Eugenol

Product Name:

Eugenol

CAS:

97-53-0

MF:

C10H12O2

MW:

164.2

EINECS:

202-589-1

Mol File:

97-53-0.mol

Melting point 

−12-−10 °C(lit.)

Boiling point 

254 °C(lit.)

density 

1.067 g/mL at 25 °C(lit.)

vapor pressure 

<0.1 hPa (25 °C)

FEMA 

2467 | EUGENOL

refractive index 

n20/D 1.541(lit.)

Fp 

>230 °F

storage temp. 

0-6°C

solubility 

2.46g/l

form 

Liquid

pka

pKa 9.8 (Uncertain)

color 

Clear pale yellow to yellow

Water Solubility 

slightly soluble

Sensitive 

Air Sensitive

JECFA Number

1529

Merck 

14,3898

BRN 

1366759

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents.

InChIKey

RRAFCDWBNXTKKO-UHFFFAOYSA-N

CAS DataBase Reference

97-53-0(CAS DataBase Reference)

NIST Chemistry Reference

Eugenol(97-53-0)

EPA Substance Registry System

Eugenol (97-53-0)

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38-42/43-38-40-43-36/38

Safety Statements 

26-36-24/25-23-36/37

RIDADR 

UN1230 - class 3 - PG 2 - Methanol, solution

WGK Germany 

1

RTECS 

SJ4375000

F 

10-23

TSCA 

Yes

HS Code 

29095090

Hazardous Substances Data

97-53-0(Hazardous Substances Data)

Toxicity

LD50 in rats, mice (mg/kg): 2680, 3000 orally (Hagan)

Production

 be synthesized by chemical method in industry. However, chemical synthesis method produces isomers. Boiling point of two isomers is very close, resulting in difficult separation. So isolation method is the main method at present.
Isolation method from natural essential oil

Chemical synthesis

Allyl bromide, o-methoxyphenol, anhydrous acetone and anhydrous potassium carbonate are added to the kettle and heated to reflux for several hours. After cooling, dilute with water and then extract with ether. The extract is washed with 10% sodium hydroxide and dried over anhydrous potassium carbonate. Recover diethyl ether and acetone after distillation at atmospheric pressure, and then distill under reduced pressure and collect fraction at 110~113 ℃ (1600Pa), finally we get o-methoxyphenyl allyl ether. The mixture is boiled and refluxed for 1 hour and then cooled. The resulting grease is dissolved in ether and extracted with 10% sodium hydroxide solution. The extract is acidified with hydrochloric acid and extracted with ether. Dry the extract over anhydrous sodium sulfate and recover the ether through air distillation, and finally we get product. We could also get product through one step reaction between o-methoxyphenol and allyl chloride with copper as catalyst at 100 ℃.
Take essential oils containing large amounts of eugenol, such as clove oil, as raw materials, and add 30% sodium hydroxide solution, and then add inorganic acid or carbon dioxide to precipitate. In addition, addition reaction between clove oil and sodium acetate is also available. 
Eugenol could be prepared by synthetic methods, but it is generally isolated from plants or aromatic oils in industry. We could take clove basil which originating from Seychelles, Comoros as raw material. In 1965, it was introduced into China from the former Soviet Union. It is cultivated in the south of the Yangtze River. The clove basil content is the highest in spike, followed by leaves, and stems are the last. The main ingredient in the oil is eugenol, accounting for 60-70%. There are linalool, parachute, ocimene and so on. We could prepare eugenol by synthetic method, in which o-methoxyphenol reacts with bromopropene. And then rearrangement is carried out with heating.

Category

Pesticide

Toxic grading

Moderate toxicity

Chemical Properties

colourless to faintly yellow liquid with a strong odour of cloves

Chemical Properties

Eugenol is the main component of several essential oils; clove leaf oil and cinnamon leaf oilmay contain>90%.Eugenol occurs in small amounts in many other essential oils. It is a colorless to slightly yellow liquid with a spicy, clove odor.
Catalytic hydrogenation (e.g., in the presence of noble metal catalysts) yields dihydroeugenol. Isoeugenol is obtained fromeugenol by shifting the double bond. Esterification and etherification of the hydroxy group of eugenol yield valuable fragrance and flavor materials (e.g., eugenol acetate and eugenol methyl ether).

Chemical Properties

Eugenol has a strong aromatic odor of clove and a spicy, pungent taste. It darkens and thickens on exposure to air.

Preparation Products

Vanillin-->ISOEUGENOL-->Clove oil-->EUGENOL ACETATE-->Methyl eugenol

Raw materials

Potassium carbonate-->CARBON DIOXIDE-->Sodium acetate trihydrate-->Allyl chloride-->Linalool-->Guaiacol-->Allyl bromide-->Eucalyptus Citriodara Oil-->Clove oil-->Basil oil-->LAUREL OIL FROM LAURUS NOBILIS-->White camphor oil-->Allyl ether-->Cassia Aurantium P.E Catechins 8% HPLC-->CINNAMON LEAVES OIL-->OCIMENE-->Violet Leaf Absolute