature; | 95% |
| Conditions | Yield |
|---|---|
| Stage #1: 4-allyl-(1-allyloxy)-2-methoxybenzene With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 2h; Inert atmosphere; Stage #2: With methanol In diethyl ether; pentane at -78℃; Inert atmosphere; | 92% |
| With ethylmagnesium chloride; iron(II) chloride In tetrahydrofuran; m-xylene at 20℃; for 1h; | 86% |
| Conditions | Yield |
|---|---|
| With lithium chloride In N,N-dimethyl-aniline at 190℃; for 3h; Reagent/catalyst; Solvent; Temperature; Time; Inert atmosphere; | 90% |
| With 2,3-Dimethylaniline at 160℃; |
- 103552-63-2
4-Allyl-1-(1-ethoxy-ethoxy)-2-methoxy-benzene
- 97-53-0
4-allylguaiacol
| Conditions | Yield |
|---|---|
| With diphosphorus tetraiodide In dichloromethane 0 degC, 25 min and room temp., 5 min; | 90% |
- 97-53-0
4-allylguaiacol
| Conditions | Yield |
|---|---|
| With diphosphorus tetraiodide In dichloromethane at 0℃; for 0.75h; | 90% |
| Conditions | Yield |
|---|---|
| With methanol; potassium permanganate at 25℃; chemoselective reaction; | 90% |
| With aluminium trichloride; potassium iodide In water; acetonitrile at 80℃; for 4h; | 83% |
| Conditions | Yield |
|---|---|
| Suzuki-Miyaura Coupling; Inert atmosphere; | 90% |
| Conditions | Yield |
|---|---|
| In N,N-dimethyl-formamide at 276 - 300℃; for 0.025h; Irradiation; | 87% |
| With boron trifluoride diacetate at 68℃; |
- 214330-24-2
3-[3-methoxy-4-(tert-butyldimethylsiloxy)phenyl]-1-propene
- 97-53-0
4-allylguaiacol
| Conditions | Yield |
|---|---|
| With sodium tetrachloroaurate(III) dihydrate In methanol at 20℃; for 7h; | 87% |
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Consensus Reports
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.
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. |