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
• General Description: Eugenol is a natural allyl phenol used in the synthesis of bio-based epoxy monomers, which demonstrate significantly lower binding affinity to the estrogen receptor α (ERα) compared to bisphenol A (BPA). This suggests that eugenol-derived epoxy compounds may serve as safer, sustainable alternatives to conventional epoxy resins with reduced endocrine-disrupting potential.

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

Synthesis of bio-based epoxy monomers from natural allyl- and vinyl phenols and the estimation of their affinity to the estrogen receptor α by molecular docking

10.1039/c6nj00782a

This study investigates the creation of sustainable epoxy monomers as alternatives to the diglycidyl ether of bisphenol A (DGEBA). The researchers synthesized diepoxydized diphenyls from eugenol, 4-vinyl guaiacol, and canolol through glycidylation with epichlorohydrin followed by cross metathesis (CM) dimerization using the Grubbs II catalyst. The synthesized products and their hydrolysed forms were then assessed for their potential endocrine-disrupting activity by estimating their binding affinity to the estrogen receptor a (ERa) using molecular docking. The study found that the epoxy forms had a moderate affinity to the antagonistic conformation of ERa, six to forty times lower than bisphenol A (BPA), while their hydrolysed forms exhibited relatively weak affinity in both agonistic and antagonistic conformations. This suggests that the synthesized bio-based epoxy monomers could serve as safer alternatives to DGEBA, with reduced potential for endocrine disruption.