Compound Summary

General Compound Information

4-allyl-1-methoxybenzene (estragol)

Description
Estragole is an olefinic compound.
Synonyms
Estragole;  4-Allylanisole;  140-67-0;  1-Allyl-4-methoxybenzene;  p-Allylanisole;
FlavorDB ID
3055
PUBCHEM ID
Molecular Weight
148.2
Molecular Formula
C10H12O
Openeye Can Smiles
COC1=CC=C(C=C1)CC=C
IUPAC Inchikey
ZFMSMUAANRJZFM-UHFFFAOYSA-N
Compound Classification
  • ClassyFire Ontology
Compound Quality
CATEGORY QUALITY THRESHOLD OCCURENCE REFERENCE
smell aniseed-like, liquorice-like 4.049e-2 µmol/L details
smell aniseed-like, liquorice-like 1.080e-1 µmol/L details
smell 4.049e-2 µmol/L licorice details
Compound Toxicity and Food Additive Safety (OFAS)
Toxicity Summary
Link to the Distributed Structure-Searchable Toxicity (DSSTox) Database
IDENTIFICATION AND USE: 1-Methoxy-4-(2-propenyl)benzene (Estragole) is a liquid. It is used in perfumes and as flavor in foods and liqueurs. It has been tested as an experimental therapy.
HUMAN STUDIES: When tested as 3% in petrolatum, it produced no irritation after a 48-hr closed-patch test on human subjects. A maximization test was carried out on 25 volunteers. The material was tested at a concentration of 3% in petrolatum and produced no sensitization reactions. It was not mutagenic when tested on human cells in vitro.
ANIMAL STUDIES: Rats given 4 daily oral doses of 605 mg/kg estragole showed minor liver damage, consisting of discoloration, mottling and blunting of lobe edge. Applied full strength to intact or abraded rabbit skin for 24 hr under occlusion estragole was moderately irritating. Estragole is a rodent liver carcinogen which requires bioactivation. It induced hepatocellular carcinomas by 15 months in 23 and 39% of the mice that received total doses of 4.4 and 5.2 umoles, respectively. In rats estragole induced dose-dependent increases in DNA damage following EndoIII or hOGG1 digestion and without enzyme treatment in liver, the cancer target organ. The formation of estragole-specific DNA adducts following conversion from estragole to the nucleophilic metabolite by sulfotransferase 1A1 (SULT1A1) has been reported.
Source: DrugBank or Hazardous Substances Data Bank (HSDB)
Food Additive Safety (OFAS)
ESTRAGOLE is used for FLAVORING AGENT OR ADJUVANT. More food additive safty information please view GRAS report.
Receptors
Receptor REFERENCE EC50 [µM] Effective Concentration [µM]
OR2T34 details Activated
OR52D1 details Activated
Consensus Spectra
Spectrum Type Spectrum View Description Polarity
Experimental GCMS view GCMS positive
Experimental LCMS view LCMS_Positive positive
Experimental LCMS view LCMS_Negative negative