Eugenol

Title: Eugenol
CAS Registry Number: 97-53-0
CAS Name: 2-Methoxy-4-(2-propenyl)phenol
Additional Names: 4-allyl-2-methoxyphenol; allylguaiacol; eugenic acid; caryophyllic acid
Molecular Formula: C10H12O2
Molecular Weight: 164.20
Percent Composition: C 73.15%, H 7.37%, O 19.49%
Literature References: Obtained from many natural sources: Beilstein vol. 6, 961. Prepn: Claisen, Ann. 418, 113 (1919); from oil of cloves: Waterman, Priester, Rec. Trav. Chim. 48, 1272 (1929). Toxicity study: E. C. Hagan et al., Toxicol. Appl. Pharmacol. 7, 18 (1965).
Properties: Colorless or pale yellow liquid, bp 255°. Darkens and thickens on exposure to air. Odor of cloves; spicy, pungent taste. mp -9.2 to -9.1°. d420 1.0664. nD20 1.5410. Practically insol in water. Misc with alcohol, chloroform, ether, oils. One ml dissolves in 2 ml 70% alcohol; sol in glacial acetic acid, in aq fixed alkali hydroxide solns. Ferric chloride, potassium permanganate. LD50 in rats, mice (mg/kg): 2680, 3000 orally (Hagan).
Melting point: mp -9.2 to -9.1°
Boiling point: bp 255°
Index of refraction: nD20 1.5410
Density: d420 1.0664
Toxicity data: LD50 in rats, mice (mg/kg): 2680, 3000 orally (Hagan)
Derivative Type: Benzoate
Additional Names: O-Benzoyleugenol
Molecular Formula: C17H16O3
Molecular Weight: 268.31
Percent Composition: C 76.10%, H 6.01%, O 17.89%
Properties: Crystals, mp 69-70°. bp 360°. Freely sol in benzene, chloroform, ether, hot alcohol. Practically insol in water.
Melting point: mp 69-70°
Boiling point: bp 360°
Use: In perfumery instead of oil of cloves; manuf vanillin. As insect attractant.
Therap-Cat: Analgesic (dental).
Keywords: Analgesic (Dental).
Euparin Eupatorin Eupatorium Euprocin Evening Primrose Oil

Eugenol
Eugenol
Eugenol 3D
Identifiers
CAS number 97-53-0 YesY
PubChem 3314
ChemSpider 13876103 YesY
UNII 3T8H1794QW YesY
KEGG D04117 YesY
ChEBI CHEBI:4917 YesY
ChEMBL CHEMBL42710 YesY
Jmol-3D images Image 1
Properties
Molecular formula C10H12O2
Molar mass 164.20 g/mol
Density 1.06 g/cm3
Melting point −7.5 °C; 18.5 °F; 265.6 K
Boiling point 254 °C; 489 °F; 527 K
Acidity (pKa) 10.19 at 25 °C
Hazards
Flash point 104 °C; 219 °F; 377 K
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Eugenol is a phenylpropene, an allyl chain-substituted guaiacol. Eugenol is a member of the phenylpropanoids class of chemical compounds. It is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, basil and bay leaf.[1][2][3][4][5] It is slightly soluble in water and soluble in organic solvents. It has a spicy, clove-like aroma.

The name is derived from the scientific name for clove, Eugenia aromaticum or Eugenia caryophyllata. Eugenol is responsible for the aroma of cloves. It is the main component in the essential oil extracted from cloves, comprising 72–90% of the total.