Eugenol

Base Information

• Chemical Name: Eugenol
• CAS No.: 97-53-0
• Molecular Formula: C10H12O2
• Molecular Weight: 164.204
• Hs Code.: 29095090
• European Community (EC) Number: 202-589-1
• NSC Number: 757030,209525,8895
• UNII: 3T8H1794QW
• DSSTox Substance ID: DTXSID9020617
• Nikkaji Number: J3.977B
• Wikipedia: Eugenol
• Wikidata: Q423357
• NCI Thesaurus Code: C75095
• RXCUI: 4186
• Pharos Ligand ID: 9H97GQT89QL1
• Metabolomics Workbench ID: 38769
• ChEMBL ID: CHEMBL42710
• Mol file: 97-53-0.mol

Synonyms:Eugenol;Phenol, 2-methoxy-4-(2-propenyl)-

Chemical Property of Eugenol

Chemical Property:

• Appearance/Colour: Clear colorless pale yellow or amber-colored liquid
• Vapor Pressure: 0.0104mmHg at 25°C
• Melting Point: -5 - -20 °C(lit.)
• Refractive Index: n20/D 1.541(lit.)
• Boiling Point: 255 °C at 760 mmHg
• PKA: pKa 9.8 (Uncertain)
• Flash Point: 119.8 °C
• PSA: 29.46000
• Density: 1.05 g/cm³
• LogP: 2.12930
• Storage Temp.: 0-6°C
• Sensitive.: Air Sensitive
• Solubility.: 2.46g/l
• Water Solubility.: slightly soluble
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 164.083729621
• Heavy Atom Count: 12
• Complexity: 145

Purity/Quality:

99% ^*data from raw suppliers

Eugenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-42/43-38-40-43-36/38
• Safety Statements: 26-36-24/25-23-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Plant-Derived Allergens
• Drug Classes: Herbal and Dietary Supplements
• Canonical SMILES: COC1=C(C=CC(=C1)CC=C)O
• Description: Sensitization to eugenol mainly occurs in those in dental professions. Eugenol is contained in the "fragrance mix".
• Uses: eugenol is a botanical fraction. It is anti-bacterial, anti-inflammatory, and pain relieving. It can also be used as a local, topical anesthetic and antiseptic. In a cosmetic formulation, it can mask odor or provide fragrance. eugenol is a yellow, oily liquid and is generally associated with clove oil. However, it is also found in nutmeg, cinnamon, and bay leaf. Eugenol is a flavoring obtained from clove oil and also found in car- nation and cinnamon leaves. it is a stable, light yellow-green liquid of clove odor. it is slightly soluble in water and miscible in alcohol. it should be stored in glass or tin, avoiding iron containers. it is used in spice oils for application in condiments and meats at 100–200 ppm and in baked goods and candy at approximately 30 ppm. analgesic (topical), antiseptic, antifungal Eugenol is a dental compound which shows cytotoxicity to human oral squamous cell carcinoma and oral cells. When glucosylated, this compound exhibits anti-inflammatory activity.
• Clinical Use: 4-Allyl-2-methoxyphenol is obtained primarily from cloveoil. It is a pale-yellow liquid with a strong aroma of clovesand a pungent taste. Eugenol is only slightly soluble in waterbut is miscible with alcohol and other organic solvents.Eugenol possesses both local anesthetic and antiseptic activityand can be directly applied on a piece of cotton to relievetoothaches. Eugenol is also used in mouthwashes because ofits antiseptic property and pleasant taste. The phenol coefficientof eugenol is 14.4.

Technology Process of Eugenol

There total 84 articles about Eugenol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

4-allyl-2-methoxy-1-(methoxymethoxy)benzene (143654-03-9) → 4-allylguaiacol (97-53-0)

Guidance literature:

With toluene-4-sulfonic acid; In neat (no solvent, solid phase); at 20 ℃; for 0.583333h; Green chemistry;

DOI:10.2174/1570178614666170321103650

Reference yield: 90.0%

5-allyl-2-hydroxy-3-methoxybenzoic acid (2216-99-1) → 4-allylguaiacol (97-53-0)

Guidance literature:

With lithium chloride; In N,N-dimethyl-aniline; at 190 ℃; for 3h; Reagent/catalyst; Solvent; Temperature; Time; Inert atmosphere;

Reference yield: 87.0%

3-[3-methoxy-4-(tert-butyldimethylsiloxy)phenyl]-1-propene (214330-24-2) → 4-allylguaiacol (97-53-0)

Guidance literature:

With sodium tetrachloroaurate(III) dihydrate; In methanol; at 20 ℃; for 7h;

DOI:10.1055/s-0034-1379032

upstream raw materials:

methyl magnesium iodide

1,2-dimethoxy-4-(2-propenyl)benzene

O-allyl guaiacol

5-allyl-2-hydroxy-3-methoxybenzoic acid

Downstream raw materials:

1-(2-hydroxyethyl)-2-methoxy-4-(2-propenyl)benzene

4-allyl-2-methoxy-6-piperidin-1-ylmethyl-phenol

4-allyl-2-methoxy-6-(morpholin-4-ylmethyl)phenol

4,4'-diallyl-6,6'-dimethoxy-2,2'-piperazine-1,4-diyldimethyl-bis-phenol

Refernces

• 1、 Neethu, P. P.,Sakthivel, A.,Sreenavya, A.. "Molybdate Stabilized Magnesium‐Iron Hydrotalcite Materials: Potential Catalysts for Isoeugenol to Vanillin and Olefin Epoxidation". . . Retrieved 2021/08/03.
• 2、 Cook, Adam,MacLean, Haydn,St. Onge, Piers,Newman, Stephen G.. "Nickel-catalyzed reductive deoxygenation of diverse C-O bond-bearing functional groups". . p. 13337 - 13347. Retrieved 2021/11/20.