Eugenol

Eugenol

Names
Preferred IUPAC name 2-Methoxy-4-(prop-2-en-1-yl)phenol
Other names 4-Allyl-2-methoxyphenol 2-Methoxy-4-(2-propenyl)phenol Eugenic acid Caryophyllic acid 1-Allyl-3-methoxy-4-hydroxybenzene Allylguaiacol 2-Methoxy-4-allylphenol 4-Allylcatechol-2-methyl ether
Identifiers
CAS Number	97-53-0 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:4917 Y
ChemSpider	13876103 Y
ECHA InfoCard	100.002.355
IUPHAR/BPS	2425
KEGG	D04117 Y
PubChem CID	3314
UNII	3T8H1794QW Y
InChI InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3 Y Key: RRAFCDWBNXTKKO-UHFFFAOYSA-N Y InChI=1/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3 Key: RRAFCDWBNXTKKO-UHFFFAOYAJ
SMILES Oc1ccc(cc1OC)CC=C
Properties
Chemical formula	C10H12O2
Molar mass	164.20 g·mol−1
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
Magnetic susceptibility (χ)	-102.1·10−6 cm3/mol
Hazards
NFPA 704	1 2 0
Flash point	104 °C (219 °F; 377 K)
Related compounds
Related compounds	2-Phenethyl propionate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Eugenol /juːdʒɪnɒl/ is a phenylpropene, an allyl chain-substituted guaiacol. Eugenol is a member of the phenylpropanoids class of chemical compounds. It is a colourless to pale yellow, aromatic oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, basil and bay leaf. It is present in concentrations of 80–90% in clove bud oil and at 82–88% in clove leaf oil.

Eugenol is used in perfumes, flavorings, and essential oils. It is also used as a local antiseptic and anaesthetic. Eugenol can be combined with zinc oxide to form zinc oxide eugenol which has restorative and prosthodontic applications in dentistry. For example, zinc oxide eugenol is used for root canal sealing.

Attempts have been made to develop eugenol derivatives as intravenous anesthetics, as an alternative to propanidid which produces unacceptable side effects around the site of injection in many patients.

It can be used to reduce the presence of Listeria monocytogenes and Lactobacillus sakei in food.

It is also used in manufacturing stabilizers and antioxidants for plastics and rubbers.